Bishydroxyl sulfoacid betaine surface active agent and synthesis method thereof

A technology of surfactants and dihydroxysulfonic acid, applied in the direction of sulfonate preparation, chemical instruments and methods, and drilling compositions, etc., can solve the problem of gemini surfactants and dibetaine surfactants, which are rarely reported and other problems, to achieve the effect of simple synthesis method, superior surface activity and mild reaction conditions

Inactive Publication Date: 2012-06-13
SOUTHWEST PETROLEUM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Domestic research on gemini surfactants started relatively late, and there is still a certain gap with foreign countries in terms of product development, performance research and application; especially bisbetaine surfactants are rarely reported

Method used

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  • Bishydroxyl sulfoacid betaine surface active agent and synthesis method thereof
  • Bishydroxyl sulfoacid betaine surface active agent and synthesis method thereof
  • Bishydroxyl sulfoacid betaine surface active agent and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of embodiment 1 DBA-12

[0034] (1) Synthesis of N-(sodium 2-hydroxypropanesulfonate)-N-dodecylamine

[0035] In a three-necked flask equipped with a stirrer placed in a constant temperature water bath, 4.63g (0.025mol) of dodecylamine, 5g (0.025mol) of 3-chloro-2-hydroxypropanesulfonate, and 100mL of 70% ethanol aqueous solution were sequentially added (as a solvent). Stir and reflux. Because dodecylamine itself is basic, and too strong basicity is unfavorable to the alkylation of amine, so 1g (20%wt) of Na was added after reflux for about 3h 2 CO 3 As an acid-binding agent, keep the pH of the system at 7-10. After refluxing for 10 h, the reaction ended (TLC monitored the end point of the reaction, and the developer was V (methanol): V (petroleum ether) = 3:10). The generated salt was filtered off while it was hot, and the filtrate was cooled to room temperature, and white crystals were precipitated. Suction filtration, wash the filter cake three ...

Embodiment 2

[0040] The preparation of embodiment 2 DBA-14

[0041] (1) Synthesis of N-(sodium 2-hydroxypropanesulfonate)-N-tetradecylamine

[0042] The reaction device is the same as in Example 1 (1), and 6.04g (0.025mol) tetradecylamine and 5g (0.025mol) 3-chloro-2-hydroxypropanesulfonate sodium are added successively in the reactor, and 100mL70% ethanol aqueous solution ( as a solvent). Stir and reflux. After reflux for about 3h, add 1.2g (20%wt) of Na 2 CO 3 As an acid-binding agent, keep the pH of the system at 7-10. After refluxing for another 12 hours, the reaction ended (TLC monitored the end point of the reaction, and the developer was V (methanol): V (petroleum ether) = 3:10). The generated salt was filtered off while it was hot, and the filtrate was cooled to room temperature, and white crystals were precipitated. Suction filtration, wash the filter cake three times with 150ml benzene to remove unreacted tetradecylamine, then recrystallize twice at room temperature with 10...

Embodiment 3

[0047] The infrared spectrogram of embodiment 3 raw material, intermediate product and target product

[0048] Raw material primary amine, the infrared spectrogram of the first-order intermediate product that obtains by embodiment example 1 and target product sees figure 1 . Among the figure, 1 is dodecylamine, 2 is N-(sodium 2-hydroxypropanesulfonate)-N-dodecylamine, and 3 is DBA-12. From the analysis of the spectrogram, it can be seen that:

[0049] In the IR spectrum of the raw material dodecylamine, there are N-H symmetric stretching (3332), asymmetric stretching (3368), and in-plane bending (1582) vibration peaks of primary amines; in the IR spectrum of the intermediate product, these primary amines The characteristic bands of all disappeared, secondary amine N-H stretching vibration (3357), O-H stretching vibration (3461), C-O stretching vibration (1052), S=O symmetrical stretching vibration (1091), asymmetric stretching vibration (1180), Characteristic bands of S-O s...

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Abstract

The invention relates to an ethylene-bishydroxyl sulfoacid betaine surface active agent (DBA for short). The synthesis method comprises the following steps: (1) adding alkyl primary amine (n=11,13,15,17) and 3-chlorine-2-hydroxysulfpropylcellulose Na into a reactor, using ethanol water as a solvent and using (Na2CO3 as a acid bonding agent, keeping a potential of hydrogen (pH) value to be equal to 7-10, performing mixing and backflow for 13-16 hours, performing leaching, cooling filtrate to the room temperature to precipitate white crystals, and performing the leaching, washing, recrystallization and drying; (2) adding a product in the step (1), the ethanol water and the Na2CO3 into the reactor to be heated and mixed, adding 1,2- dibromoethane into mixture and performing backflow for 2-3 hours after dissolution; and (3) adding superfluous bromoethane in a reaction system, performing mixing and backflow for 48-72 hours, performing leaching, standing filtrate at zero DEG C for 10-12 hours to precipitate white crystal, and performing the leaching, the washing and the recrystallization to produce a target product DBA. The synthesis method is temperate in reaction condition and simple and convenient to operate, and the product is easy to separate and refine and has high surface activity.

Description

technical field [0001] The invention relates to a novel amphoteric gemini surfactant, an ethylene-bissulfonic acid betaine surfactant and a synthesis method thereof. Background technique [0002] In 1971, Bunton et al. p-alkylene-bis(alkyldimethylammonium bromide) [C m h 2m+1 N + (CH 3 ) 2 -(CH 2 ) 5 -C m h 2m+1 N + (CH 3 ) 2 ]Br - 2 The surface activity of the surfactant was studied, and the properties of this type of surfactant were investigated when the linking groups were hydrophilic, hydrophobic, flexible and rigid groups. (C.A.Bunton, L.Robinson. Catalysis of nucleophilc substitutions by micelles of dietic detergent [J]. F.J.Org.Chem, 1971. [0003] (36):2346-2352). In 1974, Deinega et al. synthesized a group of new amphiphilic molecules, whose molecular structure sequence is: long hydrocarbon chain, ion head group, linking group, second ion head group, second hydrocarbon chain (Y.P.Zhu , A. Masuyama, Deinega, Preparation and properties of double-or-tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/14C07C303/32C09K8/584
Inventor 胡星琪耿向飞罗丽娟杨彦东
Owner SOUTHWEST PETROLEUM UNIV
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