Quaternary ammonium salt surfactant, preparation method and applications thereof

A surfactant and quaternary ammonium salt technology, which is applied in the field of high-efficiency and low-consumption quaternary ammonium salt surfactants, can solve the problems of low reactivity, strong corrosion, and harsh reaction conditions of polyols

Active Publication Date: 2020-04-28
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method needs to use bromoacetyl bromide when carrying out amidation reaction, makes reaction condition harsh likewise, is unfavorable for industrialized production
[0004] Generally speaking, with polyol or polyamine as starting material, the method for synthesizing oligomeric quaternary ammonium salt surfactant through amidation and quaternization two-step reaction has following shortcoming: (1) starting material polyamine has Strong corrosiveness and strong irritant; polyols have low reactivity and poor solubility in organic solvents; (2) toxic acid chlorides or acid bromides are used in the reaction process, and acid chlorides or acid bromides are easily deactivated when they meet water, resulting in harsh reaction conditions

Method used

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  • Quaternary ammonium salt surfactant, preparation method and applications thereof
  • Quaternary ammonium salt surfactant, preparation method and applications thereof
  • Quaternary ammonium salt surfactant, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0095] The preparation of embodiment 1 dimer quaternary ammonium salt surfactant

[0096] The preparation method of dimer quaternary ammonium salt surfactant is as follows:

[0097]

[0098] The specific method is:

[0099] (1) Synthesis steps of the intermediate product diamide: add 14.1 g (160.0 mmol) of N,N-dimethylethylenediamine to 3.2 g (20.0 mmol) of DL-dimethyl malate, and reflux at 106 ° C for 3 h . After the reaction, use a rotary evaporator to remove excess N,N-dimethylethylenediamine to obtain an intermediate with a yield of 99%.

[0100] The intermediate was characterized by ESI-MS: 275.2 (M+H), 297.2 (M+Na).

[0101] 1 H NMR (CDCl 3 , 400MHz): δ=2.24 (single peak, 12H, -N(CH 3 ) 2 ), 2.44 (multiplet, 4H, -NH-CH 2 -CH 2 -N(CH 3 ) 2 ), 2.51, 2.82 (multiplet, 2H, -NH-CO-CH 2 -CH(OH)-CO-NH-), 3.25 (multiplet, 4H, -NH-CH 2 -CH 2 -N(CH 3 ) 2 ), 4.42 (single peak, 1H, -CH-OH), 5.95 (single peak, 1H, -CH-OH), 7.04, 7.49 (single peak, 2H, -NH-CO-CH 2 -...

Embodiment 2 3

[0106] The preparation of embodiment 2 trimerized quaternary ammonium salt surfactants

[0107] The preparation method of trimerized quaternary ammonium salt surfactant is as follows:

[0108]

[0109] The specific method is:

[0110] (1) Synthesis of intermediate tripolyamide: 10.6 g (120.0 mmol) of N,N-dimethylethylenediamine was added to 2.3 g (10.0 mmol) of trimethyl citrate, and refluxed at 106° C. for 3 h. After the reaction, use a rotary evaporator to remove excess N,N-dimethylethylenediamine to obtain an intermediate with a yield of 99%.

[0111] The intermediate was characterized by ESI-MS: 403.2 (M+H), 425.3 (M+Na).

[0112] 1 H NMR (CDCl 3 , 400MHz): δ=2.24 (single peak, 18H, -N(CH 3 ) 2 ), 2.41 (multiplet, 6H, -NH-CH 2 -CH 2 -N(CH 3 ) 2 ), 2.60-2.73 (multiple peaks, 4H, -NH-CO-CH 2 -CH(OH)-), 3.32 (multiplet, 6H, -NH-CH 2 -CH 2 -N(CH 3 ) 2 ), 5.20 (unimodal, 1H, -CH-OH), 7.10, 7.47 (unimodal, 3H, -NH-CH 2 -CH 2 -N(CH 3 ) 2 ).

[0113] (2) Pre...

Embodiment 3

[0116] Embodiment 3 linking group contains the preparation of the dimeric surfactant of aromatic ring

[0117] The preparation method of the dimeric surfactant that linking group contains aromatic ring is as follows:

[0118]

[0119] The specific method is:

[0120] (1) Synthesis of intermediate dimethyl ester: 2.7 g (10.0 mmol) of azobenzene-3,3'-dicarboxylic acid was added to 50 mL of methanol, and a catalytic amount of concentrated sulfuric acid was added to reflux for 3 h. After the reaction, the solvent was removed by a rotary evaporator to obtain the intermediate dimethyl ester with a yield of 99%.

[0121] (2) Synthesis of intermediate diamine: 3.5 g (40.0 mmol) of N,N-dimethylethylenediamine was added to 3.0 g (10.0 mmol) of intermediate dimethyl ester, and refluxed at 106° C. for 3 h. After the reaction, use a rotary evaporator to remove excess N,N-dimethylethylenediamine to obtain an intermediate with a yield of 99%.

[0122] (3) The preparation of the dipolym...

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Abstract

The invention provides a quaternary ammonium salt surfactant, a preparation method and applications thereof, wherein the structure of the quaternary ammonium salt surfactant is represented by a formula (I), and each group is defined in the specification. The quaternary ammonium salt surfactant disclosed by the invention can be used as an efficient and low-consumption wetting agent in the field oftertiary oil recovery, and can effectively convert the surface of a carbonate oil reservoir wrapped by crude oil into water wettability or neutral wettability in the tertiary oil recovery process to achieve wetting reversal, so that the oil washing efficiency can be improved.

Description

technical field [0001] The invention relates to a quaternary ammonium salt surfactant, in particular to a high-efficiency and low-consumption quaternary ammonium salt surfactant. Background technique [0002] Oligomeric surfactants refer to a class of amphiphilic molecules containing two, three or more amphiphilic units in the molecule, and multiple amphiphilic units in the molecule pass through the linking group at or near the head group Groups are held together by chemical bonds. Compared with traditional single-chain surfactants, the increase in the degree of polymerization makes the synergy between multiple amphiphilic units in the oligomeric surfactant molecule stronger, thus showing excellent performance of high efficiency and low consumption, and is expected to become a new generation of surfactants. Surfactant. On the other hand, CN105561865A believes that compared with linear oligomeric surfactants, dendritic surfactants have a stronger ability to remove oil and r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C235/10C07C245/08C07D307/68B01F17/32B01F17/22C09K23/22C09K23/32
CPCC07C235/10C07C245/08C07D307/68C09K23/00
Inventor 乔富林侯研博秦冰江建林李财富高敏余伟发
Owner CHINA PETROLEUM & CHEM CORP
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