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Nonylphenol polyoxyethylene ether dimeric surfactant using piperazine as connecting group

A technology of nonylphenol polyoxyethylene ether and surfactant, which is applied in the field of nonylphenol polyoxyethylene ether dimerization surfactant and its preparation, can solve the problems of complex synthesis process, high raw material cost and high reaction temperature, Achieve the effect of avoiding by-products, clear route and high crystallinity

Inactive Publication Date: 2009-12-16
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims at the disadvantages of complex synthesis process, high reaction temperature, high energy consumption, high cost of some raw materials and high toxicity in current various preparation technologies, and provides a nonyl nonyl compound with piperazine as a linking group. A preparation method of a phenolic polyoxyethylene ether dimerized surfactant, the surfactant uses industrial nonylphenol as a raw material, the preparation method is simple, the reaction conditions are mild, the molecular structure of the target product is accurate, the crystallinity of the intermediate is high, and the product is easy to purify Separation and high conversion rate

Method used

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  • Nonylphenol polyoxyethylene ether dimeric surfactant using piperazine as connecting group
  • Nonylphenol polyoxyethylene ether dimeric surfactant using piperazine as connecting group
  • Nonylphenol polyoxyethylene ether dimeric surfactant using piperazine as connecting group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of Nonylphenol Polyoxyethylene Ether-4 Dimeric Surfactant Bis(NP)-4

[0025] The first step, intermediate N, the synthesis of N'-two (2-hydroxyl-5-nonylphenylmethyl) piperazine:

[0026] (1) Weigh the material according to the molar ratio of anhydrous piperazine:paraformaldehyde=1:2, add it to a three-necked flask, then add dehydrated alcohol 20 times the quality of anhydrous piperazine, turn on the stirring and reflux device, heat and keep The temperature of the material was 50°C, and the reaction was carried out for 2 hours to obtain the intermediate N,N'-dimethylolpiperazine.

[0027] In operation, the amount of paraformaldehyde used above is based on the molar mass of unimolecular formaldehyde (the same as in the following examples).

[0028] (2) Add commercially available industrial product nonylphenol dropwise to the reactant in the three-necked flask of the previous step reaction to continue the reaction. And keep the temperature of the material at 80...

Embodiment 2

[0032] Synthesis of Nonylphenol Polyoxyethylene Ether-30 Dimeric Surfactant Bis(NP)-30

[0033] The first step, intermediate N, the synthesis of N'-two (2-hydroxyl-5-nonylphenylmethyl) piperazine:

[0034](1) Weigh the material according to the molar ratio of anhydrous piperazine:paraformaldehyde=1:4, add it to a three-necked flask, then add dehydrated alcohol 20 times the quality of anhydrous piperazine, open the stirring and reflux device, heat and keep The temperature of the material was 60°C, and the reaction was carried out for 2 hours to obtain the intermediate N,N'-dimethylolpiperazine.

[0035] (2) Add commercially available industrial product nonylphenol dropwise to the reactant in the three-necked flask of the previous step reaction to continue the reaction, the addition of nonylphenol is 3.5 times the molar amount of anhydrous piperazine added in the previous step, heat And keep the temperature of the material at 70°C, react for 5 hours, cool, precipitate white cry...

Embodiment 3～6

[0039] The molar ratio of piperazine to formaldehyde, the molar ratio of nonylphenol to N,N'-dimethylolpiperazine and the number of moles of ethylene oxide added in Examples 3 to 6 are shown in the table below, and other synthetic process steps are implemented in the same way example 1.

[0040]

[0041] The above examples illustrate that the present invention adopts the nonylphenol polyoxyethylene ether dimerized surfactant synthesized by the classic Mannich reaction mechanism, and the intermediate is separated and purified by recrystallization, which has the advantages of easy separation and high crystallinity. Since the piperazine as the linking group is a secondary amine, the generation of other by-products can be effectively avoided. The product was characterized by H NMR, C NMR, and IR spectra to accurately analyze the structure of the product.

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Abstract

The invention discloses a nonylphenol polyoxyethylene ether dimeric surfactant using piperazine as a connecting group and a preparation method thereof. The structural formula of the substance is as the following right formula, wherein the addition mole number m is 4, 7, 10, 15, 20 or 30. The preparation method for the surfactant comprises the following steps: adding intermediate N-N'-di (2-hydroxy-5-nonylphenmethyl) piperazine and 1 percent of potassium hydroxide in percentage by mass of the intermediate into an autoclave, introducing oxacyclopropane of 2m according to the addition mole number m of the ethylene oxide group into the autoclave, heating the mixture to between 120 and 180 DEG C under stirring, reacting the mixture for 2 hours at a pressure of 1MPa, stopping reaction, cooling a reaction product, and taking the cooled reaction product out to obtain a product. The synthetic method has clear route, the synthesized product has an accurate structure, the crystallization degree of the intermediate is high, the product is easy to be separated, the generation of other byproducts is effectively avoided, and a novel dimeric nonylphenol polyoxyethylene ether surfactant is provided for the industry of fine chemicals.

Description

technical field [0001] The invention relates to a non-ionic nonylphenol polyoxyethylene ether dimeric surfactant with piperazine as a linking group and a preparation method thereof, which is a nonylphenol polyoxyethylene ether dipolymer with piperazine as a linking group Polysurfactants and methods for their preparation. Background technique [0002] Two identical or different surfactant monomer molecules are connected by a spacer group at or near their hydrophilic end groups through chemical bonds to connect their amphiphile components together to form a surface active Agents are known as dimeric surfactants or as Gemini surfactants. According to the existing data, the key technology for the preparation of alkylphenol dimeric surfactants is to determine the appropriate linking group. Regarding the synthesis, properties and applications of cationic, anionic, and nonionic oligomeric surfactants, there have been detailed reports in domestic and foreign literature, such as th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/42C08G65/04C07D295/096C09K23/42
Inventor 黎钢祁健杨芳刘荣张松梅
Owner HEBEI UNIV OF TECH
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