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Benzyl methoxy-oleoyl quaternary ammonium surfactant as well as preparation method and application thereof

A technology of surfactant and oleoyl quaternary ammonium, which is applied in the field of benzyloxy-oleoyl quaternary ammonium surfactant and its preparation, can solve the problem of large, easy to decompose when exposed to water and high temperature to form toxic gases such as sulfur dioxide and hydrogen chloride , Limiting the scope of application, unfavorable environmental protection and other problems, to achieve the effect of low toxicity, avoiding toxic gas and high yield

Active Publication Date: 2022-01-14
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this patent also has the following disadvantages and deficiencies: 1) benzene and its homologues are used as the alkylation raw materials, and benzene, toluene and other benzene homologues have been listed as carcinogens at present (benzene belongs to the first class of carcinogens, and toluene is three carcinogens, ethylbenzene is a 2B carcinogen), and the LD50 of benzene is 930mg / kg, which is moderately toxic
Toluene belongs to the precursor compound, subject to application restrictions, ethylbenzene has a strong irritant to human skin; 2) Thionyl chloride is used as the acyl chloride reagent in the synthesis process, and thionyl chloride is more irritating to humans , meeting water and high temperature, it is easy to decompose and form toxic gases such as sulfur dioxide and hydrogen chloride, which is not conducive to environmental protection; 3) the obtained surfactant is a diamine surfactant, which belongs to a cationic surfactant. Easy to decompose, which limits its scope of application

Method used

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  • Benzyl methoxy-oleoyl quaternary ammonium surfactant as well as preparation method and application thereof
  • Benzyl methoxy-oleoyl quaternary ammonium surfactant as well as preparation method and application thereof
  • Benzyl methoxy-oleoyl quaternary ammonium surfactant as well as preparation method and application thereof

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preparation example Construction

[0054] A kind of preparation method of benzyloxy-oleoyl quaternary ammonium surfactant, comprises the following steps:

[0055] 1) fatty acid, anisole, FeCl 3 mixing and carrying out an alkylation reaction at 50-85° C. for 2-8 hours to obtain the first intermediate product;

[0056] 2) Mix the first intermediate product with 3-dimethylaminopropylamine and perform amidation reaction at 135-165° C. for 5-12 hours to obtain the second intermediate product;

[0057] 3) Mix the second intermediate product, chlorinated organic acid salt, and sodium carbonate in ethanol / water solution, and perform a quaternization reaction at 85-105°C for 6-12h to obtain benzyloxy-oleoyl quaternary ammonium type surfactants.

[0058] Among them, the fatty acid is oleic acid or its methyl ester, methyl oleate; fatty acid, anisole, FeCl 3 , 3-dimethylaminopropylamine, chlorinated organic acid salt, the molar ratio of sodium carbonate is 1:(3-8):(0.5-1.2):(1-3):(1-2):(1-2 ).

[0059] For the surfac...

Embodiment 1

[0067] A kind of benzyloxy-oleoyl quaternary ammonium surfactant, its structural formula is as follows:

[0068]

[0069] The preparation method of this tensio-active agent comprises the following steps:

[0070] 1) Add 0.08mol anisole and 0.005mol catalyst FeCl to 0.01mol oleic acid 3 , and stirred at 65°C for 6h to obtain the first intermediate product;

[0071] 2) Add 0.03mol 3-dimethylaminopropylamine to 10mL ethylbenzene and mix well, then add the first intermediate product, and stir and react at 160°C for 5h, then distill off the unreacted 3-dimethylaminopropylamine, Ethylbenzene and anisole, obtain the second intermediate product;

[0072] 3) Mix 30mL ethanol and 15mL water to prepare ethanol / water solution, then add the second intermediate product, 0.01mol Na 2 CO 3 and 0.012mol 3-chloro-2-hydroxypropanesulfonate, and stirred at 95°C for 10h, then evaporated to remove ethanol and water, and dissolved the remaining solid with methanol, separated the methanol phas...

Embodiment 2

[0076] A kind of benzyloxy-oleoyl quaternary ammonium surfactant, its structural formula is as follows:

[0077]

[0078] The preparation method of this tensio-active agent comprises the following steps:

[0079] 1) Add 0.03mol anisole and 0.01mol catalyst FeCl to 0.01mol oleic acid 3 , and stirred at 50°C for 8h to obtain the first intermediate product;

[0080] 2) Add 0.01mol 3-dimethylaminopropylamine to 10mL ethylbenzene and mix well, then add the first intermediate product, and stir and react at 160°C for 5h, then evaporate unreacted 3-dimethylaminopropylamine, Ethylbenzene and anisole, obtain the second intermediate product;

[0081] 3) Mix 30mL ethanol and 15mL water to prepare ethanol / water solution, then add the second intermediate product, 0.01mol Na 2 CO 3 and 0.02mol 3-chloro-2-hydroxypropanesulfonate, and stirred at 85°C for 6h, then evaporated to remove ethanol and water, and dissolved the remaining solid with methanol, separated the methanol phase, and evap...

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Abstract

The invention relates to a benzyl methoxy-oleoyl quaternary ammonium surfactant as well as a preparation method and application thereof, wherein the structural formula of the surfactant is represented by a formula (I) or a formula (II), m is equal to 0-11, n is equal to 4-15, and m+n is equal to 15. The preparation method comprises the steps: firstly, mixing fatty acid, anisole and FeCl3, and carrying out alkylation reaction; then mixing the product with 3-dimethylaminopropylamine, and carrying out amidation reaction; and finally, mixing the obtained intermediate product with chlorinated organic acid salt and sodium carbonate in an ethanol / aqueous solution, and carrying out quaternization reaction to obtain the surfactant. Compared with the prior art, oleic acid obtained from animals and plants and anisole extracted from fennel are adopted to replace benzene as raw materials, traditional phenyl octadecanoic acid is subjected to structure optimization, and after alkylation reaction, amidation reaction and quaternization reaction are sequentially carried out, the minimum oil-water interfacial tension of the obtained surfactant can reach 5*10 <-4> mN / m, and the surfactant has great application potential in the tertiary oil recovery industry.

Description

technical field [0001] The invention belongs to the technical field of surfactants, and relates to a benzyloxy-oleoyl quaternary ammonium surfactant and a preparation method and application thereof. Background technique [0002] Surfactants can be divided into petroleum-based surfactants, bio-surfactants, bio-based surfactants, etc. according to the source of the hydrophobic group. Currently the most widely used surfactants are petroleum-based surfactants, the main source of which is petrochemicals. Bio-based surfactants, unlike traditional petroleum-based surfactants, refer to surfactants whose main source is renewable biomass. Petroleum products have been widely used as sources of hydrophobic groups for surfactants since the 1950s. Since the 1990s, due to factors such as safety, environmental protection and sustainable development, the share of petroleum-based surfactants in the total production of surfactants has gradually declined. Biomass resources are considered to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K23/24C07C303/32C07C309/14C09K8/584
CPCC07C51/367C07C231/02C07C303/32C09K8/584C07C59/64C07C235/34C07C309/14
Inventor 牟伯中杨世忠刚洪泽刘金峰郎剑桥
Owner EAST CHINA UNIV OF SCI & TECH
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