Glycidol

Last updated
Glycidol
Glycidol structure.svg
Names
Preferred IUPAC name
Oxiranylmethanol
Other names
Glycidol
2,3-Epoxy-1-propanol
3-Hydroxypropylene oxide
Epoxypropyl alcohol
Hydroxymethyl ethylene oxide
2-Hydroxymethyl oxiran
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.300 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2 Yes check.svgY
    Key: CTKINSOISVBQLD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2
    Key: CTKINSOISVBQLD-UHFFFAOYAN
  • OCC1OC1
Properties
C3H6O2
Molar mass 74.079 g·mol−1
AppearanceViscous liquid
Density 1.1143 g/cm3 [1]
Melting point −54 °C (−65 °F; 219 K) [2]
Boiling point 167 °C (333 °F; 440 K) (decomposes) [1]
miscible [3]
Vapor pressure 0.9 mmHg (25°C) [3]
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
4
2
3
Flash point 66 °C (151 °F; 339 K) [2]
Lethal dose or concentration (LD, LC):
420 mg/kg (oral, rat) [2] [4]
1980 mg/kg (dermal, rabbit) [2] [5]
450 ppm (mouse, 4 hr)
580 ppm (rat, 8 hr) [6]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 50 ppm (150 mg/m3) [3]
REL (Recommended)
TWA 25 ppm (75 mg/m3) [3]
IDLH (Immediate danger)
150 ppm [3]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Glycidol is an organic compound with the formula HOCH2CHOCH2. The molecule contains both epoxide and alcohol functional groups. Being simple to make and bifunctional, it has a variety of industrial uses. The compound is a colorless, slightly viscous liquid that is slightly unstable and is not often encountered in pure form. [7]

Contents

Synthesis and applications

Glycidol is prepared by the epoxidation of allyl alcohol. A typical catalyst is tungstic acid, and a typical O-atom source is aqueous peroxyacetic acid. [8]

Some useful products derived from glycidol are 2,3-epoxypropyloxy chloroformate (from phosgene) and glycidyl urethanes (by addition of isocyanates: [8]

HOCH2CH(O)CH2 + COCl2 → ClC(O)OCH2CH(O)CH2 + HCl
HOCH2CH(O)CH2 + RNCO → RNHC(O)OCH2CH(O)CH2

Glycidol is used as a chemical intermediate in the synthesis of other glycidyl ethers, esters, and amines. [9]

Glycidol can be O-benzylated in the presence of strong base. [10] More typically, such glycidol ethers are produced by reaction of epichlorohydrin with alkoxides. [11]

Glycidol is a precursor to diproqualone (by alkylation of 2-methylquinazolin-4(3H)-one) and dyphylline (by alkylation of theophylline).

Occurrence

Glycidyl fatty acid esters that are thought to contaminate some edible oils could be a source of traces of glycidol in the diet. These esters are formed during the deodorization step of edible oil refining, which uses vapor and high temperatures to remove impurities. The reaction conditions in that step can allow monoglyceride and diglycerides (MAG, DAG) naturally present in the oil to rearrange into glycidyl fatty acid esters. [12]

Safety

Glycidol is an irritant of the skin, eyes, mucous membranes, and upper respiratory tract. Exposure to glycidol may also cause central nervous system depression, followed by central nervous system stimulation. [13] It is listed as an IARC Group 2A Agent, meaning that it is "probably carcinogenic to humans". [14] In regards to occupational exposures, the Occupational Safety and Health Administration has set a permissible exposure limit at 50 ppm over an eight-hour work shift, while the National Institute for Occupational Safety and Health recommends a limit at 25 ppm over an eight-hour work shift. [15]

See also

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Propylene oxide</span> Chemical compound

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

<span class="mw-page-title-main">Allyl chloride</span> Chemical compound

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.

<span class="mw-page-title-main">Cyclohexanone</span> Chemical compound

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon.

<span class="mw-page-title-main">Methyl methacrylate</span> Chemical compound

Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odor.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

<span class="mw-page-title-main">2-Ethylhexanol</span> Chemical compound

2-Ethylhexanol is an organic compound with the chemical formula CH3CH2CH2CH2CH(CH2CH3)CH2OH. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.

<span class="mw-page-title-main">Epichlorohydrin</span> Chemical compound

Epichlorohydrin is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.

<span class="mw-page-title-main">3-MCPD</span> Chemical compound

3-MCPD (3-monochloropropane-1,2-diol or 3-chloropropane-1,2-diol) is an organic chemical compound with the formula HOCH2CH(OH)CH2Cl. It is a colorless liquid. The compound has attracted notoreity as the most common member of chemical food contaminants known as chloropropanols. It is suspected to be carcinogenic in humans.

<span class="mw-page-title-main">Allyl glycidyl ether</span> Chemical compound

Allyl glycidyl ether is an organic compound used in adhesives and sealants and as a monomer for polymerization reactions. It is formally the condensation product of allyl alcohol and glycidol via an ether linkage. Because it contains both an alkene and an epoxide group, either group can be reacted selectively to yield a product where the other functional group remains intact for future reactions.

