CN101774917B - Method for preparing methyl acetylricinolate - Google Patents
Method for preparing methyl acetylricinolate Download PDFInfo
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- CN101774917B CN101774917B CN 201010106843 CN201010106843A CN101774917B CN 101774917 B CN101774917 B CN 101774917B CN 201010106843 CN201010106843 CN 201010106843 CN 201010106843 A CN201010106843 A CN 201010106843A CN 101774917 B CN101774917 B CN 101774917B
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- 238000000034 method Methods 0.000 title claims abstract description 12
- SFSRMWVCKNCASA-JSUSWRHTSA-N methyl (z,12r)-2-acetyl-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(C)=O)C(=O)OC SFSRMWVCKNCASA-JSUSWRHTSA-N 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 66
- XKGDWZQXVZSXAO-UHFFFAOYSA-N ricinoleic acid methyl ester Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002608 ionic liquid Substances 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- -1 acetyl ricinoleic acid methyl ester Chemical compound 0.000 claims abstract description 26
- XKGDWZQXVZSXAO-ADYSOMBNSA-N Ricinoleic Acid methyl ester Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC XKGDWZQXVZSXAO-ADYSOMBNSA-N 0.000 claims abstract description 21
- 238000006640 acetylation reaction Methods 0.000 claims abstract description 9
- 230000035484 reaction time Effects 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract 2
- XKGDWZQXVZSXAO-SFHVURJKSA-N Ricinolsaeure-methylester Natural products CCCCCC[C@H](O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-SFHVURJKSA-N 0.000 claims description 6
- GAQPYRAIOYJQGZ-UHFFFAOYSA-N S(=O)(=O)(O)O.C(C)N1CC=CC=C1 Chemical compound S(=O)(=O)(O)O.C(C)N1CC=CC=C1 GAQPYRAIOYJQGZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 2
- OPNWGGRJSXYWRA-UHFFFAOYSA-M 1-butylpyridin-1-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+]1=CC=CC=C1 OPNWGGRJSXYWRA-UHFFFAOYSA-M 0.000 claims 1
- NCGZHLTXGNOHRO-UHFFFAOYSA-M hydrogen sulfate;1-propylpyridin-1-ium Chemical compound OS([O-])(=O)=O.CCC[N+]1=CC=CC=C1 NCGZHLTXGNOHRO-UHFFFAOYSA-M 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- 230000007797 corrosion Effects 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000011259 mixed solution Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 abstract description 2
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 4
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- RRQAKHXJCSROOH-OMDYCXLKSA-N (z,12r)-12-hydroxy-2-methyloctadec-9-enoic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCC(C)C(O)=O RRQAKHXJCSROOH-OMDYCXLKSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- AZHBOJDJBCOVKL-UHFFFAOYSA-N 1-butyl-2H-pyridine sulfuric acid Chemical compound S(O)(O)(=O)=O.C(CCC)N1CC=CC=C1 AZHBOJDJBCOVKL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- RCRNHQZAZXJMHW-UHFFFAOYSA-N S(O)(O)(=O)=O.C(CC)N1CC=CC=C1 Chemical compound S(O)(O)(=O)=O.C(CC)N1CC=CC=C1 RCRNHQZAZXJMHW-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
一种制备乙酰蓖麻油酸甲酯的方法，按下述步骤进行：(1)在常压条件，将离子液体催化剂加入到蓖麻油酸甲酯及醋酐的混合液中，搅拌，进行乙酰反应；反应温度为室温～130℃，反应时间0.1-10h；其中所述的酰蓖麻油酸甲酯与醋酐的摩尔比1∶1.5-2.5；其中所述的离子液体催化剂使用量占蓖麻油酸甲酯以质量计≥0.1％；其中所述离子液体催化剂为带-SO3H官能团的烷基磺酸吡啶类离子液体；(2)将上述步骤(1)的反应液静置分层，分出上层产品为粗乙酰蓖麻油酸甲酯，下层催化剂及少量醋酐可以不必处理，而重复利用；(3)将步骤(2)的粗乙酰蓖麻油酸甲酯进行减压蒸馏后，再水洗得精制乙酰蓖麻油酸甲酯。本发明方法简单，易于操作，反应时间短，收率高对设备腐蚀小，成本低。
A method for preparing acetyl ricinoleic acid methyl ester, carried out according to the following steps: (1) under normal pressure conditions, ionic liquid catalyst is added in the mixed solution of ricinoleic acid methyl ester and acetic anhydride, stir, carry out acetylation reaction The reaction temperature is room temperature to 130°C, and the reaction time is 0.1-10h; the molar ratio of the acyl ricinoleic acid methyl ester to acetic anhydride is 1:1.5-2.5; Methyl ester is ≥ 0.1% by mass; wherein the ionic liquid catalyst is an alkylsulfonic acid pyridine ionic liquid with a -SO 3 H functional group; (2) the reaction solution in the above step (1) is left to stand and layered, and separated Go out upper product and be crude acetyl ricinoleic acid methyl ester, lower floor catalyst and a small amount of acetic anhydride can needn't handle, and reuse; (3) after the thick acetyl acetyl ricinoleic acid methyl ester of step (2) is carried out vacuum distillation, wash again Refined acetyl ricinoleic acid methyl ester. The method of the invention is simple, easy to operate, short in reaction time, high in yield, less in equipment corrosion and low in cost.
