CN113292423A - Synthesis method of o-methyl cyclohexyl acetate - Google Patents
Synthesis method of o-methyl cyclohexyl acetate Download PDFInfo
- Publication number
- CN113292423A CN113292423A CN202110605025.4A CN202110605025A CN113292423A CN 113292423 A CN113292423 A CN 113292423A CN 202110605025 A CN202110605025 A CN 202110605025A CN 113292423 A CN113292423 A CN 113292423A
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- China
- Prior art keywords
- synthesis
- acetate
- methyl cyclohexyl
- cyclohexyl acetate
- synthesis method
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- -1 o-methyl cyclohexyl Chemical group 0.000 title claims abstract description 10
- 238000001308 synthesis method Methods 0.000 title abstract description 7
- 230000035484 reaction time Effects 0.000 claims abstract description 9
- 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 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 14
- AKIIJALHGMKJEJ-UHFFFAOYSA-N (2-methylcyclohexyl) acetate Chemical compound CC1CCCCC1OC(C)=O AKIIJALHGMKJEJ-UHFFFAOYSA-N 0.000 claims description 11
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 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
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 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
- 239000000126 substance Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 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
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 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
- 238000003756 stirring Methods 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to the field of chemical industry, and discloses a synthesis method of o-methyl cyclohexyl acetate. The synthesis method of o-methyl cyclohexyl acetate greatly shortens the reaction time by sulfonic acid catalysts, and the obtained product has high purity.
Description
Technical Field
The invention relates to the field of chemical industry, in particular to a synthesis method of o-methyl cyclohexyl acetate.
Background
At present, most of hydrogen peroxide is produced by an anthraquinone method. However, the production of hydrogen peroxide by the anthraquinone process suffers from low yield and poor product quality. Therefore, the method for solving the performance problem of the working solution is an important method for improving the yield of the hydrogen peroxide.
By adding 2-MCA into the working solution, the performance of the working solution can be effectively improved. The synthesis of o-methylcyclohexyl acetates from acetic anhydride and o-methylcyclohexanol is known.
Chinese patent (published: 10/13/2004, publication No. CN1240663C) discloses a preparation method of o-methylcyclohexyl acetate, wherein a catalyst for synthesizing 2-MCA is trimethylchlorosilane (CTMS), and the CTMS is used to reduce the operation risk coefficient, but the reaction time is too long, and the yield is low.
Therefore, a catalyst with good catalytic effect and low risk coefficient is urgently needed to improve the synthesis process of 2-MCA, so as to improve the reaction efficiency and shorten the reaction time.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for synthesizing o-methylcyclohexyl acetate, which greatly shortens the reaction time by using a sulfonic acid catalyst and obtains a product with high purity.
In order to achieve the purpose, the synthesis method of the o-methyl cyclohexyl acetate provided by the invention comprises the step of reacting o-methyl cyclohexanol with acetic anhydride under the catalysis of a sulfonic acid catalyst to generate the o-methyl cyclohexyl acetate.
Preferably, the sulfonic acid-based catalyst includes methanesulfonic acid, p-toluenesulfonic acid, benzenesulfonic acid, and trifluoromethanesulfonic acid.
Preferably, the reaction temperature is 30-60 ℃.
Preferably, the reaction time is 1 to 3 hours.
Preferably, the molar ratio of the o-methyl cyclohexanol to the acetic anhydride is 1: 1.0 to 1.5.
Preferably, the dosage of the sulfonic acid catalyst is 0.01-0.1% of the mass of the o-methylcyclohexanol.
Compared with the prior art, the invention has the following advantages:
1. simple operation, high catalytic efficiency and low catalyst consumption;
2. the yield of the finally obtained product is more than 98 percent, and the purity of the obtained product is high;
3. compared with the prior catalyst, the catalyst has more development potential and process prospect.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
Example 1
50 g of o-methylcyclohexanol and 52.7 g of acetic anhydride are added into a reactor, 0.005 g of trifluoromethanesulfonic acid is added into the reactor, the reaction temperature is controlled at 50 ℃, the reaction time is 2 hours, and the yield of o-methylcyclohexyl acetate is 98%.
Example 2
50 g of o-methylcyclohexanol and 57.9 g of acetic anhydride are added into a reactor, 0.025 g of trifluoromethanesulfonic acid is added into the reactor, the reaction temperature is controlled at 60 ℃, the reaction time is 2 hours, and the yield of o-methylcyclohexyl acetate is 98%.
