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Acetone cyanohydrin

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Name

Acetone cyanohydrin

EINECS 200-909-4
CAS No. 75-86-5 Density 0.932
PSA 44.02000 LogP 0.28088
Solubility miscible Melting Point -19ºC
Formula C4H7NO Boiling Point 82ºC
Molecular Weight 85.1057 Flash Point 73 ºC
Transport Information UN 1541 Appearance yellowish liquid
Safety Risk Codes R26/27/28;R50
Molecular Structure Molecular Structure of 75-86-5 (2-Hydroxy-2-methylpropanenitrile) Hazard Symbols
Synonyms

Lactonitrile,2-methyl- (6CI,8CI);2-Cyano-2-hydroxypropane;2-Cyano-2-propanol;2-Hydroxy-2-cyanopropane;2-Hydroxy-2-methylpropanenitrile;2-Hydroxy-2-methylpropionitrile;2-Hydroxyisobutyronitrile;2-Methyl-2-hydroxypropionitrile;2-Methyllactonitrile;2-Propanone,cyanohydrin;Acetone cyanohydrin;Dimethyl ketone cyanohydrin;NSC 131093;NSC7080;NSC 977;a-Hydroxyisobutyronitrile;

Article Data 63

Acetone cyanohydrin Synthetic route

potassium cyanide

67-64-1

acetone

75-86-5

2-hydroxy-2-methylpropanenitrile

Conditions
ConditionsYield
With acetic acid In water at 30℃; Microreactor technology; Continuous flow system;99%
With sodium metabisulfite In water at 20℃; for 0.5h;
Stage #1: acetone With sodium hydrogen sulfite In water at 0℃; for 1h;
Stage #2: potassium cyanide In water for 14h;
74-90-8

hydrogen cyanide

67-64-1

acetone

75-86-5

2-hydroxy-2-methylpropanenitrile

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid; sodium cyanide In water at 10℃; for 1.5h; pH=7.3;95%
With pyridine
With quinoline
19355-69-2

2-amino-2-cyanopropane

A

18992-13-7

2-cyano-2-nitropropane

B

40561-27-1

1-cyano-1-methylethylnitrate

C

58102-56-0

tris-(1-cyano-1-methyl-ethyl)-hydroxylamine

D

75-86-5

2-hydroxy-2-methylpropanenitrile

Conditions
ConditionsYield
With perchloric acid; sodium nitrite at 25℃; Product distribution; var. α-aminonitriles; other conditions, also radical scavengers;A 47.4%
B 0.4%
C 13.9%
D 37.3%
773837-37-9

sodium cyanide

67-64-1

acetone

75-86-5

2-hydroxy-2-methylpropanenitrile

Conditions
ConditionsYield
With sulfuric acid In water at 20℃;29%
74-90-8

hydrogen cyanide

75-86-5

2-hydroxy-2-methylpropanenitrile

Conditions
ConditionsYield
With aluminum oxide at 150 - 300℃; Beim Leiten von Aceton-Dampf im den Gemisch;
With dipotassium hydrogenphosphate; kieselguhr at 60℃; Beim Leiten von Aceton-Dampf im den Gemisch;
151-50-8

potassium cyanide

540-92-1

acetone sodium bisulfite

75-86-5

2-hydroxy-2-methylpropanenitrile

67-56-1

methanol

74-90-8

hydrogen cyanide

67-64-1

acetone

75-86-5

2-hydroxy-2-methylpropanenitrile

Conditions
ConditionsYield
at 20℃; Kinetics; Verlauf der Reaktion; auch in anderen Loesungsmitteln;
at 20℃; Rate constant; und in anderen Loesungsmitteln;
60-29-7

diethyl ether

74-90-8

hydrogen cyanide

67-64-1

acetone

75-86-5

2-hydroxy-2-methylpropanenitrile

74-90-8

hydrogen cyanide

143-33-9

sodium cyanide

67-64-1

acetone

75-86-5

2-hydroxy-2-methylpropanenitrile

74-90-8

hydrogen cyanide

151-50-8

potassium cyanide

67-64-1

acetone

75-86-5

2-hydroxy-2-methylpropanenitrile

Acetone cyanohydrin Chemical Properties

2-METHYLLACTONITRILE's Molecular formula: C4H7NO
2-METHYLLACTONITRILE's Molar mass: 85.1
EINECS: 200-909-4
melting point: -19 °C
flash point: 147 °F
boiling point: 82 °C 23 mm Hg
density: 0.932 g/mL at 25 °C
vapor pressure: 0.3 psi ( 20 °C)
refractive index: n20/D 1.399
Water Solubility: miscible
other names: Acetone cyanohydrin

Acetone cyanohydrin Uses

 Acetone cyanohydrin is an intermediate in the manufacture of methyl methacrylate.

Acetone cyanohydrin Production

 Acetone cyanohydrin is manufactured by the direct reaction of hydrogen cyanide with acetone catalyzed by base, generally In a continuous process.
       CH3COCH3 + HCN → CH3C(OH . CN)CH3

Acetone cyanohydrin Toxicity Data With Reference

1.   

orl-rat LD50:19,300 µg/kg

   GISAAA    Gigiena i Sanitariya. 58 (1)(1993),28.
2.   

ihl-rat LCLo:63 ppm/4H

   AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
3.   

scu-rat LDLo:8500 µg/kg

   BJIMAG    British Journal of Industrial Medicine. 19 (1962),283.
4.   

orl-mus LD50:14 mg/kg

   28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,161.
5.   

ihl-mus LCLo:500 mg/m3/2H

   IGIBA5    Igiena. 11 (1962),27.
6.   

ipr-mus LD50:1 mg/kg

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) No. AD277-689 .
7.   

orl-rbt LD50:13,500 µg/kg

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) No. PB214-270 .
8.   

skn-rbt LD50:17 mg/kg

   AIHAAP    American Industrial Hygiene Association Journal. 23 (1962),95.
9.   

unr-rat TDLo:242 mg/kg/26W-I

   GISAAA    Gigiena i Sanitariya. 31 (6)(1966),8.
10.
  

Acetone cyanohydrin Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.

Acetone cyanohydrin 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. See also NITRILES, HYDROCYANIC ACID, and ACETONE.

Acetone cyanohydrin Standards and Recommendations

ACGIH TLV: CL 4.7 ppm (skin)
NIOSH REL: (Nitriles) CL 4 mg/m3/15M
DOT Classification:  6.1; Label: Poison

Acetone cyanohydrin Analytical Methods

For occupational chemical analysis use NIOSH: Acetone Cyanohydrin, 2506.