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Method for preparing 2,2-dimethyl-3-hydroxy propanal

A technology of hydroxypropionaldehyde and dimethyl, which is applied in the field of preparation of chemical intermediates, can solve the problems of low conversion rate of raw materials, low product selectivity, short activity cycle, etc., and achieve easy recovery, mild reaction conditions, and simple post-treatment Effect

Active Publication Date: 2013-06-05
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The condensation reaction in CN1286673A uses anion exchange resin, and the conversion rate of HPA is between 91-93%, while the anion exchange resin often has the disadvantages of short active cycle, low raw material conversion rate and product selectivity

Method used

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  • Method for preparing 2,2-dimethyl-3-hydroxy propanal
  • Method for preparing 2,2-dimethyl-3-hydroxy propanal
  • Method for preparing 2,2-dimethyl-3-hydroxy propanal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 170g (2.12mol) of 37% aqueous formaldehyde solution in 1 liter of reactor, isobutyraldehyde 144g (2mol), N 2 Replace 3 times, add 2.80g (0.02mol) of DBU dropwise at room temperature, after the dropwise addition, the temperature of the reaction is raised to 35°C and continue to keep warm for 1h to obtain a colorless viscous liquid, evaporate unreacted isobutyraldehyde, add 50ml of deionized water, cooled to room temperature, a large amount of white solids precipitated, filtered to obtain 199.3g of 2,2-dimethyl-3-hydroxypropanal, melting point 89-90°C. 1 H NMR (400MHz, CDCl 3 , δ / ppm): 1.22 (s, 6H), 2.0 (s, 1H), 3.78 (s, 2H), 9.52 (s, 1H). The filtrate contains most of the DBU, which can be concentrated to remove most of the water and then recycled. The conversion rate of isobutyraldehyde is 99.3%, and the selectivity of hydroxypivalaldehyde is 98.4%.

Embodiment 2

[0033] Add 170g (2.12mol) of 37% aqueous formaldehyde solution in 1 liter of reactor, isobutyraldehyde 144g (2mo), N 2 Substitute 3 times, add 9-methyl-1,7-diazabicyclo[4,4,0]decene-62.80g (0.02mol) dropwise at room temperature, after the dropwise addition, the reaction temperature rises to 35°C and continues to keep warm After 1h, a colorless viscous liquid was obtained, unreacted isobutyraldehyde was evaporated, 50ml of deionized water was added, cooled to room temperature, a large amount of white solid was precipitated, filtered to obtain 198.5g of 2,2-dimethyl-3-hydroxypropane Aldehyde, melting point 89-90°C. 1 H NMR (400MHz, CDCl 3 , δ / ppm): 1.22 (s, 6H), 2.0 (s, 1H), 3.78 (s, 2H), 9.52 (s, 1H). The filtrate contains most of 9-methyl-1,7-diazabicyclo[4,4,0]decene-6, and can be recycled after being concentrated to remove most of the water. The conversion rate of isobutyraldehyde is 99.2%, and the selectivity of hydroxypivalaldehyde is 98.1%.

Embodiment 3

[0035] Add 170g (2.12mol) of 37% aqueous formaldehyde solution in 1 liter of reactor, isobutyraldehyde 144g (2mol), N 2 Substitute 3 times, add 10-methyl-1,8-diazabicyclo[5,4,0]undecene-73.08g (0.02mol) dropwise at room temperature, and the reaction temperature rises to 35°C after the dropwise addition Continue to keep warm for 1h to obtain a colorless viscous liquid, evaporate unreacted isobutyraldehyde, add 50ml deionized water, cool to room temperature, a large amount of white solid precipitates, filter to obtain 199.3g 2,2-dimethyl-3- Hydroxypropionaldehyde, melting point 89-90°C. 1 H NMR (400MHz, CDCl 3 , δ / ppm): 1.22 (s, 6H), 2.0 (s, 1H), 3.78 (s, 2H), 9.52 (s, 1H). The filtrate contains most of 10-methyl-1,8-diazabicyclo[5,4,0]undecene-7, and can be recycled after being concentrated to remove most of the water. The conversion rate of isobutyraldehyde is 99.5%, and the selectivity of hydroxypivalaldehyde is 98.2%.

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Abstract

The invention provides a method for preparing 2,2-dimethyl-e-hydroxy propanal. The method is characterized by comprising the following step of: catalyzing a condensation reaction between isobutylaldehyde and formaldehyde by taking a compound having a structure shown in the specifications as a catalyst to obtain 2,2-dimethyl-e-hydroxy propanal, wherein n is equal to 2-11, m is equal to 2-6, and R is H or alky of C1-C8. In the preparation method, the consumption of the catalyst is small, and the catalyst is easy to recycle. Moreover, the reaction condition is mild, and the post treatment is simple. The transformation rate of the isobutyl aldehyde is over 99 percent, and the selectivity of hydroxyl pivalaldehyde is over 98 percent.

Description

technical field [0001] The invention belongs to the field of preparation of chemical intermediates, in particular to the preparation of 2,2-dimethyl-3-hydroxypropanal. Background technique [0002] 2,2-Dimethyl-3-hydroxypropanal (commonly known as hydroxypivalaldehyde, 2,2-dimethyl-3-hydroxypropanal, referred to as HPA,) is a synthetic 2,2-dimethyl-1,3-propanediol (commonly known as neopentyl glycol, Neopentyl glycol, referred to as the intermediate product of NPG). As an important fine chemical product and raw material, NPG is widely used in the production of various resins, plasticizers, synthetic lubricants and surfactants. [0003] Formaldehyde solution and isobutyraldehyde (IBD) are usually used in industry at present, and triethylamine (triethlamine, referred to as TEM) is used as a catalyst to generate aldol condensation reaction to synthesize 2,2-dimethyl-3-hydroxypropionaldehyde, and hydrogenation Or disproportionation reaction to generate neopentyl glycol. This ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/19C07C45/64B01J31/02
CPCY02P20/584
Inventor 丁建生何光文黎源王中华谢增勇华卫琦
Owner WANHUA CHEM GRP CO LTD
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