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Dehydroabietic-acid-based dipeptide surfactant and performance thereof

A surfactant, abietic acid-based technology, applied in the field of synthesis and application of natural product surfactants, can solve problems such as rosin resin acid molecules being easily oxidized

Active Publication Date: 2017-11-03
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because rosin contains double bonds, the rosin resin acid molecule is easily oxidized, and to obtain a surfactant with a stable structure, it is usually necessary to modify the structure of rosin

Method used

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  • Dehydroabietic-acid-based dipeptide surfactant and performance thereof
  • Dehydroabietic-acid-based dipeptide surfactant and performance thereof
  • Dehydroabietic-acid-based dipeptide surfactant and performance thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of Compound 1: Dissolve 6-aminocaproic acid methyl ester hydrochloride (32.7g, 0.18mol) in dichloromethane, add triethylamine (72.8g, 0.72mol), 4-di Methylaminopyridine (DMAP) (0.8g, 0.006mol) and dehydroabietic acid (48g, 0.16mol), then add 2-(7-benzotriazole oxide)-N,N,N',N'- Tetramethyluronium hexafluorophosphate (HATU) (76.0g, 0.20mol), the temperature was raised to 35°C, and reacted for 5h. After the reaction, extract with dichloromethane, wash the organic layer with deionized water for 5-6 times, and wash with anhydrous Na 2 SO 4 dry. After suction filtration, dichloromethane was removed by rotary evaporation. The product was purified by column chromatography (eluent: petroleum ether: ethyl acetate = 2:1) to obtain a colorless viscous liquid.

Embodiment 2

[0027] Example 2: Synthesis of R-6: Add NaOH (5.2g, 0.13mol) and 200mL of ethanol to a 500mL single-necked bottle, stir until NaOH is completely dissolved, then add compound 1 (47.0g, 0.11mol), and heat up to 70°C, react for 1.5h. After the reaction was completed, it was cooled to room temperature, a solid was precipitated, and R-6 was obtained by suction filtration.

Embodiment 3

[0028] Example 3: Synthesis of Compound 2: Dissolve R-6 (38.3g, 0.088mol) in water, add dilute HCl to make the solution acidic, extract with ethyl acetate, wash the organic layer with deionized water 5-6 times and use Anhydrous MgSO 4 After drying and suction filtration, ethyl acetate was removed by rotary evaporation to obtain compound 2.

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Abstract

The invention relates the synthesizing and performance of dehydroabietic-acid-based dipeptide surfactant R-6-Phe and provides the molecular structure and synthesizing method of the novel dehydroabietic-acid-based dipeptide surfactant. The molecular structure of the R-6-Phe is as shown in the specification. The surfactant has the advantages that the surfactant is good in aggregation ability, the critical micelle concentration of the surfactant at 25 DEG C is 1.01mmol*L<-1>, and the surfactant is good in emulsifying performance; the main synthesizing raw material dehydroabietic acid and amino acid are natural products which are renewable, biodegradable, rich in source and easy in structural modification, conforms to the environment protection concept of green chemistry and the like, and the surfactant is applicable to fields such as detergent, household chemicals and emulsifiers.

Description

technical field [0001] The invention relates to a dipeptide surfactant synthesized from dehydroabietic acid, which belongs to the field of synthesis and application of natural product surfactants. Background technique [0002] With the concept of environmental protection and sustainable development becoming more and more popular, the research and development of mild, safe and easily degradable green surfactants has become one of the important topics concerned by the academic circles. Seeking natural products as raw materials for the synthesis of green surfactants is the development direction of the surfactant industry. Rosin is a rich renewable forest resource, which is a solid mixture of resin acid, a small amount of fatty acid and neutral substances, and is an important source of raw materials for green surfactants. The tricyclic diterpene structure of resin acid has strong hydrophobicity, and the method of chemical modification is used to introduce hydrophilic groups int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C237/22B01F17/22C09K23/22
CPCC07C231/02C07C231/12C09K23/00
Inventor 宋冰蕾王丹萍冯林
Owner JIANGNAN UNIV
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