Method for synthesizing 2,2-bis(hydroxymenthyl)propinonic acid

A technology of dimethylolpropionic acid and synthesis method, applied in the directions of oxidative preparation of carboxylic acid, organic chemistry, etc., can solve the problems such as decreased yield of 2,2 dimethylolpropionic acid, high content of by-products, etc. Low, high oxidation efficiency, high yield effect

Inactive Publication Date: 2009-03-11
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Above-mentioned method all can cause higher by-product content,

Method used

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  • Method for synthesizing 2,2-bis(hydroxymenthyl)propinonic acid
  • Method for synthesizing 2,2-bis(hydroxymenthyl)propinonic acid
  • Method for synthesizing 2,2-bis(hydroxymenthyl)propinonic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Add a certain amount of formaldehyde and Ba(OH) 2 , formaldehyde and Ba(OH) 2 The ratio of formaldehyde to propionaldehyde is 1:0.05, the mass ratio; take an appropriate amount of propionaldehyde in the dropping funnel, the ratio of formaldehyde and propionaldehyde is 2.2:1, the molar ratio; start stirring, control the pH at 10, and the temperature at 250 ° C, slowly Propionaldehyde was added dropwise, and the dropwise addition was completed, keeping the pH at 10 to continue the reaction for 4h.

[0063] Pour the prepared 2,2-dimethylolpropanal into a 250 ml four-necked bottle equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, add 100 ml of distilled water for dilution, and take an appropriate amount of 30% over The hydrogen peroxide solution is placed in the dropping funnel, the molar ratio of hydrogen peroxide to propionaldehyde is 1:1; start stirring, and after the temperature rises to 60°C and stabilizes, slowly add hydrogen peroxide ...

Embodiment 2

[0065] Embodiment 2: the influence of the selection of condensation reaction catalyst on reaction

[0066] Other is the same as embodiment 1, changes the catalyzer of condensation reaction, and experimental result is shown in table 2.

[0067] The influence of the selection of table 2 condensation reaction catalyst on reaction

[0068]

condensation catalyst

Formaldehyde and Propionaldehyde

The molar ratio of Reaction time

(h) temperature reflex

(℃)

PH value

molar yield

(%) Triethylamine (5%) 2.2:1 4 25 10 43.2 NaOH(5%) 2.2:1 4 25 10 63.1 Ca(OH)2 2.2:1 4 25 10 67.6 Triethylamine(5%)+Ca(OH) 2 2.2:1 4 25 10 87.5 Ammonia (5%) 2.2:1 4 25 10 26.1 Triethylamine (5%)+Ba(OH) 2 2.2:1 4 25 10 88.2 Ba(OH) 2 2.2:1 4 25 10 70.1

[0069]

[0070] It can be seen from the experimental results that NaOH and Ca(OH) 2 、Ba(OH) 2 When used as a catalyst, the yie...

Embodiment 3

[0072] Add triethylamine and Ca(OH) 2 mixture of formaldehyde, triethylamine and Ca(OH) 2 The mixture: formaldehyde=0.02:1, molar ratio;

[0073] Propionaldehyde is added in the dropping funnel, the ratio of formaldehyde and propionaldehyde is 2.1:1, molar ratio;

[0074] Start stirring, control pH = 10, temperature at 20°C, slowly add propionaldehyde dropwise, keep the pH at 10 and continue the reaction for 4 hours;

[0075]After the reaction, add an appropriate amount of formic acid to neutralize to pH = 7, add the reaction materials to a round bottom flask, and carry out vacuum distillation (0.4 atmospheric pressure) to remove unreacted formaldehyde and propionaldehyde; use methyl isobutyl The ketone was extracted three times to remove the side reaction product methacrolein. The volume ratio of methyl isobutyl ketone to mother liquor is 1:1, and the extraction time is 10 minutes. After standing still, divide into two layers, discard the methyl isobutyl ketone phase, and ...

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Abstract

The invention belongs to the field of fine organic synthesis. The invention uses a mixture of Ca(OH)2, Ba(OH)2, triethylamine and Ca(OH)2 or a mixture of triethylamine and Ba(OH)2 as a catalyst to prepare 2,2-hydroxymethylpropionic acid through a condensation reaction of propanal and formaldehyde under the oxidation of hydrogen peroxide or oxygen. The invention has the advantages of fewer side reactions due to preparation of the 2,2-hydroxymethylpropionic acid under alkaline conditions, higher yield of the 2,2-hydroxymethylpropionic acid and easy realization of industrialization.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to a synthesis method of 2,2-dimethylolpropionic acid. Background technique [0002] In the domestic leather chemical industry, water-emulsion polyurethane leather finishing agents, as an upgraded product of solvent-based polyurethane and water-emulsion polyacrylic acid leather finishing agents, have developed rapidly in recent years. A technical key to producing water-emulsified polyurethane leather finishing agent is to introduce hydrophilic groups into the polymer backbone so that the polymer has a self-emulsifying function. At present, the water-emulsified polyurethane leather finishing agents produced in China all adopt 2,2-dimethylolpropionic acid (DMPA) as self-emulsifying chain extender (Xie Chuan, Wang Shendian, 2,2-dimethylolpropionic acid Acid application, Sichuan Chemical Industry, 1994, 12(2), 46). [0003] 2,2-Dimethylolpropionic acid has a multifunctional reaction betw...

Claims

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Application Information

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IPC IPC(8): C07C59/105C07C51/16
Inventor 班青房士敏吴月吴建国王兰兰秦小刚张静钱山巍
Owner QILU UNIV OF TECH
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