| Identification | More | [Name]
Acetone cyanohydrin | [CAS]
75-86-5 | [Synonyms]
2-HYDROXY-2-METHYLPROPIONITRILE
2-HYDROXYISOBUTYRONITRILE
2-METHYL-LACTONITRILE
ACETONE CYANOHYDRIN
A-HYDROXYISOBUTYRONITRILE
AKOS BBS-00004270
ALPHA-HYDROXYISOBUTYRONITRILE
2-Cyano-2-hydroxypropane
2-Cyano-2-propanol
2-Cyanopropan-2-ol
2-hydroxy-2-methyl-propanenitril
2-Hydroxy-2-methylpropanenitrile
2-hydroxy-2-methyl-Propanenitrile
2-methyllacetonitrile
2-methyl-lactonitril
2-Propanone, cyanohydrin
2-propanone,cyanohydrin
Acetoncianhidrinei
acetoncianhidrinei(roumanian)
Acetoncianidrina | [EINECS(EC#)]
200-909-4 | [Molecular Formula]
C4H7NO | [MDL Number]
MFCD00004455 | [Molecular Weight]
85.1 | [MOL File]
75-86-5.mol |
| Chemical Properties | Back Directory | [Description]
Acetone cyanohydrin is an organic compound used in the production of methyl methacrylate,
the monomer of the transparent plastic polymethyl methacrylate (PMMA), also
known as acrylic. Acetone cyanohydrin is a flammable colourless liquid with a faint odour
of bitter almond. It is incompatible with sulphuric acid. Acetone cyanohydrin readily
undergoes decomposition by water to form hydrogen cyanide and acetone. Cassava tubers
contain linamarin, a glucoside of acetohydrin, and the enzyme linamarinase for hydrolysing
the glucoside. Crushing the tubers releases these compounds and produces acetone
cyanohydrin, which is potentially lethally toxic. Acetone cyanohydrin is classified as an
extremely hazardous substance in the U.S. Emergency Planning and Community Right-to-
Know Act. The principal hazards of acetone cyanohydrin arise from its ready decomposition
on contact with water, which releases highly toxic hydrogen cyanide. | [Appearance]
Acetone cyanohydrin is a flammable, colorless to light yellow liquid. Almond-like odor. | [Melting point ]
-19 °C (lit.) | [Boiling point ]
82 °C/23 mmHg (lit.) | [density ]
0.932 g/mL at 25 °C(lit.)
| [vapor pressure ]
0.3 psi ( 20 °C)
| [refractive index ]
n20/D 1.399(lit.)
| [Fp ]
147 °F
| [storage temp. ]
Refrigerator | [solubility ]
very soluble in water, alcohol, and ether; slightly soluble in petroleum
ether | [form ]
Liquid | [pka]
11.45±0.29(Predicted) | [color ]
Clear colorless to yellow | [Water Solubility ]
miscible | [Merck ]
13,68 | [Exposure limits]
Ceiling 4 mg (1.2 ppm)/m3/15 min (NIOSH).
Zholdakova et al. (1995) have recommended a maximum permissible concentration of 0.035 mg/L in water as cyanide for acetone cyanohydrin or in combination with other cyanides. | [CAS DataBase Reference]
75-86-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Propanenitrile, 2-hydroxy-2-methyl-(75-86-5) | [EPA Substance Registry System]
75-86-5(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
cetone cyanohydrin is a colorless, fl
ammable liquid with a faint odor of bitter almond.
It is an organic compound used in the production of methyl methacrylate, the monomer
of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It is
incompatible with sulfuric acid and caustics. Acetone cyanohydrin readily undergoes
decomposition by water to form hydrogen cyanide and acetone. | [General Description]
A colorless liquid. Flash point 165°F. Lethal by inhalation and highly toxic or lethal by skin absorption. Density 7.8 lb/gal (less dense than water). Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. | [Reactivity Profile]
ACETONE CYANOHYDRIN readily decomposes to acetone and poisonous hydrogen cyanide gas on contact with water, acids (sulfuric acid) or when exposed to heat. Should be kept cool and slightly acidic (pH 4-5) [Sax, 2nd ed., 1965, p. 388]. Slowly dissociates to acetone, a flammable liquid, and hydrogen cyanide, a flammable poisonous gas, under normal storage and transportation conditions. Rate of dissociation increased by contact with alkalis and/or heat. | [Health Hazard]
Acetone cyanohydrin is extremely toxic. Exposures to acetone cyanohydrin cause adverse
health effects. The symptoms of toxicity include, but are not limited to, irritation to the
eyes, skin, respiratory system, dizziness, lassitude (weakness, exhaustion), headache, con-
fusion, pulmonary edema, asphyxia convulsions, liver, kidney injury, pulmonary edema,
and asphyxia. The target organs include the eyes, skin, respiratory system, central nervous
system (CNS), cardiovascular system, liver, kidneys, and the gastrointestinal tract. | [Health Hazard]
This material is considered very hazardous and should only be handled under conditions that prevent any inhalation of vapor or skin contact. May be slightly irritating to skin and mucous membranes. | [Potential Exposure]
Used in the manufacture of insecticides and making other chemicals, such as methyl methacrylate. | [Fire Hazard]
Too dangerous to health to expose fire fighters; a few whiffs of vapor could cause death; vapor or liquid could be fatal on penetrating normal protective clothing. Vapor forms explosive mixture with air. Decomposes when heated to 248F or at lower temperature under alkaline conditions, emitting highly toxic hydrogen cyanide. May react violently with water. Contact with sulfuric acid may cause ACETONE CYANOHYDRIN, STABILIZED to explode. | [First aid]
