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Synthesis method of monoalkyl hydrocarbyl phosphonate

A technology of alkyl and cycloalkyl, which is applied in the field of synthesizing hydrocarbyl monoalkyl phosphate extractants, and can solve the problems of harsh reaction conditions, residues, and low product yields

Inactive Publication Date: 2013-05-01
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, Method 1 is the synthesis method of Japanese PC88 (ie P507), but the yield of the product obtained by applying this method is low, often accompanied by by-products such as dibasic acids and other acidic impurities that affect the extraction performance; Method 2 is the current domestic It is a general synthetic method, but the reaction conditions are harsh, the reaction yield is not very high, and the raw material phosphite diester often cannot be completely reacted, remains in the reaction intermediate, and participates in the next step of the reaction, thus affecting the overall product yield. yield and purity

Method used

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  • Synthesis method of monoalkyl hydrocarbyl phosphonate
  • Synthesis method of monoalkyl hydrocarbyl phosphonate
  • Synthesis method of monoalkyl hydrocarbyl phosphonate

Examples

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preparation example Construction

[0086] Synthetic methods include one or more of the following steps:

[0087] (a) in an inert solvent, the phosphonite diester is reacted with an alkene to obtain an alkylphosphonate diester; and / or

[0088] (b) in an inert solvent, under reflux conditions, the alkyl phosphonic acid diester obtained in step (a) is reacted with an alkali solution to obtain a compound of formula I;

[0089] In the above formulas, M and R 2 as defined above;

[0090] R 1 It is a substituted or unsubstituted C1-C18 alkyl group, a substituted or unsubstituted C3-C18 cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted C1-C3 alkylene aryl group;

[0091] or R 1 with substituted or unsubstituted -CH=CH 2 Constitute C3-C20 substituted and unsubstituted cycloalkenes together;

[0092] or R 1 with substituted or unsubstituted -CH 2 CH 2 - together form C3-C20 substituted or unsubstituted cycloalkanes;

[0093] Wherein, the definition of substitution is th...

Embodiment 1

[0121] Embodiment 1: the synthesis of 1-octylphosphonic acid monoisooctyl ester

[0122] Add 10.6 g of sodium phosphinate monohydrate, 80 mL of glacial acetic acid, 11.2 g of 1-octene, and 4 mL of tert-butyl peroxybenzoate into a three-necked flask in sequence, heat to 130 degrees under normal pressure, and reflux for 2 hours. After adding 4 mL of initiator tert-butyl peroxybenzoate, the reflux reaction was continued for 2 hours. Wash twice with water, once with saturated brine, and extract twice with ether. Combine the organic phases, wash with water, dry over anhydrous sodium sulfate, filter with suction, and remove the solvent under reduced pressure to obtain 30.6 g of the product with a yield of 73.2%. Add 52ml of ethanolamine, heat and reflux for 30 hours, recover the excess ethanolamine under reduced pressure, dissolve the residue in petroleum ether, acidify twice with 3M sulfuric acid, wash with water until neutral, remove the solvent, and dry to obtain 18.9g of product...

Embodiment 2

[0126] Example 2: Synthesis of 1,2-dimethyl-1-propylphosphonic acid monoisooctyl ester

[0127] Add 10.6 g of sodium phosphinate monohydrate, 80 mL of DMF, 7.0 g of isopentene, and 4.8 g of benzoyl peroxide into a three-necked flask in sequence, heat to 110 degrees under normal pressure, and reflux for 2 hours. After adding the initiator benzoyl peroxide 4.8g, the reflux reaction was continued for 2 hours. After adding the initiator benzoyl peroxide 4.8g again, the reflux reaction was continued for 2 hours. Wash twice with water, once with saturated brine, and extract twice with ether. Combine the organic phases, wash with water, dry over anhydrous sodium sulfate, filter with suction, and remove the solvent under reduced pressure to obtain 29.4 g of the product with a yield of 78.2%. Add 55ml of ethanolamine, heat and reflux for 30 hours, recover the excess ethanolamine under reduced pressure, dissolve the residue in petroleum ether, acidify twice with 3M sulfuric acid, wash ...

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Abstract

The invention provides a synthesis method of monoalkyl hydrocarbyl phosphonate. Particularly, the invention provides a compound shown as a formula I and a preparation method thereof. In the formula, definitions of R1, R2 and M are defined as the specification. The invention further discloses an application of taking the compound shown as the formula I as an extracting agent, and an extracting agent component prepared from the compound shown as the formula I.

Description

technical field [0001] The present invention relates to a new method for synthesizing hydrocarbyl monoalkyl phosphate extractant and the application of the synthesized compound. Background technique [0002] Hydrocarbyl phosphonic acid monoalkyl ester is a type of extractant suitable for the separation of rare earth, nickel cobalt or other metals, with high extraction performance and separation factor. Currently the most widely used extractant P507 also belongs to this type of extractant A sort of. [0003] The traditional synthetic method of P507 mainly contains the following two kinds: 1. Triisooctyl phosphonite reacts with halogenated isooctane to obtain alkylphosphonic acid diester, and then hydrolyzes to obtain the product; 2. Diisooctyl phosphonite Under the action of sodium ethoxide or sodium, alkyl esters react with halogenated isooctanes to generate alkylphosphonic acid diesters, which are then hydrolyzed to obtain monoisooctyl isooctylphosphonates. Among them, Me...

Claims

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Application Information

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IPC IPC(8): C07F9/40C22B3/38
CPCY02P10/234Y02P10/20
Inventor 肖吉昌马恒励毛婷婷张燕辉张婷殷武涛李长峰欧阳明
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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