エタノール

関: ethanol

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/12 23:26:09」(JST)

wiki ja

エタノール（ethanol）はアルコールの一つ。別名として、エチルアルコール（ethyl alcohol）や、酒類の主成分であるため「酒精」とも呼ばれる。アルコール類の中で、最も身近に使われる物質の1つである。揮発性が強く、殺菌・消毒のほか、燃料としても用いられる。

性質

詳細は「アルコール」を参照

一般的なアルコールの性質を持つ。水などの極性溶媒や炭化水素も含む各種有機溶媒など、ほとんどの溶媒と自由に混和できる。

合成

現在市場に出回っているエタノールは、大部分がアルコール発酵によって製造されている。一部は、化石燃料由来のエチレンの水和反応等の有機合成手法によっても製造される。

反応

エタノールに濃硫酸を混ぜて、130〜140℃に加熱すると、ジエチルエーテルが生成する。

また、160〜170℃に加熱するとエチレンが生成する。

エタノールに適当な酸化剤を作用させる、または脱水素反応などを施すとアセトアルデヒドに変わり、さらに強い酸化反応条件下では酢酸まで酸化される。以上の酸化の過程を簡略した化学式で表すと以下のようになる。

エタノールに金属ナトリウムあるいは水素化ナトリウムを反応させると、水素ガスを発生しながらナトリウムエトキシドを生成する。

共沸と精製

水とエタノールの混合液を蒸留によって、二つの成分に完全に分離することはできない。これは水とエタノールが共沸をするためであり、この時の共沸混合物はエタノールが96%（質量パーセント濃度）、水が4%であるため、通常の蒸留によって得られるエタノールの最高濃度はおよそ96%である。ここにペンタン^[2]などの成分が存在すると、始留に水分が集まるようになる。薬局方にある「無水エタノール」を作るときは、この三成分共沸によってさらに水分が除かれたのち、分別蒸留でさらに精製される。

利用

溶剤（有機溶媒）、有機合成原料、消毒剤などとして広く使われている。用途別の使用量としては、飲用22%・工業用10%・燃料用68%である（2003年）。工業用アルコールのうち、天然の原料から作った発酵アルコールは、食品の防腐用、みりんなどの調味料の原料などに使用され、化学合成された合成アルコールは接着剤、インク、塗料、農薬などに使用される^[3]。

飲用（酒類）及び医薬品以外のエタノール（いわゆる工業用アルコール）はほとんどが変性アルコールと呼ばれるもので、エタノールにかなりの量あるいは少量のメタノールやイソプロピルアルコール等の物質が混入されている^[4]。従って酒として販売されているもの以外のアルコールを、「エタノール」と表示されているからといって、薄めて飲むなどは極めて危険である。

外用剤や化粧品等に用いられている変性アルコールは変性剤としてメタノールを使用しておらず有害性はやや低い。メタノールよりは毒性の低いイソプロピルアルコールを添加するか、苦味や匂いを付加して飲用に適さないアルコールとしている。なお、平成12年からアルコール事業法が施行され、許可を取得すれば酒税相当分の価格を上乗せしていない無変性アルコールを取り扱えるようになった（後述）。

炎が青白色で、日中の太陽光のもとでは見えにくい。2013年8月4日、滋賀で消火訓練準備中に消防団員が火が消えたことを確認しエタノールを注ぎ足したところ爆発、女児が火だるまになる悲惨な事故が起きた^[5]。警察では火が消えたことの確認が不十分だったと見ている^[6]。

自動車燃料

近年日本では、石油の代替燃料としてのエタノールの自動車用燃料用途に注目が集まっている。

自動車の登場期にすでに燃料として使われていた。米国では、1920年代にゼネラルモーターズが石油会社と共に（会社の利益となる）有鉛ガソリンを推進するようになったため、以降ほとんど使われなくなった。

「トマス・ミジリー#エチルの発見」も参照

フランスでは、1920年代から1950年代頃には砂糖大根で作ったエタノールをガソリンに混ぜて使っていた。石油が安価に手に入るようになりほとんどの国ではエタノールを使わなくなった。

しかし、ブラジルでは、1973年の石油ショックによる原油価格の高騰に対処するため、政府が1975年からプロアルコール（Proalcool）政策を実施し、自国で豊富にとれるサトウキビから生産できるエタノールをガソリン代替にすることを進めてきた。1977年にフォルクスワーゲン・ブラジリアを皮切りに導入され、既にブラジルでは年間に販売される新車の半数以上がエタノール燃料に対応した車となっている。2003年よりブラジルでのガソリンに対するエタノール混合率は25%となっている。

アメリカ合衆国でも、1970年代から中西部のとうもろこし生産地帯においてエタノール混合率10%のガソリン「ガソホール」が販売されてきた。1990年代になると、クリーンエア・アクト（大気浄化法）にもとづき、エタノール混合に優遇措置がなされた。これらは米国では農業生産者が政治に対して力をもっているからなしえたことでもあった。2000年代になり、米国内では、州によって状況が異なるが、通常E10とよばれる10%混合ガソリンが広く販売されるようになっている。しかし、すべての米国人がその実態を知っているとはいえない程度である。エタノールとガソリンの混合燃料（フレックス燃料）に対応した車（フレックス車）の販売も増加している。通常の米国車は基本的にE10対応となっており、普通にガソリンをいれていると思いながらE10フレックス燃料をいれているようなケースも実際には多く、使用者の意識がなくともフレックスを使用している場合がある。米国ではフレックスに対応している車はE10対応、E25対応とよばれるが、E10対応はすでに標準であり、フォードではE85というような車も販売をはじめている^[7]。

日本においては、実験を進めていた経済産業省が、コストの観点から日本国内での生産よりも輸入によることによる普及促進を狙い、2006年2月にブラジルの国営石油会社ペトロブラスと日本の日本アルコール販売の50%出資で、「日伯エタノール」を設立した。2007年2月時点で経済産業省の政策に対し石油会社の協力が得られておらず、ガソリンとの混合およびその販売にはまだ明確な道筋が立っていない。日本の法制度上では、過去にメタノールが主成分のガイアックスを高濃度アルコール燃料と名指しした上で事実上の販売禁止令を発布した経緯があり、その際に自動車部品への安全性を確保する基準とされた「アルコール添加量3%以下（E3相当）」という文面が現在でも法的根拠として残り続けていることや、「高濃度アルコール燃料」に対する過度のバッシングによる悪印象が未だ尾を引いている事から、E3以上の濃度のアルコール燃料の普及の目処は全く立っていないことが現状である。

モータースポーツのインディカー・シリーズでは2007年より98%エタノール燃料（飲用防止と発火を目視できるように2%のガソリンを混ぜてある）を使用している。

詳細は「アルコール燃料」を参照

医薬品

消毒用エタノール（阪神局方製）

日本では日本薬局方により純度が規定されている。

無水エタノール（別名：無水アルコール）: 15℃でエタノールを99.5v/v%以上含む。消毒効果は消毒用エタノールに比べて小さいが、肝癌治療に応用されている。
エタノール（別名：アルコール）: 15℃でエタノールを95.1〜96.9v/v%含む。
消毒用エタノール（別名：消毒用アルコール）: 15℃でエタノールを76.9〜81.4v/v%含む。一般的な医療用消毒剤。

医薬用の（日本薬局方の）エタノールは酒税相当額が課税されている。節税のため､イソプロピルアルコールを添加したものや変性アルコールを用いたものもあり､逆性石鹸で消毒の効力を高めた物もある｡

人体への影響

詳細は「エタノールと人体」を参照

ヒトがエタノールを摂取すると、中枢神経を抑制する効果により酔いという症状が現れる。アルコール飲料を長期にわたって飲み続けると脂肪肝などが見られることがあるが、エタノールの作用というよりはアルコール飲料を中心とした偏食の結果であるという見方もある。また、脳萎縮も発生する。

「消毒用アルコール」も参照

殺菌・消毒の用途では人体への影響はほぼ無視できるが、アルコール濃度が非常に高いため飲用しては急性アルコール中毒を引き起す危険性が高い。（他にメタノール等を含むものは人体に摂取すると重篤な症状を引き起こす危険がある）また皮膚等への消毒及びアルコール類の使用は、アルコールに対してアレルギーを持つ人には有害であるとされる。またアルコールには高い揮発性があり、皮膚へ塗布した際には水分の蒸発が著しい。皮膚への過度な使用は控える必要がある。

おもな誘導体

エチルメチルエーテル
ジエチルエーテル
エチルフェニルエーテル
酢酸
酢酸エチル
ブロモエタン
メタノール

法的規制

危険物

日本では消防法により危険物第4類（アルコール類　危険等級II）に指定されている。

飲用アルコール（酒類）

容積比率で1%以上のエチルアルコールを含む飲料は、酒税法により酒類と呼ばれ^[8]、この製造や販売には所轄税務署長の免許（製造免許や販売業免許）が必要である^[9]。酒税法では、酒類を製造所から移出するとき、または保税地域から引き取る際に酒税を納めることを義務付けている^[10]。同法ではさらに、さまざまな種類の酒類を規定し^[11]、種類に応じた税率を定める^[12]。

