出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2019/07/07 11:35:19」(JST)
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| Names | |||
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| Preferred IUPAC name
Propane-1,2-diol | |||
| Other names
Propylene glycol
α-Propylene glycol 1,2-Propanediol 1,2-Dihydroxypropane Methyl ethyl glycol Methylethylene glycol | |||
| Identifiers | |||
CAS Number
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3D model (JSmol)
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| ChEBI |
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard | 100.000.307 | ||
| EC Number | 200-338-0 | ||
| E number | E1520 (additional chemicals) | ||
PubChem CID
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| RTECS number | TY6300000 | ||
| UNII |
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |||
Chemical formula
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C3H8O2 | ||
| Molar mass | 76.095 g·mol−1 | ||
| Density | 1.036 g/cm3 | ||
| Melting point | −59 °C (−74 °F; 214 K) | ||
| Boiling point | 188.2 °C (370.8 °F; 461.3 K) | ||
Solubility in water
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Miscible | ||
| Solubility in ethanol | Miscible | ||
| Solubility in diethyl ether | Miscible | ||
| Solubility in acetone | Miscible | ||
| Solubility in chloroform | Miscible | ||
| log P | -1.34[2] | ||
| Thermal conductivity | 0.34 W/m-K (50% H2O @ 90 °C (194 °F)) | ||
| Viscosity | 0.042 Pa·s | ||
| Pharmacology | |||
ATCvet code
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QA16QA01 (WHO) | ||
| Hazards | |||
| S-phrases (outdated) | S24 S25 | ||
| NFPA 704 |
1
0
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| Related compounds | |||
Related glycols
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Ethylene glycol, 1,3-propanediol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
| Y verify (what is YN ?) | |||
| Infobox references | |||
Propylene glycol (IUPAC name: propane-1,2-diol) is a synthetic organic compound with the chemical formula C3H8O2. It is a viscous, colorless liquid which is nearly odorless but possesses a faintly sweet taste. Chemically it is classed as a diol alcohol that is miscible with a broad range of solvents, including water, acetone, and chloroform. It falls within the same class of compounds as alcohols.[4]
It is produced on a large scale and is primarily used in the production of polymers, used as chemical feedstock for building materials and toner for laser printers, but also used in food processing, pharma and in airplane deicing applications. In the European Union, it has the E-number E1520 for food applications. For cosmetics and pharmacology, the number is E490. Propylene glycol is also present in propylene glycol alginate which is known as E405. Propylene glycol is a compound which is generally recognized as safe (GRAS) by the U.S. Food and Drug Administration (FDA) under 21 CFR x184.1666 and is also approved by FDA for certain uses as an indirect food additive. Propylene glycol is approved and used as a vehicle for topical, oral and some intravenous pharmaceutical preparations in U.S. and in Europe.
The compound is sometimes called (alpha) α-propylene glycol to distinguish it from the isomer propane-1,3-diol, known as (beta) β-propylene glycol.
Propylene glycol is a clear, colorless and hygroscopic liquid. Propylene glycol contains an asymmetrical carbon atom, so it exists in two enantiomers. The commercial product is a racemic mixture. Pure optical isomers can be obtained by hydration of optically pure propylene oxide.[5]
The freezing point of water is depressed when mixed with propylene glycol, owing to the effects of dissolution of a solute in a solvent (freezing-point depression). In general, glycols are non-irritating, have very low volatility and very low toxicity.
Industrially, propylene glycol is produced from propylene oxide[6] (for food-grade use), and global capacity in 1990 was 900,000 tonnes per year.[7] Different manufacturers use either non-catalytic high-temperature process at 200 °C (392 °F) to 220 °C (428 °F), or a catalytic method, which proceeds at 150 °C (302 °F) to 180 °C (356 °F) in the presence of ion exchange resin or a small amount of sulfuric acid or alkali.
Final products contain 20% propylene glycol, 1.5% of dipropylene glycol and small amounts of other polypropylene glycols.[8] Further purification produces finished industrial grade or USP/JP/EP/BP grade propylene glycol that is typically 99.5% or greater. Propylene glycol can also be converted from glycerol, a biodiesel byproduct. This starting material is usually reserved for industrial use because of the noticeable odor and taste that accompanies the final product.
S-Propanediol may be synthesized from D-mannitol, through the following scheme:[9]
Forty-five percent of propylene glycol produced is used as chemical feedstock for the production of unsaturated polyester resins. In this regard, propylene glycol reacts with a mixture of unsaturated maleic anhydride and isophthalic acid to give a copolymer. This partially unsaturated polymer undergoes further crosslinking to yield thermoset plastics. Related to this application, propylene glycol reacts with propylene oxide to give oligomers and polymers that are used to produce polyurethanes.[7] Propylene glycol is used in waterbased acrylic architectural paints to extend dry time which it accomplishes by preventing the surface from drying due to its slower evaporation rate compared to water. Propylene glycol is used as a humectant (E1520), solvent,[10] and additive in food, pharmaceutical and for tobacco products. It is also one of the major ingredients (<1–92%), along with Vegetable Glycerin (VG), of the e-liquid and cartridges used in electronic cigarettes where it is aerosolized in the atomizer.[11] It is also used in model railway and model boat applications to simulate steam or smoke, using a small heating element.
