Method for preparing cyclic carbonate

A cyclic carbonate and alkylene oxide technology, which is applied in the field of preparation of organic compounds, can solve the problems of low activity of disubstituted alkylene oxides, complex catalyst synthesis, narrow substrate application range, etc., and achieves clear structure, excellent catalytic performance, The effect of short reaction time

Inactive Publication Date: 2014-03-19
SUZHOU UNIV
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Problems solved by technology

[0005] In 2001, T. Nguyen's research group reported that (Salen)Cr(III) with 1% propylene oxide molar mass and 4-(N,N-dimethyl)pyridine at 75°C and 3.5bar CO 2 Catalytic CO under pressure 2 React with propylene oxide to prepare cyclocarbonate, and the reaction can reach 100% yield in 1.5 hours, but this method is not suitable for the larger disubstituted alkylene oxide with steric hindrance, the scope of substrate application is narrow, and the catalyst consumption is relatively large (see : R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc. , 2001, 123, 11498); in 2007, Michael North's research group reported that (Salen)Al compound with 2.5% molar weight of styrene oxide and tetrabutylammonium bromide catalyzed CO 2 Reacting with styrene oxide to prepare cyclocarbonate, the reaction can reach a yield of 98% in 24 hours, but the amount of reaction catalyst is large, and the reaction is less active or inactive for the larger disubstituted alkylene oxide with steric hindrance (see: J . Meléndez, M. North, and R. Pasquale, Eur. J. Inorg. Chem., 2007, 3323); in 2010, Arjan W. Kleij's research group reported that Zn(Salphen) compound and tetrabutylammonium iodide were mixed at 45℃, 10bar CO 2 pressure, dichloromethane as a solvent to catalyze CO 2 React with 1,2-epo...

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  • Method for preparing cyclic carbonate

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Experimental program
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Embodiment 1

[0039] Embodiment one: preparation bridged tetraaryloxy rare earth metal compound LNd (THF) (R 1 =R 2 = Bu t )

[0040] (1) Add 2.80 g of LH 4 (3.00 mmol) dissolved in tetrahydrofuran, added to the solution containing 1.23 g NdCp 3 (THF) (3.00 mmol) in tetrahydrofuran solution, stirred at room temperature for 4 hours, and the system was a blue transparent solution;

[0041] (2) Remove the solvent, add 14 ml of toluene and 0.5 ml of tetrahydrofuran, heat to 60°C for extraction, and centrifuge. The supernatant was transferred and left at room temperature until blue crystals (2.65 g, 2.31 mmol) were precipitated, with a yield of 77%. Melting point: 182-184 °C. Elemental analysis: C, 68.80; H, 9.11; N, 2.54; Nd, 12.76. Infrared spectrum (KBr, cm -1 ): 3436(s), 2957(w), 2904(s), 2869(s), 1609(s), 1479(s), 1442(s), 1411(s), 1362(s), 1304(s) ), 1276(s), 1235(s), 1204(s), 1165(s), 1132(s), 1026(s), 994(s), 912(s), 877(s), 837(s) ), 806(s), 759(s), 741(s), 683(s), 529(s), ...

Embodiment 2

[0042] Embodiment two: preparation bridged tetraaryloxy rare earth metal compound LY (THF) (R 1 =R 2 = Bu t )

[0043] (1) Add 2.80 g of LH 4 (3.00 mmol) dissolved in tetrahydrofuran, added to the solution containing 1.07 g of YCp 3 (THF) (3.00 mmol) tetrahydrofuran solution, stirring reaction at room temperature for 4 hours, the system is a light yellow transparent solution;

[0044] (2) Remove the solvent, add 15 ml of toluene and 0.5 ml of tetrahydrofuran, heat to 60°C for extraction, and centrifuge. The supernatant was transferred and left at room temperature until colorless crystals (2.59 g, 2.37 mmol) were precipitated, with a yield of 79%. Melting point: 178-180 °C. Elemental analysis: C, 72.59; H, 9.65; N, 2.62; Y, 8.57. Infrared spectrum (KBr, cm -1 ): 3437(s), 2953(w), 2904(s), 2867(s), 1603(s), 1479(s), 1442(s), 1414(s), 1362(s), 1304(s) ), 1271(s), 1238(s), 1202(s), 1167(s), 1132(s), 1108(s), 974(s), 912(s), 875(s), 837(s) ), 805(s), 770(s), 744(s), 66...