工業用アルコール

工業用のアルコールが酒税法で定める酒類に転用されるを防ぐために、昭和12年（1937年）に制定された旧アルコール専売法や平成12年（2000年）に制定されたアルコール事業法では、容積比で90%のエタノールを含むアルコールの製造・使用・流通を制限ないし管理している。

旧アルコール専売法の下では公示価格が設定され^[13]、酒類に転用するには高すぎる価格（酒税相当分が加算された価格）で販売された。工業用に使用するアルコールにはこの公示価格は適用されなかったが、その場合は添加物を加えて飲用不可の状態とすること（変性アルコール）が義務づけられていた^[14]。

アルコール事業法が施行され、専売制が廃止された後は、変性アルコールでないアルコール（一般アルコール^[15]、無変性アルコール^[16]、事業法アルコール^[17]などと呼ばれる。）も自由に取引できるようになった。ただし、製造・輸入・使用・販売には経済産業大臣の許可が必要である^[18]。なお、製造業者や輸入業者は省令で定められた加算額を含む価格で工業用アルコールを販売することができ、これを特定アルコール^[19]という。特定アルコールは許可を受けずに誰でも購入して自由に使用することができる。

工業用アルコールには、その原料・製造方法の違いにより発酵アルコールと合成アルコールの二種類がある。発酵アルコールはサトウキビから作った糖蜜などを原料として、それを発酵させて作る。合成アルコールはエチレンから化学的に合成されたものである。合成アルコールは、旧食品衛生法でいうところの化学的合成品^[20]にあたり、添加物としても食品に使用できない^[21]。

脚注

^ D.D. Wagman, W.H. Evans, V.B. Parker, R.H. Schumm, I. Halow, S.M. Bailey, K.L. Churney, R.I. Nuttal, K.L. Churney and R.I. Nuttal, The NBS tables of chemical thermodynamics properties, J. Phys. Chem. Ref. Data 11 Suppl. 2 (1982).
^ かつては、ベンゼンが用いられていたが、発がん性、毒性のため、近年ではペンタンが用いられている。例えば、[1]参照。
^ 総務省のウェブサイトにある資料 - アルコール専売事業（2001年に廃止）の仕組みをあらわしたもの（2010年12月01日閲覧）。
^ 変性アルコールの例（2010年11月29日閲覧）。平成12年12月26日付け厚生省の通達であるが、文書の末尾にアルコール専売法施行規則別表「工業用アルコール変性標準」の抜粋がある。
^ “消火訓練で10人やけど　滋賀、アルコールが飛散”. 日経新聞. (2013年8月4日)
^ “エタノールの「見えない炎」、消火訓練準備で10人やけど”. TBS. (2013年8月5日)
^ [2]
^ 酒税法第二条
^ 同第七条、第九条
^ 同第六条
^ 同第三条
^ 同第二十三条
^ アルコール専売法十九条
^ 同第二十六条
^ 使用例：三協化学株式会社のウェブサイト（2010年11月29日閲覧）
^ 使用例：平成12年１2月26日付け厚生省の通達（2010年11月29日閲覧）
^ 使用例：日本アルコール販売のウェブサイト（2010年11月29日閲覧）
^ アルコール事業法第三条、第十六条、第二十一条、第二十六条。
^ 同第二条
^ 旧食品衛生法第二条第三項
^ 食品衛生法第十条。食品衛生法施工規則第十二条別表第一（使用を認められている添加物の一覧表）も参照。

外部リンク

エタノール（エチルアルコール）　理科ねっとわーく（一般公開版） - 科学技術振興機構

wiki en

[Wiki en表示]

Commonly referred to simply as alcohol or spirits, ethanol /ˈɛθənɒl/ is also called ethyl alcohol, and drinking alcohol. It is the principal type of alcohol found in alcoholic beverages, produced by the fermentation of sugars by yeasts. It is a neurotoxic^[6]^[7] psychoactive drug and one of the oldest recreational drugs used by humans. It can cause alcohol intoxication when consumed in sufficient quantity. Ethanol is used as a solvent, an antiseptic, a fuel and the active fluid in modern (post-mercury) thermometers. It is a volatile, flammable, colorless liquid with the structural formula CH
3CH
2OH, often abbreviated as C
2H
5OH or C
2H
6O.

1 Etymology
2 Chemical formula
3 Natural occurrence
4 Pharmacology
- 4.1 Activity profile
- 4.2 Properties
- 4.3 Short-term
  - 4.3.1 Effects on the central nervous system
  - 4.3.2 Effects on metabolism
  - 4.3.3 Drug interactions
  - 4.3.4 Alcohol and digestion
  - 4.3.5 Alcohol and gastrointestinal diseases
  - 4.3.6 Magnitude of effects
- 4.4 Long-term
  - 4.4.1 Birth defects
  - 4.4.2 Cancer
  - 4.4.3 Other effects
5 History
6 Properties
- 6.1 Physical properties
- 6.2 Solvent properties
- 6.3 Flammability
7 Production
- 7.1 Ethylene hydration
- 7.2 Fermentation
  - 7.2.1 Cellulose
  - 7.2.2 Hydrocarbon
- 7.3 Testing
8 Research
9 Purification
- 9.1 Distillation
- 9.2 Molecular sieves and desiccants
- 9.3 Membranes and reverse osmosis
- 9.4 Other techniques
10 Grades of ethanol
- 10.1 Denatured alcohol
- 10.2 Absolute alcohol
- 10.3 Rectified spirits
11 Reactions
- 11.1 Ester formation
- 11.2 Dehydration
- 11.3 Combustion
- 11.4 Acid-base chemistry
- 11.5 Halogenation
- 11.6 Oxidation
12 Other uses
- 12.1 Motor fuel
- 12.2 Household heating
- 12.3 Feedstock
- 12.4 Antiseptic
- 12.5 Solvent
13 Charts
14 History
15 See also
16 References
17 Further reading
18 External links

Etymology

Ethanol is the systematic name defined by the International Union of Pure and Applied Chemistry (IUPAC) for a molecule with two carbon atoms (prefix "eth-"), having a single bond between them (suffix "-ane"), and an attached functional group-OH group (suffix "-ol").^[1]

The prefix ethyl was coined in 1834 by the German chemist Justus Liebig.^[8] Ethyl is a contraction of the French word ether (any substance that evaporated or sublimated readily at room temperature) and the Greek word ύλη (hyle, substance).^[9]

The name ethanol was coined as a result of a resolution that was adopted at the International Conference on Chemical Nomenclature that was held in April 1892 in Geneva, Switzerland.^[10]

The term "alcohol" now refers to a wider class of substances in chemistry nomenclature, but in common parlance it remains the name of ethanol. Ultimately a medieval loan from Arabic al-kuḥl,^[11] use of alcohol in this sense is modern, introduced in the mid 18th century. Before that time, Middle Latin alcohol referred to "powdered ore of antimony; powdered cosmetic", by the later 17th century "any sublimated substance; distilled spirit" use for "the spirit of wine" (shortened from a full expression alcohol of wine) recorded 1753. The systematic use in chemistry dates to 1850.

Chemical formula

Ethanol is a 2-carbon alcohol. Its molecular formula is CH₃CH₂OH. An alternative notation is CH₃–CH₂–OH, which indicates that the carbon of a methyl group (CH₃–) is attached to the carbon of a methylene group (–CH₂–), which is attached to the oxygen of a hydroxyl group (–OH). It is a constitutional isomer of dimethyl ether. Ethanol is sometimes abbreviated as EtOH, using the common organic chemistry notation of representing the ethyl group (C₂H₅) with Et.

Natural occurrence

Ethanol is a byproduct of the metabolic process of yeast. As such, ethanol will be present in any yeast habitat. Ethanol can commonly be found in overripe fruit.^[12] Ethanol produced by symbiotic yeast can be found in Bertam Palm blossoms. Although some animal species such as the Pentailed Treeshrew exhibit ethanol-seeking behaviors, most show no interest or avoidance of food sources containing ethanol.^[13] Ethanol is also produced during the germination of many plants as a result of natural anerobiosis.^[14] Ethanol has been detected in outer space, forming an icy coating around dust grains in interstellar clouds.^[15] Minute quantity amounts (244 ppb) of endogenous ethanol and acetaldehyde were found in the exhaled breath of healthy volunteers.^[16]

Pharmacology

Activity profile

Ethanol is known to possess the following direct pharmacodynamic actions:^[17]

GABA_A receptor positive allosteric modulator (primarily of δ subunit-containing receptors)
NMDA receptor negative allosteric modulator
Glycine receptor positive and negative allosteric modulator
5-HT₃ receptor positive allosteric modulator
nACh receptor positive and negative allosteric modulator
L-type calcium channel blocker
GIRK channel opener
Glycine reuptake inhibitor^[18]
Adenosine reuptake inhibitor^[19]

Some of its actions on ligand-gated ion channels, specifically the nACh receptors and the glycine receptor, are dose-dependent, with potentiation or inhibition occurring dependent on ethanol concentration. This is because ethanol's effects on these channels are a summation of positive and negative allosteric modulatory actions.^[17]

Properties

The removal of ethanol from the human body, through oxidation by alcohol dehydrogenase in the liver, is limited. Hence, the removal of a large concentration of alcohol from blood may follow zero-order kinetics. This means that alcohol leaves the body at a constant rate, rather than having an elimination half-life.^[20]

The rate-limiting steps for one substance may be in common with other substances. As a result, the blood alcohol concentration can be used to modify the rate of metabolism of methanol and ethylene glycol. Methanol itself is not highly toxic, but its metabolites formaldehyde and formic acid are; therefore, to reduce the rate of production and concentration of these harmful metabolites, ethanol can be ingested.^{[citation needed]} Ethylene glycol poisoning can be treated in the same way.

