化工进展 ›› 2023, Vol. 42 ›› Issue (S1): 400-410.DOI: 10.16085/j.issn.1000-6613.2023-0424

• 精细化工 • 上一篇    下一篇

双子表面活性剂癸炔二醇的绿色合成

王正坤(), 黎四芳()   

  1. 厦门大学化学化工学院,福建 厦门 361005
  • 收稿日期:2023-03-21 修回日期:2023-07-09 出版日期:2023-10-25 发布日期:2023-11-30
  • 通讯作者: 黎四芳
  • 作者简介:王正坤(1993—),男,硕士研究生,研究方向为精细化工。E-mail:zkwang@stu.xmu.edu.cn

Green synthesis of gemini surfactant decyne diol

WANG Zhengkun(), LI Sifang()   

  1. College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China
  • Received:2023-03-21 Revised:2023-07-09 Online:2023-10-25 Published:2023-11-30
  • Contact: LI Sifang

摘要:

双子表面活性剂癸炔二醇(S104),即2,4,7,9-四甲基-5-癸炔-4,7-二醇,是一种用途广泛的炔二醇类表面活性剂。S104由甲基异丁基酮和乙炔在碱催化下进行炔化反应合成,目前的合成工艺有两种:固体KOH催化炔化法和液氨-KOH催化炔化法,但都存在严重的环保问题等缺点。为此本研究以悬浮于溶剂二甲苯中的固体异丁醇钾为催化剂催化乙炔和甲基异丁基酮的反应合成S104。采用单因素实验探究了各工艺条件对甲基异丁基酮转化率和S104收率的影响,并以此基础进行了响应面实验优化。在优选反应条件(反应温度35℃,反应时间9h,异丁醇钾与甲基异丁基酮摩尔比1.5∶1,溶剂二甲苯与甲基异丁基酮的质量比4.5∶1)下,S104的收率为86.52%±2.02%。将反应结束后水解得到的氢氧化钾溶液返回到异丁醇钾制备阶段循环使用,甲基异丁基酮转化率和S104收率无明显变化。该工艺在常压下进行,废碱液循环使用,避免了废水排放,安全环保,具有较高的绿色价值。

关键词: 合成, 2,4,7,9-四甲基-5-癸炔-4,7-二醇, 乙炔, 催化, 优化

Abstract:

Gemini surfactant decyne diol (S104), namely 2,4,7,9-tetramethyl-5-decyne-4,7-diol, is a widely used alkyne diol surfactant. S104 is synthesized by ethynylation of methyl isobutyl ketone with acetylene in the presence of alkali catalyst. Currently, there are two types of synthesis processes: solid KOH catalytic ethynylation and liquid ammonia-KOH catalytic ethynylation, but both have serious environmental problems and other shortcomings. In this paper, the synthesis of S104 from acetylene and methyl isobutyl ketone by solid potassium isobutoxide catalyst suspended in solvent xylene was studied. The effects of various process conditions on the conversion of methyl isobutyl ketone and the yield of S104 were investigated by using single factor experiments. Based on this, a response surface experiment was applied for optimization. Under optimized reaction conditions (reaction temperature 35℃, reaction time 9h, molar ratio of potassium isobutoxide to methyl isobutyl ketone 1.5∶1, mass ratio of solvent xylene to methyl isobutyl ketone 4.5∶1), the yield of S104 was 86.52% ± 2.02%. The KOH solution obtained by hydrolysis after the reaction was returned to the potassium isobutoxide preparation step for recycling, and no significant changes in the conversion of methyl isobutyl ketone and the yield of S104 were observed. The process was carried out under atmospheric pressure and the waste alkali liquor was recycled, avoiding wastewater discharge. It was safe, environmentally friendly, and had high green value.

Key words: synthesis, 2,4,7,9-tetramethyl-5-decyne-4,7-diol, acetylene, catalysis, optimization

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