Description
技术领域 technical field
本发明涉及一种乙酰蓖麻油酸甲酯的制备方法，尤其涉及蓖麻油酸甲酯为原料，离子液体作催化剂制备乙酰蓖麻油酸甲酯的方法。The invention relates to a method for preparing methyl acetyl ricinoleate, in particular to a method for preparing methyl acetyl ricinoleate as a raw material and using an ionic liquid as a catalyst.
背景技术 Background technique
乙酰蓖麻油酸甲酯是种淡黄色透明粘稠液体，不溶于水，易溶于乙醚、乙醇、苯和油脂等。可以用做聚氯乙烯、天然橡胶、合成橡胶、聚醋酸乙烯酯等的耐寒增塑剂，改善它们在低温下脆、硬、不易软化等缺点。尤其它还具有无毒、不易燃、可降解等优点，能够赋予衍生物良好的性能。可以用于于加工各种与食物接触的包装材料、玩具和医疗器械等行业，所以乙酰蓖麻油酸甲酯的发展空间是广阔的。Acetyl ricinoleic acid methyl ester is a light yellow transparent viscous liquid, insoluble in water, soluble in ether, ethanol, benzene and oil, etc. It can be used as a cold-resistant plasticizer for polyvinyl chloride, natural rubber, synthetic rubber, polyvinyl acetate, etc., to improve their shortcomings such as brittleness, hardness, and difficulty in softening at low temperatures. In particular, it also has the advantages of non-toxic, non-flammable, and degradable, which can endow derivatives with good performance. It can be used in the processing of various packaging materials in contact with food, toys and medical equipment and other industries, so the development space of methyl acetyl ricinoleate is broad.
目前，蓖麻油酸甲酯与醋酐的酰化反应制备乙酰蓖麻油酸甲酯，是在比较高的温度下，不加催化剂进行反应[内蒙古民族大学学报，2006，21(1)：39-40]。郑顺姬等报道了羊毛脂(主要成分为脂肪酸甘油三酯)的乙酰化过程(陕西科技大学学报，2003，21(1)：31～34)，采用无催化高温(140℃)羊毛脂与醋酐进行乙酰化反应，转化率84.7％。由于蓖麻油酸甲酯中羟基键在高温下可以发生烷氧化和脱水反应的发生，使产品的纯度下降；蓖麻油酸甲酯分子中含有一个不饱和双健，在高温下容易发生聚合反应，并影响反应产品的收率与色泽，产品需脱色处理；由于在比较高的温度下反应，能耗比较大。At present, the acylation reaction of ricinoleic acid methyl ester and acetic anhydride to prepare acetyl ricinoleic acid methyl ester is to react at a relatively high temperature without adding a catalyst [Journal of Inner Mongolia University for Nationalities, 2006, 21 (1): 39- 40]. Zheng Shunji et al reported the acetylation process of lanolin (mainly composed of fatty acid triglycerides) (Journal of Shaanxi University of Science and Technology, 2003, 21(1): 31-34), using non-catalyzed high temperature (140°C) lanolin and acetic anhydride The acetylation reaction was carried out, and the conversion rate was 84.7%. Owing to the occurrence of alkoxylation and dehydration reactions in the methyl ricinoleic acid methyl ester can occur at high temperature, the purity of the product is reduced; the methyl ricinoleic acid molecule contains an unsaturated double bond, which is prone to polymerization at high temperatures. And affect the yield and color of the reaction product, the product needs to be decolorized; due to the reaction at a relatively high temperature, the energy consumption is relatively large.
