Acetone cyanohydrin is an organic substance , the simplest cyanohydrin . It is widely used in the chemical industry for the production of methyl methacrylate - a raw material ( monomer ) for the production of polymethyl methacrylate ("organic glass").
| Acetone cyanohydrin | |
|---|---|
 | |
 | |
| Are common | |
| Systematic name | 2-hydroxy-2-methylpropannitrile |
| Traditional names | Acetone cyanohydrin, α-hydroxyisobutyronitrile, nitrile-α-hydroxyisobutyric acid |
| Chem. formula | C 4 H 7 NO |
| Rat formula | (CH 3 ) 2 C (OH) CN |
| Physical properties | |
| condition | colorless liquid with a characteristic smell of bitter almonds |
| Molar mass | 85.1045 ± 0.0042 g / mol |
| Density | 0.93 g / cm³ |
| Thermal properties | |
| T. melt. | -19 ° C |
| T. bale. | 95 ° C |
| T. decomp. | 120 ° C |
| T. aux. | |
| T. svpl. | 668 ° C |
| Etc. blast | 2.2-12% |
| Steam pressure | 110 Pa |
| Chemical properties | |
| Solubility in water | 93.2 g / 100 ml |
| Optical properties | |
| Refractive index | 1,3992 |
| Classification | |
| Reg. CAS number | 75-86-5 |
| PubChem | |
| Reg. EINECS number | 200-909-4 |
| Smiles | |
| Inchi | |
| RTECS | |
| Chebi | |
| UN number | |
| ChemSpider | |
| Security | |
| MPC | 0.9 mg / m 3 |
| LD 50 | 18.65 mg / kg (rat, oral) |
| Toxicity | highly toxic, SDYA , irritant     |
| NFPA 704 |  2 four 2 |
It is extremely dangerous, because when it interacts with water it decomposes with the release of highly toxic hydrocyanic acid .
Physical Properties
It is a colorless, odorless liquid (concentrated solutions have the smell of bitter almonds ), readily soluble in water , ethanol , diethyl ether and other polar organic solvents , poorly in benzene , carbon disulfide and non-polar solvents. In solution, it hydrolyzes to form acetone and hydrocyanic acid . At a saturated vapor pressure of 23 mm Hg boils at 82 ° C; decomposes at 120 ° C [2] . At normal atmospheric pressure, the melting point is -19 ° C, the boiling point is 95 ° C. The mixture with air is explosive (ignition limits - from 2.2 to 12.0% by volume).
Getting
In laboratory synthesis, it can be obtained from acetone by treatment with sodium cyanide , followed by acidification [3]
Application
In the cyanohydrin method for producing polymethylmethacrylate (“organic glass”), acetone cyanohydrin is treated with sulfuric acid to form methacrylamide sulfate, the transesterification of which with methanol gives ammonium hydrosulfate and methyl methacrylate , a polymethacrylate monomer [4] .
Toxicology
Acetone cyanohydrin is a highly toxic compound. Poisoning of the body is possible through the respiratory tract , gastrointestinal tract and exposed areas of the skin (especially damaged ones). In the body, it easily dissociates into acetone and hydrocyanic acid ; therefore, it is similar in toxicity to it and other cyanides [5] .
Precautions
When working with acetone cyanohydrin, it is necessary to comply with safety rules established for working with potent toxic substances [6] . It is quite flammable, it easily ignites from a spark, spontaneously ignites in the sun and near heating appliances.
See also
- Cyanhydrins
Notes
- ↑ http://www.cdc.gov/niosh/npg/npgd0005.html
- ↑ Barg E.I. Technology of synthetic plastics. - Goskhimizdat. - L. , 1954. - 656 p.
- ↑ Cox, RFB & Stormont, RT, " Acetone Cyanohydrin ", Org. Synth. , < http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0007 > ; Coll. Vol. T. 2: 7
- ↑ William Bauer, Jr. Methacrylic Acid and Derivatives // Ullmann's Encyclopedia of Industrial Chemistry. - Weinheim: Wiley-VCH, 2002. - ISBN 3-527-30673-0 . - DOI : 10.1002 / 14356007.a16_441 .
- ↑ Harmful substances in industry. Handbook for chemists, engineers and doctors. / Ed. merit activist science prof. N.V. Lazareva and Dr. honey. Sciences E.N. Levina. - Ed. 7th, per. and add. - L .: "Chemistry", 1976. - T. I. - S. 340-341. - 592 p. - 49,000 copies.
- ↑ Bezugly V.D. Analysis of Polymerization Plastics / Ed. V.D. Non-carbonless. - M .; L .: Chemistry, 1965 .-- 512 p. - 6700 copies.