| Identification | More | [Name]
Glycidol | [CAS]
556-52-5 | [Synonyms]
2,3-EPOXY-1-PROPANOL
2,3-EPOXYPROPAN-1-OL
2,3-EPOXYPROPANOL-1
3-HYDROXY-1,2-EPOXYPROPANE
3-HYDROXYPROPYLENE OXIDE
GLYCEROGLYCIDE
GLYCEROLGLYCIDE
(+/-)-GLYCIDOL
GLYCIDOL
(+/-)-OXIRANE-2-METHANOL
OXYRANYL METHANOL
(±)-Oxiranyl-methanol
(RS)-Glycidol
±-Oxiranyl-methanol
1,2-Epoxy-3-hydroxypropane
1-Hydroxy-2,3-epoxypropane
1-Propanol, 2,3-epoxy-
1-Propanol,2,3-epoxy-
2-(Hydroxymethyl)oxirane
2,3-epoxy-1-propano | [EINECS(EC#)]
209-128-3 | [Molecular Formula]
C3H6O2 | [MDL Number]
MFCD00005147 | [Molecular Weight]
74.08 | [MOL File]
556-52-5.mol |
| Chemical Properties | Back Directory | [Definition]
an epoxide | [Appearance]
Glycidol is a colorless liquid. | [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. ]
2-8°C
| [solubility ]
Soluble in acetone, alcohol, benzene, chloroform, and ether (Weast, 1986) | [form ]
Powder, Crystals or Chunks | [pka]
14.62±0.10(Predicted) | [color ]
White to light yellow-beige | [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. | [Water Solubility ]
soluble | [Merck ]
13,4503 | [BRN ]
383562 | [Exposure limits]
TLV-TWA 75 mg/m3
(25 ppm) (ACGIH);
150 mg/m3
(50 ppm) (OSHA); IDLH
500 ppm (NIOSH). | [InChIKey]
CTKINSOISVBQLD-UHFFFAOYSA-N | [LogP]
-0.95 at 25℃ | [CAS DataBase Reference]
556-52-5(CAS DataBase Reference) | [IARC]
2A (Vol. 77) 2000 | [NIST Chemistry Reference]
Glycidol(556-52-5) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
556-52-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R45:May cause cancer.
R60:May impair fertility.
R21/22:Harmful in contact with skin and if swallowed .
R23:Toxic by inhalation.
R36/37/38:Irritating to eyes, respiratory system and skin .
R68:Possible risk of irreversible effects. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [OEB]
A | [OEL]
TWA: 25 ppm (75 mg/m3) | [RIDADR ]
UN 2810 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
UB4375000
| [F ]
10-21 | [Autoignition Temperature]
780 °F | [Hazard Note ]
Toxic | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29109000 | [Safety Profile]
Confirmed 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. | [Hazardous Substances Data]
556-52-5(Hazardous Substances Data) | [Toxicity]
Acute oral LD50 for mice 431 mg/kg, rats 420 mg/kg (quoted, RTECS, 1985). | [IDLA]
150 ppm |
| Hazard Information | Back Directory | [General Description]
Odorless clear colorless liquid. | [Reactivity Profile]
GLYCIDOL(556-52-5) is sensitive to moisture. GLYCIDOL(556-52-5) is also sensitive to light. GLYCIDOL(556-52-5) may polymerize if heated above room temperature. GLYCIDOL(556-52-5) may darken on storage. Stability studies of this chemical stored for two week protected from light indicated definite decomposition at 140° F, and strongly indicated instability at 77° F. A solution of this compound in water was found to be unstable when stored at room temperature, even after one day in the dark. This chemical is incompatible with strong oxidizers. GLYCIDOL(556-52-5) 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(556-52-5) is also incompatible with nitrates. GLYCIDOL(556-52-5) will attack some forms of plastics, rubber and coatings. | [Air & Water Reactions]
Sensitive to moisture. | [Hazard]
Toxic material. Probable carcinogen. | [Potential Exposure]
Glycidol is used as an intermediate in
the synthesis of glycerol, glycidyl ethers, esters, and amines. | [Fire Hazard]
This chemical is combustible. | [First aid]
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, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, includ ing resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medi cal attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a qualified med ical professional might consider administering a corticoste roid spray. Cigarette smoking may exacerbate pulmonary
injury and should be discouraged for at least 72 hours
following exposure. If symptoms develop or overexposure
is suspected, chest X-ray should be considered. | [Shipping]
UN2810 Toxic liquids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. | [Incompatibilities]
May 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. | [Description]
Glycidol 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 Properties]
colourless liquid | [Chemical Properties]
Glycidol is a colorless liquid. | [Waste Disposal]
Concentrated 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. | [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.
| [Uses]
Glycidol is used as a stabilizer for natural oilsand vinyl polymers, as a demulsifier, and asa leveling agent for dyes. | [Uses]
Stabilizer in manufacturing of vinyl polymers; intermediate in synthesis of glycerol, glycidyl ethers, and amines; additive for oil and synthetic hydraulic fluids; epoxy resin diluent. | [Health Hazard]
Glycidol 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. | [Flammability and Explosibility]
Nonflammable | [Synthesis]
A method for directly preparing glycidol from glycerol is shown as following steps: putting a mixed solvent in a glass or enamel reaction kettle, adding glycerol to the mixed solvent, controlling the concentration of glycerol in the reaction liquid within the range of 0.5-3.0 mol/L, then adding a catalyst, and controlling the quantity of the catalyst to account for 0.01-0.20 of the weight of the glycerol; increasing the temperature of the mixed reaction liquid to the range of 40-100 ℃ under stirring condition and reacting at a constant temperature for 2-20 hours; and after reaction, filtering off the catalyst from the reaction liquid, then distilling the mixed reaction liquid, and collecting the fraction in the range of 160-161 ℃, thereby obtaining the product 2,3-glycidol. | [Carcinogenicity]
Glycidol is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. | [Environmental Fate]
Chemical/Physical. May hydrolyze in water forming glycerin (Lyman et al., 1982). | [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 evaluation]
Glycidol 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. |
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