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Enhanced environment friendly surfactant production by the glycerolysis of castor oil using amino acid ionic liquid as a catalyst
Industrial Crops and Products ( IF 5.9 ) Pub Date : 2021-06-01 , DOI: 10.1016/j.indcrop.2021.113680
Yaping Lv , Shangde Sun , Xiaowei Chen

Monoacylglycerol (MAG) is one kind of the oil-based nonionic surfactant, which has the excellent emulsifying property and biodegradability. In this work, several novel and green amino acid ionic liquids (AAILs) were developed as eco-friendly catalysts to promote the glycerolysis of castor (Ricinus communis L.) oil for the green castor oil-based MAG production. Nine AAILs, consisting of an amino acid anion (arginine (Arg), lysine (Lys) and histidine (His)), and an organic hydroxide cation (choline hydroxide (ChOH), tetramethylhydroxide ammonium (TMAOH) and tetrabutylammonium hydroxide (TBAOH)), were synthesized by a simple and green chemical route and used as catalysts to catalyze the glycerolysis of castor oil. Effects of the structural composition of AAILs, reaction time (0-120 min), castor oil and glycerol molar ratio (1:2-1:10), AAIL load (4-12%), and temperature (60-120℃) on the glycerolysis were evaluated and optimized by Box–Behnken methodology. Particularly, the effect of free fatty acid content in castor oil (0-25%) was also investigated to analyze the fatty acid tolerance of AAILs. Among the tested AAILs, [Ch][Arg], [TMA][Arg], and [TBA][Arg] showed the outstanding catalysis performance. Especially, [Ch][Arg] as reaction catalyst for the glycerolysis of castor oil exhibited the best catalysis activity, and high selectivity for MAG formation. The maximum TAG conversion (99.6 ± 0.4%) and MAG content (83.3 ± 1.6%) were obtained under the optimized conditions: 93.7℃, 60.7 min, [Ch][Arg] load 12.3%, and substrate molar ratio 1:6.4. Besides, [Ch][Arg] still had 80% catalytic activity when the free fatty acid content was 20% in castor oil. Kinetic analysis of the glycrolysis was also evaluated. Accordingly, activation energy (Ea) and average reaction order (a) of the glycerolysis were obtained as 59.7 kJ/mol and 1.69, respectively.



中文翻译:

以氨基酸离子液体为催化剂,通过甘油解蓖麻油提高环境友好型表面活性剂生产

单酰基甘油(MAG)是一种油基非离子表面活性剂,具有优良的乳化性和生物降解性。在这项工作中,开发了几种新型绿色氨基酸离子液体(AAILs)作为环保催化剂,以促进蓖麻的甘油分解。L.) 用于生产绿色蓖麻油基 MAG 的油。九个 AAIL,由氨基酸阴离子(精氨酸 (Arg)、赖氨酸 (Lys) 和组氨酸 (His))和有机氢氧化物阳离子(氢氧化胆碱 (ChOH)、四甲基氢氧化铵 (TMAOH) 和四丁基氢氧化铵 (TBAOH))组成, 是通过简单的绿色化学路线合成的,并用作催化剂来催化蓖麻油的甘油分解。AAILs的结构组成、反应时间(0-120 min)、蓖麻油与甘油摩尔比(1:2-1:10)、AAIL负载量(4-12%)、温度(60-120℃)的影响通过 Box-Behnken 方法评估和优化对甘油分解的影响。特别是,还研究了蓖麻油中游离脂肪酸含量 (0-25%) 的影响,以分析 AAILs 的脂肪酸耐受性。在测试的 AAILs 中,[Ch][Arg]、[TMA][Arg]、[TBA][Arg]表现出优异的催化性能。特别是[Ch][Arg]作为蓖麻油甘油解反应催化剂表现出最好的催化活性和高MAG形成选择性。在93.7℃、60.7 min、[Ch][Arg]负载12.3%、底物摩尔比1:6.4的优化条件下获得了最大TAG转化率(99.6±0.4%)和MAG含量(83.3±1.6%)。此外,当蓖麻油中游离脂肪酸含量为20%时,[Ch][Arg]仍有80%的催化活性。还评估了糖酵解的动力学分析。因此,甘油分解的活化能 (Ea) 和平均反应级数 (a) 分别为 59.7 kJ/mol 和 1.69。[Ch][Arg]作为蓖麻油甘油解反应催化剂表现出最好的催化活性和高选择性形成MAG。在93.7℃、60.7 min、[Ch][Arg]负载12.3%、底物摩尔比1:6.4的优化条件下获得了最大TAG转化率(99.6±0.4%)和MAG含量(83.3±1.6%)。此外,当蓖麻油中游离脂肪酸含量为20%时,[Ch][Arg]仍有80%的催化活性。还评估了糖酵解的动力学分析。因此,甘油分解的活化能 (Ea) 和平均反应级数 (a) 分别为 59.7 kJ/mol 和 1.69。[Ch][Arg]作为蓖麻油甘油解反应催化剂表现出最好的催化活性和高选择性形成MAG。在93.7℃、60.7 min、[Ch][Arg]负载12.3%、底物摩尔比1:6.4的优化条件下获得了最大TAG转化率(99.6±0.4%)和MAG含量(83.3±1.6%)。此外,当蓖麻油中游离脂肪酸含量为20%时,[Ch][Arg]仍有80%的催化活性。还评估了糖酵解的动力学分析。因此,甘油分解的活化能 (Ea) 和平均反应级数 (a) 分别为 59.7 kJ/mol 和 1.69。与底物摩尔比为1:6.4。此外,当蓖麻油中游离脂肪酸含量为20%时,[Ch][Arg]仍有80%的催化活性。还评估了糖酵解的动力学分析。因此,甘油分解的活化能 (Ea) 和平均反应级数 (a) 分别为 59.7 kJ/mol 和 1.69。与底物摩尔比为1:6.4。此外,当蓖麻油中游离脂肪酸含量为20%时,[Ch][Arg]仍有80%的催化活性。还评估了糖酵解的动力学分析。因此,甘油分解的活化能 (Ea) 和平均反应级数 (a) 分别为 59.7 kJ/mol 和 1.69。

更新日期:2021-06-01
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