Example 3
50 g of o-methylcyclohexanol and 57.9 g of acetic anhydride are charged into a reactor, 0.05 g of p-toluenesulfonic acid is charged into the reactor, and stirring is carried out until it is dissolved. The reaction temperature is controlled at 60 ℃, the reaction time is 2 hours, and the yield of the o-methylcyclohexyl acetate is 99 percent.
The synthesis method of o-methyl cyclohexyl acetate has the advantages of simple and convenient operation, high catalytic efficiency and low catalyst consumption; the yield of the finally obtained product is more than 98 percent, and the purity of the obtained product is high; compared with the prior catalyst, the catalyst has more development potential and process prospect.
Claims (6)
1. A method for synthesizing o-methyl cyclohexyl acetate is characterized in that: the o-methyl cyclohexanol and acetic anhydride react under the catalysis of sulfonic acid catalyst to produce o-methyl cyclohexyl acetate.
2. The process for the synthesis of o-methylcyclohexyl acetate as claimed in claim 1, wherein: the sulfonic acid catalyst includes methanesulfonic acid, p-toluenesulfonic acid, benzenesulfonic acid and trifluoromethanesulfonic acid.
3. The process for the synthesis of o-methylcyclohexyl acetate as claimed in claim 1, wherein: the reaction temperature is 30-60 ℃.
4. The process for the synthesis of o-methylcyclohexyl acetate as claimed in claim 1, wherein: the reaction time is 1-3 hours.
5. The process for the synthesis of o-methylcyclohexyl acetate as claimed in claim 1, wherein: the mol ratio of the o-methyl cyclohexanol to the acetic anhydride is 1: 1.0 to 1.5.
6. The process for the synthesis of o-methylcyclohexyl acetate as claimed in claim 1, wherein: the dosage of the sulfonic acid catalyst is 0.01-0.1% of the mass of the o-methylcyclohexanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110605025.4A CN113292423B (en) | 2021-05-31 | 2021-05-31 | Synthesis method of o-methyl cyclohexyl acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110605025.4A CN113292423B (en) | 2021-05-31 | 2021-05-31 | Synthesis method of o-methyl cyclohexyl acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113292423A true CN113292423A (en) | 2021-08-24 |
| CN113292423B CN113292423B (en) | 2023-12-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110605025.4A Active CN113292423B (en) | 2021-05-31 | 2021-05-31 | Synthesis method of o-methyl cyclohexyl acetate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113292423B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050010065A1 (en) * | 2001-11-15 | 2005-01-13 | Alexander Wartini | Method for producing (meth) acrylic acid esters of polyhydric alcohols |
| CN104557526A (en) * | 2014-11-27 | 2015-04-29 | 浙江金科过氧化物股份有限公司 | Method for preparing ortho-methylcyclohexyl acetate under solvent-free conditions |
| CN105315156A (en) * | 2014-07-31 | 2016-02-10 | 广西田东达盛化工科技有限公司 | Synthesis method for 2-methylcyclohexyl acetate |
-
2021
- 2021-05-31 CN CN202110605025.4A patent/CN113292423B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050010065A1 (en) * | 2001-11-15 | 2005-01-13 | Alexander Wartini | Method for producing (meth) acrylic acid esters of polyhydric alcohols |
| CN105315156A (en) * | 2014-07-31 | 2016-02-10 | 广西田东达盛化工科技有限公司 | Synthesis method for 2-methylcyclohexyl acetate |
| CN104557526A (en) * | 2014-11-27 | 2015-04-29 | 浙江金科过氧化物股份有限公司 | Method for preparing ortho-methylcyclohexyl acetate under solvent-free conditions |
Non-Patent Citations (4)
| Title |
|---|
| 向德轩 等: "甲基丙烯酸八氟戊酯的合成", 《精细石油化工》 * |
| 周扬志 等: "三氟甲磺酸催化合成柠檬酸酯", 《现代化工》 * |
| 李玉文 等: "三氟甲磺酸催化合成阿司匹林", 《应用化工》 * |
| 李玉文: "三氟甲磺酸催化便捷高效合成2,4-滴丁酯除草剂", 《应用化工》 * |
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| Publication number | Publication date |
|---|---|
| CN113292423B (en) | 2023-12-12 |
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