Pure ethanol will irritate the skin and eyes.^[21] Nausea, vomiting and intoxication are symptoms of ingestion. Long-term use by ingestion can result in serious liver damage.^[22] Atmospheric concentrations above one in a thousand are above the European Union Occupational exposure limits.^[22]

Short-term

BAC (g/L)	BAC (% v/v)	Symptoms^[23]
0.5	0.05%	Euphoria, talkativeness, relaxation
1	0.1 %	Central nervous system depression, nausea, possible vomiting, impaired motor and sensory function, impaired cognition
>1.4	>0.14%	Decreased blood flow to brain
3	0.3%	Stupefaction, possible unconsciousness
4	0.4%	Possible death
>5.5	>0.55%	Death

Effects on the central nervous system

Ethanol is a central nervous system depressant and has significant psychoactive effects in sublethal doses; for specifics, see "Effects of alcohol on the body by dose". Based on its abilities to change the human consciousness, ethanol is considered a psychoactive drug.^[24] Death from ethanol consumption is possible when blood alcohol level reaches 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1% can cause intoxication, with unconsciousness often occurring at 0.3–0.4%.^[25]

The amount of ethanol in the body is typically quantified by blood alcohol content (BAC), which is here taken as weight of ethanol per unit volume of blood. The table at the right summarizes the symptoms of ethanol consumption. Small doses of ethanol, in general, produce euphoria and relaxation; people experiencing these symptoms tend to become talkative and less inhibited, and may exhibit poor judgment. At higher dosages (BAC > 1 g/L), ethanol acts as a central nervous system depressant, producing at progressively higher dosages, impaired sensory and motor function, slowed cognition, stupefaction, unconsciousness, and possible death.

Ethanol acts in the central nervous system primarily by binding to the GABA_A receptor, increasing the effects of the inhibitory neurotransmitter GABA (i.e., it is a positive allosteric modulator).^[26]

Prolonged heavy consumption of alcohol can cause significant permanent damage to the brain and other organs. See Alcohol consumption and health.

According to the US National Highway Traffic Safety Administration, in 2002 about "41% of people fatally injured in traffic crashes were in alcohol related crashes".^[27] The risk of a fatal car accident increases exponentially with the level of alcohol in the driver's blood.^[28] Most drunk driving laws governing the acceptable levels in the blood while driving or operating heavy machinery set typical upper limits of blood alcohol content (BAC) between 0.02% and 0.08%.^{[citation needed]}

Discontinuing consumption of alcohol after several years of heavy drinking can also be fatal. Alcohol withdrawal can cause anxiety, autonomic dysfunction, seizures, and hallucinations. Delirium tremens is a condition that requires people with a long history of heavy drinking to undertake an alcohol detoxification regimen.

The reinforcing effects of alcohol consumption are also mediated by acetaldehyde generated by catalase and other oxidizing enzymes such as cytochrome P-4502E1 in the brain.^[29] Although acetaldehyde has been associated with some of the adverse and toxic effects of ethanol, it appears to play a central role in the activation of the mesolimbic dopamine system.^[30]

Effects on metabolism

Ethanol within the human body is converted into acetaldehyde by alcohol dehydrogenase and then into the acetyl in acetyl CoA by acetaldehyde dehydrogenase. Acetyl CoA is the final product of both carbohydrate and fat metabolism, where the acetyl can be further used to produce energy or for biosynthesis. As such, ethanol can be compared to an energy-bearing macronutrient, yielding approximately 7 kcal per gram consumed.^[31] However, the product of the first step of this breakdown, acetaldehyde,^[32] is more toxic than ethanol. Acetaldehyde is linked to most of the clinical effects of alcohol. It has been shown to increase the risk of developing cirrhosis of the liver^[33] and multiple forms of cancer.

During the metabolism of alcohol via the respective dehydrogenases, NAD (Nicotinamide adenine dinucleotide) is converted into reduced NAD. Normally, NAD is used to metabolise fats in the liver, and as such alcohol competes with these fats for the use of NAD. Prolonged exposure to alcohol means that fats accumulate in the liver, leading to the term 'fatty liver'. Continued consumption (such as in alcoholism) then leads to cell death in the hepatocytes as the fat stores reduce the function of the cell to the point of death. These cells are then replaced with scar tissue, leading to the condition called cirrhosis.

Drug interactions

Ethanol can intensify the sedation caused by other central nervous system depressant drugs such as barbiturates, benzodiazepines, opioids, non-benzodiazepines (such as Zolpidem and Zopiclone), antipsychotics, sedative antihistamines, and antidepressants.^[25] It interacts with cocaine in vivo to produce cocaethylene, another psychoactive substance.^[34] Ethanol enhances the bioavailability of methylphenidate (elevated plasma d-MPH).^[35] In combination with cannabis, ethanol increases plasma THC levels, which suggets that ethanol may increase the absorption of THC.^[36]

Alcohol and metronidazole

One of the most important drug/food interactions that should be noted is between alcohol and metronidazole.

Metronidazole is an antibacterial agent that kills bacteria by damaging cellular DNA and hence cellular function.^[37] Metronidazole is usually given to people who have diarrhea caused by Clostridium difficile bacteria. C. difficile is one of the most common microorganisms that cause diarrhea and can lead to complications such as colon inflammation and even more severely, death.

Patients who are taking metronidazole are strongly advised to avoid alcohol, even after 1 hour after the last dose. The reason is that alcohol and metronidazole can lead to side effects such as flushing, headache, nausea, vomiting, abdominal cramps, and sweating.^[38]^[39]^[39] These symptoms are often called the disulfiram-like reaction. The proposed mechanism of action for this interaction is that metronidazole can bind to an enzyme that normally metabolizes alcohol. Binding to this enzyme may impair the liver's ability to process alcohol for proper excretion.^[40]

Alcohol and digestion

Digestive system

A part of ethyl alcohol is hydrophobic. This hydrophobic or lipophilic end can diffuse across cells that line the stomach wall. In fact, alcohol is one of the rare substances that can be absorbed in the stomach. Most food substances are absorbed in the small intestine. However, even though alcohol can be absorbed in the stomach, it is mostly absorbed in the small intestine because the small intestine has a large surface area that promotes absorption. Once alcohol is absorbed in the small intestine, it delays the release of stomach contents from emptying into the small intestine. Thus, alcohol can delay the rate of absorption of nutrients.^[41] After absorption, alcohol reaches the liver where it is metabolized.

Breathalyzers
Alcohol that is not processed by the liver goes to the heart. The liver can process only a certain amount of alcohol per unit time. Thus, when a person drinks too much alcohol, more alcohol can reach the heart. In the heart, alcohol reduces the force of heart contractions. Consequently, the heart will pump less blood, lowering overall body blood pressure.^[42] Also, blood that reaches the heart goes to the lungs to replenish blood's oxygen concentration. It is at this stage that a person can breathe out traces of alcohol.^[42] This is the underlying principle of the alcohol breath testing (or breathalyzers) to determine if a driver has been drinking and driving.^[43]

From the lungs, blood returns to the heart and will be distributed throughout the body. Interestingly, alcohol increases levels of high-density lipoproteins(HDLs), which carry cholesterol.^[42] Alcohol is known to make blood less likely to clot, reducing risk of heart attack and stroke. This could be the reason why alcohol could produce health benefits when consumed in moderate amounts.^[44] Also, alcohol dilates blood vessels. Consequently, a person will feel warmer, and their face turns flush and pink.^[42]

Loss of balance
When alcohol reaches the brain, it has the ability to delay signals that are sent between nerve cells that control balance, thinking and movement.^[42]

Frequent urination
Moreover, alcohol can affect the brain's ability to produce antidiuretic hormones. These hormones are responsible for controlling the amount of urine that is produced. Alcohol prevents the body from reabsorbing water, and consequently a person who recently drank alcohol will urinate frequently.^[42]

Alcohol and gastrointestinal diseases

Diagram of mucosal layer

Alcohol stimulates gastric juice production, even when food is not present. In other words, when a person drinks alcohol, the alcohol will stimulate stomach's acidic secretions that are intended to digest protein molecules. Consequently, the acidity has potential to harm the inner lining of the stomach. Normally, the stomach lining is protected by a mucus layer that prevents any acids from reaching the stomach cells.

