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Method for preparing formyl methylene triphenylphosphine

A formyl methylene triphenyl phosphine and a technology for triphenyl phosphine are applied in the field of preparing formyl methylene triphenyl phosphine and can solve the problems of poor purity, low yield of quaternary phosphorus salt, unsatisfactory reaction effect, etc. problem, to achieve the effect of easy operation, high yield, and less three wastes

Inactive Publication Date: 2020-12-01
石家庄欧特佳化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the literature related to this method, an entrainer is first added to remove water in chloroacetaldehyde, otherwise the reaction effect is very unsatisfactory.
In addition, in the azeotropic dehydration process, due to long-term heating, some side reactions such as condensation of chloroacetaldehyde will occur, and finally the quaternary phosphorus salt (Ph 3 P + CH 2 CHOCl - ) with low yield and poor purity

Method used

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  • Method for preparing formyl methylene triphenylphosphine

Examples

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Comparison scheme
Effect test

Embodiment 1

[0020] A method for preparing formyl methylene triphenylphosphine, comprising the steps of:

[0021] 1. Add 500g of chloroacetaldehyde dimethyl acetal [FW124.6], 52.5g of triphenylphosphine (0.20mol) and 0.74g of tetrabutyl iodide into a 1L three-necked flask equipped with mechanical stirring, thermometer and dropping funnel base ammonium, heated at 80°C for 10 hours with stirring.

[0022] 2. Naturally cool to room temperature, filter the generated white solid to obtain 72g of quaternary phosphorus salt I, and the yield of the first step is 93%.

[0023] 3. Add the solid of the above-mentioned quaternary phosphorus salt I to 200mL water, add 1g of 30% HCl, heat to 40°C, stir for 2 hours to hydrolyze it into a uniform solution of the quaternary phosphorus salt II.

[0024] 4. Add the above quaternary phosphorus salt II solution dropwise to 100mL water dissolved with 7.7g NaOH, control the temperature at 20-30°C, and finish the dropwise addition in about 30 minutes. After dry...

Embodiment 2

[0026] A method for preparing formyl methylene triphenylphosphine, comprising the steps of:

[0027] 1. In a 1L three-neck flask equipped with a mechanical stirrer, a thermometer and a dropping funnel, add the mother liquor in the first step of the above-mentioned Example 1, 25g of chloroacetaldehyde dimethyl acetal [FW124.6], 52.5g of triphenylphosphine (0.20mol), heated at 80°C for 10 hours with stirring.

[0028] 2. Naturally cool to room temperature, filter the generated white solid to obtain 73.5g of quaternary phosphorus salt I, and the yield of the first step is 95%.

[0029] 3. Add the solid of the above-mentioned quaternary phosphorus salt I to 200mL water, add 1g98%H 2 S0 4 , heated to 40 degrees, stirred for 2h to make it hydrolyzed into a uniform solution of quaternary phosphorus salt II.

[0030] 4. Add the solution of the above-mentioned quaternary phosphorus salt II to 100mL water dissolved with 7.9g NaOH, control the temperature at 20-30°C, and complete the ...

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Abstract

The invention discloses a method for preparing formyl methylene triphenylphosphine. The method comprises the following steps: reacting triphenylphosphine with excessive chloroacetaldehyde dimethyl acetal under the catalysis of a proper catalyst to obtain corresponding quaternary phosphonium salt; dissolving quaternary phosphonium salt in water, adding a trace amount of inorganic acid to hydrolyzethe quaternary phosphonium salt, dropwise adding the hydrolyzed quaternary phosphonium salt into an aqueous solution of alkali according to a conventional method, and filtering and washing precipitates to directly obtain formyl methylene triphenylphosphine. The method has the advantages of no use of expensive reagents, simple operation, high yield, less three wastes, and easy realization of industrialization.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing formylmethylene triphenylphosphine. Background technique [0002] Formylmethylenetriphenylphosphine, also known as formylmethylenetriphenylphosphine (CAS: 2136-75-6), is a Wittig reagent for the construction of α, β-unsaturated aldehydes. Because the Wittig reagent contains formyl group, it is relatively stable and has low reactivity, and can selectively undergo Wittig reaction with the aldehyde carbonyl group in the substrate molecule. [0003] At present, the preparation methods of formylmethylenetriphenylphosphine mainly contain methylenetriphenylphosphine formylation method, bromoacetaldehyde method and chloroacetaldehyde method, and the former adopts methylenetriphenylphosphine (Ph 3 P=CH 2 ) react with ethyl formate or other formylating reagents (such as formyl imidazole) in benzene to prepare formylmethylene triphenylphosphine, but this t...

Claims

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Application Information

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IPC IPC(8): C07F9/54
CPCC07F9/5442
Inventor 张文勤曹立军许江涛
Owner 石家庄欧特佳化工有限公司