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Preparation method of sulfonate type gemini surfactant

A Gemini-surface, sulfonate-type technology, applied in the preparation of sulfonates, ethers, and esters to prepare ethers, etc., can solve the problems that the yield of intermediates cannot be further improved and the reaction temperature is high.

Inactive Publication Date: 2016-05-11
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are certain deficiencies in this intermediate reaction, such as high reaction temperature and intermediate yield can not be further improved, etc.

Method used

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  • Preparation method of sulfonate type gemini surfactant
  • Preparation method of sulfonate type gemini surfactant
  • Preparation method of sulfonate type gemini surfactant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Step 1: In a 250mL four-necked flask equipped with a reflux condenser and a thermometer, add 2.02mol (22.22g) of nonylphenol and 2.00g of tetrabutylammonium bromide, and then add 100mL of 20% sodium hydroxide Aqueous solution, mechanical stirring, turn on the ultrasonic cleaner, set the power to 250W. Set the temperature, when the temperature rises to 55°C, add 0.05mol 1,4-dibromobutane, continue to heat up to 65°C, use thin-layer chromatography to track the reaction process during the reaction, the developer is V (petroleum ether): V (acetic acid ethyl ester)=15:1. After 1.5 hours of reaction, the reaction was completed. The product separated into two phases. After the system was cooled to room temperature, it was extracted with ether (50 mL×3), and the extract was washed with deionized water (50 mL×3), and then dried over anhydrous magnesium sulfate overnight. Suction filtration under reduced pressure and evaporation of the solvent to obtain the bis-ether intermedi...

Embodiment 2

[0024] Step 1: In a 250mL four-necked flask equipped with a reflux condenser and a thermometer, add 2.02mol (22.22g) of nonylphenol and 2.00g of tetrabutylammonium bromide, and then add 100mL of 20% sodium hydroxide Aqueous solution, mechanical stirring, turn on the ultrasonic cleaner, set the power to 250W. Set the temperature, when the temperature rises to 55°C, add 0.05mol 1,6-dibromohexane, continue to heat up to 65°C, use thin-layer chromatography to track the reaction process during the reaction, the developer is V (petroleum ether): V (acetic acid ethyl ester)=15:1. After 1.5 hours of reaction, the reaction was completed. The product separated into two phases. After the system was cooled to room temperature, it was extracted with ether (50 mL×3), and the extract was washed with deionized water (50 mL×3), and then dried over anhydrous magnesium sulfate overnight. Suction filtration under reduced pressure and evaporation of the solvent to obtain the bis-ether intermedi...

Embodiment 3

[0027] Embodiment 3 (effect example)

[0028] The HLB value can be used to measure the emulsification effect of the emulsifier. The formula for calculating the HLB value by the structure factor method: HLB=7+∑hydrophilic base number-∑lipophilic base number. The HLB value of the target product in Example 1 can be obtained by substituting the group numbers of the HLB values ​​of the hydrophilic group and the lipophilic group into the formula. HLB=7+9.4×2+1.9×6+1.3×2-34×0.475-2×1.662=20.326.

[0029] Compound the target product in Example 1 with Span80 to emulsify methyl silicone oil. It can be seen from relevant data that the HLB value required for methyl silicone oil to form a stable O / W emulsion is 10.5. It can be seen from the calculation that the mass ratio of the target product to Span80 in Example 1 is 39:61.

[0030] Add 20g of the prepared compound emulsifier and 340ml of water into a large beaker. After the emulsifier is completely dissolved, turn on the high-shear ...

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Abstract

The invention discloses a preparation method of a sulfonate type gemini surfactant. According to the method, alkylphenol, sodium hydroxide and dibromoalkane generate a bisether intermediate under the action of a phase transfer catalyst tetrabutylammonium bromide in a nucleophilic substitution reaction under an ultrasonic condition; the bisether intermediate and chlorosulfonic acid are subjected to a sulfonation reaction with dichloromethane being a solvent under an ice-water bath condition, and then an alkaline solution is added to generate the sulfonate type gemini surfactant. According to the method, the reaction process is accelerated by the cavatition of ultrasonic waves, selectivity of a target product is improved, and therefore the yield of the intermediate is increased to 94.5% at present from 87% achieved through a common method.

Description

technical field [0001] The invention belongs to the field of fine chemical industry and relates to a preparation method of a sulfonate type gemini surfactant. Background technique [0002] Gemini surfactants consist of two hydrophilic groups, two hydrophobic groups and a linking group. The special structure makes it have many excellent properties, such as higher surface activity, easier to form micelles, low Krafft point and excellent wettability, etc., so it has become a hot spot in many research fields. It has very broad application prospects. Due to the double sulfonate structure, the sulfonate-type gemini surfactant has good water solubility, improved surface activity, and greatly improved decontamination performance, dispersion ability, hard water resistance and stability. [0003] Literature (Zhu Sen, Cheng Fa, Zheng Baojiang, etc. Aggregation properties of Gemini anionic surfactant in aqueous solution [J]. Acta Physicochemical Sinica, 2004, 20(10): 1245-1248.) once ...

Claims

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Application Information

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IPC IPC(8): B01F17/12C07C303/32C07C309/42C07C41/16C07C43/205C09K23/12
Inventor 刘笑妍汤胜会朱广军
Owner NANJING UNIV OF SCI & TECH
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