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Method for preparing benzoic acid esters

A technology of benzoic acid ester and benzoic acid, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of hindering acid discharge, impossible and inefficient reuse of benzoic acid, etc. Improved processability, reduced downtime, increased productivity

Active Publication Date: 2020-05-05
PUBLIC SIBUR HLDG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of using a neutralizer is also that the neutralization of the benzoic acid during its removal leads to the situation that the re-use of the benzoic acid becomes impossible during the esterification
[0010]The use of vacuum distillation of benzoic acid from the reaction mass is also inefficient, given that benzoic acid is a sublimated species which can be used in the esterification process Incrustations on equipment surfaces, covering reactor and piping surfaces, gradually clogging them, which hinders further discharge of acid

Method used

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  • Method for preparing benzoic acid esters
  • Method for preparing benzoic acid esters
  • Method for preparing benzoic acid esters

Examples

Experimental program
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Effect test

Embodiment 1

[0084] In a steel esterification reactor with a volume of 15 1 equipped with heating elements and stirring means, 3550 g of benzoic acid, 1500 g of diethylene glycol, and 13 g of titanium(IV) isopropoxide are added.

[0085] Xylene was added to the separator in an amount of 2500 g before the heat treatment. The reaction was carried out by constantly feeding xylene from the separator to the reaction mass at a rate of 3 1 / hour by means of a circulation pump. The reaction mass was heated to a temperature of 200°C, the temperature was increased to 220°C within one hour after the start of heating, and to 240°C within two hours after the start of heating.

[0086] Within 3 hours after starting the heating, the pressure in the reactor was reduced to 15 kPa, and within a further 30 minutes, the pressure in the reactor was reduced to 5 kPa. Within 4 hours after the start of heating, the reaction mass was cooled.

[0087] 4400 g of a reaction mass containing 0.5% by weight of benzoic ...

Embodiment 2

[0088] Embodiment 2 (comparative example)

[0089] In a steel esterification reactor with a volume of 15 1 equipped with heating elements and stirring means, 6500 g of benzoic acid, 2650 g of diethylene glycol and 23 g of titanium(IV) isopropoxide are added.

[0090] Xylene was added to the separator in an amount of 2500 g before the heat treatment. The reaction mass was heated to a temperature of 200°C. The esterification process was carried out under atmospheric pressure. The temperature was raised to 220°C within 4 hours of starting heating, to 240°C within 6 hours of starting heating, and the reaction mass was cooled within 8 hours after starting heating.

[0091] 8290 g of a reaction mass containing 7.8% by weight of benzoic acid, 9% by weight of diethylene glycol benzoate and 83.2% by weight of diethylene glycol dibenzoate were discharged from the esterification reactor. A phase comprising 856 g of water, 15 g of benzoic acid was discharged from the separator.

Embodiment 3

[0092] Embodiment 3 (comparative example)

[0093] This example was carried out according to Example 2, except that 4.5 g of titanium(IV) isopropoxide were added. The reaction mass was heated to a temperature of 200°C, the temperature was raised to 220°C within one hour after the start of heating, the temperature was raised to 240°C within two hours after the start of heating, and the temperature was raised to 240°C within 4 hours after the start of heating. The reaction mass is cooled.

[0094] 8255 g of a reaction mass comprising 7.6% by weight of benzoic acid, 4.5% by weight of diethylene glycol benzoate and 87.5% by weight of diethylene glycol dibenzoate were discharged from the esterification reactor. A phase comprising 878 g of water, 35 g of benzoic acid was discharged from the separator.

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Abstract

The invention relates to the method of preparing benzoic acid esters which provides high selectivity of the process, and high yield of the desired product, as well as the reduction of the duration ofthe esterification process, comprising esterification of benzoic acid with monohydric alcohols having a number of carbon atoms from 6 to 12, or polyhydric alcohols having a number of carbon atoms from2 to 10, in the presence of metal containing catalyst in the media of aromatic solvent at the stepwise buildup of the temperature of the process to 180-200 DEG C, further to 200-220 DEG C, and then to 240-250 DEG C.

Description

[0001] The present invention relates to the field of organic synthesis, in particular, by combining benzoic acid with monohydric alcohols selected from 6 to 12 carbon atoms or 2 to 2 carbon atoms in the presence of a metal-containing catalyst and an aromatic compound-based solvent. 10 polyhydric alcohols, monobasic aliphatic alcohols or polyhydric alcohols are esterified to prepare benzoic acid esters. The esters obtained according to the invention can be used in coatings, inks or lacquers, in plastisols, adhesives or adhesive components, sealing compositions and plasticizers in plastics, or in plastic components, in particular It is used as a plasticizer for polyvinyl chloride (PVC). Background technique [0002] Benzoates relate in particular to monobenzoates such as isodecyl benzoate, isononyl benzoate, 2-ethylhexyl benzoate, dipropylene glycol monobenzoate, diethylene glycol monobenzoate, and dibenzoates such as diethylene glycol dibenzoate, dipropylene glycol dibenzoate,...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C67/54C07C67/60C07C69/78
CPCC07C67/08C07C67/54C07C69/78
Inventor 阿列克塞伊·亚历山德罗维奇·诺西科夫伊万·阿纳托列维奇·巴宾叶戈尔·叶夫根尼耶维奇·波波夫采夫瓦尔瓦拉·彼得罗夫娜·伊加舍娃
Owner PUBLIC SIBUR HLDG
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