Glycidol

Glycidol Basic information
Product Name:Glycidol
Synonyms:GLYCEROLGLYCIDE;(+/-)-GLYCIDOL;GLYCIDOL;GLYCEROGLYCIDE;3-HYDROXY-1,2-EPOXYPROPANE;3-HYDROXYPROPYLENE OXIDE;2,3-EPOXY-1-PROPANOL;2,3-EPOXYPROPAN-1-OL
CAS:556-52-5
MF:C3H6O2
MW:74.08
EINECS:209-128-3
Product Categories:Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;556-52-5
Mol File:556-52-5.mol
Glycidol Structure
Glycidol Chemical Properties
Melting point -54 °C
Boiling point 61-62 °C/15 mmHg (lit.)
density 1.117 g/mL at 25 °C (lit.)
vapor density 2.15 (vs air)
vapor pressure 0.9 mm Hg ( 25 °C)
refractive index n20/D 1.433(lit.)
Fp 178 °F
storage temp. -20°C
solubility Soluble in acetone, alcohol, benzene, chloroform, and ether (Weast, 1986)
form Powder, Crystals or Chunks
pka14.62±0.10(Predicted)
color White to light yellow-beige
Water Solubility soluble
Merck 13,4503
BRN 383562
Exposure limitsTLV-TWA 75 mg/m3 (25 ppm) (ACGIH); 150 mg/m3 (50 ppm) (OSHA); IDLH 500 ppm (NIOSH).
Stability:Stability Stable, but may explode on contact with strong acids, strong bases, heavy metals, heavy metal salts. May decompose on exposure to water or moist air.
InChIKeyCTKINSOISVBQLD-UHFFFAOYSA-N
LogP-0.95 at 25℃
CAS DataBase Reference556-52-5(CAS DataBase Reference)
IARC2A (Vol. 77) 2000
NIST Chemistry ReferenceGlycidol(556-52-5)
EPA Substance Registry SystemGlycidol (556-52-5)
Safety Information
Hazard Codes T
Risk Statements 45-60-21/22-23-36/37/38-68
Safety Statements 53-45-36/37-26
RIDADR UN 2810 6.1/PG 3
WGK Germany 3
RTECS UB4375000
10-21
Autoignition Temperature780 °F
Hazard Note Toxic
HazardClass 6.1(b)
PackingGroup III
HS Code 29109000
Hazardous Substances Data556-52-5(Hazardous Substances Data)
ToxicityAcute oral LD50 for mice 431 mg/kg, rats 420 mg/kg (quoted, RTECS, 1985).
IDLA150 ppm
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
Glycidol Usage And Synthesis
DescriptionGlycidol is a chiral molecule with epoxide and primary alcohol functional groups. It is racemic mixture and exists in the dextrorotatory and the levorotatory enantiomeric forms. Several synthetic methods are available for preparation of glycidol. However, it is commercially prepared from the epoxidation of allyl alcohol with hydrogen peroxide and a catalyst (tungsten or vanadium), or from the reaction of epichlorohydrin with caustic. Glycidol has been used in the industrial synthesis of pharmaceutical products since the 1970s. However, its use for research purposes has been reported since 1956. Available information indicates that glycidol is manufactured by several companies in Japan, Germany, and the United States.
Chemical Propertiescolourless liquid
Chemical PropertiesGlycidol is a colorless liquid.
UsesGlycidol is used as a stabilizer for natural oilsand vinyl polymers, as a demulsifier, and asa leveling agent for dyes.
UsesStabilizer in manufacturing of vinyl polymers; intermediate in synthesis of glycerol, glycidyl ethers, and amines; additive for oil and synthetic hydraulic fluids; epoxy resin diluent.
Uses

Glycidol is a Stabilizer in the manufacture of vinyl polymers; chemical intermediate in preparation of glycerol, glycidyl ethers, esters, and amines; in pharmaceuticals; in sanitary chemicals.

