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Rosinyl quaternary ammonium salt type gemini surfactant and method for preparing same

A rosin-based quaternary ammonium salt and gemini surface technology, which is applied in the preparation of amino hydroxy compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of high product price, high product purity, unfavorable sustainable development, etc. The effect of increasing added value and reducing product toxicity

Inactive Publication Date: 2008-10-15
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, quaternary ammonium salt gemini surfactants are mainly synthesized by long-time reflux method, which consumes high energy and has many impurities in the product. Microwave-assisted synthesis can be completed in a short period of time, and the product has high purity.
Many surfactant raw materials used today are derived from petroleum products, which is not conducive to sustainable development
Simultaneously, adopt straight-chain alkanes as the lipophilic component of gemini surfactant at present, product price is high, and the two ends of lipophilic group are the quaternary ammonium salt type gemini surfactant of high-yielding natural product rosin-based tricyclic diterpene structure ester. Literature report

Method used

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  • Rosinyl quaternary ammonium salt type gemini surfactant and method for preparing same
  • Rosinyl quaternary ammonium salt type gemini surfactant and method for preparing same
  • Rosinyl quaternary ammonium salt type gemini surfactant and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A kind of rosin base quaternary ammonium salt type gemini surfactant, its general structural formula is as follows:

[0029]

[0030] In the formula, R is a rosin-based tricyclic diterpene structure, X is an integer of Br or I, 1≤n≤10, for example, n can be selected as 2, 3, 4, 5, 6, 7, 8, 9, 10 .

[0031] In this embodiment, R is one of the following substituents:

[0032] Tricyclic phenanthrene structure of dehydroabietic acid Or the tricyclic phenanthrene structure of disproportionated rosin.

Embodiment 2

[0034] A method for preparing a rosin-based quaternary ammonium salt-type gemini surfactant. Firstly, dehydroabietic acid or disproportionated rosin is used to prepare rosin-based tertiary amine, and then rosin-based quaternary ammonium is obtained through quaternization reaction with rosin-based tertiary amine and dihaloalkane Salt type gemini surfactant.

[0035] In the present embodiment, the synthesis of rosin-based tertiary amine comprises the following steps:

[0036] to PCl 3 As an acylation reagent, convert dehydroabietic acid or disproportionated rosin into an active acid chloride intermediate, and then combine the acid chloride intermediate with N,N-dimethylethanolamine to obtain a rosin base in the presence of triethylamine as an acid-binding agent tertiary amine. The molar ratio of acid chloride, N,N-dimethylethanolamine and triethylamine is 0.1:0.1:0.11.

[0037] The quaternization reaction condition of described rosin-based tertiary amine and dihaloalkane is: ...

Embodiment 3

[0044]A preparation method of a rosin-based quaternary ammonium salt type gemini surfactant, comprising the following steps:

[0045] The first step: the synthesis of rosin-based tertiary amine.

[0046] In a dropping funnel, anhydrous CaCl 2 Add 20 mL of PCl to the four-neck flask of the drying tube and the reflux condenser 3 20-25mL CHCl 3 Solution, dissolve 100g of dehydroabietic acid or disproportionated rosin in 80-100mL CHCl 3 Slowly add it to the flask, and after the dropwise addition, raise the temperature to 30-65°C for 3-20 hours to obtain a light amber transparent liquid for use. ) in a dropping funnel, anhydrous CaCl 2 Add (0.1mol) N,N-dimethylethanolamine to the four-necked flask of the drying tube and condenser tube, add 50-60mL toluene to dissolve, add (0.11mol) triethylamine, and (0.1mol) dehydroabietic acid chloride Dissolve in 50-60mL toluene, slowly add dropwise to the toluene solution of amine under ice-water cooling, during the reaction, white precipi...

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Abstract

The invention discloses a rosinyl bis-quaternary ammonium surfactant, the general molecular formula of which is as follows. In the formula, R is a rosinyl ricyclic diterpene structure, X is Br or I, and n is larger than or equal to 1 and smaller than or equal to 10. The invention also discloses a method for preparing the compound: firstly, dehydroabietic acid or disproportionated rosin is adopted to prepare rosinyl tertiary amine, and then the rosinyl tertiary amine and saturated dihalide are prepared into the rosinyl bis-quaternary ammonium surfactant through quaternization. The synthesis of the rosinyl tertiary amine comprises the following steps: the dehydroabietic acid or the disproportionated rosin is converted into active acyl chloride intermediate, and then the acyl chloride intermediate and N,N-dimethyl ethanolamine are prepared into the rosinyl tertiary amine in the presence of the triethylamine which is used as the acid-binding agent. The rosinyl tertiary amine and the saturated dihalide are reacted in the solvent isopropyl alcohol, and then vacuum drying is performed after filtration. The prepared surface active agent has good surface activity performance; the raw material is inexpensive and easy to obtain, and can be biodegraded; the synthetic method is assisted with microwave, the reaction time is short, and the product purity is high.

Description

technical field [0001] The invention relates to a quaternary ammonium salt type gemini surfactant and a preparation method thereof, in particular to a rosin-based quaternary ammonium salt type gemini surfactant and a preparation method thereof. Background technique [0002] Rosin has a unique chemical structure and chemical properties. Because of its rich resources and low price, it has attracted widespread attention. It is an important natural renewable resource in my country. Its deep-processed products are widely used in various departments of daily life. In the national economic life It occupies an important position and is an indispensable chemical raw material. The tricyclic phenanthrene structure of rosin has good lipophilic properties, and can be used as a good surfactant after being connected with a hydrophilic group. Due to the strong hydrophobic property of rosin, the compound obtained after linking with hydrophilic groups has strong surface active properties. A ...

Claims

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Application Information

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IPC IPC(8): C07C219/12C07C213/08B01F17/18C09K23/18
Inventor 饶小平贾卫红宋湛谦商士斌
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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