Embodiment 3

[0045] Embodiment three: preparation bridged tetraaryloxy rare earth metal compound LSm (THF) (R 1 =R 2 = Bu t )

[0046] (1) Add 2.80 g of LH 4 (3.00 mmol) dissolved in tetrahydrofuran, added to the solution containing 1.25 g of SmCp 3 (THF) (3.00 mmol) in tetrahydrofuran solution, stirring reaction at room temperature for 4 hours, the system is a yellow transparent solution;

[0047] (2) Remove the solvent, add 14 ml of hexane and 0.5 ml of tetrahydrofuran, heat to 60°C for extraction, and centrifuge. The supernatant was transferred and left at room temperature until yellow crystals (2.50 g, 2.16 mmol) were precipitated, with a yield of 72%. Melting point: 199-201 °C. Elemental analysis: C, 68.52; H, 8.69; N, 2.53; Sm, 13.27. Infrared spectrum (KBr, cm -1 ): 3423(s), 2960(w), 2904(s), 2869(s), 1603(s), 1477(s), 1440(s), 1414(s), 1362(s), 1301(s) ), 1276(s), 1240(s), 1202(s), 1167(s), 997(s), 969(s), 959(s), 913(s), 875(s), 833(s) ), 808(s), 770(s), 741(s), 691(s...

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Abstract

The invention discloses a method for preparing cyclic carbonate. The method specifically comprises the following step: with a quadri-aryloxy bridged rare earth metal compound as a catalyst, catalyzing carbon dioxide and alkylene oxide to react in the present of quaternary ammonium salt, wherein the general formula of the quadriaryloxy bridged rare earth metal compound is LLn(THF), wherein L refers to ethanediamine group bridged quadri-aryloxy, Ln refers to rare earth metal ions, and the quaternary ammonium salt is one of tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctyl ammonium bromide, bis(triphenylphosphine) ammonium chloride and benzyl butyl ammonium bromide. The rare earth catalyst in the catalysis system is clear in structure, easy to synthesize, high in catalysis activity, less in using amount, mild in reaction conditions and wide in universality to alkylene oxide. According to the preparation method disclosed by the invention, raw materials are easily available, the reaction conditions are wild, a reaction substrate is wide in universality, the reaction time is short, the yield of the target product, namely the cyclic carbonate is high, and the reaction operation and the posttreatment process are simple.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method of cyclocarbonate. Background technique [0002] Cyclocarbonate is a kind of good polar aprotic solvent, which can be used as the electrolyte of lithium battery, and can also be used as polymerized monomer (such as synthetic polyurethane) and pharmaceutical intermediate in industry. Therefore, it is of great application value to study the synthesis of cyclocarbonate. [0003] As a major greenhouse gas, carbon dioxide has aroused widespread concern in the society for its impact on the environment. Carbon dioxide is cheap, non-toxic, non-flammable, and rich in resources. Through the chemical conversion of carbon dioxide, the resource utilization of carbon dioxide can not only solve the problem of greenhouse effect caused by it, but also turn waste into treasure. [0004] In fact, carbon dioxide can be used as a very valua...

Claims

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Application Information

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IPC IPC(8): C07D317/36B01J31/26
CPCB01J31/2213B01J2531/36B01J2531/38C07D317/36C07D317/44C07D317/46
Inventor 姚英明秦杰
Owner SUZHOU UNIV
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