Definitionan epoxide
General DescriptionOdorless clear colorless liquid.
Air & Water ReactionsSensitive to moisture.
Reactivity ProfileGlycidol is sensitive to moisture. Glycidol is also sensitive to light. Glycidol may polymerize if heated above room temperature. Glycidol may darken on storage. Stability studies of Glycidol stored for two week protected from light indicated definite decomposition at 140° F, and strongly indicated instability at 77° F. A solution of Glycidol in water was found to be unstable when stored at room temperature, even after one day in the dark. Glycidol is incompatible with strong oxidizers. Glycidol will undergo explosive decomposition in the presence of strong acids or bases, salts (such as aluminum chloride, iron(III)chloride or tin(IV) chloride) or metals (such as copper and zinc). Glycidol is also incompatible with nitrates. Glycidol will attack some forms of plastics, rubber and coatings.
HazardToxic material. Probable carcinogen.
Health HazardGlycidol is an eye, lung, and skin irri-tant. The pure compound caused severebut reversible corneal injury in rabbit eyes(ACGIH 1986). Exposure to its vapor causedirritation of lung in mice, resulting in pneu-monitis. There is no evidence of any cumula-tive toxicity. From the limited toxicity data,it appears that the health hazard to humansfrom its exposure is, primarily, respiratoryirritation, stimulation of the central nervoussystem, and depression.
Glycidol is mutagenic, testing positive inthe histidine reversion–Ames test. There isno report of its carcinogenic action. Oraland intraperitoneal administration of gly-cidol in rats showed harmful effects onfertility.
Fire HazardGlycidol is combustible.
Flammability and ExplosibilityNonflammable
Safety ProfileConfirmed carcinogen with carcinogenic data reported. Poison by intraperitoneal route. Moderately toxic by ingestion, inhalation, and sh contact. Experimental teratogenic and reproductive effects. A skin irritant. Human mutation data reported. Animal experiments suggest somewhat lower toxicity than for related epoxy compounds. Readdy absorbed through the skin. Causes nervous excitation followed by depression. Explodes when heated or in the presence of strong acids,bases, metals (e.g., copper, zinc), and metal salts (e.g., aluminum chloride, iron(II1) chloride, tin(Iy chloride). When heated to decomposition it emits acrid smoke and fumes. See also DIGLYCIDYL ETHER.
Potential ExposureGlycidol is used as an intermediate in the synthesis of glycerol, glycidyl ethers, esters, and amines.
CarcinogenicityGlycidol is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental fateChemical/Physical. May hydrolyze in water forming glycerin (Lyman et al., 1982).
ShippingUN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Purification Methods[S(-)-isomer, § also available on polymer support, has b 49-50o/7mm, 66-67o/19mm, [ ] D -1 5o(neat)], [R(+)-isomer has b 56 -5 6 . 5o/11mm, d 4 1.117, n D 1.429, [ ] D +15o (neat)]. Purify glycidol by fractional distillation.
Toxicity evaluationGlycidol is a small molecule possessing a chemically reactive epoxide group. Therefore, it acts as a direct alkylating agent. Nucleophilic bioactive compounds such as glutathione react readily with glycidol. Glycidol decreases glutathione content in rat liver by direct binding to the glutathione. In vitro experiments revealed that glycidol reacts with purified DNA to form the DNA adducts. This is likely to be responsible for the genotoxic activity of the compound without a requirement for metabolic activation.
IncompatibilitiesMay form explosive mixture with air. Violent reaction with strong oxidizers, nitrates. Decomposes on contact (especially in the presence of heat) with strong acids, strong bases, water, metal salts, e.g., alu minum chloride, ferric chloride, and tin chloride), or metals (copper and zinc), causing fire and explosion hazard. Contact with barium, lithium, sodium, magnesium, and tita nium may cause polymerization. Attacks some plastics, rubber, and coatings.
Waste DisposalConcentrated waste contain ing no peroxides: discharge liquid at a controlled rate near a pilot flame. Concentrated waste containing peroxides: perforation of a container of the waste from a safe distance followed by open burning.
1,3-Butadiene diepoxide Glycidol phenyl ether ETHYLENE OXIDE disodium epoxysuccinate EPOXY (2R,3R)-(+)-3-(4-NITROPHENYL)GLYCIDOL) Phenolic epoxy resin Glycidol methacrylate Allyl glycidyl ether R-GlycidolS-Glycidol 4-CHLOROPHENYL GLYCIDYL ETHER GLYCIDAMIDE Epoxy coating of terrace Epichlorohydrin Isopropyl alcohol CHLOROPHOSPHONAZO III 1-Propanol Propylene oxide

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