CN105439834B - α,β‑环氧羧酸酯连续水解制备C14醛的装置和方法 - Google Patents
α,β‑环氧羧酸酯连续水解制备C14醛的装置和方法 Download PDFInfo
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- CN105439834B CN105439834B CN201410390651.6A CN201410390651A CN105439834B CN 105439834 B CN105439834 B CN 105439834B CN 201410390651 A CN201410390651 A CN 201410390651A CN 105439834 B CN105439834 B CN 105439834B
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- Prior art keywords
- raw material
- alkali lye
- aldehyde
- tower
- hydrolysis
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims abstract description 43
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 34
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 31
- 150000002148 esters Chemical class 0.000 title abstract description 5
- 239000004593 Epoxy Substances 0.000 title abstract 5
- 150000001735 carboxylic acids Chemical class 0.000 title abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000003513 alkali Substances 0.000 claims abstract description 67
- 239000002994 raw material Substances 0.000 claims abstract description 61
- 239000002351 wastewater Substances 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 230000005484 gravity Effects 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 140
- -1 epoxide carboxylate Chemical class 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 238000004821 distillation Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000003208 petroleum Substances 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 230000003472 neutralizing effect Effects 0.000 claims description 6
- 239000002699 waste material Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 4
- 230000008676 import Effects 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- FFIDVTCKFVYQCZ-UHFFFAOYSA-N 1,3,3-trimethylcyclohexene Chemical compound CC1=CC(C)(C)CCC1 FFIDVTCKFVYQCZ-UHFFFAOYSA-N 0.000 claims description 3
- YKNYRRVISWJDSR-UHFFFAOYSA-N methyl oxirane-2-carboxylate Chemical class COC(=O)C1CO1 YKNYRRVISWJDSR-UHFFFAOYSA-N 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 238000012805 post-processing Methods 0.000 claims description 2
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 3
- 238000012545 processing Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 24
- 238000000605 extraction Methods 0.000 abstract description 4
- 238000010931 ester hydrolysis Methods 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 60
- 150000007942 carboxylates Chemical class 0.000 description 22
- 150000002924 oxiranes Chemical class 0.000 description 22
- 239000012071 phase Substances 0.000 description 21
- 239000012043 crude product Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 3
- 235000019155 vitamin A Nutrition 0.000 description 3
- 239000011719 vitamin A Substances 0.000 description 3
- 229940045997 vitamin a Drugs 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- 238000003476 Darzens condensation reaction Methods 0.000 description 1
- 229930183419 Irisone Natural products 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 201000000909 keratomalacia Diseases 0.000 description 1
- WOCOGWMEEYJGLH-CSKARUKUSA-N methyl 3-methyl-3-[(e)-2-(2,6,6-trimethylcyclohex-2-en-1-yl)ethenyl]oxirane-2-carboxylate Chemical compound COC(=O)C1OC1(C)\C=C\C1C(C)(C)CCC=C1C WOCOGWMEEYJGLH-CSKARUKUSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN201410390651.6A CN105439834B (zh) | 2014-08-08 | 2014-08-08 | α,β‑环氧羧酸酯连续水解制备C14醛的装置和方法 |
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CN201410390651.6A CN105439834B (zh) | 2014-08-08 | 2014-08-08 | α,β‑环氧羧酸酯连续水解制备C14醛的装置和方法 |
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CN105439834A CN105439834A (zh) | 2016-03-30 |
CN105439834B true CN105439834B (zh) | 2018-02-13 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2987550A (en) * | 1958-09-25 | 1961-06-06 | Pfizer & Co C | Process for the manufacture of c14 aldehyde |
US3246038A (en) * | 1961-05-05 | 1966-04-12 | Bayer Ag | Process for the production of 4-[2', 6', 6'-trimethylcyclohexen-(1')-yl]-2-methylbuten-(3)-al |
CN1348947A (zh) * | 2000-10-18 | 2002-05-15 | 浙江新和成股份有限公司 | 维生素a中间体的制备工艺 |
CN101892126A (zh) * | 2010-04-14 | 2010-11-24 | 江苏永林油脂化工有限公司 | 一种植物油脂酸化油连续水解的方法 |
-
2014
- 2014-08-08 CN CN201410390651.6A patent/CN105439834B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2987550A (en) * | 1958-09-25 | 1961-06-06 | Pfizer & Co C | Process for the manufacture of c14 aldehyde |
US3246038A (en) * | 1961-05-05 | 1966-04-12 | Bayer Ag | Process for the production of 4-[2', 6', 6'-trimethylcyclohexen-(1')-yl]-2-methylbuten-(3)-al |
CN1348947A (zh) * | 2000-10-18 | 2002-05-15 | 浙江新和成股份有限公司 | 维生素a中间体的制备工艺 |
CN101892126A (zh) * | 2010-04-14 | 2010-11-24 | 江苏永林油脂化工有限公司 | 一种植物油脂酸化油连续水解的方法 |
Non-Patent Citations (1)
Title |
---|
油脂连续高压水解制备脂肪酸的工艺和技术;忻耀年等;《中国油脂》;20021231;第27卷(第6期);55-57 * |
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CN105439834A (zh) | 2016-03-30 |
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Application publication date: 20160330 Assignee: ZHEJIANG NHU SPECIAL MATERIALS Co.,Ltd. Assignor: SHANGYU NHU BIO-CHEM Co.,Ltd. Contract record no.: X2023980043740 Denomination of invention: a,b- Device and Method for Continuous Hydrolysis of Epoxy Carboxylate Esters to Prepare C14 Aldehydes Granted publication date: 20180213 License type: Common License Record date: 20231019 Application publication date: 20160330 Assignee: ZHEJIANG NHU PHARMACEUTICAL Co.,Ltd. Assignor: SHANGYU NHU BIO-CHEM Co.,Ltd. Contract record no.: X2023980043734 Denomination of invention: a,b- Device and Method for Continuous Hydrolysis of Epoxy Carboxylate Esters to Prepare C14 Aldehydes Granted publication date: 20180213 License type: Common License Record date: 20231019 |
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