However, in patients who have a peptic ulcer disease (PUD), this mucus layer is broken down. PUD is commonly associated with a bacteria H. pylori. H. pylori secretes a toxin that weakens the mucosal wall. As a result, acid and protein enzymes penetrate the weakened barrier. Because alcohol stimulates a person's stomach to secrete acid, a person with PUD should avoid drinking alcohol on an empty stomach. Drinking alcohol would cause more acid release to damage the weakened stomach wall.^[45] Complications of this disease could include a burning pain in the abdomen, bloating and in severe cases, the presence of dark black stools indicate internal bleeding.^[46] A person who drinks alcohol regularly is strongly advised to reduce their intake to prevent PUD aggravation.^[46]

Magnitude of effects

Some individuals have less effective forms of one or both of the metabolizing enzymes, and can experience more severe symptoms from ethanol consumption than others. However, those having acquired alcohol tolerance have a greater quantity of these enzymes, and metabolize ethanol more rapidly.^[47]

Long-term

Birth defects

Ethanol is classified as a teratogen. See fetal alcohol syndrome and fetal alcohol spectrum disorder.

Cancer

IARC list ethanol in alcoholic beverages as Group 1 carcinogens and arguments "There is sufficient evidence for the carcinogenicity of acetaldehyde (the major metabolite of ethanol) in experimental animals.".^[48]

Other effects

Frequent drinking of alcoholic beverages has been shown to be a major contributing factor in cases of elevated blood levels of triglycerides.^[49]

Ethanol is also widely used, clinically and over the counter, as an antitussive agent.^[50]

History

The fermentation of sugar into ethanol is one of the earliest biotechnologies employed by humans. The intoxicating effects of ethanol consumption have been known since ancient times. Ethanol has been used by humans since prehistory as the intoxicating ingredient of alcoholic beverages. Dried residue on 9,000-year-old pottery found in China suggests that Neolithic people consumed alcoholic beverages.^[51]

Although distillation was well known by the early Greeks and Arabs, the first recorded production of alcohol from distilled wine was by the School of Salerno alchemists in the 12th century.^[52] The first to mention absolute alcohol, in contrast with alcohol-water mixtures, was Raymond Lull.^[52]

In 1796, German-Russian chemist Johann Tobias Lowitz obtained pure ethanol by mixing partially purified ethanol (the alcohol-water azeotrope) with an excess of anhydrous alkali and then distilling the mixture over low heat.^[53] French chemist Antoine Lavoisier described ethanol as a compound of carbon, hydrogen, and oxygen, and in 1807 Nicolas-Théodore de Saussure determined ethanol's chemical formula.^[54]^[55] Fifty years later, Archibald Scott Couper published the structural formula of ethanol. It was one of the first structural formulas determined.^[56]

Ethanol was first prepared synthetically in 1825 by Michael Faraday. He found that sulfuric acid could absorb large volumes of coal gas.^[57] He gave the resulting solution to Henry Hennell, a British chemist, who found in 1826 that it contained "sulphovinic acid" (ethyl hydrogen sulfate).^[58] In 1828, Hennell and the French chemist Georges-Simon Sérullas independently discovered that sulphovinic acid could be decomposed into ethanol.^[59]^[60] Thus, in 1825 Faraday had unwittingly discovered that ethanol could be produced from ethylene (a component of coal gas) by acid-catalyzed hydration, a process similar to current industrial ethanol synthesis.^[61]

Ethanol was used as lamp fuel in the United States as early as 1840, but a tax levied on industrial alcohol during the Civil War made this use uneconomical. The tax was repealed in 1906.^[62] Use as an automotive fuel dates back to 1908, with the Ford Model T able to run on petrol(gasoline) or ethanol.^[63] It remains a common fuel for spirit lamps.

Ethanol intended for industrial use is often produced from ethylene.^[64] Ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. In chemistry, it is both a solvent and a feedstock for the synthesis of other products. It has a long history as a fuel for heat and light, and more recently as a fuel for internal combustion engines.

Properties

Physical properties

Ethanol burning with its spectrum depicted

Ethanol is a volatile, colorless liquid that has a slight odor. It burns with a smokeless blue flame that is not always visible in normal light.

The physical properties of ethanol stem primarily from the presence of its hydroxyl group and the shortness of its carbon chain. Ethanol's hydroxyl group is able to participate in hydrogen bonding, rendering it more viscous and less volatile than less polar organic compounds of similar molecular weight, such as propane.

Ethanol is slightly more refractive than water, having a refractive index of 1.36242 (at λ=589.3 nm and 18.35 °C or 65.03 °F).^[65]

The triple point for ethanol is 150 K at a pressure of 4.3 × 10⁻⁴ Pa.^[66]

Solvent properties

Ethanol is a versatile solvent, miscible with water and with many organic solvents, including acetic acid, acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, ethylene glycol, glycerol, nitromethane, pyridine, and toluene.^[65]^[67] It is also miscible with light aliphatic hydrocarbons, such as pentane and hexane, and with aliphatic chlorides such as trichloroethane and tetrachloroethylene.^[67]

Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms), whose water miscibility decreases sharply as the number of carbons increases.^[68] The miscibility of ethanol with alkanes is limited to alkanes up to undecane: mixtures with dodecane and higher alkanes show a miscibility gap below a certain temperature (about 13 °C for dodecane^[69]). The miscibility gap tends to get wider with higher alkanes and the temperature for complete miscibility increases.

Ethanol-water mixtures have less volume than the sum of their individual components at the given fractions. Mixing equal volumes of ethanol and water results in only 1.92 volumes of mixture.^[65]^[70] Mixing ethanol and water is exothermic, with up to 777 J/mol^[71] being released at 298 K.

Mixtures of ethanol and water form an azeotrope at about 89 mole-% ethanol and 11 mole-% water^[72] or a mixture of about 96 volume percent ethanol and 4% water at normal pressure and T = 351 K. This azeotropic composition is strongly temperature- and pressure-dependent and vanishes at temperatures below 303 K.^[73]

Hydrogen bonding in solid ethanol at −186 °C

Hydrogen bonding causes pure ethanol to be hygroscopic to the extent that it readily absorbs water from the air. The polar nature of the hydroxyl group causes ethanol to dissolve many ionic compounds, notably sodium and potassium hydroxides, magnesium chloride, calcium chloride, ammonium chloride, ammonium bromide, and sodium bromide.^[67] Sodium and potassium chlorides are slightly soluble in ethanol.^[67] Because the ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances, including most essential oils^[74] and numerous flavoring, coloring, and medicinal agents.

The addition of even a few percent of ethanol to water sharply reduces the surface tension of water. This property partially explains the "tears of wine" phenomenon. When wine is swirled in a glass, ethanol evaporates quickly from the thin film of wine on the wall of the glass. As the wine's ethanol content decreases, its surface tension increases and the thin film "beads up" and runs down the glass in channels rather than as a smooth sheet.

Flammability

An ethanol-water solution that contains 40% ABV (alcohol by volume) will catch fire if heated to about 26 °C (79 °F) and if an ignition source is applied to it. This is called its flash point.^[75] The flash point of pure ethanol is 16.60 °C (61.88 °F), less than average room temperature.^{[citation needed]}

The flash points of ethanol concentrations from 10% ABV to 96% ABV are shown below:^[76]

10% — 49 °C (120 °F)
20% — 36 °C (97 °F)
30% — 29 °C (84 °F)
40% — 26 °C (79 °F)
50% — 24 °C (75 °F)
60% — 22 °C (72 °F)
70% — 21 °C (70 °F)
80% — 20 °C (68 °F)
90% — 17 °C (63 °F)
96% — 17 °C (63 °F)

Alcoholic beverages that have a low concentration of ethanol will burn if sufficiently heated and an ignition source (such as an electric spark or a match) is applied to them. For example, the flash point of ordinary wine containing 12.5% ethanol is about 52 °C (126 °F).^[77]

Dishes using burning alcohol for culinary effects are called Flambé.

Production

94% denatured ethanol sold in a bottle for household use

Ethanol is produced both as a petrochemical, through the hydration of ethylene and, via biological processes, by fermenting sugars with yeast.^[78] Which process is more economical depends on prevailing prices of petroleum and grain feed stocks.

Ethylene hydration

Ethanol for use as an industrial feedstock or solvent (sometimes referred to as synthetic ethanol) is made from petrochemical feed stocks, primarily by the acid-catalyzed hydration of ethylene, represented by the chemical equation

C
2H
4 + H
2O → CH
3CH
2OH

The catalyst is most commonly phosphoric acid,^[79]^[80] adsorbed onto a porous support such as silica gel or diatomaceous earth. This catalyst was first used for large-scale ethanol production by the Shell Oil Company in 1947.^[81] The reaction is carried out with an excess of high pressure steam at 300 °C (572 °F). In the U.S., this process was used on an industrial scale by Union Carbide Corporation and others, but now only LyondellBasell uses it commercially.

