Nonylphenol polyoxyethylene ether trimeric surfactant using piperazine as connecting group

A technology of nonylphenol polyoxyethylene ether and surfactant, which is applied in the field of non-ionic nonylphenol polyoxyethylene ether trimerized surfactant and its preparation, which can solve equipment corrosion, acid cannot be removed cleanly, increase Product production costs and other issues to achieve the effect of avoiding the formation of by-products, the structure of the synthetic product is accurate, and the route is clear

Inactive Publication Date: 2011-05-11
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The main disadvantages of the above method in the process of preparing polymeric surfactants are: due to the use of distillation dehydration to remove acid, not only the acid cannot be removed cleanly, which affects the quality of subsequent products, but also the acidic water vapor has strong corrosion on equipment Effect; use NaHCO 3 Washing the phenolic trimer product obtained by using potassium hydroxide as a catalyst with aqueous solution and saturated salt water requires a large amount of washing liquid, and the subsequent treatment of a large amount of wastewater will greatly increase the production cost of the product and easily lead to environmental pollution; using solid acid Catalysis requires high reaction temperature and high energy consumption

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of Nonylphenol Polyoxyethylene Ether-7 Trimeric Surfactant Tri(NP)-7

[0024] The first step, the synthesis of intermediate 2,6-bis{N-[N'-(2-hydroxyl-5-nonylbenzyl)piperazinyl]methyl}-4-nonylphenol:

[0025] (1) According to the molar ratio, anhydrous piperazine: paraformaldehyde = 1: 2.5 weighs the material, adds in the there-necked flask, then adds n-butanol with 20 times the quality of anhydrous piperazine, and the temperature is at 80°C, and the reaction After 1h, the intermediate N,N'-dimethylolpiperazine was obtained.

[0026] (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 70°C, react for 3 hours, then introduce the Dean-Stark reactor into the reaction system, react at 120°C for 5 hours to evaporate the water in the system, cool to room temperature, precipitate light yellow crystals, and re...

Embodiment 2

[0031] Synthesis of Nonylphenol Polyoxyethylene Ether-20 Trimeric Surfactant Tri(NP)-20

[0032] The first step, the synthesis of intermediate 2,6-bis{N-[N'-(2-hydroxy-5-nonylbenzyl)piperazinyl]methyl}-4-nonylphenol

[0033] (1) The molar ratio is anhydrous piperazine: paraformaldehyde = 1: 3. Weigh the material, add it to a three-necked flask, then add n-butanol 20 times the mass of anhydrous piperazine, and react for 1 h at a temperature of 80°C. , to obtain the intermediate N, N'-dimethylolpiperazine.

[0034](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 100°C, react for 3 hours, then introduce the Dean-Stark reactor into the reaction system, react at 110°C for 5 hours, evaporate the water in the system, cool to room temperature, precipitate light yellow crystals, and recrystallize three times from ethanol to...

Embodiment 3～6

[0038] 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.

[0039]

[0040] The above examples illustrate that the present invention adopts the classic Mannich reaction mechanism to synthesize the nonylphenol polyoxyethylene ether dimerized surfactant, 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 nonionic surfactant 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 2,6-di{N-[N'-(2-hydroxy-5-nonylphenmethyl)piperazinyl] methyl}-4-nonylphenol and 1 percent of potassium hydroxide in percentage by mass of the intermediate into an autoclave, introducing oxacyclopropane of 3m according to the addition mole number m of theethylene 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, and cooling a reaction product 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 trimeric 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 trimerized surfactant with piperazine as a connecting group and a preparation method thereof, belonging to a non-ionic nonylphenol polyoxyethylene ether surfactant and its preparation method. Background technique [0002] There are few reports in the literature that three identical or different surfactant monomer molecules are connected together by chemical bonds with linking groups to form trimeric surfactants. US 3919429 proposes to use hydrochloric acid, sulfuric acid, phosphoric acid and oxalic acid as catalysts, alkylphenol and formaldehyde condensation reaction, and rely on distillation dehydration to remove acid to obtain alkylphenol aldehyde polymer intermediates, and then use ethylene oxide addition, can prepare A polymeric surfactant with a degree of polymerization of 1-9. CN 200510126038.4 proposes to use potassium hydroxide as a catalyst, and to condense nonylphenol wi...

Claims

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Application Information

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