出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/09/19 21:06:26」(JST)
| Names | |
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| Preferred IUPAC name
Prop-2-enoic acid
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| Other names
Acrylic acid
Acroleic acid |
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| Identifiers | |
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CAS Number
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3D model (JSmol)
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| ChEBI |
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| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.001.071 |
| EC Number | 201-177-9 |
| KEGG |
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PubChem CID
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| RTECS number | AS4375000 |
| UNII |
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InChI
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SMILES
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| Properties | |
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Chemical formula
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C3H4O2 |
| Molar mass | 72.06 g·mol−1 |
| Appearance | clear, colorless liquid |
| Odor | acrid[2] |
| Density | 1.051 g/mL |
| Melting point | 14 °C (57 °F; 287 K) |
| Boiling point | 141 °C (286 °F; 414 K) |
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Solubility in water
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Miscible |
| Vapor pressure | 3 mmHg[2] |
| Acidity (pKa) | 4.25[3] |
| Viscosity | 1.3 cP at 20 °C (68 °F) |
| Hazards | |
| Main hazards | Corrosive (C), Dangerous for the |
| Safety data sheet | MSDS |
| R-phrases (outdated) | R10 R20/21/22 R35 R50 |
| S-phrases (outdated) | S26 S36/37/39 S45 S61 |
| NFPA 704 |
2
3
2
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| Flash point | 68 °C (154 °F; 341 K) |
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Autoignition
temperature |
429 °C (804 °F; 702 K) |
| Explosive limits | 2.4%-8.02%[2] |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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none[2] |
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REL (Recommended)
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TWA 2 ppm (6 mg/m3) [skin][2] |
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IDLH (Immediate danger)
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N.D.[2] |
| Related compounds | |
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Other anions
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acrylate |
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Related carboxylic acids
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acetic acid propionic acid |
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Related compounds
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allyl alcohol propionaldehyde |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) | |
| Infobox references | |
Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.[4]
Acrylic acid is produced from propylene which is a byproduct of ethylene and gasoline production.
Because propane is a significantly cheaper raw material than propylene, considerable research efforts are undertaken to develop a process based on the one-step selective oxidation of propane to acrylic acid.[5][6][7][8] Ethylene can be carboxylated to acrylic acid under supercritical carbon dioxide condition.[9]
Because acrylic acid and its esters have long been valued commercially, many other methods have been developed but most have been abandoned for economic or environmental reasons. An early method was the hydrocarboxylation of acetylene ("Reppe chemistry"):
This method requires nickel carbonyl and high pressures of carbon monoxide. It was once manufactured by the hydrolysis of acrylonitrile which is derived from propene by ammoxidation, but was abandoned because the method cogenerates ammonium derivatives. Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.[4]
Dow Chemical Company and a partner, OPX Biotechnologies, are investigating using fermented sugar to produce 3-hydroxypropionic acid (3HP), an acrylic acid precursor.[10] The goal is to reduce greenhouse gas emissions. [11]
Acrylic acid undergoes the typical reactions of a carboxylic acid. When reacted with an alcohol, it forms the corresponding ester. The esters and salts of acrylic acid are collectively known as acrylates (or propenoates). The most common alkyl esters of acrylic acid are methyl, butyl, ethyl, and 2-ethylhexyl acrylate.
Acrylic acid and its esters readily combine with themselves (to form polyacrylic acid) or other monomers (e.g. acrylamides, acrylonitrile, vinyl compounds, styrene, and butadiene) by reacting at their double bond, forming homopolymers or copolymers which are used in the manufacture of various plastics, coatings, adhesives, elastomers, as well as floor polishes, and paints.
As a substituent acrylic acid can be found as an acyl group or a carboxyalkyl group depending on the removal of the group from the molecule. More specifically these are:
Acrylic acid is severely irritating and corrosive to the skin and the respiratory tract. Eye contact can result in severe and irreversible injury. Low exposure will cause minimal or no health effects, while high exposure could result in pulmonary edema. The LD50 is 340 mg/kg (rat, oral).
Acrylic acid is a constituent of tobacco smoke.[12]
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| リンク元 | 「acrylate」「アクリル酸」 |
| 拡張検索 | 「4-imidazoleacrylic acid」「methacrylic acid」 |
| 関連記事 | 「acrylic」「acryl」 |