In an older process, first practiced on the industrial scale in 1930 by Union Carbide,^[82] but now almost entirely obsolete, ethylene was hydrated indirectly by reacting it with concentrated sulfuric acid to produce ethyl sulfate, which was hydrolyzed to yield ethanol and regenerate the sulfuric acid:^[83]

C
2H
4 + H
2SO
4 → CH
3CH
2SO
4H

CH
3CH
2SO
4H + H
2O → CH
3CH
2OH + H
2SO
4

Fermentation

Ethanol for use in alcoholic beverages, and the vast majority of ethanol for use as fuel,^[84] is produced by fermentation. When certain species of yeast (e.g., Saccharomyces cerevisiae) metabolize sugar in reduced-oxygen conditions they produce ethanol and carbon dioxide. The chemical equations below summarize the conversion:

C
6H
12O
6 → 2 CH
3CH
2OH + 2 CO₂

C
12H
22O
11 + H
2O → 4 CH
3CH
2OH + 4 CO₂

Fermentation is the process of culturing yeast under favorable thermal conditions to produce alcohol. This process is carried out at around 35–40 °C (95–104 °F). Toxicity of ethanol to yeast limits the ethanol concentration obtainable by brewing; higher concentrations, therefore, are usually obtained by fortification or distillation. The most ethanol-tolerant strains of yeast can survive up to approximately 18% ethanol by volume (Red Star Pasteur Champagne wine yeast, Lalvin EC-1118 wine yeast) and 20% or greater using "Turbo Yeast" as sold for spirit and fuel distillation.

To produce ethanol from starchy materials such as cereal grains, the starch must first be converted into sugars. In brewing beer, this has traditionally been accomplished by allowing the grain to germinate, or malt, which produces the enzyme amylase. When the malted grain is mashed, the amylase converts the remaining starches into sugars. For fuel ethanol, the hydrolysis of starch into glucose can be accomplished more rapidly by treatment with dilute sulfuric acid, fungally produced amylase, or some combination of the two.^[85]

Cellulose

Sugars for ethanol fermentation can be obtained from cellulose.^[86]^[87] Until recently, however, the cost of the cellulase enzymes capable of hydrolyzing cellulose has been prohibitive. The Canadian firm Iogen brought the first cellulose-based ethanol plant on-stream in 2004.^[88] Its primary consumer so far has been the Canadian government, which, along with the United States Department of Energy, has invested heavily in the commercialization of cellulosic ethanol. Deployment of this technology could turn a number of cellulose-containing agricultural by-products, such as corncobs, straw, and sawdust, into renewable energy resources. Other enzyme companies are developing genetically engineered fungi that produce large volumes of cellulase, xylanase, and hemicellulase enzymes. These would convert agricultural residues such as corn stover, wheat straw, and sugar cane bagasse and energy crops such as switchgrass into fermentable sugars.^[89]

Cellulose-bearing materials typically contain other polysaccharides, including hemicellulose. Hydrolysis of hemicellulose gives mostly five-carbon sugars such as xylose. S. cerevisiae, the yeast most commonly used for ethanol production, cannot metabolize xylose. Other yeasts and bacteria are under investigation to ferment xylose and other pentoses into ethanol.

Hydrocarbon

A process developed and marketed by Celanese Corporation under the name TCX Technology uses hydrocarbons such as natural gas or coal for ethanol production rather than using fermented crops such as corn or sugarcane.^[90]

Testing

Infrared reflection spectra of liquid ethanol, showing the -OH band centered at ~3300 cm⁻¹ and C-H bands at ~2950 cm⁻¹.

Near infrared spectrum of liquid ethanol.

Breweries and biofuel plants employ two methods for measuring ethanol concentration. Infrared ethanol sensors measure the vibrational frequency of dissolved ethanol using the CH band at 2900 cm⁻¹. This method uses a relatively inexpensive solid state sensor that compares the CH band with a reference band to calculate the ethanol content. The calculation makes use of the Beer-Lambert law. Alternatively, by measuring the density of the starting material and the density of the product, using a hydrometer, the change in specific gravity during fermentation indicates the alcohol content. This inexpensive and indirect method has a long history in the beer brewing industry.

Research

Research on ethanol production includes working from alternative source materials, novel catalysts and new chemical processes.

Purification

Distillation

Ethylene hydration or brewing produces an ethanol–water mixture. For most industrial and fuel uses, the ethanol must be purified. Fractional distillation can concentrate ethanol to 95.6% by volume (89.5 mole%). This mixture is an azeotrope with a boiling point of 78.1 °C (172.6 °F), and cannot be further purified by distillation. Addition of an entraining agent, such as benzene, cyclohexane, or heptane, allows a new ternary azeotrope comprising the ethanol, water, and the entraining agent to be formed. This lower-boiling ternary azeotrope is removed preferentially, leading to water-free ethanol.^[80]

At pressures less than atmospheric pressure, the composition of the ethanol-water azeotrope shifts to more ethanol-rich mixtures, and at pressures less than 70 torr (9.333 kPa), there is no azeotrope, and it is possible to distill absolute ethanol from an ethanol-water mixture. While vacuum distillation of ethanol is not presently economical, pressure-swing distillation is a topic of current research. In this technique, a reduced-pressure distillation first yields an ethanol-water mixture of more than 95.6% ethanol. Then, fractional distillation of this mixture at atmospheric pressure distills off the 95.6% azeotrope, leaving anhydrous ethanol at the bottom.^{[citation needed]}

Molecular sieves and desiccants

Molecular sieves can be used to selectively absorb the water from the 95.6% ethanol solution. Synthetic zeolite in pellet form can be used, as well as a variety of plant-derived absorbents, including cornmeal, straw, and sawdust. The zeolite bed can be regenerated essentially an unlimited number of times by drying it with a blast of hot carbon dioxide. Cornmeal and other plant-derived absorbents cannot readily be regenerated, but where ethanol is made from grain, they are often available at low cost. Absolute ethanol produced this way has no residual benzene, and can be used to fortify port and sherry in traditional winery operations.

Apart from distillation, ethanol may be dried by addition of a desiccant, such as molecular sieves, cellulose, and cornmeal. The desiccants can be dried and reused.^[80]

Membranes and reverse osmosis

Membranes can also be used to separate ethanol and water. Membrane-based separations are not subject to the limitations water-ethanol azeotrope because separation is not based on vapor-liquid equilibria. Membranes are often used in the so-called hybrid membrane distillation process. This process uses a pre-concentration distillation column as first separating step. The further separation is then accomplished with a membrane operated either in vapor permeation or pervaporation mode. Vapor permeation uses a vapor membrane feed and pervaporation uses a liquid membrane feed.

Other techniques

A variety of other techniques have been discussed, including the following:^[80]

Liquid-liquid extraction of ethanol from an aqueous solution;
Extraction of ethanol from grain mash by supercritical carbon dioxide;
Pervaporation;
Pressure swing adsorption.^[91]

Grades of ethanol

Ethanol is available in a range of purities that result from its production or, in the case of denatured alcohol, are introduced intentionally.

Denatured alcohol

Pure ethanol and alcoholic beverages are heavily taxed as psychoactive drugs, but ethanol has many uses that do not involve consumption by humans. To relieve the tax burden on these uses, most jurisdictions waive the tax when an agent has been added to the ethanol to render it unfit to drink. These include bittering agents such as denatonium benzoate and toxins such as methanol, naphtha, and pyridine. Products of this kind are called denatured alcohol.^[92]^[93]

Absolute alcohol

Absolute or anhydrous alcohol refers to ethanol with a low water content. There are various grades with maximum water contents ranging from 1% to a few parts per million (ppm) levels. Absolute alcohol is not intended for human consumption. If azeotropic distillation is used to remove water, it will contain trace amounts of the material separation agent (e.g. benzene).^[94] Absolute ethanol is used as a solvent for laboratory and industrial applications, where water will react with other chemicals, and as fuel alcohol. Spectroscopic ethanol is an absolute ethanol with a low absorbance in ultraviolet and visible light, fit for use as a solvent in ultraviolet-visible spectroscopy.^[95]

Pure ethanol is classed as 200 proof in the U.S., equivalent to 175 degrees proof in the UK system.^[96]

Rectified spirits

Rectified spirit, an azeotropic composition of 96% ethanol containing 4% water, is used instead of anhydrous ethanol for various purposes. Wine spirits are about 94% ethanol (188 proof). The impurities are different from those in 95% (190 proof) laboratory ethanol.^[97]

Reactions

Ethanol is classified as a primary alcohol, meaning that the carbon its hydroxyl group attaches to has at least two hydrogen atoms attached to it as well. Many ethanol reactions occur at its hydroxyl group.

Ester formation

In the presence of acid catalysts, ethanol reacts with carboxylic acids to produce ethyl esters and water:

RCOOH + HOCH₂CH₃ → RCOOCH₂CH₃ + H₂O

This reaction, which is conducted on large scale industrially, requires the removal of the water from the reaction mixture as it is formed. Esters react in the presence of an acid or base to give back the alcohol and a salt. This reaction is known as saponification because it is used in the preparation of soap. Ethanol can also form esters with inorganic acids. Diethyl sulfate and triethyl phosphate are prepared by treating ethanol with sulfur trioxide and phosphorus pentoxide respectively. Diethyl sulfate is a useful ethylating agent in organic synthesis. Ethyl nitrite, prepared from the reaction of ethanol with sodium nitrite and sulfuric acid, was formerly used as a diuretic.

