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Selenium-containing surfactant having pH and redox double-coincidence switch response

A surfactant and solvent technology, used in the field of selenium-containing surfactants, can solve problems such as interfering with the production process, and achieve the effects of low skin irritation, mild synthesis conditions, and excellent antioxidant properties.

Inactive Publication Date: 2017-05-31
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, more and more practice has proved that surfactants and systems containing surfactants often want to stop the function of surfactants after a certain process has played the role of surfactants, otherwise it will interfere with the subsequent production process

Method used

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  • Selenium-containing surfactant having pH and redox double-coincidence switch response
  • Selenium-containing surfactant having pH and redox double-coincidence switch response
  • Selenium-containing surfactant having pH and redox double-coincidence switch response

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Production of Dibenzyl Diselenide

[0034] Take 63.6g of selenium powder (0.4mol) and mix with 520g of water to cool in an ice water bath under the protection of nitrogen; another 66.7g of sodium borohydride (1.6mol) is completely dissolved in ice water and added to the mixed solution of selenium powder and water at room temperature After reacting for 20-50 minutes, add 0.4mol selenium powder and heat to 70 degrees Celsius to react for 20-30 minutes, then add the benzyl bromide dissolved in tetrahydrofuran in advance at 55 degrees Celsius and stir for 20-30 minutes according to the molar ratio of benzyl bromide: selenium 2:1 After 18 hours, the organic phase was extracted with dichloromethane, dehydrated and dried and the solvent was evaporated. The residue was recrystallized with ethyl acetate to obtain yellow crystals of dibenzyl diselenide. The yield of dibenzyl diselenide was 87.6%.

Embodiment 2

[0035] Example 2: Production of 11-benzylselenoundecanoate

[0036] Under the protection of nitrogen, dissolve 4.08 g of dibenzyl diselenide in 40 mL of tetrahydrofuran, and add dropwise 2.36 g of sodium borohydride dissolved in 50 mL of ice water under ice-water bath conditions. After reaction in the ice-water bath for 2.5 hours, add 30 mL dropwise containing 5.38 g11-Bromo-undecanoic acid in tetrahydrofuran, reacted in an ice-water bath for 0.5 hours, and then evaporate under reduced pressure to remove tetrahydrofuran. The resulting aqueous solution of 11-benzylselenoundecanoate was adjusted to pH 1 with hydrochloric acid and filtered under vacuum 11-benzylselenundecanoic acid crude product, and then the obtained crude 11-benzylselenundecanoic acid product was dissolved in ethyl acetate and washed with deionized water several times to obtain the ethyl acetate of 11-benzylselenundecanoic acid The solution was dried with anhydrous sodium sulfate, and the filtrate obtained by filt...

Embodiment 3

[0039] Example 3: Production of 5-benzylselenovalerate

[0040] Under the protection of nitrogen, dissolve 8.16 g of dibenzyl diselenide in 65 mL of tetrahydrofuran, add dropwise a solution of 7.26 g of sodium borohydride dissolved in 75 mL of ice water under ice-water bath conditions, and after reaction in the ice-water bath for 2.5 hours, add 50 mL dropwise containing 1.73 g 5-bromo-pentanoic acid in tetrahydrofuran, reacted in an ice-water bath for 0.5 hours, and then steamed to remove tetrahydrofuran. The resulting aqueous solution of 5-benzylselenovalerate was adjusted to pH 1 with hydrochloric acid, and filtered under reduced pressure to obtain 5- The crude product of benzylselenovaleric acid, then the obtained crude product of 5-benzylselenovaleric acid was dissolved in ethyl acetate and washed with deionized water three times, and the ethyl acetate solution of the obtained 5-benzylselenovaleric acid was used anhydrous sulfuric acid After drying with sodium, the filtrate o...

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PUM

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Abstract

The invention discloses a selenium-containing surfactant having pH and redox double-coincidence switch response and belongs to the technical field of the daily chemical industry. The selenium-containing surfactant is a benzyl selenoalkyl fatty acid salt and has the advantages of simple preparation method, mild synthesis conditions, no special equipment requirement, low energy consumption, easy availability of raw materials and no brominated carboxylate in the product. The selenium-containing surfactant has high surface activity and has excellent foaming and foam stabilization properties. The selenium-containing surfactant has a hydrophilic group similar to a hydrophilic group of the common fatty acid salt surfactant and has low skin irritation. The selenium-containing surfactant has unique pH and redox dual-response properties, excellent antioxidant properties and free radical scavenging ability, and low cytotoxicity and aquatic organism acute toxicity.

Description

Technical field [0001] The invention relates to a selenium-containing surfactant with a dual switch response of pH and redox, and belongs to the technical field of daily chemical industry. Background technique [0002] Selenium (Se) is an element with important physiological activity. It exists in the form of selenoprotein in living organisms. It is often the active center of selenoprotease and has good redox response ability. Surfactants are a large class of fine chemicals widely used in industry, agriculture and personal toiletries industry, and are known as industrial monosodium glutamate. However, more and more practice has proved that surfactants and surfactant-containing systems often hope that the function of surfactants will stop after a certain process has completed the function of surfactants, otherwise it will interfere with subsequent production processes. For example, as a detergent surfactant, when the washing process is completed, the emulsification and foaming pr...

Claims

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Application Information

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IPC IPC(8): C11D1/04C07C391/00A61K8/58A61Q5/02A61Q19/10
CPCC11D1/04A61K8/58A61Q5/02A61Q19/10C07C391/00
Inventor 刘雪锋杨成成陈晖
Owner JIANGNAN UNIV
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