上述不足因此仍有值得改进的地方。Therefore, the above-mentioned deficiencies still have room for improvement.
发明内容 Contents of the invention
本发明目的在于克服上述现有技术的不足，提供一种反应效率高，反应温度低，环境友好、高活性、催化剂可循环利用的催化蓖麻油酸甲酯乙酰化反应的方法，它不挥发、可循环使用和可灵活修饰等优点，克服了其它催化剂的强腐蚀性和污染环境的缺点，实现本发明目的。The purpose of the present invention is to overcome above-mentioned deficiencies in the prior art, provide a kind of reaction efficiency height, reaction temperature is low, the method for the catalyzed ricinoleic acid methyl ester acetylation reaction of environmental friendliness, high activity, catalyzer recyclability, it does not volatilize, The advantages of recyclable use, flexible modification and the like overcome the disadvantages of strong corrosion and environmental pollution of other catalysts, and realize the object of the invention.
本发明的蓖麻油酸甲酯与醋酐的乙酰化化学反应式如下：The acetylation chemical reaction formula of ricinoleic acid methyl ester of the present invention and acetic anhydride is as follows:
本发明目的实现，选择采用带-SO3H官能团的烷基磺酸吡啶类离子液体作催化剂，催化制备乙酰蓖麻油酸甲酯的方法，所述方依次按如下步骤进行：The purpose of the present invention is realized, and the alkylsulfonic acid pyridine ionic liquid with -SO3H functional group is selected as a catalyst to catalyze the method for preparing methyl acetyl ricinoleate, and the method is carried out as follows:
(1)在常压条件，将离子液体催化剂加入到蓖麻油酸甲酯及醋酐的混合液中，搅拌，进行乙酰反应；反应温度为室温～130℃，优选反应温度为60-80℃；反应时间0.1-10h，反应压力为常压；(1) Under normal pressure conditions, the ionic liquid catalyst is added to the mixed solution of methyl ricinoleate and acetic anhydride, stirred, and the acetylation reaction is carried out; the reaction temperature is room temperature to 130°C, and the preferred reaction temperature is 60-80°C; The reaction time is 0.1-10h, and the reaction pressure is normal pressure;
其中所述的酰蓖麻油酸甲酯与醋酐的摩尔比1∶1.5-2.5；其中所述的离子液体催化剂使用量占蓖麻油酸甲酯以质量计≥0.1％；优选以质量计为0.5-1.5％，其中所述的带-SO3H官能团的烷基磺酸吡啶类离子液体，其结构式分别为：The molar ratio of the acyl ricinoleic acid methyl ester and acetic anhydride is 1: 1.5-2.5; wherein the ionic liquid catalyst usage accounts for ricinoleic acid methyl ester ≥ 0.1% by mass; preferably 0.5% by mass -1.5%, wherein the alkylsulfonic acid pyridinium ionic liquid with -SO 3 H functional group, its structural formula is respectively:
其中上式离子液体催化剂中烷基R0的烷基碳链长为1-10个碳原子，R1-R5的烷基碳链长0-20个碳原子，R0-R5中碳原子超过10个，则催化性能下降，没有实际用途。离子液体催化剂中阴离子X-为HSO4 -；Wherein the alkyl carbon chain length of alkyl R in the above formula ionic liquid catalyst is 1-10 carbon atoms, R 1 - R The alkyl carbon chain length of 0-20 carbon atoms, R 0 -R 5 middle carbon If the number of atoms is more than 10, the catalytic performance will be lowered, and there is no practical use. The anion X - in the ionic liquid catalyst is HSO 4 - ;
优选离子液体催化剂分子式如下：Preferred ionic liquid catalyst molecular formula is as follows:
N-乙基吡啶硫酸氢盐离子液体：
N-丙基吡啶硫酸氢盐离子液体：
N-丁基吡啶硫酸氢盐离子液体：
N-戊基吡啶硫酸氢盐离子液体
(2)将上述步骤(1)的反应液静置分层，分出上层产品为粗乙酰蓖麻油酸甲酯，下层催化剂及少量醋酐可以不必处理，而重复利用；(2) the reaction solution of the above-mentioned steps (1) is left to stand for layering, and the upper strata product is separated to be crude acetyl ricinoleic acid methyl ester, and the lower floor catalyst and a small amount of acetic anhydride can be reused without processing;
(3)将步骤(2)的粗乙酰蓖麻油酸甲酯进行减压蒸馏后，再水洗得精制乙酰蓖麻油酸甲酯。(3) After the crude acetyl ricinoleic acid methyl ester of step (2) is carried out underpressure distillation, then wash with water to obtain the refined acetyl acetyl ricinoleic acid methyl ester.
