Solketal

Base Information

• Chemical Name: Solketal
• CAS No.: 100-79-8
• Deprecated CAS: 22323-83-7,36543-79-0,2263936-21-4,36543-79-0
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 29329970
• European Community (EC) Number: 202-888-7
• ICSC Number: 0790
• NSC Number: 59720
• UNII: 3XK098O8ZW
• DSSTox Substance ID: DTXSID9021845
• Nikkaji Number: J20.693H
• Wikipedia: Solketal
• Wikidata: Q2968854
• Metabolomics Workbench ID: 131398
• ChEMBL ID: CHEMBL3342436
• Mol file: 100-79-8.mol

Synonyms:2,2-dimethyl-1,3-dioxolane-4-methanol;2,2-dimethyl-1,3-dioxolane-4-methanol, (DL)-isomer;2,2-dimethyl-1,3-dioxolane-4-methanol, (R)-isomer;2,2-dimethyl-1,3-dioxolane-4-methanol, (S)-isomer;2,2-dimethyl-1,3-dioxolane-4-methanol, monosodium salt;2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane;2,3-isopropylidene-sn-glycerol;2,3-O-isopropylideneglycerol;glycerol acetonide

Chemical Property of Solketal

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 0.164mmHg at 25°C
• Melting Point: -27℃
• Refractive Index: n20/D 1.434
• Boiling Point: 188.499 °C at 760 mmHg
• PKA: 14.20±0.10(Predicted)
• Flash Point: 80 °C
• PSA: 38.69000
• Density: 1.034 g/cm³
• LogP: 0.13020
• Storage Temp.: 2-8°C
• Solubility.: 172g/l soluble
• Water Solubility.: miscible
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

1,2-O-Isopropylideneglycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Other Solvents
• Canonical SMILES: CC1(OCC(O1)CO)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Uses: A MEK inhibitor Solketal is useful for synthesis of mono-, di- and triglycerides. It is used as the starting reagent for synthesis of tulipaline derivatives. It acts as a fuel additive in gasoline. It is an inhibitor of Methyl ethyl ketone . DL-1,2-Isopropylideneglycerol was used as the starting reagent for synthesis of tulipaline derivatives.

Technology Process of Solketal

There total 50 articles about Solketal 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%

acetone (67-64-1) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0)

Guidance literature:

With sulfuric acid; at 40 ℃; Reagent/catalyst;

DOI:10.1134/S1070427216100094

Reference yield: 99.0%

oxiranyl-methanol (556-52-5) + acetone (67-64-1) → (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0)

Guidance literature:

erbium(III) triflate; at 20 ℃; for 48h;

DOI:10.1002/adsc.200505096

Reference yield: 96.0%

1,2-isopropyliden-3-O-allyloxycarbonyl-sn-glycerin (1333925-44-2) + 2-propanethiol (75-33-2) → allylisopropyl sulfide (50996-72-0) + carbon dioxide (124-38-9,18923-20-1) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0)

Guidance literature:

With Roussin's red salt ester; tetrabutylammomium bromide; potassium hydride; In tetrahydrofuran; ethanol; at 40 ℃;

DOI:10.1021/ol202270g

upstream raw materials:

oxiranyl-methanol

trifluoroborane diethyl ether

acetone

glycerol

Downstream raw materials:

glyceryl tribenzoate

2,3-dihydroxypropyl hexanoate

(S)-1,2-O-isopropylidene glycerol propionate

(R)-1,2-O-isopropylidene glycerol propionate

Refernces

• 1、 Gonzalez-Arellano, Camino,De, Sudipta,Luque, Rafael. "Selective glycerol transformations to high value-added products catalysed by aluminosilicate-supported iron oxide nanoparticles". . p. 4242 - 4249. Retrieved 2014.
• 2、 Khayoon,Hameed. "Solventless acetalization of glycerol with acetone to fuel oxygenates over Ni-Zr supported on mesoporous activated carbon catalyst". . p. 191 - 199. Retrieved 2013.
• 3、 Matsumoto, Yoshihiko,Mita, Keisuke,Hashimoto, Keiji,Iio, Hideo,Tokoroyama, Takashi. "Selective cleavage of ethers using silica-alumina gel catalysts prepared by the sol-gel method". . p. 9387 - 9398. Retrieved 1996.
• 4、 Deutsch,Martin,Lieske. "Investigations on heterogeneously catalysed condensations of glycerol to cyclic acetals". . p. 428 - 435. Retrieved 2007.
• 5、 Vivian, Alvise,Soumoy, Loraine,Fusaro, Luca,Fiorilli, Sonia,Debecker, Damien P.,Aprile, Carmela. "Surface-functionalized mesoporous gallosilicate catalysts for the efficient and sustainable upgrading of glycerol to solketal". . p. 354 - 366. Retrieved 2021.
• 6、 Auroux, Aline,Chowdhury, Biswajit,Das, Avik,Ghosh, Anindya,Sen, Debasis,Singha, Aniruddha. "A green approach for the preparation of a surfactant embedded sulfonated carbon catalyst towards glycerol acetalization reactions". . p. 4827 - 4844. Retrieved 2020.
• 7、 Dmitriev,Zanaveskin,Terekhov,Samoilov,Kozlovskii,Maksimov. "Technologies for Processing of Crude Glycerol from Biodiesel Production: Synthesis of Solketal and Its Hydrolysis to Obtain Pure Glycerol". . p. 1478 - 1485. Retrieved 2018.
• 8、 Vol'Eva,Belostotskaya,Malkova,Komissarova,Kurkovskaya,Usachev,Makarov. "New approach to the synthesis of 1,3-dioxolanes". . p. 638 - 641. Retrieved 2012.
• 9、 Le Cocq,Ballou. "-". . p. 976,979. Retrieved 1964.
• 10、 Viswanadham, Nagabhatla,Debnath, Suman,Sreenivasulu, Peta,Nandan, Devaki,Saxena, Sandeep K.,Al-Muhtaseb, Ala'a H.. "Nano porous hydroxyapatite as a bi-functional catalyst for bio-fuel production". . p. 67380 - 67383. Retrieved 2015.