Dehydration

Strong acid desiccants cause the partial dehydration of ethanol to form diethyl ether and other byproducts. If the dehydration temperature exceeds around 160 °C (320 °F), full dehydration will occur and ethylene will be the main product.

2 CH₃CH₂OH → CH₃CH₂OCH₂CH₃ + H₂O (ca. 120 °C)

CH₃CH₂OH → H2C=CH2 + H₂O (above 160 °C)

Combustion

Complete combustion of ethanol forms carbon dioxide and water:

C₂H₅OH (l) + 3 O₂ (g) → 2 CO₂ (g) + 3 H₂O (liq); −ΔH_c = 1371 kJ/mol^[98] = 29.8 kJ/g = 327 kcal/mol = 7.1 kcal/g

C₂H₅OH (l) + 3 O₂ (g) → 2 CO₂ (g) + 3 H₂O (g); −ΔH_c = 1236 kJ/mol = 26.8 kJ/g = 295.4 kcal/mol = 6.41 kcal/g^[99]

Specific heat = 2.44 kJ/(kg·K)

Acid-base chemistry

Ethanol is a neutral molecule and the pH of a solution of ethanol in water is nearly 7.00. Ethanol can be quantitatively converted to its conjugate base, the ethoxide ion (CH₃CH₂O⁻), by reaction with an alkali metal such as sodium:^[68]

2 CH₃CH₂OH + 2 Na → 2 CH₃CH₂ONa + H₂

or a very strong base such as sodium hydride:

CH₃CH₂OH + NaH → CH₃CH₂ONa + H₂

The acidity of water and ethanol are nearly the same, as indicated by their pKa of 15.7 and 16 respectively. Thus, sodium ethoxide and sodium hydroxide exist in an equilbrium that is closely balanced:

CH₃CH₂OH + NaOH CH₃CH₂ONa + H₂O

Halogenation

Ethanol is not used industrially as a precursor to ethyl halides, but the reactions are illustrative. Ethanol reacts with hydrogen halides to produce ethyl halides such as ethyl chloride and ethyl bromide via an S_N2 reaction:

CH₃CH₂OH + HCl → CH₃CH₂Cl + H₂O

These reactions require a catalyst such as zinc chloride.^[83] HBr requires refluxing with a sulfuric acid catalyst.^[83] Ethyl halides can, in principle, also be produced by treating ethanol with more specialized halogenating agents, such as thionyl chloride or phosphorus tribromide.^[68]^[83]

CH₃CH₂OH + SOCl₂ → CH₃CH₂Cl + SO₂ + HCl

Upon treatment with halogens in the presence of base, ethanol gives the corresponding haloform (CHX₃, where X = Cl, Br, I). This conversion is called the haloform reaction.^[100] " An intermediate in the reaction with chlorine is the aldehyde called chloral:

4 Cl₂ + CH₃CH₂OH → CCl₃CHO + 5 HCl

Oxidation

Ethanol can be oxidized to acetaldehyde and further oxidized to acetic acid, depending on the reagents and conditions.^[83] This oxidation is of no importance industrially, but in the human body, these oxidation reactions are catalyzed by the enzyme liver alcohol dehydrogenase. The oxidation product of ethanol, acetic acid, is a nutrient for humans, being a precursor to acetyl CoA, where the acetyl group can be spent as energy or used for biosynthesis.

Other uses

Motor fuel

Energy content of some fuels compared with ethanol:^[101]
Fuel type	MJ/L	MJ/kg	Research octane number
Dry wood (20% moisture)		~19.5
Methanol	17.9	19.9	108.7^[102]
Ethanol	21.2^[103]	26.8^[103]	108.6^[102]
E85 (85% ethanol, 15% gasoline)	25.2	33.2	105
Liquefied natural gas	25.3	~55
Autogas (LPG) (60% propane + 40% butane)	26.8	50.
Aviation gasoline (high-octane gasoline, not jet fuel)	33.5	46.8	100/130 (lean/rich)
Gasohol (90% gasoline + 10% ethanol)	33.7	47.1	93/94
Regular gasoline/petrol	34.8	44.4^[104]	min. 91
Premium gasoline/petrol			max. 104
Diesel	38.6	45.4	25
Charcoal, extruded	50	23

The largest single use of ethanol is as a motor fuel and fuel additive. More than any other major country, Brazil relies on ethanol as a motor fuel. Gasoline sold in Brazil contains at least 25% anhydrous ethanol. Hydrous ethanol (about 95% ethanol and 5% water) can be used as fuel in more than 90% of new cars sold in the country. Brazilian ethanol is produced from sugar cane and noted for high carbon sequestration.^[105] The US uses Gasohol (max 10% ethanol) and E85 (85% ethanol) ethanol/gasoline mixtures.

USP grade ethanol for laboratory use.

Ethanol may also be utilized as a rocket fuel, and is currently in lightweight rocket-powered racing aircraft.^[106]

Australian law limits the use of pure ethanol sourced from sugarcane waste to up to 10% in automobiles. It has been recommended that older cars (and vintage cars designed to use a slower burning fuel) have their valves upgraded or replaced.^[107]

According to an industry advocacy group for promoting ethanol called the American Coalition for Ethanol, ethanol as a fuel reduces harmful tailpipe emissions of carbon monoxide, particulate matter, oxides of nitrogen, and other ozone-forming pollutants.^[108] Argonne National Laboratory analyzed the greenhouse gas emissions of many different engine and fuel combinations. Comparing ethanol blends with gasoline alone, they showed reductions of 8% with the biodiesel/petrodiesel blend known as B20, 17% with the conventional E85 ethanol blend, and that using cellulosic ethanol lowers emissions 64%.^[109]

Ethanol combustion in an internal combustion engine yields many of the products of incomplete combustion produced by gasoline and significantly larger amounts of formaldehyde and related species such as acetaldehyde.^[110] This leads to a significantly larger photochemical reactivity that generates much more ground level ozone.^[111] These data have been assembled into The Clean Fuels Report comparison of fuel emissions^[112] and show that ethanol exhaust generates 2.14 times as much ozone as does gasoline exhaust.^{[citation needed]} When this is added into the custom Localised Pollution Index (LPI) of The Clean Fuels Report the local pollution (pollution that contributes to smog) is 1.7 on a scale where gasoline is 1.0 and higher numbers signify greater pollution.^{[citation needed]} The California Air Resources Board formalized this issue in 2008 by recognizing control standards for formaldehydes as an emissions control group, much like the conventional NOx and Reactive Organic Gases (ROGs).^[113]

Ethanol pump station in São Paulo, Brazil where the fuel is available commercially.

World production of ethanol in 2006 was 51 gigalitres (1.3×10¹⁰ US gal), with 69% of the world supply coming from Brazil and the United States.^[114] More than 20% of Brazilian cars are able to use 100% ethanol as fuel, which includes ethanol-only engines and flex-fuel engines.^[115] Flex-fuel engines in Brazil are able to work with all ethanol, all gasoline or any mixture of both. In the US flex-fuel vehicles can run on 0% to 85% ethanol (15% gasoline) since higher ethanol blends are not yet allowed or efficient. Brazil supports this population of ethanol-burning automobiles with large national infrastructure that produces ethanol from domestically grown sugar cane. Sugar cane not only has a greater concentration of sucrose than corn (by about 30%), but is also much easier to extract. The bagasse generated by the process is not wasted, but is used in power plants to produce electricity.^{[citation needed]}

A Ford Taurus "fueled by clean burning ethanol" owned by New York City.

The United States fuel ethanol industry is based largely on corn. According to the Renewable Fuels Association, as of October 30, 2007, 131 grain ethanol bio-refineries in the United States have the capacity to produce 7.0 billion US gallons (26,000,000 m³) of ethanol per year. An additional 72 construction projects underway (in the U.S.) can add 6.4 billion US gallons (24,000,000 m³) of new capacity in the next 18 months. Over time, it is believed that a material portion of the ≈150-billion-US-gallon (570,000,000 m³) per year market for gasoline will begin to be replaced with fuel ethanol.^[116]

United States Postal Service vehicle running on E85, a "flex-fuel" blend in Saint Paul, Minnesota.

Sweet sorghum is a potential source of ethanol, which is suitable for growing in dryland conditions. It is being investigated by the International Crops Research Institute for the Semi-Arid Tropics (ICRISAT) for its potential to provide fuel, along with food and animal feed, in arid parts of Asia and Africa.^[117] The water requirement of sweet sorghum is one-third that of sugarcane on a comparable time scale. Also, sweet sorghum requires about 22% less water than corn also known as maize. The world’s first sweet sorghum-based ethanol production distillery began commercial ethanol production in 2007 in Andhra Pradesh, India.^[118]

Ethanol's high miscibility with water means that it cannot be shipped through modern pipelines like liquid hydrocarbons.^[119] Mechanics have seen increased cases of damage to small engines, in particular, the carburetor, attributable to the increased water retention by ethanol in fuel.^[120]

Household heating

An example of a bio-ethanol fire in the form of a traditional fireplace, using fire-proof ceramic simulated wood logs for effect.

