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

A technology for the synthesis of dimethylolbutyric acid, which is applied in the fields of oxidative preparation of carboxylic acids, organic chemistry, etc., can solve the problems of reduced yield and high content of by-products, and achieve low cost, high oxidation efficiency, and high yield Effect

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

AI Technical Summary

Problems solved by technology

[0013] Above-mentioned method all can cause higher by-product content, thereby 2,2 dime

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

[0063] Add 37% formaldehyde aqueous solution and catalyzer in the 250ml four-neck flask that agitator, reflux condenser, dropping funnel and thermometer are equipped, the ratio of formaldehyde and catalyzer is 1:0.02, molar ratio; Described catalyzer is Ba( Oh) 2 ;

[0064] Propionaldehyde is added in the dropping funnel, the ratio of formaldehyde and butyraldehyde is 2:1, molar ratio;

[0065] Start stirring, control pH=11, temperature at 25°C, slowly add butyraldehyde dropwise, keep the pH at 11 and continue the reaction for 3 hours after the dropwise addition is complete;

[0066] 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 (0.4-0.8 atmospheric pressure) to remove unreacted formaldehyde and butyraldehyde; Butyl ketone was extracted three times to remove the side reaction product methacrolein. The volume ratio of extractant to mother liquor is 1:...

Embodiment 2

[0070] Add paraformaldehyde and catalyzer in the 250ml four-necked bottle that agitator, reflux condenser, dropping funnel and thermometer are equipped with, described as Na 2 CO 3 (solid); the ratio of paraformaldehyde and catalyst is 1:0.06, molar ratio;

[0071] Propionaldehyde is added in the dropping funnel, the ratio of formaldehyde and butyraldehyde is 2.1:1, molar ratio;

[0072] Start stirring, control pH = 10, temperature at 40°C, slowly add butyraldehyde dropwise, after the dropwise addition, keep the pH at 10 and continue the reaction for 4 hours;

[0073] 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 (0.4-0.8 atmospheric pressure) to remove unreacted formaldehyde and butyraldehyde;

[0074] The above product is added to distilled water, and the addition amount is 3 times of the volume of the obtained solution, the volume ratio. Heat to 7...

Embodiment 3

[0078] Add formaldehyde and catalyzer in the 250ml four-neck flask that agitator, reflux condenser, dropping funnel and thermometer are equipped with, described catalyzer is triethylamine and Na 2 CO 3 (solid) mixture; the ratio of formaldehyde and catalyst is 1:0.04, molar ratio;

[0079] Propionaldehyde is added in the dropping funnel, the ratio of formaldehyde and butyraldehyde is 2.2:1, molar ratio;

[0080] Start stirring, control pH = 10, temperature at 35°C, slowly add butyraldehyde dropwise, keep the pH at 10 and continue the reaction for 5 hours;

[0081]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 (0.4-0.8 atmospheric pressure) to remove unreacted formaldehyde and butyraldehyde; Butyl ketone was extracted three times to remove the side reaction product methacrolein. The volume ratio of extractant to mother liquor is 1:1, and the extraction...

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Abstract

The invention belongs to the field of fine organic synthesis. The invention selects the mixture of NaCO3, Ba(OH)2, triethylamine and NaCO3, or the mixture of triethylamine and Ba(OH)2 as a catalyst, and makes use of butyraldehyde and formaldehyde to prepare 2, 2-hydroxymethyl butyric acid under the oxidation of hydrogen peroxide or oxygen through aldol condensation reaction. The invention prepares the 2, 2-hydroxymethyl butyric acid in the alkaline condition, thus the side reaction is less, the yield of the 2, 2-hydroxymethyl butyric acid is higher, and the industrialization of the invention is easy to realize.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to a synthesis method of 2,2-dimethylol butyric acid. Background technique [0002] The structural formula of 2,2-dimethylolbutanoic acid is: [0003] [0004] 2,2-Dihydroxymethylbutanoic acid has two hydroxymethyl groups, one carboxyl group and one ethyl group attached to a quaternary carbon atom. The proximity of the four groups in terms of space volume and the covalent structure of the quaternary carbon atoms similar to diamond determine the relative stability of the compound to light and heat; and the two reactive functional groups make the molecule both alcohols, It also has the characteristics of acid compounds. The lipophilic carbon skeleton and hydrophilic functional group structure make it have unique solubility characteristics, and become a crosslinking agent and organic intermediate with excellent performance. The application reports are increasing year by year. It is ...

Claims

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Application Information

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