2463-45-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 725, 1995 DOI: 10.1021/jo00108a042

Safety Profile

Poison by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cl-.

InChI:InChI=1/C4H5ClO3/c5-1-3-2-7-4(6)8-3/h3H,1-2H2

Upstream product

• 75-44-5 phosgene 
• 96-24-2 3-monochloro-1,2-propanediol 
• 15719-64-9 methylammonium carbonate 
• 106-89-8 epichlorohydrin 
• 124-38-9 carbon dioxide 
• 5911-08-0 chloro(cyclopropyl)methane 
• 107-05-1 3-chloroprop-1-ene 
• 122-60-1 Phenyl glycidyl ether 
• 201230-82-2 carbon monoxide 
• 57-13-6 urea 
• 4540-44-7 1-bromo-3-chloro-propan-2-ol 
• 102-09-0 bis(phenyl) carbonate 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 

Downstream Products

• 34950-70-4 4H,4'H-4,4'-(2-hydroxy-propane-1,3-diyl)-bis-pyrido[3,2-b][1,4]oxazin-3-one 
• 379220-30-1 tert-butyl glycidyl carbonate 
• 106-89-8 epichlorohydrin 
• 4437-83-6 4-(phenoxy)methyl-1,3-dioxolane-2-one 
• 1352955-20-4 C₁₂H₂₃Cl₂N₃O₆ 
• 96-24-2 3-monochloro-1,2-propanediol 
• 616-38-6 carbonic acid dimethyl ester 
• 597-49-9 3-ethylpentan-3-ol 
• 119-61-9 benzophenone 
• 76-84-6 triphenylmethyl alcohol 
• 92-52-4 biphenyl 
• 3477-94-9 3-chloro-2-hydroxyprop-1-yl benzoate 
• 36847-79-7 1-chloro-3-hydroxy-2-propyl benzoate 
• 777094-79-8 ammoniumcarbonate 

Relevant academic research and scientific papers

CYCLIC CARBONATES OBTAINED BY REACTIONS OF ALKALI METAL CARBONATES WITH EPIHALOHYDRINS.

A study has been carried out on the reaction of alkali metal carbonates with epihalohydrins in the presence of cation complexing agents e. g. crown ethers. 3-Glycidyloxypropylene carbonate was found to be formed as the main product of the reaction of epichlorohydrin with potassium carbonate promoted by 18-crown-6. The effect of various epihalohydrins and alkali metal carbonates on the reaction course was examined. It was found that the reaction of potassium hydrogencarbonate with epichlorohydrin gives 4-hydroxymethyl-1,3-dioxolan-2-one. When the reaction of epihalohydrins with potassium carbonates was carried out in the atmosphere of carbon dioxide the products contained linear carbonate linkage apart from cyclic one.

Catalytic activity of metal organic framework Cu3(BTC) 2 in the cycloaddition of CO2 to epichlorohydrin reaction

We demonstrate the novel, catalytic activity of metal organic framework of Cu3(BTC)2 catalysts in the synthesis of chloropropene carbonate from CO2 and epichlorohydrin. The catalysts display moderate epoxide conversions, and moderate selectivities to chloropropene carbonate at 100 °C. No solvents or co-catalysts were required. It is suggested that Lewis acid copper (II) sites in the Cu3(BTC) 2 framework promoted the adsorption of carbon dioxide on the solid surface and its further conversion to the carbonate.

A highly augmented, (12,3)-connected Zr-MOF containing hydrated coordination sites for the catalytic transformation of gaseous CO2 to cyclic carbonates

A porous Zr-based MOF, [Zr6(BTEB)4(μ3-O)4(μ3-OH)4(H2O)4], which contains partially hydrated, 12-connected {Zr6} nodes and extended carboxylate ligands (BTEB3-), was synthesized and physicochemically characterised. The resulting (12,3)-connected, 3D framework adopts an uncommon llj topology with a large, solvent accessible void volume of ca. 79% of the unit cell volume. The porous structure facilitates the uptake of N2 and activated samples give rise to BET surface areas of >1000 m2 g-1. Furthermore, the porosity and accessibility of Lewis acidic Zr(iv) sites promote the catalytic transformation of gaseous CO2 to cyclic carbonates via cycloaddition reactions using epoxide reactants, whereby solvated MOFs exhibit higher catalytic performance than thermally treated samples.

New reaction of glycidols with oxalyl chloride and phosgene - An approach to cyclic esters

2,3-Epoxy alcohols (glycidols) react with carboxylic acid dichlorides to form cyclic esters of 3-chloro-1,2-diols. The reaction proceeds with complete retention of the configuration of the C(2) atom of the initial glycidol and with predominant (but not complete) inversion of the configuration of the C(3) atom in the final heterocycle.

