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Preparation method of chloromethylated cardanol

A technology of chloromethylation and chloromethylation reagents, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of low reactivity, many by-products, long reaction time, etc. The process is simple and easy to control, conducive to large-scale production, and the effect of mild reaction conditions

Active Publication Date: 2013-04-03
SHANDONG SHENGQUAN NEW MATERIALS CO LTD
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Problems solved by technology

The method for carrying out chloromethylation modification in the prior art is mainly obtained by chlorination reaction using alkyltoluene as a raw material. Due to the low single-pass conversion rate of alkyl benzyl chloride, the degree of chlorination is not easy to control, and there are many by-products, resulting in product The selectivity and productive rate are all low, and this method uses poisonous chlorine; In order to improve an environmentally friendly chloromethylation method, the prior art has developed a chloromethyl source that adopts formaldehyde or paraformaldehyde and hydrochloric acid to form Chloromethylation reagents are used to carry out chloromethylation reactions with such chloromethylation reagents and raw materials to complete the modification of chloromethylation. Although the chloromethylation reagents composed of formaldehyde and hydrochloric acid are cheap, their reaction Low activity, long reaction time, low yield of chloromethylated cardanol

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  • Preparation method of chloromethylated cardanol
  • Preparation method of chloromethylated cardanol
  • Preparation method of chloromethylated cardanol

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preparation example Construction

[0022] The invention provides a kind of preparation method of chloromethylated cardanol, comprising the following steps:

[0023] Mix cardanol, chloromethylation reagent and Lewis acid to carry out chloromethylation reaction to obtain chloromethylated cardanol having the structure shown in formula (I), and the chloromethylation reagent is chloromethyl alkane or chloromethyl alkyl ether;

[0024]

[0025] Wherein, n is 0~3, preferably an integer between 0~3.

[0026] The method provided by the invention takes chloromethyl alkane or chloromethyl alkyl ether as chloromethylation reagent, takes Lewis acid as catalyzer, the chloromethylation reagent and catalyzer that the present invention adopts all have higher reactivity, improve The conversion rate of cardanol to chloromethylated cardanol is improved, thereby improving the yield of the reaction product. Moreover, the raw materials used in the present invention are non-toxic, and the reaction process can be completed in one ...

Embodiment 1

[0039] Add 300.00g of cardanol into a 1000mL four-necked flask equipped with an electric stirrer and a thermometer, start the stirrer, keep the temperature at 15°C~25°C, add 10.00g of tin tetrachloride to it, and stir for 5 minutes. Obtain a uniform reaction system; keep the temperature at 15°C~25°C, add 93.50g of 1,4-dichloromethoxybutane dropwise to it, and finish adding dropwise within 20min~40min; then continue the constant temperature reaction for 6h to end; Add 30.00 g of hydrochloric acid with a mass concentration of 0.5%, wash for 20 min, and then stand for stratification; wash the obtained upper layer product three times with distilled water to obtain a reaction product.

[0040] The present invention detects the chlorine content in the reaction product, and the result shows that the chlorine content in the reaction product obtained in this embodiment is 1%, which shows that the chloromethylated cardanol obtained by the method provided by the present invention.

[004...

Embodiment 2

[0043] Add 300.00g of cardanol into a 1000mL four-necked flask equipped with an electric stirrer and a thermometer, start the stirrer, keep the temperature at 25°C~30°C, add 15.00g of zinc chloride to it, and stir for 5 minutes to obtain Uniform reaction system; keep the temperature at 25°C~30°C, add 187.00g of 1,4-dichloromethoxybutane dropwise to it, and finish adding dropwise within 20min~40min; then continue the constant temperature reaction for 8h to end; add 30.00 g of hydrochloric acid with a mass concentration of 0.5% was washed for 20 minutes and then allowed to stand for stratification; the obtained upper layer product was washed three times with distilled water to obtain a reaction product.

[0044] The present invention detects the chlorine content in the reaction product, and the results show that the chlorine content in the reaction product obtained in this embodiment is 0.8%, which shows that the chloromethylated cardanol obtained by the method provided by the pr...

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Abstract

The invention provides a preparation method of chloromethylated cardanol. The preparation method comprises the following steps: mixing cardanol, a chloromethylation reagent and Lewis acid, carrying out a chloromethylation reaction to obtain cardanol with a structured shown as a formula (I); the chloromethylation reagent is chloromethyl alkane or chloromethyl alkyl ether; and n is the formula (I) is 0-3. The chloromethyl alkane or chloromethyl alkyl ether is used as the chloromethylation reagent in the preparation method provided by the invention; the chloromethyl alkane or chloromethyl alkyl ether also has high reaction cavity and can completely carry out chloromethylation on the reaction raw material cardanol. The Lewis acid is used as a catalyst for carrying out one-step chloromethyl functionalization for the cardanol in the method provided by the invention; and the catalyst also has the high reaction activity and can enhance conversion from the raw material cardanol to the chloromethylated cardanol, so that the yield of the reaction product chloromethylated cardanol is enhanced.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of chloromethylated cardanol. Background technique [0002] Cardanol is extracted from natural cashew nut shell oil and can replace or partially replace phenol for the manufacture of epoxy curing agents, liquid phenolic resins, and liquid or powdered thermosetting phenolic resins. Cardanol also has the following characteristics due to its special chemical structure: First, it has high temperature resistance due to its benzene ring structure; second, the polar hydroxyl group in its structure can provide the system with wetting and activity on the contact surface; in addition, The carbon chain with unsaturated double bonds in the meta position can provide the system with good toughness, excellent hydrophobicity, low permeability and self-drying property. [0003] Because cardanol has the above excellent properties, it is widely used in the modificati...

Claims

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Application Information

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IPC IPC(8): C07C39/373C07C37/62
Inventor 江成真陈英军刘卫
Owner SHANDONG SHENGQUAN NEW MATERIALS CO LTD
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