Glycidol

Base Information

• Chemical Name: Glycidol
• CAS No.: 556-52-5
• Deprecated CAS: 61915-27-3,98913-54-3,1852481-80-1,98913-54-3
• Molecular Formula: C3H6O2
• Molecular Weight: 74.0794
• Hs Code.: 2910.90 Oral rat LD50: 420 mg/kg
• European Community (EC) Number: 209-128-3
• ICSC Number: 0159
• NSC Number: 46096
• UN Number: 2810
• UNII: S54CF1DV9A
• DSSTox Substance ID: DTXSID4020666
• Nikkaji Number: J2.660C
• Wikipedia: Glycidol
• Wikidata: Q418265
• NCI Thesaurus Code: C44387
• ChEMBL ID: CHEMBL1530150
• Mol file: 556-52-5.mol

Synonyms:2,3-epoxypropan-1-ol;2,3-epoxypropanol;epihydrin alcohol;glycidol;glycidol, (+-)-isomer;glycidol, (R)-isomer

Chemical Property of Glycidol

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.9 mm Hg ( 25 °C)
• Melting Point: -54 °C
• Refractive Index: 1.4287
• Boiling Point: 162.358 °C at 760 mmHg
• PKA: 14.62±0.10(Predicted)
• Flash Point: 81.111 °C
• PSA: 32.76000
• Density: 1.179 g/cm³
• LogP: -0.62250
• Storage Temp.: 2-8°C
• Solubility.: Soluble in acetone, alcohol, benzene, chloroform, and ether (Weast, 1986)
• Water Solubility.: soluble
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 74.036779430
• Heavy Atom Count: 5
• Complexity: 35.9
• Transport DOT Label: Poison

Purity/Quality:

90%,98% ^*data from raw suppliers

Glycidol(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-60-21/22-23-36/37/38-68
• Safety Statements: 53-45-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Epoxides
• Canonical SMILES: C1C(O1)CO
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. Exposure far above the OEL could cause lowering of consciousness.
• Effects of Long Term Exposure: This substance is probably carcinogenic to humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• 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.
• Uses: Glycidol is used as a stabilizer for natural oilsand vinyl polymers, as a demulsifier, and asa leveling agent for dyes. 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. 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.

Technology Process of Glycidol

There total 72 articles about Glycidol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

allyl alcohol (107-18-6) → oxiranyl-methanol (556-52-5)

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In chlorobenzene; at 80 ℃; for 5h;

DOI:10.1021/jo971270b

Reference yield: 98.5%

3-monochloro-1,2-propanediol (96-24-2) → oxiranyl-methanol (556-52-5)

Guidance literature:

With sodium hydroxide; In ethanol; water; at -5 - 15 ℃; for 6h; Large scale;

Reference yield: 98.2%

4-hydroxymethyl-1,3-dioxolan-2-one (931-40-8) → oxiranyl-methanol (556-52-5)

Guidance literature:

With zinc(II) nitrate; 1-butyl-3-methylimidazolium nitrate; at 175 ℃; for 2.5h; under 20.027 Torr;

DOI:10.1016/j.jcat.2012.10.015

upstream raw materials:

[1,3]-dioxolan-2-one

glycerol

3-iodo-propane-1,2-diol

silver⁽¹⁺⁾ stearate

Downstream raw materials:

glycidyl acetate

3-diisobutylamino-propane-1,2-diol

4-chloro-benzenesulfonic acid-(2,3-dihydroxy-propylamide)

4-chloro-benzenesulfonic acid-[bis-(2,3-dihydroxy-propyl)-amide]

Refernces

• 1、 Zhang, Xuelan,Wang, Dengfeng,Ma, Jie,Wei, Wei. "Fluorinated Mg–Al Hydrotalcites Derived Basic Catalysts for Transesterification of Glycerol with Dimethyl Carbonate". . p. 1181 - 1196. Retrieved 2017.
• 2、 Zhou, Yan,Ouyang, Fan,Song, Zhi-Bin,Yang, Zhen,Tao, Duan-Jian. "Facile one-pot synthesis of glycidol from glycerol and dimethyl carbonate catalyzed by tetraethylammonium amino acid ionic liquids". . p. 25 - 29. Retrieved 2015.
• 3、 Munshi, Mudassir K.,Biradar, Pradeep S.,Gade, Swapna M.,Rane, Vilas H.,Kelkar, Ashutosh A.. "Efficient synthesis of glycerol carbonate/glycidol using 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) based ionic liquids as catalyst". . p. 17124 - 17128. Retrieved 2014.
• 4、 Munshi, Mudassir K.,Gade, Swapna M.,Mane, Manoj V.,Mishra, Deepti,Pal, Sourav,Vanka, Kumar,Rane, Vilas H.,Kelkar, Ashutosh A.. "1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU): A highly efficient catalyst in glycerol carbonate synthesis". . p. 144 - 149. Retrieved 2014.
• 5、 Munshi, Mudassir K.,Gade, Swapna M.,Rane, Vilas H.,Kelkar, Ashutosh A.. "Role of cation-anion cooperation in the selective synthesis of glycidol from glycerol using DABCO-DMC ionic liquid as catalyst". . p. 32127 - 32133. Retrieved 2014.
• 6、 Arjunan,Rani,Santhanam,Mohan. "Structural characteristics and harmonic vibrational analysis of the stable conformer of 2,3-epoxypropanol by quantum chemical methods". . p. 24 - 34. Retrieved 2012.
• 7、 Ha, Ji Hae,Kim, Ji Sun,Kim, Myung Hwan,Lee, Kwan Young,Lee, Man Sig. "Synthesis of glycidol by decarboxylation of glycerol carbonate over Zn-La catalysts with different molar ratio". . p. 10898 - 10902. Retrieved 2016.
• 8、 Song, Xianghai,Pan, Donghui,Wu, Yuanfeng,Cheng, Pin,Wei, Ruiping,Gao, Lijing,Zhang, Jin,Xiao, Guomin. "Synthesis of glycerol carbonate over porous La-Zr based catalysts: The role of strong and super basic sites". . p. 828 - 837. Retrieved 2018.
• 9、 Devarajan, Arulselvan,Thiripuranthagan, Sivakumar,Radhakrishnan, Ramakrishnan,Kumaravel, Sakthivel. "Solvent free transesterification of glycerol into glycerol carbonate over nanostructured CaAl hydrotalcite catalyst". . p. 4588 - 4599. Retrieved 2018.
• 10、 Sulimov,Danov,Ovcharova,Ovcharov,Flid. "Regularities of glycidol synthesis by the liquid-phase epoxidation of allyl alcohol with hydrogen peroxide". . p. 2647 - 2651. Retrieved 2014.