油酸直接马来酸化制备C22 -三元羧酸Preparation of C22-tricarboxylic acid by Maleinisation of oleic acid
为解决C22-三元羧酸合成过程中均相催化剂残留、原料价格较高等问题，以油酸为原料，在路易斯酸催化下与马来酸酐进行Alder-ene加成反应，水解后得到C22-三元羧酸。对C22-三元羧酸的合成条件进行优化并对产物进行了鉴定；制备C22-三元酸钠表面活性剂并研究其表面性能。结果表明：C22-三元羧酸合成的最佳条件为以FePO4为催化剂、催化剂用量3%（以油酸物质的量计）、马来酸酐与油酸物质的量比3∶ 1、反应温度180 ℃、反应时间10 h，在此条件下C22-三元羧酸产率达到78%，油酸转化率为77.4%；通过质谱及核磁共振表征证明得到了较纯的C22-三元羧酸；催化剂经过5次回收利用并未出现明显...
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| Language: | English |
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中粮工科（西安）国际工程有限公司
2023-01-01
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| Series: | Zhongguo youzhi |
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| Online Access: | http://tg.chinaoils.cn/ch/reader/create_pdf.aspx?file_no=20230111&year_id=2023&quarter_id=1&falg=1 |
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| author | 陈治家，赵杰，张铭远，邓林江，钮腾飞 CHEN Zhijia，ZHAO Jie，ZHANG Mingyuan，DENG Linjiang，NIU Tengfei |
| author_facet | 陈治家，赵杰，张铭远，邓林江，钮腾飞 CHEN Zhijia，ZHAO Jie，ZHANG Mingyuan，DENG Linjiang，NIU Tengfei |
| author_sort | 陈治家，赵杰，张铭远，邓林江，钮腾飞 CHEN Zhijia，ZHAO Jie，ZHANG Mingyuan，DENG Linjiang，NIU Tengfei |
| collection | DOAJ |
| description | 为解决C22-三元羧酸合成过程中均相催化剂残留、原料价格较高等问题，以油酸为原料，在路易斯酸催化下与马来酸酐进行Alder-ene加成反应，水解后得到C22-三元羧酸。对C22-三元羧酸的合成条件进行优化并对产物进行了鉴定；制备C22-三元酸钠表面活性剂并研究其表面性能。结果表明：C22-三元羧酸合成的最佳条件为以FePO4为催化剂、催化剂用量3%（以油酸物质的量计）、马来酸酐与油酸物质的量比3∶ 1、反应温度180 ℃、反应时间10 h，在此条件下C22-三元羧酸产率达到78%，油酸转化率为77.4%；通过质谱及核磁共振表征证明得到了较纯的C22-三元羧酸；催化剂经过5次回收利用并未出现明显的活性降低；以C22-三元羧酸为原料制备的C22-三元酸钠表面活性剂的临界胶束浓度为3.61×10-3 mol/L，在临界胶束浓度下的表面张力为28.39 mN/m。综上，油酸在FePO4催化下直接马来酸化制备C22-三元羧酸，工艺绿色，原料成本较低，并可作为表面活性剂制备的良好原料。
To solve the problems of homogeneous catalyst residue and high raw material price in the synthesis of C22-tricarboxylic acid, using oleic acid as the raw material, Lewis acid as catalyst, the Alder-ene addition reaction of oleic acid and maleic anhydride was realized, and C22-tricarboxylic acid was obtained after hydrolysis. The synthesis conditions of C22-tricarboxylic acid were optimized and the product was identified, and its product was neutralized to prepare C22-tribasic acid sodium surfactant and its surface properties were studied. The results showed that the optimal conditions for C22-tricarboxylic acid synthesis were obtained as follows: with Lewis acid FePO4 as catalyst, dosage of catalyst 3% (calculated by the mole of oleic acid ), molar ratio of maleic anhydride to oleic acid 3∶ 1, reaction temperature 180 ℃, and reaction time 10 h. Under the optimal conditions, the yield of C22-tricarboxylic acid could reach 78% and oleic acid conversion rate was 77.4%. It was proved that C22-tricarboxylic acid was obtained through mass spectrometry and nuclear magnetic resonance characterization. There was no obvious decrease in activity of catalyst after 5 times of recycling. The critical micelle concentration of C22-tribasic acid sodium surfactant prepared by C22-tricarboxylic acid was 3.61×10-3 mol/L, and the surface tension(γ) reached 28.39 mN/m. In conclusion, the preparation process of C22-tricarboxylic acid by the Alder-ene addition reaction of oleic acid and maleic anhydride with FePO4 as catalyst is green and the cost of materials is low， and the C22-tricarboxylic acid prepared can used as good material for surfactant preparation. |
| first_indexed | 2024-03-13T02:21:49Z |
| format | Article |
| id | doaj.art-404fa6ea5c374cdfafc97bc9a6bbdf29 |
| institution | Directory Open Access Journal |
| issn | 1003-7969 |
| language | English |
| last_indexed | 2024-03-13T02:21:49Z |
| publishDate | 2023-01-01 |
| publisher | 中粮工科（西安）国际工程有限公司 |
| record_format | Article |
| series | Zhongguo youzhi |
