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Preparation method and application of cardanol-based chlorohydrin ether

A cardanol-based chlorohydrin technology and cardanol technology are applied in the preparation field of cardanol-based chlorohydrin, can solve the problems of poor surfactant performance, long synthesis route, low yield and the like, and achieve high reaction yield, Simple preparation process and high purity effect

Pending Publication Date: 2022-08-05
PETROCHINA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The main purpose of the present invention is to provide a preparation method and application of cardanol-based chlorohydrins, so as to overcome the defects of poor performance of cardanol-related surfactants in the prior art, long synthetic route, low yield and low purity

Method used

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  • Preparation method and application of cardanol-based chlorohydrin ether
  • Preparation method and application of cardanol-based chlorohydrin ether
  • Preparation method and application of cardanol-based chlorohydrin ether

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preparation example Construction

[0023] The invention discloses a preparation method of cardanol-based chlorohydrin, comprising the following steps:

[0024] S1, add cardanol, epichlorohydrin and organic alcohol in the reactor, stir and dissolve, wherein the mol ratio of cardanol and epichlorohydrin is 1: 1~1: 8, and the mol ratio of cardanol and organic alcohol is 1:10~1:80;

[0025] S2, adding an organic alcohol solution containing a phase transfer catalyst into the reactor, and performing constant temperature reaction at 60-100° C. for 4-10 hours;

[0026] S3, removing organic alcohol and unreacted epichlorohydrin after completion of the reaction, washing the product, and removing the phase transfer catalyst to obtain cardanol-based chlorohydrin.

[0027] In one embodiment, the cardanol is technical grade unsaturated cardanol.

[0028] In one embodiment, the organic alcohol of the present invention is a short-chain alcohol; in another embodiment, the short-chain alcohol of the present invention is one or...

Embodiment 1

[0044] Preparation of Surfactant Cardanol-Based Chlorohydrin:

[0045] Add 5.80g (0.02mol) technical grade unsaturated cardanol, 3.70g (0.04mol) epichlorohydrin and 80mL ethanol to the reactor, stir and dissolve at room temperature; then add 20mL mass fraction of 3% tetrabutyl bromide The ethanol solution of ammonium chloride was reacted at a constant temperature of 80 ° C for 6 hours; after the reaction was completed, the solvent and unreacted epichlorohydrin were removed by distillation under reduced pressure, the distilled water was used to wash the distillation product for many times, and tetrabutylammonium bromide was removed to obtain cashew nuts. Phenol chlorohydrin ether, the yield was 95.3%, and the purity was 98.2%. Infrared spectrum of cardanol chlorohydrin see figure 1 , as can be seen from the figure, the wave number is 3411cm -1 The left and right are the O-H stretching vibration absorption peaks in the alcoholic hydroxyl group; 2927cm -1 , 2886cm -1 Left and...

Embodiment 2

[0047] Add 5.80g (0.02mol) technical grade unsaturated cardanol, 11.10g (0.12mol) epichlorohydrin and 80mL isopropanol to the reactor, stir and dissolve at room temperature; then add 20mL mass fraction of 2% tetradecanol The isopropanol solution of alkyl trimethyl ammonium chloride was reacted at a constant temperature of 80 ° C for 8 hours; after the reaction was completed, the solvent and unreacted epichlorohydrin were removed by distillation under reduced pressure, and the distilled water was used to wash the distillation product several times to remove ten Tetraalkyltrimethylammonium chloride was obtained to obtain cardanol chlorohydrins with a yield of 91.5% and a purity of 97.6%.

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Abstract

The invention provides a preparation method and application of cardanol-based chlorohydrin ether.The preparation method comprises the following steps that S1, cardanol, epichlorohydrin and organic alcohol are added into a reactor and stirred to be dissolved, the molar ratio of cardanol to epichlorohydrin is 1: 1-1: 8, and the molar ratio of cardanol to organic alcohol is 1: 10-1: 80; s2, adding an organic alcohol solution containing a phase transfer catalyst into the reactor, and reacting at the constant temperature of 60-100 DEG C for 4-10 hours; and S3, after the reaction is finished, removing the organic alcohol and unreacted epoxy chloropropane, washing the product, and removing the phase transfer catalyst to obtain the cardanol-based chlorohydrin ether. In the preparation method disclosed by the invention, the yield and the purity of the target product are improved through proper selection of a catalyst system and a solvent system.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method and application of cardanol-based chlorohydrin. Background technique [0002] Cashew nut shell liquid (CNSL) is a by-product of cashew processing, and its content accounts for about 25%-30% of cashew nuts. The world's annual output is about 500,000 tons. It is a cheap and abundant renewable resource. The main component of CNSL is cardanol, the content of which can reach 90%. From the structural point of view, cardanol is a derivative of phenol, which is substituted by a straight chain of 15 carbons (containing 0-3 carbon-carbon double bonds) at the meta position of phenol. Cardanol can be modified to synthesize many derivatives, including functional small molecules and polymers, which are of great application value in coatings, friction materials, antioxidants, insecticides and fungicides. [0003] Many useful compounds, such ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/03C07C41/42C07C43/23C09K23/42
CPCC07C41/03C07C41/42C09K23/42C07C43/23Y02P20/584
Inventor 张志翔李翠勤徐显明王俊张忠涛施伟光张永军李玉龙王凤荣关伟宏李影辉于翠艳苑慧敏张娜王淑兰
Owner PETROCHINA CO LTD
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