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Surfactant containing adamantane and preparation method thereof

A technology of surfactant and adamantane, which is applied in the field of surfactant and its preparation, can solve the problems that have not been reported, and achieve the effects of good lipophilicity, high product yield and purity, and high biological activity

Inactive Publication Date: 2011-08-31
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the use of this special group of adamantane for the preparation of Bola-type surfactants.

Method used

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  • Surfactant containing adamantane and preparation method thereof
  • Surfactant containing adamantane and preparation method thereof
  • Surfactant containing adamantane and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of 1,3-dibromoadamantane: In a 150ml three-neck flask equipped with a reflux condensation and tail gas absorption device, add 20g (0.147mol) of adamantane, 20ml of dichloromethane, and 0.8g (0.014mol) of iron powder, and feed Nitrogen, under the temperature condition of 0~5℃, slowly add 18ml bromine (54g, 0.34mol) dropwise while stirring, then react at the temperature condition of 15~25℃ for 8 hours, add saturated sodium bisulfite solution and stir well, remove Excess bromine, the resulting solid was washed with water, dried, and recrystallized from methanol / water to obtain 32.4 g of 1,3-dibromoadamantane, with a yield of 75.0%.

[0028] Synthesis of 1,3-di(4-hydroxyphenyl)adamantane: In a 150ml reaction bottle equipped with reflux condensation and tail gas absorption device, add 6g (20.4mmol) of dried 1,3-dibromoadamantane, phenol 40g (0.425mol), heated to 80-85°C, added 1.36g (10.2mmol) of aluminum trichloride, reacted for 10 hours, washed with hot water to ...

Embodiment 2

[0032] The synthesis steps of 1,3-dibromoadamantane and 1,3-bis(4-hydroxyphenyl)adamantane are shown in Example 1.

[0033] Synthesis of adamantane-1,3-diphenethyl ether sulfonic acid: Add 0.80 g (2.5 mmol) of 1,3-bis(4-hydroxyphenyl) adamantane and anhydrous N to a 150 ml three-necked flask equipped with a reflux condenser , N-dimethylformamide 25ml, stir until completely dissolved, add sodium hydroxide 0.40g (10mmol), slowly heat up to 50°C while stirring and maintain for 2 hours, pass through N 2 protection, and slowly added 1.16 g (5.5 mmol) of sodium 2-bromoethylsulfonate. Then heat up to 80°C to continue the reaction for 5 hours, add 100ml of water, stir for a while, filter to remove insoluble impurities, acidify to pH 4 with hydrochloric acid to precipitate a large amount of white solid, filter with suction, and dry the resulting solid at 45°C for 12 hours to constant temperature. 1.50 g was obtained, and 1.05 g of white flaky crystals were obtained after recrystalliza...

Embodiment 3

[0036] Synthesis of adamantane-1,3-diphenylethyl ether sulfonic acid: add anhydrous N,N-dimethylformamide 50ml to a 150ml three-necked flask equipped with a reflux condenser, N 2 After replacement, add 1.60 g (40 mmol) of sodium hydride, stir evenly, add 3.20 g (10 mmol) of 1,3-bis(4-hydroxyphenyl)adamantane, slowly raise the temperature to 40°C while stirring and keep it for 1 hour, and pass through N 2 After protection, until no bubbles continue to be generated, 5.25 g (25 mmol) of sodium 2-bromoethylsulfonate was added slowly, and the addition was completed in 1 hour. Then heat up to 60°C to continue the reaction for 4 hours, add 100ml of water, stir for a while, filter to remove insoluble impurities, acidify with hydrochloric acid to pH 4, precipitate a large amount of white solid, filter with suction, dry the resulting solid at 45°C for 12 hours to constant weight , 7.15g was obtained, and 4.73g of white flaky crystals were obtained after methanol / water recrystallization,...

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Abstract

The invention discloses a surfactant containing adamantane, namely 1,3-di(4-(2-sodium ethoxysulfonate)-phenyl)adamantane which is called adamantane-1,3-diphenyl ether sodium sulfonate for short and has a structural formula shown in the specification of the invention. In the preparation method of adamantane-1,3-diphenyl ether sodium sulfonate, adamantane is used as starting raw material; and the method comprises the following four steps of reactions: 1) firstly brominating adamantane to prepare 1,3-dibromoadamantane; 2) alkylating 1,3-dibromoadamantane to obtain 1,3-di(4-hydroxyphenyl)adamantane; 3) alkalifying 1,3-di(4-hydroxyphenyl)adamantane to obtain 1,3-di(4-hydroxyphenyl)adamantane sodium salt; and 4) finally performing condensation reaction between 1,3-di(4-hydroxyphenyl)adamantane sodium salt and halogenated sulfone alkylating reagent to synthesize adamantane-1,3-diphenyl ether sodium sulfonate. The method is simple to operate and has the advantages of higher product yield and the like, and the prepared product has high purity; and adamantane-1,3-diphenyl ether sodium sulfonate has potential application prospect in the fields of household chemicals, medicines, materials, chemical engineering and the like.

Description

technical field [0001] The invention relates to a surfactant containing adamantane and a preparation method thereof. Background technique [0002] Surfactant is an important branch of the fine chemical industry and an important part of the national economy. It is known as "industrial monosodium glutamate" and has a wide range of uses due to its good surface properties and application properties. The difference in its molecular structure will lead to obvious differences in the performance of surfactants. Studies have shown that the factors affecting surface activity are mainly the structure of hydrophilic groups and hydrophobic groups and their connection methods. When two hydrophilic groups are connected to a hydrophobic chain in the surfactant molecule to form an amphiphilic compound, the structure is similar to a simple weapon of the South American natives, Bola (made by connecting a small ball at both ends of a thin rope). into), which is a novel Bola-type surfactant [F...

Claims

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Application Information

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IPC IPC(8): C07C309/11C07C303/22B01F17/10B01F17/42A01N41/02A01P1/00A01P3/00C09K23/10C09K23/42
Inventor 郭建维付长安杨楚芬彭进平崔亦华孙保兴
Owner GUANGDONG UNIV OF TECH
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