Ethanol fuels flue-less, real flame fireplaces. Ethanol is kept in a burner containing a wick such as glass wool, a safety shield to reduce the chances of accidents and an extinguisher such as a plate or shutter to cut off oxygen.

It provides almost the same visual benefits of a real flame log or coal fire without the need to vent the fumes via a flue as ethanol produces very little hazardous carbon monoxide, and little or no noticeable scent. It does emit carbon dioxide and requires oxygen. Therefore, external ventilation of the room containing the fire is needed to ensure safe operation.

An additional benefit is that, unlike a flue based fireplace, 100% of the heat energy produced enters the room. This serves to offset some of the heat loss from an external air vent, as well as offset the relatively high cost of the fuel compared to other forms of heating.

Feedstock

Ethanol is an important industrial ingredient and has widespread use as a base chemical for other organic compounds. These include ethyl halides, ethyl esters, diethyl ether, acetic acid, ethyl amines, and, to a lesser extent, butadiene.

Antiseptic

Ethanol is used in medical wipes and in most common antibacterial hand sanitizer gels at a concentration of about 62% v/v as an antiseptic. Ethanol kills organisms by denaturing their proteins and dissolving their lipids and is effective against most bacteria and fungi, and many viruses, but is ineffective against bacterial spores.^[121]

Solvent

Ethanol is miscible with water and is a good general purpose solvent. It is found in paints, tinctures, markers, and personal care products such as perfumes and deodorants.

Charts

Thermophysical properties of mixtures of ethanol with water and dodecane

Excess volume of the mixture of ethanol and water (volume contraction)	Heat of mixing of the mixture of ethanol and water	Vapor-liquid equilibrium of the mixture of ethanol and water (including azeotrope)

Solid-liquid equilibrium of the mixture of ethanol and water (including eutecticum)	Miscibility gap in the mixture of dodecane and ethanol

History

Ethanol was commonly used as fuel in early bipropellant rocket (liquid propelled) vehicles, in conjunction with an oxidizer such as liquid oxygen. The German V-2 rocket of World War II, credited with beginning the space age, used ethanol, mixed with 25% of water to reduce the combustion chamber temperature.^[122]^[123] The V-2's design team helped develop U.S. rockets following World War II, including the ethanol-fueled Redstone rocket which launched the first U.S. satellite.^[124] Alcohols fell into general disuse as more efficient rocket fuels were developed.^[123]

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External links

Look up alcohol or ethanol in Wiktionary, the free dictionary.

Wikimedia Commons has media related to Ethanol.

Alcohol (Ethanol) at The Periodic Table of Videos (University of Nottingham)
International Labour Organization ethanol safety information
National Pollutant Inventory – Ethanol Fact Sheet
CDC – NIOSH Pocket Guide to Chemical Hazards – Ethyl Alcohol
National Institute of Standards and Technology chemical data on ethanol
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Industrial ethanol production process flow diagram using ethylene and sulphuric acid

Pathophysiology of ethanol

Pharmacology of ethanol

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1. アルコール使用障害：疫学、病因、臨床症状、有害事象、および診断 risky drinking and alcohol use disorder epidemiology pathogenesis clinical manifestations course assessment and diagnosis
2. アルコール摂取の利益とリスクの概要 overview of the risks and benefits of alcohol consumption
3. 成人におけるエタノール中毒 ethanol intoxication in adults
4. 外来における医師監督下のアルコール離脱症状の治療 medically supervised alcohol withdrawal in the ambulatory setting
5. アルコール使用障害の心理社会的治療 psychosocial treatment of alcohol use disorder

English Journal

Antioxidant and antimicrobial activities of ethanol and aqueous extracts from Urtica urens.

Mzid M1, Ben Khedir S1, Ben Salem M2, Regaieg W2, Rebai T1.
Pharmaceutical biology.Pharm Biol.2017 Dec;55(1):775-781. doi: 10.1080/13880209.2016.1275025.
PMID 28084125

A case of advanced gastric cancer achieved a pathological complete response by chemotherapy.

Tada K1, Etoh T2, Shitomi Y1, Ueda Y3, Tojigamori M1, Shiroshita H1, Shiraishi N3, Inomata M1.
Surgical case reports.Surg Case Rep.2017 Dec;3(1):68. doi: 10.1186/s40792-017-0344-9. Epub 2017 May 12.
PMID 28500392

Potential environmental impact of bioethanol production chain from fiber sorghum to be used in passenger cars.

Forte A1, Zucaro A2, Fagnano M3, Fierro A4.
The Science of the total environment.Sci Total Environ.2017 Nov 15;598:365-376. doi: 10.1016/j.scitotenv.2017.03.244. Epub 2017 Apr 24.
PMID 28448928

Japanese Journal

Synthesis, Structure, and Clathration Ability of Two-Dimensional Coordination Networks with Inclined Interpenetration

宮城教育大学紀要 = Bulletin of Miyagi University of Education 50, 121-126, 2016-01-29
NAID 120005695676

Heme oxygenase-1 alleviates alcoholic liver steatosis: histopathological study

Journal of Toxicologic Pathology 29(1), 7-15, 2016
NAID 130005126477

Toward 10 Gfps : Factors Limiting the Frame Rate of the BSI MCG Image Sensor (情報センシング)

映像情報メディア学会技術報告 39(35), 41-44, 2015-09-11
NAID 110009990382

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拡張検索	「EtOH ppt」

「EtOH ppt」

Ethanol
	Systematic name Ethanol
Identifiers
CAS number	64-17-5
Jmol-3D images	Image 1
	SMILES CCO ;
	InChI InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 ; Key: LFQSCWFLJHTTHZ-UHFFFAOYSA-N InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3; Key: LFQSCWFLJHTTHZ-UHFFFAOYAB ;
Properties
Molecular formula	C2H6O
Molar mass	46.07 g mol−1
Density	0.789 g/cm3 (at 25°C)
Melting point	−114 °C (−173 °F; 159 K)
Boiling point	78.37 °C (173.07 °F; 351.52 K)
Acidity (pKa)	15.9 (H2O), 29.8 (DMSO)
Hazards
MSDS	External MSDS
R-phrases	R11
S-phrases	(S2), S7, S16
Flash point	16 °C (61 °F; 289 K)
Autoignition temperature	365 °C (689 °F; 638 K)
LD50	7060 mg/kg (oral, rat)
Related compounds
Related compounds	Methanol; Ethane
Supplementary data page
Structure and; properties	n, εr, etc.
Thermodynamic; data	Phase behaviour; Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	(verify) (what is: /?)
	Infobox references

エタノール
	IUPAC名エタノール
	別称エチルアルコール
識別情報
CAS登録番号	64-17-5
ChemSpider	682
KEGG	C00469
RTECS番号	KQ6300000
	SMILES CCO;
特性
化学式	C2H6O
モル質量	46.07 g mol−1
外観	無色液体
密度	0.789 g/cm3
融点	−114.3 ℃
沸点	78.37 ℃
水への溶解度	水と任意に混合
酸解離定数 pKa	15.9
粘度	1.200 mPa s (cP) at 20.0 ℃
双極子モーメント	5.64 fC fm (1.69 D) (gas)
熱化学
標準生成熱 ΔfHo	-277.69 kJ mol-1
標準燃焼熱 ΔcHo	1367.6 J mol-1K-1
標準モルエントロピー So	160.7 J mol-1K-1
標準定圧モル比熱, Cpo	111.46 J mol-1K-1
危険性
EU分類	F
NFPA 704	3 1 0
Rフレーズ	R11 R20 R21 R22 R36
Sフレーズ	(S2) S7 S16
引火点	13 ℃
関連する物質
関連物質	メタノール; プロパノール
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

　　[★] エタノール沈殿

関: ethanol precipitation、precipitate with ethanol

[Parker-1] D.D. Wagman, W.H. Evans, V.B. Parker, R.H. Schumm, I. Halow, S.M. Bailey, K.L. Churney, R.I. Nuttal, K.L. Churney and R.I. Nuttal, The NBS tables of chemical thermodynamics properties, J. Phys. Chem. Ref. Data 11 Suppl. 2 (1982).

[2] かつては、ベンゼンが用いられていたが、発がん性、毒性のため、近年ではペンタンが用いられている。例えば、[1]参照。

[3] 総務省のウェブサイトにある資料 - アルコール専売事業（2001年に廃止）の仕組みをあらわしたもの（2010年12月01日閲覧）。

[4] 変性アルコールの例（2010年11月29日閲覧）。平成12年12月26日付け厚生省の通達であるが、文書の末尾にアルコール専売法施行規則別表「工業用アルコール変性標準」の抜粋がある。

[5] “消火訓練で10人やけど　滋賀、アルコールが飛散”. 日経新聞. (2013年8月4日)

[6] “エタノールの「見えない炎」、消火訓練準備で10人やけど”. TBS. (2013年8月5日)

[7] [2]

[8] 酒税法第二条

[9] 同第七条、第九条

[10] 同第六条

[11] 同第三条

[12] 同第二十三条

[13] アルコール専売法十九条

[14] 同第二十六条

[15] 使用例：三協化学株式会社のウェブサイト（2010年11月29日閲覧）

[16] 使用例：平成12年１2月26日付け厚生省の通達（2010年11月29日閲覧）

[17] 使用例：日本アルコール販売のウェブサイト（2010年11月29日閲覧）

[18] アルコール事業法第三条、第十六条、第二十一条、第二十六条。

[19] 同第二条

[20] 旧食品衛生法第二条第三項

[21] 食品衛生法第十条。食品衛生法施工規則第十二条別表第一（使用を認められている添加物の一覧表）も参照。

[Pubchem-1] "Ethanol – Compound Summary". The PubChem Project. USA: National Center for Biotechnology Information.

