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Alkylbenzene sulfonate Gemini surfactant and preparation method thereof

A technology of alkylbenzene sulfonate and surfactant, applied in the field of alkylbenzene sulfonate Gemini surfactant and its preparation, can solve the problems of complex synthesis process, low critical micelle concentration surface tension, and high cost, To achieve the effect of broad application prospects

Inactive Publication Date: 2012-05-16
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] US Patent 6043391 discloses a method using SO 3 Sulfonated with olefins, using the sulfonic acid obtained by sulfonation to directly mix with aromatic hydrocarbons to synthesize anionic Gemini surfactants, using strong acid as a catalyst or adding water as a cocatalyst to react at 150°C for 4 hours, there are hydrolysis, high temperature dehydration, etc. in the reaction process Steps, complex process, high energy consumption and high cost
[0007] Compared with traditional single-chain surfactants, Gemini surfactant needles have a lower critical micelle concentration and a stronger ability to reduce surface tension, but its high price and complex synthesis process limit its large-scale industrial use. Promote application

Method used

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  • Alkylbenzene sulfonate Gemini surfactant and preparation method thereof
  • Alkylbenzene sulfonate Gemini surfactant and preparation method thereof
  • Alkylbenzene sulfonate Gemini surfactant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1 (10-3-10 synthesis)

[0060] Step 1: 2.82g (30mmol) phenol, 2.02g (10mmol) 1,3-dibromopropane, 1.2g (30mmol) sodium hydroxide and 0.16g (0.5mmol) tetrabutylammonium bromide are dissolved in 25ml water, and Raise the temperature to 95°C, keep a slight boil and stir vigorously. The mixture was refluxed for three hours and then cooled, extracted with anhydrous diethyl ether (20ml×3) at room temperature, combined and extracted organic phases, and dried over anhydrous sodium sulfate for 12 hours, the organic solvent was distilled off under reduced pressure, and the residue was dissolved in anhydrous Crystallized in water and ethanol, 1.76 g of product was isolated with a yield of 77%. The product is white needle-like crystals.

[0061] Step 2: 6.15g (27mmol) diethers were added dropwise to 11.88g (54mmol) of brominated n-decane and 7.12g (54mmol) of aluminum trichloride in anhydrous 1,2-dichloroethane solution, at 0.3 Stir the reaction at MPa and 80°C for 5 h...

Embodiment 2

[0063] Embodiment 2 (12-3-12 synthesis)

[0064] Step 1: 2.82g (30mmol) phenol, 2.02g (10mmol) 1,3-dibromopropane, 1.2g (30mmol) sodium hydroxide and 0.16g (0.5mmol) tetrabutylammonium bromide are dissolved in 25ml water, and Raise the temperature to 95°C, keep a slight boil and stir vigorously. The mixture was refluxed for three hours and then cooled, extracted with anhydrous diethyl ether (20ml×3) at room temperature, combined and extracted organic phases, and dried over anhydrous sodium sulfate for 12 hours, the organic solvent was distilled off under reduced pressure, and the residue was dissolved in anhydrous Crystallized in water and ethanol, 1.76 g of product was isolated with a yield of 77%. The product is white needle-like crystals.

[0065] Step 2: In, add 6.13g (27mmol) bis-ether dropwise to 13.40g (54mmol) of n-dodecane bromide and 7.12g (54mmol) of aluminum trichloride in anhydrous 1,2-dichloroethane solution , the reaction was stirred at 0.3MPa and 80°C for 5 ...

experiment example 1

[0068] Surface tension curves were measured by the drop volume method. To achieve surface adsorption equilibrium, the formation of each droplet is divided into two steps: first, approximately 90% of the entire droplet volume is quickly extruded, and then the droplet hangs for a sufficient time until the entire droplet falls down automatically. Each surface tension value was averaged from at least three experimental values. The measurement temperature is 25.0±0.1°C. Triple distilled water was used for the solution configuration in this experiment.

[0069] Example 2

[0070] In this experiment, the interfacial tension of the hexadecane / water interface was measured by the spinning drop method (TEX500 rotating interfacial tensiometer), the sample rotation speed was maintained at 5000 rpm, and the measurement temperature was 30.0±0.1°C. Triple distilled water was used for the solution configuration in this experiment. The interfacial tension value can be calculated by the foll...

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Abstract

The invention relates to an alkylbenzene sulfonate Gemini surfactant and a preparation method thereof. The method comprises the following steps of: undergoing a substitution reaction: undergoing a substitutive etherification reaction at the temperature of 65-70 DEG C for 6 hours on phenol and dihalogenated alkane under the action of a phase transfer catalyst to generate bisether, wherein the molar ratio of the phenol to saturated dihalide is 1:3, the saturated dihalide is head-to-end dibromoalkane, the quantity of atoms C of the dibromoalkane is larger than 2, and the phase transfer catalyst is tetrabutylammonium bromide; performing Fourier alkylation: making the bis-ether react with an alkyl halide at the temperature of 80 DEG C and under the pressure of 0.3 MPa under the action of a Louis acid catalyst to generate dialkyl phenylate, wherein the molar ratio of the bis-ether to the alkyl halide is 1:2; undergoing a sulfonation reaction: undergoing a sulfonation reaction on the dialkyl phenylate and a chlorosulfonic acid in the molar ratio of 1:4 by taking dichloromethane as a solvent at the temperature of 0 DEG C; and undergoing a salt-forming reaction: adding an alkali to generate a target product. The alkylbenzene sulfonate Gemini surfactant has very high interfacial activity and a very low critical micelle concentration.

Description

technical field [0001] The invention relates to an alkylbenzene sulfonate Gemini surfactant with good surface / interface activity and a preparation method thereof. Background technique [0002] The emergence of Gemini surfactants has opened up broad prospects for the development of surfactants. Compared with traditional single-chain surfactants, Gemini surfactants have extremely low CMC, strong ability to reduce surface tension, singular aggregation morphology, special phase behavior and rheological properties, etc. A major change in the field. The reason is that the Gemini surfactant molecule contains two polar heads and two hydrophobic chains, and the polar head is composed of a linking group (spacer) connected by a chemical bond, and its structure is shown in the figure. On the one hand, this structure enhances the hydrophobic effect of the hydrocarbon chains, which increases the tendency of hydrophobic groups to escape from the aqueous solution and aggregate into micell...

Claims

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Application Information

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IPC IPC(8): C07C309/42C07C303/32B01F17/12C09K8/584C09K23/12
Inventor 张群朱友益
Owner PETROCHINA CO LTD
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