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Monofunctional acrylamide compound with capsaicinoid functional structure and preparation method and application thereof

A technology of acrylamide and monofunctionality, which is applied in the field of acrylamide compounds with monofunctionality and capsaicin-like functional structure, which can solve the problems of unfeasible price on a large scale, low yield, and difficulty in large-scale promotion and use.

Inactive Publication Date: 2014-07-30
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the application of capsaicin extracted from capsicum in antifouling coatings is not feasible either in terms of scale or price, and the steps of artificially fully synthesizing capsaicin are cumbersome, with low yield and high cost
Not only that, whether it is capsaicin extracted from pepper or artificially synthesized capsaicin, it can only be used as an additive antifouling agent in antifouling coatings, and its function is relatively single, so it is difficult to promote the use on a large scale

Method used

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  • Monofunctional acrylamide compound with capsaicinoid functional structure and preparation method and application thereof
  • Monofunctional acrylamide compound with capsaicinoid functional structure and preparation method and application thereof
  • Monofunctional acrylamide compound with capsaicinoid functional structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Example 1: Preparation of N-(3,5-dimethyl-4-hydroxybenzyl)acrylamide

[0080] Add 122g (1mol) of 2,6-xylenol and 151.5g (1.5mol) of N-methylol acrylamide (2,6-xylenol and N-methylol acrylamide molar ratio 1:1.5), then add 30 mL of concentrated sulfuric acid catalyst (36% by weight of 2,6-xylenol) and 115 mL of ethanol solvent (by weight of 2,6-xylenol) in turn 60%). The reaction was stirred in a water bath at a temperature of 35 °C for 15 hours, and a white precipitate was formed, which was filtered with suction. The obtained filter cake was repeatedly washed with water until neutral, and then recrystallized in absolute ethanol to obtain a white crystal.

[0081] The yield of white crystals in this example was 84.4%.

[0082] The melting point of the white crystals was 140-141°C according to melting point determination.

[0083] Infrared spectra were measured under the following conditions:

[0084] Instrument used: NICOLETAVATAR-360 infrared absorption spectrometer...

Embodiment 2

[0094] Example 2: Preparation of N-(4-hydroxy-3-methylbenzyl)acrylamide

[0095] In a 500 mL three-necked flask equipped with an electric stirring device, a condenser tube and a thermometer, add 74 mL of acetone (55% of the weight of o-cresol), 107 g (1 mol) of o-cresol, 101 g (1 mol) of N-methylolpropene amide (the molar ratio of o-cresol and N-methylol acrylamide is 1:1), then add 13g of anhydrous aluminum trichloride (12% of the weight of o-cresol) to the system, and heat in a water bath at 40°C Stir the reaction. The reaction was terminated after 36 hours, a large amount of solid was precipitated in the system, and the filter cake was washed repeatedly with dilute hydrochloric acid until neutral, and then recrystallized in absolute ethanol to obtain a white crystal.

[0096] According to the method described in Example 1, the following results were obtained:

[0097] The yield of white crystals was 80%, and the melting point was 141-142°C.

[0098] IR(KBr)υ / cm -1 : 330...

Embodiment 3

[0101] Example 3: Preparation of N-(2-hydroxy-4,5-methylenedioxybenzyl)acrylamide

[0102] Into a 1000mL three-necked flask equipped with an electric stirring device, a condenser tube and a thermometer, add 175mL of ethanol (100% by weight of 3,4-methylenedioxyphenol), 137g (1mol) of 3,4-methylenediol Oxyphenol, 101g (1mol) N-methylol acrylamide (3,4-methylenedioxyphenol and N-methylol acrylamide molar ratio 1:1), and then add 40mL of concentrated sulfuric acid to the system (54% by weight of 3,4-methylenedioxyphenol), heated and stirred in a water bath at 30°C for 24 hours, a large amount of solid was precipitated in the system, filtered, and the filter cake was repeatedly washed with water until neutral.

[0103] Subsequent recrystallization from absolute ethanol gave a white crystal.

[0104] According to the method described in Example 1, the following results were obtained:

[0105] The yield of white crystals was 90.2%, and the melting point was 128-129°C.

[0106] IR...

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Abstract

The invention relates to a new monofunctional acrylamide compound with a capsaicinoid functional structure and a preparation method and application thereof. The acrylamide compound has the chemical structural formula (I) in the specification, wherein in the formula, R1, R2, R3 or R4 represents alkyl, OH group, OCH3 and other substituent groups. The monofunctional acrylamide compound with the capsaicinoid functional structure contains not only a capsaicin important active group, but also active double-bonds capable of performing polymerization reaction, the synthesis method is simple and easy to operate, the yield is high, and the monofunctional acrylamide compound can make up for the defect that the mass production of natural capsaicin is limited by complicated extraction processes and the output of hot pepper and simultaneously make up for the insufficiency that the natural capsaicin can only be used as a pure additive. The monofunctional acrylamide compound with the capsaicinoid functional structure, provided by the invention, has very good application prospects in preparation of marine antifouling coatings or antibacterial and mildew-proof coatings.

Description

【Technical field】 [0001] The invention belongs to the technical field of acrylamide chemistry. More specifically, the present invention relates to a monofunctional acrylamide compound having a capsaicinoid functional structure, a preparation method of the acrylamide compound, and a use of the acrylamide compound. 【Background technique】 [0002] Capsaicin is the main spicy ingredient in peppers, its structure It is an amide compound formed by fatty acid and vanillylamine. It is a structurally stable alkaloid with antibacterial, antitumor, analgesic and anti-inflammatory effects. It has been used in medicine, health care, biological pesticides, diet, chemical industry, security defense and other technical fields . The use of capsaicin for marine antifouling has also been reported. For example, US5226380 and US5397385 disclose that capsaicin is used as an additive for antifouling coatings, which can effectively prevent the attachment of marine fouling organisms. my country ...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/20C07C233/31C07D317/64C09D5/16C09D5/14C09D4/02
Inventor 于良民姜晓辉李霞闫雪峰张志明李昌诚夏树伟于晓琳
Owner OCEAN UNIV OF CHINA
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