反应原料与现有技术相同，可以是通常采用的蓖麻油酸甲酯。The reaction raw material is the same as the prior art, and can be commonly used ricinoleic acid methyl ester.
本发明的优点是：The advantages of the present invention are:
1、本发明是采用烷基磺酸吡啶类离子液体作为催化剂，催化剂的用量少，反应结束后可以催化剂和产物可自动分相，离子液体回收后，可以不必处理即可重复利用，活性略有下降，可以补充少量离子液体。1. The present invention uses alkylsulfonic acid pyridine ionic liquids as catalysts, and the amount of catalysts is small. After the reaction, the catalyst and the product can be automatically phase-separated. After the ionic liquids are recovered, they can be reused without treatment, and the activity is slightly If there is a decline, a small amount of ionic liquid can be added.
2、反应过程中催化剂与反应物能够充分接触，在一定程度上降低了乙酰化温度。因为不需太高温度，避免了蓖麻油酸甲酯中羟基键在高温下发生烷氧化和脱水反应的发生，还可以提高产品的纯度。2. During the reaction process, the catalyst and the reactants can fully contact, which reduces the acetylation temperature to a certain extent. Because too high temperature is not needed, the occurrence of alkoxylation and dehydration reactions of hydroxyl bonds in the methyl ricinoleate at high temperatures is avoided, and the purity of the product can also be improved.
3、制得的粗乙酰蓖麻油酸甲酯减压蒸馏出未反应的醋酐后，水洗，脱水后，产品色泽明亮，不必进行脱色处理。3. After the unreacted acetic anhydride is distilled out of the crude acetyl ricinoleic acid methyl ester obtained under reduced pressure, after washing and dehydration, the product has a bright color and does not need to be decolorized.
4、本发明方法简单，易于操作，反应时间短，收率高对设备腐蚀小，既可以减少能源，又可以降低成本。其突出的优点是蓖麻油酸甲酯的乙酰化反应温度从140℃降低到60-80℃，降低了能耗，产品的色泽得到了改善4. The method of the present invention is simple, easy to operate, short in reaction time, high in yield and less in corrosion to equipment, which can reduce both energy and cost. Its outstanding advantage is that the acetylation reaction temperature of methyl ricinoleate is reduced from 140°C to 60-80°C, which reduces energy consumption and improves the color of the product
本发明给出的区间值，并非数学概念的精确端值，而试验选择有协当区间，适当偏离端值并非不可以。The interval value given by the present invention is not the exact end value of the mathematical concept, but there is a coordinated interval in the test selection, and it is not impossible to deviate from the end value appropriately.
附图说明 Description of drawings
图1为本发明离子液体催化剂重复性实验结果。Fig. 1 is the repeatability experiment result of the ionic liquid catalyst of the present invention.
具体实施方式 Detailed ways
对比实施例：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶2)，不加催化剂，在140℃下反应2小时，转化率为83.4％。Comparative example: in a 0.25L reactor, add ricinoleic acid methyl ester and acetic anhydride (molar mass ratio 1: 2), do not add catalyst, react at 140 ℃ for 2 hours, the conversion rate is 83.4%.
