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Biquaternary ammonium salt and bisulfonate surfactant and synthesis method thereof

A technology of surfactants and bissulfonates, applied in the preparation of sulfonates, chemical instruments and methods, organic chemistry, etc., can solve the problems of late Gemini surfactants and limited types of Gemini surfactants, and achieve a synthesis method. Simple, excellent surface activity, easy to operate

Inactive Publication Date: 2010-05-12
SOUTHWEST PETROLEUM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the relatively late start of research on Gemini surfactants in China, the types of Gemini surfactants developed are relatively limited, especially the surfactants whose linking groups connect two amphoteric surfactant molecules have hardly been reported.

Method used

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  • Biquaternary ammonium salt and bisulfonate surfactant and synthesis method thereof
  • Biquaternary ammonium salt and bisulfonate surfactant and synthesis method thereof
  • Biquaternary ammonium salt and bisulfonate surfactant and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of embodiment 1 TM-12

[0034] (1) Synthesis of N, N'-(di-p-benzenesulfonic acid)ethylenediamine

[0035] In a 250mL three-necked flask placed in a constant temperature water bath and equipped with a stirrer, a thermometer, and a reflux condenser, add 4 g (0.0231 mol) of p-aminobenzenesulfonic acid and an aqueous sodium hydroxide solution of ethanol, and slowly add 1,2-bis Bromoethane 2.1604g (0.0115mol) solution, adjust the pH value at 8-10, stir and reflux at a water bath temperature of 65-85°C, and react for 35-40 hours. The reaction solution was slowly evaporated to dryness at 50° C. to obtain 4.17 g of white solid (yield about 97%).

[0036] (2) Synthesis of N, N'-(sodium dialkyl di-p-benzenesulfonate) ethylenediamine

[0037] Add 4g (0.01074mol) of the intermediate to a three-necked flask equipped with a stirrer and a thermometer placed in a constant temperature water bath, then add 100mL of distilled water / ethanol (v:v=2:3) mixed solvent to diss...

Embodiment 2

[0040] The preparation of embodiment 2 TM-10

[0041] (1) Synthesize N, N'-(di-p-benzenesulfonic acid) ethylenediamine and N, N'-(sodium dialkyldi-p-benzenesulfonate) respectively by the method of Example 1 (1), (2) Ethylenediamine.

[0042] (2) Synthesis of TM-10

[0043] In a 250mL three-necked flask placed in a constant temperature water bath and equipped with a stirrer and a reflux condenser, add 4 g (0.0053 mol) of the intermediate N, N'-(sodium dialkyldi-p-benzenesulfonate) ethylenediamine, and then add 50mL of distilled water / ethanol (v:v=2:3) mixed solvent, stir to dissolve, slowly add bromoethane 1.2510g (0.01148mol) dropwise, adjust the pH value to about 8, in the water bath temperature is 30 ~ 50 ℃ React for 7 to 10 hours. After the reaction, a precipitate precipitated out, cooled overnight, filtered with suction, and dried at 50°C to obtain a white solid powder which is TM-10. Weighed 3.9908g (76% yield).

Embodiment 3

[0044] The infrared spectrum of embodiment 3 target product TM surfactant

[0045] The IR spectrogram of the target substance TM-12 obtained by embodiment 1 is shown in figure 1 .

[0046] The attribution analysis of each characteristic band in the spectrum is as follows: 3490.7, 3383.6, 3332.4cm -1 It is O-H stretching vibration on amine group and sulfonic acid group; 3077.9cm -1 It is the stretching vibration peak of =C-H on the benzene ring; 2960cm -1 for CH 3 Upper stretching vibration peaks; 2922.9 and 2852.2 cm -1 is-CH 2 - C-H stretching vibration; 1905.4 is the out-of-plane bending vibration peak of Ar-H; 1605.5 and 1503.0cm -1 It is the stretching vibration peak of the skeleton on the benzene ring; 1580 and 1450cm -1 It is the third band of substituted benzene ring (characteristic band of conjugated substituted benzene); 1465cm -1 for -CH 2 - deformation vibration; 1299.8 and 1280.5 cm -1 It is the stretching vibration peak of -C-N on the aryl carbon; 1224.3...

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Abstract

The invention relates to a biquaternary ammonium salt and bisulfonate surfactant, which is N,N'-ethylene bis[ethyl alkyl (sodium) p-benzene-sulfonate ammonium bromide]. The synthesis method of the biquaternary ammonium salt and bisulfonate surfactant comprises the following steps of: (1) dissolving a sodium hydroxide in a mixed solvent of ethanol and water to prepare solution, adding the solution into a three-necked flask with a stirrer and a return condenser, then adding a sulfanilic acid into the flask and slowly dripping 1,2-dibromoethane under a condition of a pH value of 8 to 10; (2) adding the product generated by step (1) in a reactor, adding a long-chain bromoalkane with stirring, adjusting the pH to around 8 and iltering out and drying a precipitate precipitated after the reaction is completed; and (3) adding the product generated by step (2) into a reactor, adding a mixed solution of distilled water and ethanol, stirring the solution to dissolve the product, adding an bromoethane, adjusting the pH to around 8, cooling the solution, filtering out under vacuum, washing and drying precipitate precipitated when the reaction is completed and thus obtaining the surfactant. The surfactant has the advantages of very high surface activity, simple synthesis method, mild reaction condition, simple and convenient operation, easy purification and separation and very good formulation performance.

Description

technical field [0001] The invention relates to a gemini amphoteric surfactant and a synthesis method thereof, in particular to a diquaternary ammonium disulfonate surfactant and a synthesis method thereof. Background technique [0002] In 1971, Bunton et al. studied alkylene-α, ω-bis(alkyl dimethyl ammonium bromide) [C m h 2m+1 N + (CH 3 ) 2 Br - ] m (CH 2 ) x Recorded as (m-x-m, 2Br - ) surface activity, and then discussed the properties (C.A.Bunton, L.Robinson.Catalysis of nucleophilc substitutions bymicelles of dietationic detergent [J] F.J.Org.Chem, 1971. (36): 2346-2352). In 1974, Deinega et al. synthesized disulfonic acid (salt) surfactants and studied its properties (Y.P.Zhu, A.Masuyama, Deinega, Preparation and properties of double-or-triple-chain surfactants with two sulfonategroups designed from N- acyldiethanolamines [J] J. Am. Oil Chem. Soc, 1991 (68): 539-543). In 1991, Menger synthesized a double alkane chain surfactant with a rigid group linking a...

Claims

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Application Information

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IPC IPC(8): B01F17/18B01F17/12C07C309/46C07C303/32C09K23/18C09K23/12
Inventor 胡星琪杨彦东李嘉方裕燕
Owner SOUTHWEST PETROLEUM UNIV
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