Over time, there has been a reported increase in the use of PG in personal care products in the United States. In a 1994 safety assessment, the Cosmetic Ingredient Review noted use of PG in 5676 products listed in the Voluntary Cosmetic Registry; in the Cosmetic Ingredient Review 2012 update, this Voluntary Cosmetic Registry reported 9094 products containing PG.[12]
Propylene glycol is also used in various edible items such as coffee-based drinks, liquid sweeteners, ice cream, whipped dairy products and soda.[13][14] Vaporizers used for delivery of pharmaceuticals or personal-care products often include propylene glycol among the ingredients.[7] In alcohol-based hand sanitizers, it is used as a humectant to prevent the skin from drying.[15] Propylene glycol is used as a solvent in many pharmaceuticals, including oral, injectable and topical formulations, such as for diazepam and lorazepam which are insoluble in water.[16] Certain formulations of artificial tears, such as Systane, use proplyene glycol as an ingredient.[17]
Propylene glycol is able to lower the freezing point of water, and so it is used as aircraft de-icing fluid.[7][18] Water-propylene glycol mixtures dyed pink to indicate the mixture is relatively nontoxic are sold under the name of RV or marine antifreeze. Propylene glycol is frequently used as a substitute for ethylene glycol in low toxicity, environmentally friendly automotive antifreeze. It is also used to winterize the plumbing systems in vacant structures.[19] The eutectic composition/temperature is 60:40 propylene glycol:water/-60 °C.[20][21] The −50 °F/−45 °C commercial product is, however, water rich; a typical formulation is 40:60.[22]
Propylene glycol is used in veterinary medicine as an oral treatment for hyperketonaemia in ruminants. Glucose, which can be used in non-ruminants for this purpose, is not effective due to its consumption by the resident microbes of the rumen. Propylene glycol is partially metabolized in the rumen to propionate which can be used as an energy source. The remainder is absorbed into the bloodstream and used by the liver for gluconeogenesis.[23]
A study by Corrie Moreau and colleagues showed that propylene glycol was similar to 95% ethanol as a preservative for ant DNA, which is important because Propylene glycol is much less flammable (so is preferable for air travel or shipment), and does not evaporate quickly (so is preferable for use in e.g., insect pitfall traps).[24]
The acute oral toxicity of propylene glycol (E1520) is very low, and large quantities are required to cause perceptible health effects in humans; in fact, propylene glycol is three times less toxic than ethanol [25]. Propylene glycol is metabolized in the human body into pyruvic acid (a normal part of the glucose-metabolism process, readily converted to energy), acetic acid (handled by ethanol-metabolism), lactic acid (a normal acid generally abundant during digestion),[26] and propionaldehyde (a potentially hazardous substance).[27][28][29] According to the Dow Chemical Company, The LD50 (Lethal Dose that kills in 50% of tests) for rats is 20 g/kg (rat/oral).[30] [31]
Toxicity generally occurs at plasma concentrations over 4 g/L, which requires extremely high intake over a relatively short period of time, or when used as a vehicle for drugs or vitamins given intravenously or orally in large bolus doses.[32] It would be nearly impossible to reach toxic levels by consuming foods or supplements, which contain at most 1 g/kg of PG, except for alcoholic beverages in the US which are allowed 5 percent = 50g/kg.[33] Cases of propylene glycol poisoning are usually related to either inappropriate intravenous administration or accidental ingestion of large quantities by children.[34]
The potential for long-term oral toxicity is also low. In one study, in 1972, 12 rats were provided with feed containing as much as 5% PG over a period of 2 years, and showed no apparent ill effects; no data on offspring were offered.[35] Because of its low chronic oral toxicity, propylene glycol was classified by the U. S. Food and Drug Administration as "generally recognized as safe" (GRAS) for use as a direct food additive, including frozen foods such as ice cream and frozen desserts.[33][36] The GRAS designation is specific to its use in food, and does not apply to other uses.[37]
Prolonged contact with propylene glycol (E490) is essentially non-irritating to the skin.[38] Undiluted propylene glycol is minimally irritating to the eye, producing slight transient conjunctivitis; the eye recovers after the exposure is removed. A recent human volunteer study found that 10 male and female subjects undergoing 4 hours exposures to concentrations of up to 442 mg/m3 and 30 minutes exposures to concentrations of up to 871 mg/m3 in combination moderate exercise did not show pulmonary function deficits, or signs of ocular irritation, with only slight symptoms of respiratory irritation reported [39]. Inhalation of propylene glycol vapors appears to present no significant hazard in ordinary applications.[40]. Due to the lack of chronic inhalation data data, it is recommended that propylene glycol not be used in inhalation applications such as theatrical productions, or antifreeze solutions for emergency eye wash stations.[41] Recently, propylene glycol (commonly alongside glycerol) has been included as a carrier for nicotine and other additives in e-cigarette liquids, the use of which presents a novel form of exposure. The potential hazards of chronic inhalation of propylene glycol or the latter substance as a whole are as-yet unknown.[citation needed]
