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Method for synthesizing alpha - olefinic bond functional cyclic carbonate from alpha ¿C alkynyl tertiary carbon alcohol and carbon dioxide

A cyclic carbonate, carbon dioxide technology, applied in the direction of organic chemistry, can solve the problems of harmfulness to human body and environment, harsh equipment requirements, non-compliance, etc., and achieve the effect of high purity

Inactive Publication Date: 2006-07-05
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

All of the above are harmful to the human body and the environment, or have relatively strict requirements on equipment, which do not meet the needs of the current development of green chemistry and chemical industry.

Method used

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  • Method for synthesizing alpha - olefinic bond functional cyclic carbonate from alpha ¿C alkynyl tertiary carbon alcohol and carbon dioxide
  • Method for synthesizing alpha - olefinic bond functional cyclic carbonate from alpha ¿C alkynyl tertiary carbon alcohol and carbon dioxide
  • Method for synthesizing alpha - olefinic bond functional cyclic carbonate from alpha ¿C alkynyl tertiary carbon alcohol and carbon dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: Cuprous chloride catalyzes the synthesis of α-methenyl-β, β-dimethylethylene carbonate in benzenesulfonic acid 1-methyl-3-butylimidazole ionic liquid

[0026]

[0027] In a 500ml autoclave equipped with magnetic stirring, gas valve and temperature control device, add 1-methyl-3-butylimidazole benzenesulfonate ([BMIm]PhSO 3 ) 29.6g (0.1mol) of ionic liquid, 16.8g (0.2mol) of 2-methyl-3-butyn-2-ol, 0.198g (0.002mol) of cuprous chloride, 15 kg of carbon dioxide, stirred at 120°C After reacting for 8 hours, it was cooled to room temperature and distilled under reduced pressure. The product was analyzed qualitatively and quantitatively by HP1790 gas chromatograph. The yield of α-methenyl-β,β-dimethylethylene carbonate was 97%, and the purity was 99%.

Embodiment 2

[0028] Example 2: Synthesis of α-methylenyl-β-methyl-β-ethyl ethylene carbonate catalyzed by cuprous chloride in p-toluenesulfonic acid 1-methyl-3-butylimidazolium ionic liquid

[0029]

[0030] With 31.0g (0.1mol) 1-methyl-3-butylimidazole p-toluenesulfonate ([BMIm]p-MePhSO 3 ) ionic liquid to replace [BMIm]PhSO 3 , 19.6g (0.2mol) 3-methyl-1-pentyn-3-alcohol replaces 2-methyl-3-butyn-2-alcohol, and the rest are the same as in Example 1. The yield of α-methenyl-β-methyl-β-ethyl ethylene carbonate was 96%, and the purity was 99%.

Embodiment 3

[0031] Example 3: Synthesis of α-methylenyl-β-methyl-β-isobutyl ethylene carbonate catalyzed by cuprous bromide in benzenesulfonic acid 1-methyl-3-butylimidazole ionic liquid

[0032]

[0033] Cuprous chloride is replaced by 0.287g (0.002mol) of cuprous bromide, 25.2g (0.2mol) of 3,5-dimethyl-1-hexyn-3-ol is replaced by 2-methyl-3-butyne- 2-alcohol, all the other are with embodiment 1. The yield of α-methenyl-β-methyl-β-isobutyl ethylene carbonate was 94%, and the purity was 99%.

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Abstract

This invention relates to a synthesis method for alpha-olefinic bond-functionalized cyclic carbonates from alpha-alkynyl tertiary alcohols and carbon dioxide. In this method, ionic liquids which consist of alkylpyridines or 1,3-dialkylimidazole cations and inorganic or organic anions and have a liquid state at room temperature are adopted as reaction media, univalent or bivalent copper salts are adopted as catalysts; and alpha-alkynyl tertiary alcohols and carbon dioxide are catalyzed to react with each other at a pressure of 0.1~2.0MPa and a temperature of 40~180 deg.C for 1~20 hours so as to produce alpha-olefinic bond-functionalized cyclic carbonates. It is characteristics of this method that no more organic solvents or organic bases are needed, and compared to conventional catalytic process; it has the advantages of low carbon dioxide pressure, high reaction rate, high product purity and reusability of ionic liquids and is thus pretty promising for industrial application.

Description

technical field [0001] The invention relates to a method for synthesizing α-alkene functionalized cyclic carbonate with α-alkynyl tertiary carbon alcohol and carbon dioxide. technical background [0002] The α-ethylenic functionalized cyclic carbonate is an important organic synthesis intermediate and a promising functionalized carbonate because of its C=C double bond and cyclic structure. Synthesis of α-ethylenic functionalized cyclic carbonates by the reaction of α-alkynyl tertiary alcohols with carbon dioxide has long been considered an effective method for the synthesis of carbonates by carbon dioxide fixation. However, from the results reported in the literature, this reaction is generally carried out in a volatile organic solvent, and requires a high carbon dioxide pressure (about 50 kilograms), and also needs to use organic bases as auxiliary agents, such as tributyl Phosphine, triethylamine, pyridine, etc. All of the above are harmful to the human body and the envi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/34
Inventor 邓友全顾彦龙张娟段志英
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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