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Method for preparing monoalkyl hypophosphite

A technology of mono-alkyl hypophosphorous acid and mono-alkyl phosphorus oxidation, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc. instability, etc.

Inactive Publication Date: 2017-09-01
南京宏福高端膦技术研发中心有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, for short-chain (1 to 4 carbon atoms) primary phosphines, no relevant reports have been found to demonstrate the selective monosubstituted hypophosphorous acid; Stable, prone to disproportionation reactions such as formula V and exothermic so much that it is difficult to control

Method used

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  • Method for preparing monoalkyl hypophosphite

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 methyl hypophosphorous acid

[0028] Add the aqueous solution that contains 96.5g methyl phosphine hydrochloride (2.01mol) in the there-necked flask that is equipped with mechanical stirring and dropping funnel two liters, and add 457.3 grams of 30% aqueous hydrogen peroxide ( 4.03 mol). The flask was placed in a cooling tank set at a temperature between 0°C and -20°C. After the aqueous hydrogen peroxide solution was added dropwise for 8 hours, the internal temperature of the flask was returned to room temperature with stirring. After removing volatile matter under reduced pressure, 171.5 grams of colorless liquid were obtained. According to the results of nuclear magnetic resonance, acid value and total phosphorus, 150.8 grams of methyl hypophosphorous acid and 4.9 grams of methyl phosphoric acid were contained therein, and the yields were 93.8% and 2.6% respectively. .

[0029] NMR data: 31 P { 1 H}NMR (CDCl 3 ): 32.35ppm(s); 31 P N...

Embodiment 22

[0031] Embodiment 22, the synthesis of 4,4-trimethyl-1-pentyl hypophosphorous acid

[0032]Add the aqueous solution that contains 95.6 grams of 2,4,4-trimethyl-1-pentyl phosphine hydrochloride (0.65mol) in the three-neck flask that is equipped with mechanical stirring and dropping funnel two liters, and in dripping 146.9 grams of 30% aqueous hydrogen peroxide (1.30 mol) was added to the funnel. The flask was placed in a cooling tank set at a temperature between 0°C and -20°C. After the aqueous hydrogen peroxide solution was added dropwise for 8 hours, the internal temperature of the flask was returned to room temperature with stirring. After removing volatile matter under reduced pressure, 92.6 g of colorless liquid was obtained, and the yield was 80% according to the results of nuclear magnetic resonance, acid value and total phosphorus.

[0033] NMR data: 31 P { 1 H}NMR (CDCl 3 ): 37.58ppm(s); 31 P NMR (CDCl 3 ): 32.35ppm (dm, 1 J H，P = 549Hz).

[0034] Total phosph...

Embodiment 3

[0035] The synthesis of embodiment 3 isobutyl hypophosphorous acid

[0036] Add the aqueous solution that contains 111.2 grams of isobutyl phosphine hydrochloride (1.25mol) in the there-necked flask that is equipped with mechanical stirring and dropping funnel two liters, and add 278.9 grams of 30% aqueous hydrogen peroxide in the dropping funnel (2.46 mol). The flask was placed in a cooling tank set at a temperature between 0°C and -20°C. After the aqueous hydrogen peroxide solution was added dropwise for 8 hours, the internal temperature of the flask was returned to room temperature with stirring. After removing volatile matter under reduced pressure, 149.0 grams of colorless liquid were obtained. According to the results of nuclear magnetic resonance, acid value and total phosphorus, 120.0 grams of methyl hypophosphorous acid and 25.5 grams of methyl phosphoric acid were contained, and the yields were 80.8% and 17.1% respectively. .

[0037] NMR data: 31 P { 1 H} NMR (C...

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Abstract

The invention relates to a method for preparing monoalkyl hypophosphite. The method comprises the steps of oxidizing monoalkyl hydrogen phosphide halate solution by virtue of hydrogen peroxide, wherein the molar ratio of the monoalkyl hydrogen phosphide halate solution to hydrogen peroxide is 1 to 2 or 1 to 2.1, and the reaction temperature is between (-50)-(20) DEG C. The molecular formula of monoalkyl hypophosphite is RP(H)OOH, wherein R is C1-C10 straight-chain, branched-chain alkyl groups. The method for preparing monoalkyl hypophosphite has the beneficial effects that the reaction yield is more than 80%, and water and halogen hydride can be easily evaporated at a reduced pressure after the reaction is finished and can be recycled by virtue of a sodium hydroxide solution and are not the main content of the invention, so that the method described by the invention is safe, environment-friendly and economic.

Description

technical field [0001] The invention relates to a method for preparing organic phosphine compounds, in particular to a method for preparing monoalkyl hypophosphorous acid, which realizes safe and controllable reactions. Background technique [0002] Trivalent monoalkyl hypophosphorous acid can be regarded as a product in which a hydrogen atom connected to phosphorus in hypophosphorous acid is replaced by an alkyl group. Such compounds exist in their corresponding interconvertible isomeric forms, as shown in formula I: [0003] R-P(H)(=O)OH←→R-P(OH) 2 Formula I [0004] Such compounds can be easily esterified into corresponding monoesters, and the hydrogen attached to phosphorus can be further transformed to obtain dialkyl substituted derivatives, such as free radical addition or Michael addition with different alkenes, such as formula II, Shown in formula III and formula IV [0005] R-P(H)(=O)OH+R 1 OH→R-P(H)(=O)OR 1 +H 2 O Formula II [0006] R-P(H)(=O)OR 1 +R 2 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30
CPCC07F9/302
Inventor 诺伯特·韦福林张栓明王康王瑞敏周中凯
Owner 南京宏福高端膦技术研发中心有限公司