[2] Ballinger, P., Long, F.A. (1960). "Acid Ionization Constants of Alcohols. II. Acidities of Some Substituted Methanols and Related Compounds1,2". Journal of the American Chemical Society 82 (4): 795. doi:10.1021/ja01489a008.

[3] Arnett, E.M., Venkatasubramaniam, K.G. (1983). "Thermochemical acidities in three superbase systems". J. Org. Chem. 48 (10): 1569. doi:10.1021/jo00158a001.

[4] "ChemIDplus - 64-17-5 - LFQSCWFLJHTTHZ-UHFFFAOYSA-N - Alcohol [USP] - Similar structures search, synonyms, formulas, resource links, and other chemical information.". Retrieved 13 October 2014.

[5] "Ethanol Material Safety Data Sheet – Europe". Distill.com. Retrieved 2014-01-18.

[6] "10th Special Report to the U.S. Congress on Alcohol and Health: Highlights from Current Research". National Institute of Health. National Institute on Alcohol Abuse and Alcoholism. June 2000. p. 134. Retrieved 21 October 2014. "The brain is a major target for the actions of alcohol, and heavy alcohol consumption has long been associated with brain damage. Studies clearly indicate that alcohol is neurotoxic, with direct effects on nerve cells. Chronic alcohol abusers are at additional risk for brain injury from related causes, such as poor nutrition, liver disease, and head trauma."

[7] Brust, John C.M. (4 April 2010). "Ethanol and Cognition: Indirect Effects, Neurotoxicity and Neuroprotection: A Review". International Journal of Environmental Research and Public Health. Int. J. Environ. Res. Public Health. pp. 1540–1557. doi:10.3390/ijerph7041540. Retrieved 21 October 2014. "Ethanol affects cognition in a number of ways. Indirect effects include intoxication, withdrawal, brain trauma, central nervous system infection, hypoglycemia, hepatic failure, and Marchiafava-Bignami disease. Nutritional deficiency can cause pellagra and Wernicke-Korsakoff disorder. Additionally, ethanol is a direct neurotoxin and in sufficient dosage can cause lasting dementia. However, ethanol also has neuroprotectant properties and in low-to-moderate dosage reduces the risk of dementia, including Alzheimer type."

[8] Liebig, Justus (1834) "Ueber die Constitution des Aethers und seiner Verbindungen" (On the constitution of ether and its compounds), Annalen der Pharmacie, 9 : 1–39. From page 18: "Bezeichnen wir die Kohlenwasserstoffverbindung 4C + 10H als das Radikal des Aethers mit E₂ und nennen es Ethyl, …" (Let us designate the hydrocarbon compound 4C + 10H as the radical of ether with E₂ and name it ethyl …).

[9] Harper, Douglas. "ethyl". Online Etymology Dictionary.

[10] For a report on the 1892 International Conference on Chemical Nomenclature, see:

Armstrong, Henry (1892). "The International Conference on Chemical Nomenclature". Nature 46 (1177): 56–59. doi:10.1038/046056c0.

Armstrong's report is reprinted with the resolutions in English in: Armstrong, Henry (1892). "The International Conference on Chemical Nomenclature". The Journal of Analytical and Applied Chemistry 6: 390–400 (398). "The alcohols and the phenols will be called after the name of the hydrocarbon from which they are derived, terminated with the suffix ol (ex. pentanol, pentenol, etc.)."

[32] Armstrong, Henry (1892). "The International Conference on Chemical Nomenclature". Nature 46 (1177): 56–59. doi:10.1038/046056c0.

[33] Armstrong's report is reprinted with the resolutions in English in: Armstrong, Henry (1892). "The International Conference on Chemical Nomenclature". The Journal of Analytical and Applied Chemistry 6: 390–400 (398). "The alcohols and the phenols will be called after the name of the hydrocarbon from which they are derived, terminated with the suffix ol (ex. pentanol, pentenol, etc.)."

[11] OED; etymonline.com

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[Forbes-52] Forbes, Robert James (1948) A short history of the art of distillation, Brill, p. 89, ISBN 9004006176.

[53] Lowitz, T. (1796) "Anzeige eines, zur volkommen Entwasserung des Weingeistes nothwendig zu beobachtenden, Handgriffs" (Report of a task that must be done for the complete dehydration of wine spirits [i.e., alcohol-water azeotrope]), (Crell's) Chemische Annalen …, vol. 1, pp. 195–204. See pp. 197–198: Lowitz dehydrated the azeotrope by mixing it with a 2:1 excess of anhydrous alkali and then distilling the mixture over low heat.

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[55] Saussure, Théodore (1807) "Mémoire sur la composition de l'alcohol et de l'éther sulfurique," Journal de physique, de chimie, d'histoire naturelle et des arts, vol. 64, pp. 316–354. In his 1807 paper, Saussure determined ethanol's composition only roughly; a more accurate analysis of ethanol appears on page 300 of his 1814 paper: de Saussure, Théodore (1814) "Nouvelles observations sur la composition de l'alcool et de l'éther sulfurique," Annales de Chimie, 89: 273–305.

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[58] Hennell, H. (1826) "On the mutual action of sulphuric acid and alcohol, with observations on the composition and properties of the resulting compound," Philsophical Transactions of the Royal Society, vol. 116, pages 240–249. On page 248, Hennell mentions that Faraday gave him some sulfuric acid in which coal gas had dissolved and that he (Hennell) found that it contained "sulphovinic acid" (ethyl hydrogen sulfate).

[Hennell-59] Hennell, H. (1828). "On the mutual action of sulfuric acid and alcohol, and on the nature of the process by which ether is formed". Philosophical Transactions of the Royal Society of London 118: 365–371. doi:10.1098/rstl.1828.0021. On page 368, Hennell produces ethanol from "sulfovinic acid" (ethyl hydrogen sulfate).

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[61] In 1855, the French chemist Marcellin Berthelot confirmed Faraday's discovery by preparing ethanol from pure ethylene. Marcellin Berthelot (1855) "Sur la formation de l'alcool au moyen du bicarbure d'hydrogène" (On the formation of alcohol by means of ethylene), Annales de chimie et de physique, series 3, vol. 43, pp. 385–405. (Note: The chemical formulas in Berthelot's paper are wrong because chemists at that time used the wrong atomic masses for the elements; e.g., carbon (6 instead of 12), oxygen (8 instead of 16), etc.)

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エタノール


IUPAC名エタノール
別称エチルアルコール
識別情報
CAS登録番号	64-17-5
ChemSpider	682
KEGG	C00469
RTECS番号	KQ6300000
SMILES CCO
特性
化学式	C₂H₆O
モル質量	46.07 g mol⁻¹
外観	無色液体
密度	0.789 g/cm³
融点	−114.3 ℃
沸点	78.37 ℃
水への溶解度	水と任意に混合
酸解離定数 pK_a	15.9
粘度	1.200 mPa s (cP) at 20.0 ℃
双極子モーメント	5.64 fC fm (1.69 D) (gas)
熱化学
標準生成熱 Δ_fH^o	-277.69 kJ mol^-1^[1]
標準燃焼熱 Δ_cH^o	1367.6 J mol^-1K^-1
標準モルエントロピー S^o	160.7 J mol^-1K^-1
標準定圧モル比熱, C_p^o	111.46 J mol^-1K^-1
危険性
EU分類	F
NFPA 704	3 1 0
Rフレーズ	R11 R20 R21 R22 R36
Sフレーズ	(S2) S7 S16
引火点	13 ℃
関連する物質
関連物質	メタノールプロパノール
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

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EtOH

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性質

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利用

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医薬品

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飲用アルコール（酒類）

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外部リンク

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Contents

Etymology

Chemical formula

Natural occurrence

Pharmacology

Activity profile

Properties

Short-term

Effects on the central nervous system

Effects on metabolism

Drug interactions

Alcohol and digestion

Alcohol and gastrointestinal diseases

Magnitude of effects

Long-term

Birth defects

Cancer

Other effects

History

Properties

Physical properties

Solvent properties

Flammability

Production

Ethylene hydration

Fermentation

Cellulose

Hydrocarbon

Testing

Research

Purification

Distillation

Molecular sieves and desiccants

Membranes and reverse osmosis

Other techniques

Grades of ethanol

Denatured alcohol

Absolute alcohol

Rectified spirits

Reactions

Ester formation

Dehydration

Combustion

Acid-base chemistry

Halogenation

Oxidation

Other uses

Motor fuel

Household heating

Feedstock

Antiseptic

Solvent

Charts

History

See also