According to a 2010 study by Karlstad University, the concentrations of PGEs (counted as the sum of propylene glycol and glycol ethers) in indoor air, particularly bedroom air, has been linked to increased risk of developing numerous respiratory and immune disorders in children, including asthma, hay fever, eczema, and allergies, with increased risk ranging from 50% to 180%. This concentration has been linked to use of water-based paints and water-based system cleansers. However, the study authors write that glycol ethers and not propylene glycol are the likely culprit.[42][43][44]
Propylene glycol has not caused sensitization or carcinogenicity in laboratory animal studies, nor has it demonstrated genotoxic potential.[45][46]
Studies with intravenously administered propylene glycol have resulted in LD50 values in rats and rabbits of 7 mL/kg BW.[47] Ruddick (1972) also summarized intramuscular LD50 data for rat as 13-20 mL/kg BW, and 6 mL/kg BW for the rabbit. Adverse effects to intravenous administration of drugs that use propylene glycol as an excipient have been seen in a number of people, particularly with large bolus dosages. Responses may include CNS depression, "hypotension, bradycardia, QRS and T abnormalities on the ECG, arrhythmia, cardiac arrhythmias, seizures, agitation, serum hyperosmolality, lactic acidosis, and haemolysis".[48] A high percentage (12% to 42%) of directly-injected propylene glycol is eliminated or secreted in urine unaltered depending on dosage, with the remainder appearing in its glucuronide-form. The speed of renal filtration decreases as dosage increases,[49] which may be due to propylene glycol's mild anesthetic / CNS-depressant -properties as an alcohol.[50] In one case, intravenous administration of propylene glycol-suspended nitroglycerin to an elderly man may have induced coma and acidosis.[51] However, no confirmed lethality from propylene glycol was reported.
Propylene glycol is an approved food additive for dog and sugar glider food under the category of animal feed and is generally recognized as safe for dogs,[52] with an LD50 of 9 mL/kg. The LD50 is higher for most laboratory animals (20 mL/kg).[53] However, it is prohibited for use in food for cats due to links to Heinz body formation and a reduced lifespan of red blood cells.[54] Heinz body formation from MPG has not been observed in dogs, cattle, or humans.
Individuals who cannot tolerate propylene glycol experience inflamed dry skin in the facial area, or small red dots on the body. Estimates on the prevalence of propylene glycol allergy range from 0.8% (10% propylene glycol in aqueous solution) to 3.5% (30% propylene glycol in aqueous solution).[55][56][57] The North American Contact Dermatitis Group (NACDG) data from 1996 to 2006 showed that the most common site for propylene glycol contact dermatitis was the face (25.9%), followed by a generalized or scattered pattern (23.7%).[55] Investigators believe that the incidence of allergic contact dermatitis to propylene glycol may be greater than 2% in patients with eczema or fungal infections, which are very common in countries with lesser sun exposure and lower-than-normal vitamin D balances. Therefore, propylene glycol allergy is more common in those countries.[58]
Because of its potential for allergic reactions and frequent use across a variety of topical and systemic products, propylene glycol was named the American Contact Dermatitis Society's Allergen of the Year for 2018.[59][60] Recent publication from The Mayo Clinic reported 0.85% incidence of positive patch tests to propylene glycol (100/11,738 patients) with an overall irritant rate of 0.35% (41/11,738 patients) during a 20-year period of 1997–2016 [61]. 87% of the reactions were classified as weak and 9% as strong. The positive reaction rates were 0%, 0.26%, and 1.86% for 5%, 10%, and 20% propylene glycol respectively, increasing with each concentration increase. The irritant reaction rates were 0.95%, 0.24%, and 0.5% for 5%, 10%, and 20% propylene glycol, respectively. Propylene glycol skin sensitization occurred in patients sensitive to a number of other concomitant positive allergens, most common of which were: Myroxylon pereirae resin, benzalkonium chloride, carba mix, potassium dichromate, neomycin sulfate; for positive propylene glycol reactions, the overall median of 5 and mean of 5.6 concomitant positive allergens was reported.
Propylene glycol is expected to degrade rapidly in water from biological processes, but is not expected to be significantly influenced by hydrolysis, oxidation, volatilization, bioconcentration, or adsorption to sediment [62]. Propylene glycol is readily biodegradable under aerobic conditions in freshwater, in seawater and in soil. Therefore, propylene glycol is considered as not persistent in the environment.
Propylene glycol exhibits a low degree of toxicity toward aquatic organisms. There are several guideline studies available for freshwater fish with the lowest observed effect concentration of 96-h LC50 value of 40,613 mg/l in a study with Oncorhynchus mykiss. Similarly, the effect concentration determined in marine fish is a 96-h LC50 of >10,000 mg/l in Scophthalmus maximus.
air containing these vapors in amounts up to the saturation point is completely harmless
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| リンク元 | 「プロピレングリコール」「propanediol」 |
| 拡張検索 | 「propylene glycolate cefatrizine」「propylene glycolum」 |
| 関連記事 | 「glyco」「propylene」 |