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4-(diethoxy-phosphoryl)-2-methyl-but-2-enoate preparation method

A diethoxy and phosphoryl technology, which is applied in the field of preparation of organic synthesis intermediates, can solve the problems of strong oxidative waste water discharge, strong corrosive waste gas discharge, low total yield, etc., and achieves simple separation and huge environmental protection benefits. , the effect of saving organic solvents

Active Publication Date: 2020-01-07
SHANGYU NHU BIOCHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] The raw materials of this route are cheap, but there are still disadvantages
The chlorination process adopted in the route, the mixed solvent of DMF and toluene used is unfavorable for recovery, and thionyl chloride is used as the chlorination agent, a large amount of strong corrosive waste gas is discharged during the reaction; a large amount of strong oxidative waste water is discharged during the oxidation reaction ; The total yield is lower than the methyl ketene method, about 41.9%

Method used

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  • 4-(diethoxy-phosphoryl)-2-methyl-but-2-enoate preparation method

Examples

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Embodiment 1

[0052] In reaction vessel, add 40% (wt%) the aqueous solution of aceguvaldehyde aqueous solution 162g (0.90mol) and 49 grams of sodium carbonate solid configurations, add palladium bismuth molybdenum / carbon catalyst 3.6g. Oxygen was introduced into the reaction solution, the temperature was raised to 40° C., the reaction was stirred for 3 hours, the stirring was stopped and filtered to obtain an aqueous solution of pyruvic acid / sodium pyruvic acid.

[0053] Dissolve 50 grams of sodium ethoxide in 300 grams of ethanol, then slowly add dropwise to 218.7 g (0.72 mol) of tetraethyl ethylene diphosphate dissolved in 150 ml of dichloromethane solution, stir for 10 minutes after the addition is complete, then drop rapidly Add pyruvic acid / sodium pyruvic acid aqueous solution, keep warm in a water bath at room temperature (20°C, within plus or minus 2°C), react for 30 minutes, and then pass in carbon dioxide for acidification. After the acidification, the liquid was separated, and the...

Embodiment 2

[0056] Add the aqueous solution of 40% (wt%) aceglyoxal aqueous solution 162g (0.9mol) and 80 gram solid sodium bicarbonate configurations in reaction vessel, add palladium bismuth molybdenum / carbon catalyst 3.6g. Oxygen was introduced into the reaction solution, and the temperature was raised to 20°C. The reaction time is 6h. Stop stirring and filter to obtain pyruvic acid / sodium pyruvic acid aqueous solution.

[0057] Dissolve 50 grams of sodium ethoxide in 300 grams of ethanol, then slowly add dropwise to 218.7 g (0.72 mol) of tetraethyl ethylene diphosphate dissolved in 150 ml of dichloromethane solution, stir for 10 minutes after the addition is complete, then drop rapidly Add pyruvic acid / sodium pyruvic acid aqueous solution, keep warm at 0°C with a freezing tank, react for 60 minutes, and then pass in carbon dioxide for acidification. After the acidification, the liquid was separated, and the oil layer was taken for the next reaction.

[0058] 140 ml of ethanol was a...

Embodiment 3

[0060] Add the aqueous solution of 40% (wt%) aceglyoxal aqueous solution 162g (0.9mol) and 37 sodium hydroxide configurations in reaction vessel, add palladium bismuth molybdenum / carbon catalyst 3.6g. Oxygen was introduced into the reaction liquid, and the temperature was raised to 60°C. Reaction time 3h. Stop stirring and filter to obtain pyruvic acid / sodium pyruvic acid aqueous solution.

[0061] Dissolve 50 grams of sodium ethoxide in 300 grams of ethanol, then slowly add dropwise to 218.7 g (0.72 mol) of tetraethyl ethylene diphosphate dissolved in 150 ml of dichloromethane solution, stir for 10 minutes after the addition is complete, then drop rapidly Add pyruvic acid / sodium pyruvate aqueous solution, keep warm in a water bath at room temperature (30°C, within plus or minus 2°C), react for 20 minutes, and then pass in carbon dioxide for acidification. After the acidification, the liquid was separated, and the oil layer was taken for the next reaction.

[0062] 80 ml of...

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Abstract

The invention discloses a 4-(diethoxy-phosphoryl)-2-methyl-but-2-enoate preparation method, which comprises: (a) carrying out an oxidation reaction on a pyruvic aldehyde aqueous solution to obtain a pyruvic acid / pyruvate aqueous solution; and (b) carrying out a reaction on the pyruvic acid / pyruvate aqueous solution and tetraethyl ethylene diphosphate, and performing an esterification reaction withan alcohol to obtain 4-(diethoxy-phosphoryl)-2-methyl-but-2-enoate. The method of the invention has advantages of cheap and easily available raw materials, simple operation of each step, high yield of the whole route, and high industrial application value.

Description

technical field [0001] The invention relates to a preparation method of an organic synthesis intermediate, in particular to a preparation method of 4-(diethoxy-phosphoryl)-2-methyl-but-2-enoate. Background technique [0002] 8'-Apo-β-ethyl carotate, the chemical system is named (all cis)-2,6,11,15-tetramethyl-17-(2,6,6)-trimethylcyclohexene Base)-2,4,6,8,10,12,14,16-heptadecaoctaenoic acid ethyl ester, referred to as ethyl apocarotene, or apoester, its molecular formula is C 32 h 44 o 2 , whose structure is shown in the following formula. [0003] [0004] 8'-Apo-β-ethyl carotate is red or purple-red crystal or crystal powder, and the industrial product is yellow to orange oil or organic solvent, with stable performance. It is insoluble in water and glycerin, very poorly soluble in ethanol, and easily soluble in chloroform. 8'-Apo-β-ethyl carotate is mainly used as a food additive. [0005] At present, the synthesis methods of 8'-apo-β-carotinic acid ethyl ester are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40
CPCC07F9/4015
Inventor 曾庆宇谭均华吕国锋傅一苇田金金单国红夏小忠乔胜超
Owner SHANGYU NHU BIOCHEM IND
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