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Organic acid base catalyst for synthesizing aryl ester carboxylic acid by interesterification

A technology for synthesizing aryl carboxylate and catalyst, which is applied in the fields of organic chemistry and catalytic chemistry, can solve the problems of slow reaction rate, long production and operation cycle, easy loss of active center metal ions, etc., and achieve good catalyst performance and mild operating conditions , the effect of short reaction time

Inactive Publication Date: 2011-05-11
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the transesterification method, phenol and dimethyl carbonate transesterification reaction synthesis diphenyl carbonate method research is more, as JP323654, US5426207, DE2528142, patents such as CN1803282 (200610020205.1) have reported, the raw material dimethyl carbonate used in this method Cheap and easy to obtain, the problem of this process is that methanol and dimethyl carbonate form an azeotrope, which increases the difficulty of separation of raw materials and products; the reaction rate is too slow, and the production operation cycle is too long
In the above-mentioned patents, when dimethyl oxalate is used as a raw material to prepare the raw material for synthesizing diphenyl carbonate, that is, methyl phenyl oxalate or diphenyl oxalate, the catalysts used include supported titanium dioxide and composite titanium dioxide. Silicon oxide, supported molybdenum trioxide, supported Mo-Sn double metal oxide, etc., these catalysts are all weak Lewis acid catalysts. When reacting in a batch reactor, the activity of the catalyst and the main product diphenyl oxalate The selectivity is not high, especially the selectivity of diphenyl oxalate is less than 47.5%, and the active center metal ion in the heterogeneous catalyst is easy to lose in the reaction mass in the transesterification reaction

Method used

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  • Organic acid base catalyst for synthesizing aryl ester carboxylic acid by interesterification
  • Organic acid base catalyst for synthesizing aryl ester carboxylic acid by interesterification

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Embodiment 1

[0023] The embodiment of the present invention is to investigate under the catalytic reaction conditions of the catalyst of the present invention, using dimethyl oxalate and phenol as an example to prepare methyl phenyl oxalate and diphenyl oxalate. The reaction process is the same as that in the background technology. (4)-(6) The reaction steps are the same.

[0024] The specific process is carried out in a 100ml three-necked flask, heated by heat-collecting electromagnetic stirring, equipped with a thermometer to display the temperature of the reaction system. The consumption of technical grade dimethyl oxalate is 17 millimoles, the consumption of analytical pure phenol is 85 millimoles, 0.3 gram Cp ' (CH 2 ) 3 -MCM-41 is a heterogeneous catalyst (containing 0.38 mmoles of alkene in 0.3 g of catalyst), added under normal pressure. Stir and heat up, the reaction temperature is controlled at 180±2°C, and the reaction time is 2 hours. (4)-(6) The reaction equilibrium constan...

Embodiment 2-5

[0026] With the cyclocene material Cp’(CH) immobilized on Si-MCM-41 2 ) 3-MCM-41 is a heterogeneous catalyst, and the catalyst consumption is 0.3 grams (containing 0.38 millimoles in 0.3 grams of catalysts), and the reaction time is carried out respectively for 4, 6, 8, and 10 hours. Under the circumstances, carry out transesterification reaction and form embodiment 2-5, examine reaction result.

[0027] Table 1: Cp'(CH 2 ) 3 -Reaction evaluation when MCM-41 is used as catalyst

[0028]

Embodiment 6-10

[0030] With 0.38 mmol Cp'(CH 2 ) 3 -MCM-41 is a homogeneous catalyst, the amount of catalyst is 0.38 mmol, and the reaction time is carried out respectively for 2, 4, 6, 8, and 10 hours. Embodiment 6-10, investigate reaction result.

[0031] Table 2: Cp'(CH 2 ) 3 Si(OEt) 3 Reaction evaluation when used as a catalyst

[0032]

[0033] Comparing Examples 1-5 and 6-10, it can be seen that after the immobilization of the cyclocene is not only conducive to the separation of the reaction material and the catalyst, but also under the condition that the activity of the catalyst is kept little changed, the total selectivity of the catalyst to the main product MPO and DPO Improvement, especially in the selectivity of the final product DPO. In Example 5, when reacting for 10 hours, the yield of diphenyl oxalate reached 41.5%.

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Abstract

The invention belongs to the technical fields of organic chemistry and catalytic chemistry, and relates to an organic acid-base catalyst which is used for carboxylic acid aryl-ester groups which are compounded by ester exchanges. The organic base in the organic acid-base catalyst refers to an organic compound which contains nitrogen, phosphorus and halogen elements and solid-carrying organic base of the organic base, while the organic acid mainly refers to organic sulfonic acid, organic phosphorus acid, organic carboxyl acid, urea and the like and solid-carrying organic acid of the organicacid. The invention can be used as organic matters such as amino acid and the like which has double functions of organic acid and base and as catalysts which can be used to solid support the organic acid base on a same carrier. The catalyst of the invention has good catalytic performance and is easy to be separated from reaction systems, ester exchange conditions are temperate, the invention is convenient to continue, the conversion rate of oxalic dim-ethyl ester can reach over 90%, the selectivity to phenyloxalate can reach over 70%, and the invention is suitable for industry applications.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and catalytic chemistry, and relates to a class of organic acid-base catalysts for synthesizing monoaryl carboxylate and diaryl carboxylate by transesterification of dialkyl carboxylate and monoaryl hydroxyl compound. Background technique [0002] Diaryl carbonate is an important organic carbonate with low toxicity and no pollution. It can be used to synthesize many important organic compounds and polymer materials. ) reaction, non-phosgene transesterification polycondensation into high-quality polycarbonate, which has high economic value. The synthesis methods of diaryl carbonate mainly include phosgene method, transesterification method and oxidative carbonylation method of monoaryl hydroxyl compound. The traditional diaryl carbonate synthesis process uses the phosgene method, but the phosgene used in the phosgene method is highly toxic and difficult to transport, and the by-product H...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07C69/96C07C68/00
Inventor 贾明君赵国明刘燕张文祥刘钢王振旅吴淑杰石景慧
Owner JILIN UNIV
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