Move victim to fresh air; call emergency medical care. If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, quickly remove contaminated clothing and wash with large amounts of water. Speed in removing material from skin is of extreme importance. Seek medical attention immediately. When this chemical has been swallowed, get medical attention immediately. If this chemical has been inhaled, remove from exposure, and transfer promptly to a medical facility. If not breathing, give artificial respiration (avoid mouth to mouth resuscitation). If breathing is difficult, give oxygen. If heart has stopped begin CPR. Keep victim quiet and maintain normal body temperature. Effects may be delayed; keep victim under observation. Avoid contact with contaminated skin. A cyanide antidote kit should be kept in the immediate work area and must be rapidly available. Kit ingredients should be replaced every 1 2 years to ensure freshness. Persons trained in the use of this kit; oxygen use, and CPR must be available within 1 2 minutes of exposure | [Shipping]
UN1541 Acetone cyanohydrin, stabilized, Hazard Class: 6.1; Labels: 6.1-Poison Inhalation Hazard, Inhalation Hazard Zone B. | [Incompatibilities]
May form explosive mixture with air. Not compatible with strong reducers, strong bases; strong oxidizers, and strong acids, such as hydrochloric, sulfuric (explosive), and nitric. Contact with strong acid and strong bases may cause explosions. Slowly decomposes to acetone and hydrogen cyanide gas at room temperatures; rate is accelerated by an increase in pH, contact with water, or temperature. | [Waste Disposal]
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Add with stirring to strong alkaline calcium hypochlorite solution. Alternatively dissolve in flammable solvent and burn in incinerator with afterburner and scrubber. | [Uses]
Acetone cyanohydrin is used as a raw material for insecticides manufacture and also to produce ethyl α-hydroxyisobutryate, a pharmaceutical intermediate. It has been used as a complexing agent for metals refining and separation. | [Uses]
Acetone cyanohydrin is used to make methyl methacrylate; in the production of pharmaceuticals, foaming agents, and insecticides; and to produce polymerization initiators. | [Uses]
In preparative organic chemistry for transcyanohydrination, such as preparing the 17-monocyanohydrin of a 3,17-diketo steroid by hydrogen cyanide exchange with the reagent, e.g. Ercoli, de Ruggieri, J. Am. Chem. Soc. 75, 650 (1953). | [Definition]
ChEBI: 2-hydroxy-2-methylpropanenitrile is a cyanohydrin. | [Production Methods]
Acetone cyanohydrin is formed by adding acetone to sodium or potassium cyanide in water and treating with H2S04 or by reaction of acetone with hydrogen cyanide
(HSDB 1988; Windholz et al 1983). Technical acetone cyanohydrin may contain
as much as 0.2% free hydrogen cyanide. U.S. production in 1984 is estimated at
546,000 tons (HSDB 1988). | [Production Methods]
Acetone cyanohydrin is manufactured by the direct reaction of hydrogen cyanide with acetone, catalyzed by base, generally in a continuous process. | [Industrial uses]
Actone cyanohydrin is used primarily in the preparation of methyl methacrylate,
which is polymerized to form various plastics, including plexiglas, and as intermediate
for resins (Hawley 1981). It also is employed for the manufacture of
insecticides; to produce oc-hydroxy-isobutyrate, a pharmaceutical intermediate; as
a complexing agent for metals; and as a reagent for chemical synthesis. | [Metabolism]
Acetone cyanohydrin is readily absorbed by all routes (Hartung 1981). Shkodich
(1966) found no evidence of cumulative effects of acetone cyanohydrin in white
mice or albino rats over a period of 20 d in which daily doses of one-fifth of the
LD50s were given. Rapid detoxication and excretion were presumed to occur.
Acetone cyanohydrin may be largely metabolized to yield free cyanide (H?rtung
1981). | [Purification Methods]
Dry the cyanohydrin with Na2SO4, and distil it as rapidly as possible under vacuum to avoid decomposition. Discard fractions boiling below 78-82o/15mm. Store it in the dark. USE AN EFFICIENT FUME HOOD as HCN (POISONOUS) is always present. [Cox & Stormont Org Synth Coll.Vol. II 7 1940, Beilstein 3 H 316, 3 IV 785.] |
| Safety Data | Back Directory | [Hazard Codes ]
T+,N | [Risk Statements ]
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed .
R50:Very Toxic to aquatic organisms.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S27:Take off immediately all contaminated clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S7/9:Keep container tightly closed and in a well-ventilated place . | [RIDADR ]
UN 1541 6.1/PG 1
| [WGK Germany ]
3
| [RTECS ]
OD9275000
| [HazardClass ]
6.1(a) | [PackingGroup ]
I | [HS Code ]
29269095 | [Safety Profile]
Poison by ingestion,
skin contact, inhalation, intraperitoneal, and
subcutaneous routes. Readily decomposes to
HCN and acetone. Keep cool and do not
store for long periods. Combustible when
exposed to heat or flame. To fight fire, use
CO2, dry chemical, alcohol foam. Vigorous
reaction with H2SO4. When heated to
decomposition it emits toxic fumes of CN-. | [Hazardous Substances Data]
75-86-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 0.17 g/kg (Smyth) |
|