| spelling | doaj.art-404fa6ea5c374cdfafc97bc9a6bbdf292023-06-30T07:47:55Zeng中粮工科（西安）国际工程有限公司Zhongguo youzhi1003-79692023-01-014816065https://doi.org/10.19902/j.cnki.zgyz.1003-7969.210720油酸直接马来酸化制备C22 -三元羧酸Preparation of C22-tricarboxylic acid by Maleinisation of oleic acid陈治家，赵杰，张铭远，邓林江，钮腾飞 CHEN Zhijia，ZHAO Jie，ZHANG Mingyuan，DENG Linjiang，NIU Tengfei0江南大学 化学与材料工程学院，江苏 无锡 214122School of Chemical and Material Engineering，Jiangnan University，Wuxi 214122，Jiangsu，China)为解决C22-三元羧酸合成过程中均相催化剂残留、原料价格较高等问题，以油酸为原料，在路易斯酸催化下与马来酸酐进行Alder-ene加成反应，水解后得到C22-三元羧酸。对C22-三元羧酸的合成条件进行优化并对产物进行了鉴定；制备C22-三元酸钠表面活性剂并研究其表面性能。结果表明：C22-三元羧酸合成的最佳条件为以FePO4为催化剂、催化剂用量3%（以油酸物质的量计）、马来酸酐与油酸物质的量比3∶ 1、反应温度180 ℃、反应时间10 h，在此条件下C22-三元羧酸产率达到78%，油酸转化率为77.4%；通过质谱及核磁共振表征证明得到了较纯的C22-三元羧酸；催化剂经过5次回收利用并未出现明显的活性降低；以C22-三元羧酸为原料制备的C22-三元酸钠表面活性剂的临界胶束浓度为3.61×10-3 mol/L，在临界胶束浓度下的表面张力为28.39 mN/m。综上，油酸在FePO4催化下直接马来酸化制备C22-三元羧酸，工艺绿色，原料成本较低，并可作为表面活性剂制备的良好原料。 To solve the problems of homogeneous catalyst residue and high raw material price in the synthesis of C22-tricarboxylic acid, using oleic acid as the raw material, Lewis acid as catalyst, the Alder-ene addition reaction of oleic acid and maleic anhydride was realized, and C22-tricarboxylic acid was obtained after hydrolysis. The synthesis conditions of C22-tricarboxylic acid were optimized and the product was identified, and its product was neutralized to prepare C22-tribasic acid sodium surfactant and its surface properties were studied. The results showed that the optimal conditions for C22-tricarboxylic acid synthesis were obtained as follows: with Lewis acid FePO4 as catalyst, dosage of catalyst 3% (calculated by the mole of oleic acid ), molar ratio of maleic anhydride to oleic acid 3∶ 1, reaction temperature 180 ℃, and reaction time 10 h. Under the optimal conditions, the yield of C22-tricarboxylic acid could reach 78% and oleic acid conversion rate was 77.4%. It was proved that C22-tricarboxylic acid was obtained through mass spectrometry and nuclear magnetic resonance characterization. There was no obvious decrease in activity of catalyst after 5 times of recycling. The critical micelle concentration of C22-tribasic acid sodium surfactant prepared by C22-tricarboxylic acid was 3.61×10-3 mol/L, and the surface tension(γ) reached 28.39 mN/m. In conclusion, the preparation process of C22-tricarboxylic acid by the Alder-ene addition reaction of oleic acid and maleic anhydride with FePO4 as catalyst is green and the cost of materials is low， and the C22-tricarboxylic acid prepared can used as good material for surfactant preparation.http://tg.chinaoils.cn/ch/reader/create_pdf.aspx?file_no=20230111&year_id=2023&quarter_id=1&falg=1油酸；马来酸酐；c22-三元羧酸；alder-ene反应oleic acid; maleic anhydride; c22-tricarboxylic acid; alder-ene addition reaction |
| spellingShingle | 陈治家，赵杰，张铭远，邓林江，钮腾飞 CHEN Zhijia，ZHAO Jie，ZHANG Mingyuan，DENG Linjiang，NIU Tengfei 油酸直接马来酸化制备C22 -三元羧酸Preparation of C22-tricarboxylic acid by Maleinisation of oleic acid Zhongguo youzhi 油酸；马来酸酐；c22-三元羧酸；alder-ene反应 oleic acid; maleic anhydride; c22-tricarboxylic acid; alder-ene addition reaction |
| title | 油酸直接马来酸化制备C22 -三元羧酸Preparation of C22-tricarboxylic acid by Maleinisation of oleic acid |
| title_full | 油酸直接马来酸化制备C22 -三元羧酸Preparation of C22-tricarboxylic acid by Maleinisation of oleic acid |
| title_fullStr | 油酸直接马来酸化制备C22 -三元羧酸Preparation of C22-tricarboxylic acid by Maleinisation of oleic acid |
| title_full_unstemmed | 油酸直接马来酸化制备C22 -三元羧酸Preparation of C22-tricarboxylic acid by Maleinisation of oleic acid |
| title_short | 油酸直接马来酸化制备C22 -三元羧酸Preparation of C22-tricarboxylic acid by Maleinisation of oleic acid |
| title_sort | 油酸直接马来酸化制备c22 三元羧酸preparation of c22 tricarboxylic acid by maleinisation of oleic acid |
| topic | 油酸；马来酸酐；c22-三元羧酸；alder-ene反应 oleic acid; maleic anhydride; c22-tricarboxylic acid; alder-ene addition reaction |
| url | http://tg.chinaoils.cn/ch/reader/create_pdf.aspx?file_no=20230111&year_id=2023&quarter_id=1&falg=1 |
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