CN114456072A - 一种3-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯的制备方法 - Google Patents
一种3-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯的制备方法 Download PDFInfo
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- CN114456072A CN114456072A CN202210204927.1A CN202210204927A CN114456072A CN 114456072 A CN114456072 A CN 114456072A CN 202210204927 A CN202210204927 A CN 202210204927A CN 114456072 A CN114456072 A CN 114456072A
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- tert
- hydroxyphenyl
- butyl
- propionate
- methyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 229940017219 methyl propionate Drugs 0.000 title claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 49
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 17
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 16
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 16
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000007524 organic acids Chemical class 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 4
- PXMJCECEFTYEKE-UHFFFAOYSA-N Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester Chemical compound COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PXMJCECEFTYEKE-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- -1 trichlorobutylsilane methanol Chemical compound 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical compound CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical group [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical class [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 238000005086 pumping Methods 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000007086 side reaction Methods 0.000 abstract description 5
- 229920001971 elastomer Polymers 0.000 abstract description 3
- 239000005060 rubber Substances 0.000 abstract description 3
- 239000004597 plastic additive Substances 0.000 abstract description 2
- 238000004321 preservation Methods 0.000 abstract description 2
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- 239000003963 antioxidant agent Substances 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 229940031826 phenolate Drugs 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN116836367A (zh) * | 2023-08-09 | 2023-10-03 | 东莞市宏成新材料有限公司 | 一种异氰酸酯组合物及其制备方法 |
Citations (10)
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JPH05238989A (ja) * | 1992-02-28 | 1993-09-17 | Dainippon Ink & Chem Inc | アルキル−β−(3,5−ジアルキル−4−ヒドロキシフェニル)プロピオネートの製法 |
US20050192455A1 (en) * | 2004-02-27 | 2005-09-01 | Albemarle Corporation | Preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
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US20100210872A1 (en) * | 2009-02-13 | 2010-08-19 | Nan Ya Plastics Corporation | Method for making hindered phenolic antioxidant |
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WO2012158250A1 (en) * | 2011-05-13 | 2012-11-22 | Amyris, Inc. | Plasticizers |
CN104387274A (zh) * | 2014-11-21 | 2015-03-04 | 黄峰 | 一种β-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯的生产工艺 |
CN104910007A (zh) * | 2015-04-24 | 2015-09-16 | 新乡市瑞丰新材料股份有限公司 | 3-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯的合成工艺 |
CN109651438A (zh) * | 2019-01-31 | 2019-04-19 | 安徽顺利生物有限公司 | 一种改性氧化镁的制备及其在维生素c磷酸酯镁中的应用 |
-
2022
- 2022-03-02 CN CN202210204927.1A patent/CN114456072B/zh active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05238989A (ja) * | 1992-02-28 | 1993-09-17 | Dainippon Ink & Chem Inc | アルキル−β−(3,5−ジアルキル−4−ヒドロキシフェニル)プロピオネートの製法 |
US20050192455A1 (en) * | 2004-02-27 | 2005-09-01 | Albemarle Corporation | Preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
CN1733692A (zh) * | 2004-08-12 | 2006-02-15 | 天津市晨光化工有限公司 | β-(3.5-二叔丁基-4羟基苯基)丙酸十八醇酯的两步法工业合成方法 |
CA2573695A1 (en) * | 2006-01-25 | 2007-07-25 | Rohm And Haas Company | Encapsulated michael addition catalyst |
US20100210872A1 (en) * | 2009-02-13 | 2010-08-19 | Nan Ya Plastics Corporation | Method for making hindered phenolic antioxidant |
CN102476995A (zh) * | 2010-11-25 | 2012-05-30 | 中国石油化工股份有限公司 | 液体受阻酚羧酸酯抗氧剂的制备方法 |
WO2012158250A1 (en) * | 2011-05-13 | 2012-11-22 | Amyris, Inc. | Plasticizers |
CN104387274A (zh) * | 2014-11-21 | 2015-03-04 | 黄峰 | 一种β-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯的生产工艺 |
CN104910007A (zh) * | 2015-04-24 | 2015-09-16 | 新乡市瑞丰新材料股份有限公司 | 3-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯的合成工艺 |
CN109651438A (zh) * | 2019-01-31 | 2019-04-19 | 安徽顺利生物有限公司 | 一种改性氧化镁的制备及其在维生素c磷酸酯镁中的应用 |
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李燕芸, 刘霞, 刘颍, 李海军, 祝九娣: "3-(3, 5-二叔丁基-4-羟基苯基)丙酸甲酯的合成", 精细石油化工, no. 03, pages 1 - 3 * |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116836367A (zh) * | 2023-08-09 | 2023-10-03 | 东莞市宏成新材料有限公司 | 一种异氰酸酯组合物及其制备方法 |
CN116836367B (zh) * | 2023-08-09 | 2023-12-08 | 东莞市宏成新材料有限公司 | 一种异氰酸酯组合物及其制备方法 |
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