CN113292423B - 邻甲基环已基醋酸酯的合成方法 - Google Patents
邻甲基环已基醋酸酯的合成方法 Download PDFInfo
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- 238000001308 synthesis method Methods 0.000 title claims abstract description 9
- -1 o-methyl cyclohexyl Chemical group 0.000 title claims abstract description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000003377 acid catalyst Substances 0.000 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims abstract description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- AKIIJALHGMKJEJ-UHFFFAOYSA-N (2-methylcyclohexyl) acetate Chemical compound CC1CCCCC1OC(C)=O AKIIJALHGMKJEJ-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000012224 working solution Substances 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
- B01J31/0227—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
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- Engineering & Computer Science (AREA)
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明涉及化工领域，公开了一种邻甲基环已基醋酸酯的合成方法，将邻甲基环己醇和醋酸酐在磺酸类催化剂的催化条件下发生反应，生成邻甲基环己基醋酸酯。本发明邻甲基环已基醋酸酯的合成方法，通过磺酸类催化剂极大的缩短了反应时间，得到的产物纯度高。
Description
技术领域
本发明涉及化工领域，具体涉及一种邻甲基环已基醋酸酯的合成方法。
背景技术
目前，绝大部分双氧水由蒽醌法生产。但是，使用蒽醌法生产双氧水会遇到产量低、产品质量差的问题。因此解决工作液的性能问题就成为了提高双氧水产量的重要方法。
通过向工作液中加入2-MCA，可以有效的提高工作液的性能。以醋酸酐和邻甲基环己醇为原料合成邻甲基环已基醋酸酯是已知的。
中国专利(公开日：2004年10月13日、公开号：CN1240663C) 公开了公开了一种邻甲基环己基醋酸酯的制备方法，合成2-MCA的催化剂为三甲基氯硅烷(CTMS)，使用CTMS虽然减少了操作危险系数，但反应时间过长，产率低。
因此，急需一种催化效果好，同时危险系数低的催化剂来改善 2-MCA的合成工艺，以提高反应效率，缩短反应时间。
发明内容
本发明的目的就是针对上述技术的不足，提供一种邻甲基环已基醋酸酯的合成方法，通过磺酸类催化剂极大的缩短了反应时间，得到的产物纯度高。
为实现上述目的，本发明所设计的邻甲基环已基醋酸酯的合成方法，将邻甲基环己醇和醋酸酐在磺酸类催化剂的催化条件下发生反应，生成邻甲基环己基醋酸酯。
优选的，所述磺酸类催化剂包括甲磺酸、对甲苯磺酸、苯磺酸和三氟甲磺酸。
优选的，反应温度为30～60℃。
优选的，反应时间为1～3小时。
优选的，邻甲基环己醇和醋酸酐的摩尔比为1：1.0～1.5。
优选的，所述磺酸类催化剂用量为邻甲基环己醇质量的 0.01％～0.1％。
本发明与现有技术相比，具有以下优点：
1、操作简便，催化效率高，催化剂用量低的优势；
2、最终得到产物收率98％以上，得到的产物纯度高；
3、相比于以往的催化剂更具有发展潜力和工艺前景。
具体实施方式
下面结合具体实施例对本发明作进一步的详细说明。
实施例1
将50克邻甲基环己醇和52.7克醋酸酐加入到反应器中，取0.005 克三氟甲磺酸加入到反应器中，控制反应温度在50℃，反应时间2 小时，得到邻甲基环已基醋酸酯的产率为98％。
实施例2
将50克邻甲基环己醇和57.9克醋酸酐加入到反应器中，取0.025 克三氟甲磺酸加入到反应器中，控制反应温度为60℃，反应时间2 小时，得到邻甲基环已基醋酸酯的产率为98％。
实施例3
将50克邻甲基环己醇和57.9克醋酸酐加入到反应器中，取0.05 克对甲苯磺酸加入到反应器中，搅拌待其溶解。控制反应温度为60℃，反应时间2小时，得到邻甲基环已基醋酸酯的产率为99％。
本发明邻甲基环已基醋酸酯的合成方法，操作简便，催化效率高，催化剂用量低的优势；最终得到产物收率98％以上，得到的产物纯度高；相比于以往的催化剂更具有发展潜力和工艺前景。
Claims (1)
1.一种邻甲基环已基醋酸酯的合成方法，其特征在于：将邻甲基环己醇和醋酸酐在磺酸类催化剂的催化条件下发生反应，生成邻甲基环己基醋酸酯，所述磺酸类催化剂包括甲磺酸、对甲苯磺酸、苯磺酸和三氟甲磺酸，反应温度为30～60℃，反应时间为1～3小时，邻甲基环己醇和醋酸酐的摩尔比为1：1.0～1.5，所述磺酸类催化剂用量为邻甲基环己醇质量的0.01％～0.1％。
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Citations (2)
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|---|---|---|---|---|
| CN104557526A (zh) * | 2014-11-27 | 2015-04-29 | 浙江金科过氧化物股份有限公司 | 一种无溶剂制备邻甲基环己醋酸酯的方法 |
| CN105315156A (zh) * | 2014-07-31 | 2016-02-10 | 广西田东达盛化工科技有限公司 | 2-甲基环己基醋酸酯的合成方法 |
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| DE10156116A1 (de) * | 2001-11-15 | 2003-06-26 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern mehrwertiger Alkohole |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105315156A (zh) * | 2014-07-31 | 2016-02-10 | 广西田东达盛化工科技有限公司 | 2-甲基环己基醋酸酯的合成方法 |
| CN104557526A (zh) * | 2014-11-27 | 2015-04-29 | 浙江金科过氧化物股份有限公司 | 一种无溶剂制备邻甲基环己醋酸酯的方法 |
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