Trimethylene carbonate

Base Information

• Chemical Name: Trimethylene carbonate
• CAS No.: 2453-03-4
• Molecular Formula: C4H6O3
• Molecular Weight: 102.09
• Hs Code.: 29147000
• European Community (EC) Number: 607-395-4
• UNII: 4316AQ174Q
• DSSTox Substance ID: DTXSID20953766
• Nikkaji Number: J277.252C
• Wikipedia: Trimethylene_carbonate
• Wikidata: Q161506
• Mol file: 2453-03-4.mol

Synonyms:1,3-carbonyldioxypropane;1,3-dioxan-2-one;trimethylene carbonate

Chemical Property of Trimethylene carbonate

Chemical Property:

• Vapor Pressure: 0.0165mmHg at 25°C
• Melting Point: 45.0 to 49.0 °C
• Refractive Index: 1.425
• Boiling Point: 255.2 °C at 760 mmHg
• Flash Point: 148.6 °C
• PSA: 35.53000
• Density: 1.2 g/cm³
• LogP: 0.54330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 102.031694049
• Heavy Atom Count: 7
• Complexity: 71

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dioxan-2-one ^*data from reagent suppliers

Safty Information:

• Statements: 22-36
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC(=O)OC1

Technology Process of Trimethylene carbonate

There total 33 articles about Trimethylene carbonate 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%

trimethylene oxide (503-30-0) + carbon dioxide (124-38-9,18923-20-1) → trimethylene carbonate (2453-03-4,31852-84-3)

Guidance literature:

With bis(acetylacetonate)oxovanadium; tetrabutylammomium bromide; In toluene; at 60 ℃; for 8h; under 26252.6 Torr; chemoselective reaction; Autoclave; Cooling with ice;

DOI:10.1039/c0gc00136h

Reference yield: 99.0%

4-(trifluoromethoxy)benzonitrile (332-25-2) + trimethyleneglycol (504-63-2) → trimethylene carbonate (2453-03-4,31852-84-3)

Guidance literature:

With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 24h; Reagent/catalyst; Inert atmosphere; Irradiation; Sealed tube;

DOI:10.1002/chem.201804603

Reference yield: 95.0%

carbon dioxide (124-38-9,18923-20-1) + 1-chloro-3-hydroxypropane (627-30-5) → trimethylene carbonate (2453-03-4,31852-84-3)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 40 ℃; for 15h; under 760.051 Torr; Reagent/catalyst; Temperature; Inert atmosphere; Glovebox; Green chemistry;

DOI:10.1039/c3gc40790j

upstream raw materials:

Diethyl carbonate

trimethyleneglycol

trimethylene oxide

carbon dioxide

Downstream raw materials:

trimethylene sulphide

3-phenyl-1,3-oxazinan-2-one

3-hydroxy-N-phenylpropylamine

trimethyleneglycol

Refernces

• 1、 Klys, Arkadiusz,Czardybon, Wojciech,Warkentin, John,Werstiuk, Nick Henry. "Synthesis and thermolysis of a spiro-fused oxadiazoline - Evidence for sequential formation of carbene and oxirane intermediates, and for oxirane dimerization". . p. 1769 - 1773. Retrieved 2004.
• 2、 Hough,Priddle. "-". . p. 581,583. Retrieved 1961.
• 3、 Calabrese, Carla,Liotta, Leonarda F.,Giacalone, Francesco,Gruttadauria, Michelangelo,Aprile, Carmela. "Supported Polyhedral Oligomeric Silsesquioxane-Based (POSS) Materials as Highly Active Organocatalysts for the Conversion of CO2". . p. 560 - 567. Retrieved 2019.
• 4、 Reithofer, Michael R.,Sum, Yin Ngai,Zhang, Yugen. "Synthesis of cyclic carbonates with carbon dioxide and cesium carbonate". . p. 2086 - 2090. Retrieved 2013.
• 5、 Darensbourg, Donald J.,Moncada, Adriana I.,Choi, Wonsook,Reibenspies, Joseph H.. "Mechanistic studies of the copolymerization reaction of oxetane and carbon dioxide to provide aliphatic polycarbonates catalyzed by (salen)CrX complexes". . p. 6523 - 6533. Retrieved 2008.
• 6、 Darensbourg, Donald J.,Horn Jr., Adolfo,Moncada, Adriana I.. "A facile catalytic synthesis of trimethylene carbonate from trimethylene oxide and carbon dioxide". . p. 1376 - 1379. Retrieved 2010.
• 7、 Tan, Eddy W. P.,Hedrick, James L.,Arrechea, Pedro L.,Erdmann, Tim,Kiyek, Vivien,Lottier, Simon,Yang, Yi Yan,Park, Nathaniel H.. "Overcoming Barriers in Polycarbonate Synthesis: A Streamlined Approach for the Synthesis of Cyclic Carbonate Monomers". . p. 1767 - 1774. Retrieved 2021/03/01.