实施例1：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶2)，催化剂N-丙基吡啶磺酸硫酸氢盐离子液体加入量为1.5％，在70℃下反应1小时，转化率达到93.37％Embodiment 1: in 0.25L reactor, add ricinoleic acid methyl ester and acetic anhydride (molar mass ratio 1: 2), catalyst N-propylpyridinesulfonic acid bisulfate ionic liquid add-on is 1.5%, at 70 Reaction at ℃ for 1 hour, the conversion rate reached 93.37%
实施例2：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶2)，催化剂N-丙基吡啶磺酸硫酸氢盐离子液体加入量为0.5％，在80℃下反应2小时，转化率达到96.21％Embodiment 2: in 0.25L reactor, add ricinoleic acid methyl ester and acetic anhydride (molar mass ratio 1: 2), catalyst N-propylpyridinesulfonic acid bisulfate ionic liquid add-on is 0.5%, at 80 Reaction at ℃ for 2 hours, the conversion rate reached 96.21%
实施例3：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶2)，催化剂N-丙基吡啶磺酸硫酸氢盐离子液体加入量为1％，在60℃下反应3小时，转化率达到90.36％Embodiment 3: in 0.25L reactor, add ricinoleic acid methyl ester and acetic anhydride (molar mass ratio 1: 2), catalyst N-propylpyridinesulfonic acid bisulfate ionic liquid add-on is 1%, at 60 Reaction at ℃ for 3 hours, the conversion rate reached 90.36%
实施例4：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶2.5)，催化剂N-丁基吡啶磺酸硫酸氢盐离子液体加入量为1％，在70℃下反应1小时，转化率达到93.64％Embodiment 4: in 0.25L reactor, add ricinoleic acid methyl ester and acetic anhydride (molar mass ratio 1: 2.5), catalyst N-butylpyridinesulfonic acid bisulfate ionic liquid add-on is 1%, at 70 Reaction at ℃ for 1 hour, the conversion rate reached 93.64%
实施例5：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶2.5)，催化剂N-丙基吡啶磺酸硫酸氢盐离子液体加入量为0.5％，在60℃下反应2小时。转化率达到90.31％Embodiment 5: in 0.25L reactor, add ricinoleic acid methyl ester and acetic anhydride (molar mass ratio 1: 2.5), catalyst N-propylpyridinesulfonic acid bisulfate ionic liquid add-on is 0.5%, at 60 °C for 2 hours. The conversion rate reached 90.31%
实施例6：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶2.5)，催化剂N-丙基吡啶磺酸硫酸氢盐离子液体加入量为1.5％，在80℃下反应3小时。转化率达到96.35％Embodiment 6: in 0.25L reactor, add ricinoleic acid methyl ester and acetic anhydride (molar mass ratio 1: 2.5), catalyst N-propylpyridinesulfonic acid bisulfate ionic liquid add-on is 1.5%, at 80 °C for 3 hours. The conversion rate reached 96.35%
实施例7：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶1.5)，催化剂N-戊基吡啶硫酸氢盐离子液体加入量为0.5％，在60℃下反应1小时。转化率达到85.59％Example 7: In a 0.25L reactor, add methyl ricinoleate and acetic anhydride (molar mass ratio 1: 1.5), the catalyst N-pentylpyridinium bisulfate ionic liquid addition is 0.5%, at 60 ° C React for 1 hour. The conversion rate reached 85.59%
实施例8：在0.25L反应器中，加入蓖麻油酸甲酯和乙酸酐(摩尔质量比1∶1.5)，催化剂N-乙基吡啶硫酸氢盐离子液体加入量为1％，在70℃下反应2小时。转化率达到90.39％Example 8: In a 0.25L reactor, add methyl ricinoleate and acetic anhydride (molar mass ratio 1: 1.5), the catalyst N-ethylpyridine bisulfate ionic liquid addition is 1%, at 70 ° C React for 2 hours. The conversion rate reached 90.39%
实施例9：除以下不同外，其余与上述实例6相同，考察催化剂重复性实验结果。从图中可以看出离子液体回收后，可以不必处理即可重复利用，活性略有下降，可以补充少量离子液体提高其活性。Embodiment 9: Except for the following differences, all the others are the same as the above-mentioned Example 6, and investigate the catalyst repeatability experiment results. It can be seen from the figure that after the ionic liquid is recovered, it can be reused without treatment, and the activity is slightly reduced, and a small amount of ionic liquid can be added to improve its activity.
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