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.

2-Ethylhexyl glycidyl ether is a liquid organic molecule with formula C11H22O2 an industrial chemical used to reduce the viscosity of epoxy resins. These are then used in adhesives, sealants, and paints or coatings. It has the CAS Registry Number of 2461-15-6. It has the IUPAC name of 2-(2-ethylhexoxymethyl)oxirane. It also finds use in other polymer based applications.

1,6-Hexanediol diglycidyl ether is an organic chemical in the glycidyl ether family. It is an aliphatic compound that is a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction whilst flexibilizing. It is REACH registered.

<span class="mw-page-title-main">Castor oil glycidyl ether</span> Chemical compound

Castor oil glycidyl ether is a liquid organic chemical in the glycidyl ether family. It is sometimes called castor oil triglycidyl ether. It has the theoretical formula C66H116O12. There are two CAS numbers in use, 14228-73-0 and 74398-71-3. The IUPAC name is 2,3-bis[[(E)-12-(oxiran-2-ylmethoxy)octadec-9-enoyl]oxy]propyl (E)-12-(oxiran-2-ylmethoxy)octadec-9-enoate. A key use is acting as a modifier for epoxy resins as a reactive diluent that adds flexibility and improved mechanical properties.

<span class="mw-page-title-main">Phenyl glycidyl ether</span> Chemical compound

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds. It has the formula C9H10O2. It has the CAS Registry Number 122-60-1 and the IUPAC name of 2-(phenoxymethyl)oxirane. A key use is in the viscosity reduction of epoxy resin systems. It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.

Batyl alcohol is an organic compound with the formula HOCH2CH(OH)CH2OC18H37. It is a colorless solid. Batyl alcohol is a monoether formed by condensation of stearyl alcohol with one of the two primary alcohol sites of glycerol. Together with S-selachyl alcohol and S-chimyl alcohol, S-batyl alcohol is a component of some lipid membranes.

Selachyl alcohol is an organic compound with the formula HOCH2CH(OH)CH2OC18H35. It is a colorless oil. Selachyl alcohol is a monoether formed by condensation of oleyl alcohol with one of the two primary alcohol sites of glycerol. Together with S-batyl alcohol and S-chimyl alcohol, S-selachyl alcohol is a component of some lipid membranes. It is found in the liver of the shark Centrophorus squamosus. The name selachyl is derived from a classification of sharks, the neoselachii. Like other glyceryl ethers, those derived from selachyl alcohol are not saponifiable.

References

  1. 1 2 Merck Index, 11th Edition, 4385
  2. 1 2 3 4 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0303". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Food and Cosmetics Toxicology. Vol. 19, Pg. 347, 1981
  5. ↑ AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956
  6. ↑ "Glycidol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. ↑ Johnson, Roy A.; Burgos-Lepley, Carmen E. (2001). "Glycidol". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rg005. ISBN   0-471-93623-5.
  8. 1 2 Guenter Sienel, Robert Rieth, Kenneth T. Rowbottom "Epoxides" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi : 10.1002/14356007.a09_531
  9. ↑ Glycidol at chemicalland21.com
  10. ↑ Bruce H. Lipshutz, Robert Moretti, and Robert Crow (1990). "Mixed Higher-Order Cyanocuprate-Induced Epoxide Openings: 1-Benzyloxy-4-Penten-2-Ol". Organic Syntheses. 69: 80. doi:10.15227/orgsyn.069.0080.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  11. ↑ Sutter, Marc; Silva, Eric Da; Duguet, Nicolas; Raoul, Yann; Métay, Estelle; Lemaire, Marc (2015). "Glycerol Ether Synthesis: A Bench Test for Green Chemistry Concepts and Technologies" (PDF). Chemical Reviews. 115 (16): 8609–8651. doi:10.1021/cr5004002. PMID   26196761.
  12. ↑ Cheng, Wei-wei; Liu, Guo-qin; Wang, Li-qing; Liu, Zeng-she (2017). "Glycidyl Fatty Acid Esters in Refined Edible Oils: A Review on Formation, Occurrence, Analysis, and Elimination Methods". Comprehensive Reviews in Food Science and Food Safety. 16 (2): 263–281. doi: 10.1111/1541-4337.12251 . ISSN   1541-4337. PMID   33371535.
  13. ↑ "OSHA guidelines for glycidol". Archived from the original on 2012-09-25. Retrieved 2006-10-20.
  14. ↑ "List of Classifications, Agents classified by the IARC Monographs, Volumes 1–124". IARC Monographs on the Evaluation of Risk to Humans. IARC. July 7, 2019. Retrieved July 14, 2019.
  15. ↑ CDC - NIOSH Pocket Guide to Chemical Hazards

Further reading

This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.