One-step assembly of a hierarchically porous phenolic resin-type polymer with high stability for CO2 capture and conversion

A hierarchically porous phenolic resin-type polymer has been successfully prepared by a solvothermal reaction. Given the relatively high surface area, hierarchical pores, good stability and abundant -OH reactive groups, this polymer exhibits high CO2 adsorption and efficient catalytic conversion for CO2 cycloaddition.

A green catalysis of CO2 fixation to aliphatic cyclic carbonates by a new ionic liquid system

A mixed ionic liquid system has been developed for the efficient catalysis of CO2 addition to aliphatic epoxides without involving any transition metal catalysts or other additives. The ionic liquid integrated with pyridinium and pyrrolidinium groups (1·(Br)3) together with a non-polar ionic liquid (3·(Ntf)2) effectively transformed non-polar aliphatic epoxides to cyclic carbonates by the reaction with CO 2 under mild CO2 pressure (3.0 MPa) and reaction temperature (80 C). The presence of 3·(Ntf)2 remarkably improved the catalytic activity of 1·(Br)3 towards non-polar epoxides by increasing the miscibility of catalyst with the substrates. The mixed ionic liquid system is robust enough to be recycled without any significant loss of catalytic activity. GC-MS studies were performed to reveal the reaction pathways to the cyclic carbonates and a feasible model accounting for the effective CO2 activation in the ionic liquid system was proposed using density functional theory (DFT) calculations.

Method for preparing cyclic carbonate through catalysis of hydrogen bond donor functionalized polymeric ionic liquid

The invention provides a preparation method of a hydrogen bond donor functionalized polymerization ionic liquid catalyst, and a method for synthesizing cyclic carbonate by catalyzing CO2 and epoxide with the catalyst. According to the method, an imidazolyl ionic liquid monomer and a hydrogen bond donor monomer are subjected to cross-linking polymerization in proportion to form the polymerized ionic liquid catalyst, the catalyst can efficiently catalyze CO2 and epoxide to be converted into cyclic carbonate under the optimal reaction condition, and the yield can reach 99%. Compared with a traditional catalyst, the polymerization ionic liquid catalyst has the advantages that a hydrogen bond donor and ionic liquid are effectively combined in a free radical polymerization manner to form a heterogeneous catalyst which has the advantages of rich hydrogen bond donor, dispersed active sites, good catalytic effect, simple preparation method, good cycle performance, simple separation and the like, and huge industrial application potential is achieved.

METHOD FOR SUSTAINABLE CHEMICAL FIXATION OF CO2

A method for sustainable fixation of CO2, is disclosed herein. A sustainable chemical fixation of CO2 into epoxide to form value added product such as cyclic carbonates using bimetallic spinel oxide hollow microspheres as an efficient and recyclable catalyst under solvent free and mild reaction conditions.

Acylamino-bridged hexacarboxylic acid ligand, metal organic framework material, and preparation method and application of acylamino-bridged hexacarboxylic acid ligand and metal organic framework material

The invention relates to the field of metal organic framework materials, and discloses an acylamino-bridged hexacarboxylic acid ligand, a metal organic framework material and a preparation method and application of the acylamino-bridged hexacarboxylic acid ligand and the metal organic framework material. The acylamino-bridged hexacarboxylic acid ligand has a structure as shown in a formula (I). The method for preparing the acylamino-modified metal organic framework material has the characteristics that the synthesis raw materials are cheap and easy to obtain, the reaction condition is mild, the operation is simple, byproducts are few, and large-scale preparation is easy. The acylamino-modified metal organic framework material provided by the invention has the characteristics of stable property, large specific surface area, easy regulation and control of performance, strong selective CO2 adsorption capacity, high catalytic activity, good catalytic conversion effect and recyclability.

Highly disordering nanoporous frameworks of lanthanide-dicarboxylates for catalysis of CO2 cycloaddition with epoxides

A series of nanoporous [LnIII4(di-nitro-BPDC)4(NO2)3(OH)(H2O)5]·n(methanol) (LnIII ?= ?PrIII, NdIII, SmIII, EuIII, GdIII, PrIII/GdIII and PrIII/EuIII; di-nitro-BPDC2- ?= ?2,2′-dinitrobiphenyl-4,4′-dicarboxylate) was synthesized and characterized. Founded on Lewis acidic LnIII possessing vacant coordination sites and functional groups of di-nitro-BPDC2-, their catalytic activities were evaluated based on the CO2 cycloaddition reactions with epoxides under ambient pressure and solvent-free conditions. Depending on catalytic conditions, satisfying turnover number and turnover frequency of 1106 and 276 h-1, respectively, could be yielded with ≥79(±4)% conversion and 87(±1)% selectivity. The correlation between the catalysis performance and structural factors is proposed on a basis of experimental and computation results. These include the restrained transportation even in the nanoporous framework and crystallographic disorder in the LnIII coordination environment. The excellent robustness of the catalysts, effects of lanthanide contraction, and synergistic activities of the heterometallic PrIII/GdIII and PrIII/EuIII catalysts are also included.