DE112019002562B4 - Verfahren zur Herstellung von ungesättigten Ketonen - Google Patents
Verfahren zur Herstellung von ungesättigten Ketonen Download PDFInfo
- Publication number
- DE112019002562B4 DE112019002562B4 DE112019002562.7T DE112019002562T DE112019002562B4 DE 112019002562 B4 DE112019002562 B4 DE 112019002562B4 DE 112019002562 T DE112019002562 T DE 112019002562T DE 112019002562 B4 DE112019002562 B4 DE 112019002562B4
- Authority
- DE
- Germany
- Prior art keywords
- unsaturated ketones
- acidic resin
- preparation
- methanol
- unsaturated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 150000002576 ketones Chemical class 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 42
- 239000011347 resin Substances 0.000 claims abstract description 41
- 229920005989 resin Polymers 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims abstract description 5
- -1 alkyl tributyl ammonium chloride Chemical group 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 83
- 239000003054 catalyst Substances 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 230000004048 modification Effects 0.000 claims description 7
- 238000012986 modification Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003607 modifier Substances 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003729 cation exchange resin Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 9
- 239000000243 solution Substances 0.000 description 18
- 238000005984 hydrogenation reaction Methods 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical group COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000006555 catalytic reaction Methods 0.000 description 7
- ZNVPGYAGXVEAFP-SDNWHVSQSA-N (6e)-3,7,11-trimethyldodeca-6,10-dien-1-yn-3-ol Chemical compound CC(C)=CCC\C(C)=C\CCC(C)(O)C#C ZNVPGYAGXVEAFP-SDNWHVSQSA-N 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical group [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003186 propargylic group Chemical group 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- FSGHEPDRMHVUCQ-UHFFFAOYSA-N 2-ethoxyprop-1-ene Chemical group CCOC(C)=C FSGHEPDRMHVUCQ-UHFFFAOYSA-N 0.000 description 1
- FKTLISWEAOSVBS-UHFFFAOYSA-N 2-prop-1-en-2-yloxyprop-1-ene Chemical compound CC(=C)OC(C)=C FKTLISWEAOSVBS-UHFFFAOYSA-N 0.000 description 1
- LGSXJEDIGQMTRC-UHFFFAOYSA-N 6,10,14-trimethylpentadeca-3,5-dien-2-one Chemical compound CC(C)CCCC(C)CCCC(C)=CC=CC(C)=O LGSXJEDIGQMTRC-UHFFFAOYSA-N 0.000 description 1
- KOEOXTZSYDFLAC-UHFFFAOYSA-N 6,10,14-trimethylpentadeca-4,5-dien-2-one Chemical compound CC(C)CCCC(C)CCCC(C)=C=CCC(C)=O KOEOXTZSYDFLAC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JPTOCTSNXXKSSN-UHFFFAOYSA-N methylheptenone Chemical compound CCCC=CC(=O)CC JPTOCTSNXXKSSN-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910001843.6A CN109503342B (zh) | 2019-01-02 | 2019-01-02 | 一种不饱和酮的制备方法 |
| CN201910001843.6 | 2019-01-02 | ||
| PCT/CN2019/095192 WO2020140414A1 (zh) | 2019-01-02 | 2019-07-09 | 一种不饱和酮的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE112019002562T5 DE112019002562T5 (de) | 2021-02-25 |
| DE112019002562B4 true DE112019002562B4 (de) | 2023-03-02 |
Family
ID=65757252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE112019002562.7T Active DE112019002562B4 (de) | 2019-01-02 | 2019-07-09 | Verfahren zur Herstellung von ungesättigten Ketonen |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN109503342B (zh) |
| DE (1) | DE112019002562B4 (zh) |
| WO (1) | WO2020140414A1 (zh) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503342B (zh) * | 2019-01-02 | 2019-11-12 | 山东新和成维生素有限公司 | 一种不饱和酮的制备方法 |
| CN110227512B (zh) * | 2019-06-17 | 2022-01-07 | 万华化学集团股份有限公司 | 一种用于Saucy-Marbet反应制备不饱和酮的催化剂的制法及其应用 |
| CN111039769B (zh) * | 2019-12-18 | 2023-01-13 | 万华化学集团股份有限公司 | 一种甲基丁炔醇合成甲基庚烯酮的方法 |
| CN114149310A (zh) * | 2021-11-23 | 2022-03-08 | 万华化学(四川)有限公司 | 一种不饱和酮的制备方法 |
| CN114950535B (zh) * | 2022-05-18 | 2023-12-19 | 万华化学集团股份有限公司 | 一种固体酸催化剂的制备方法及其在不饱和酮合成中的应用 |
| CN114933518B (zh) * | 2022-06-16 | 2023-11-28 | 山东新和成药业有限公司 | 一种乙基庚烯酮的合成方法及杂多酸催化剂的应用 |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029287A (en) | 1958-08-01 | 1962-04-10 | Hoffmann La Roche | Preparation of unsaturated ketones |
| US5113021A (en) | 1989-09-21 | 1992-05-12 | Givaudan Corporation | Process for the manufacture of a mixture of α- and β-irone |
| US6184420B1 (en) | 1997-09-10 | 2001-02-06 | Basf Aktiengesellschaft | Preparation of unsaturated ketones |
| US6380437B1 (en) | 1999-10-15 | 2002-04-30 | Degussa Ag | Process for the preparation of unsaturated 4,5-allene ketones, 3,5-diene ketones and the corresponding saturated ketones |
| US6586635B2 (en) | 2001-04-28 | 2003-07-01 | Degussa Ag | Process for the preparation of unsaturated ketones |
| CN100392045C (zh) | 2006-02-20 | 2008-06-04 | 周千淇 | 一种采用固定床气相酯化制备脂肪酸甲酯的方法 |
| WO2010046199A2 (en) | 2008-10-21 | 2010-04-29 | Dsm Ip Assets B.V. | Manufacture of gamma-delta-unsaturated ketones |
| CN101723828A (zh) | 2008-10-27 | 2010-06-09 | 谷长安 | 一种连续酯化制备己酸乙酯的方法 |
| CN204509222U (zh) | 2015-03-24 | 2015-07-29 | 浙江大学 | 一种具有焦油降解功能的u型固定床气化-催化反应装置 |
| CN105154239A (zh) | 2015-07-28 | 2015-12-16 | 宜春大海龟生命科学有限公司 | 一种植物油脱臭馏出物固定床连续酯化的方法 |
| CN106917163A (zh) | 2017-03-13 | 2017-07-04 | 中国科学院过程工程研究所 | 一种碳氢化合物裂解制备碳纤维的反应系统及其处理方法和用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2109597A1 (en) * | 2007-01-30 | 2009-10-21 | DSM IP Assets B.V. | Process for preparing dienones |
| CN109503342B (zh) * | 2019-01-02 | 2019-11-12 | 山东新和成维生素有限公司 | 一种不饱和酮的制备方法 |
-
2019
- 2019-01-02 CN CN201910001843.6A patent/CN109503342B/zh active Active
- 2019-07-09 DE DE112019002562.7T patent/DE112019002562B4/de active Active
- 2019-07-09 WO PCT/CN2019/095192 patent/WO2020140414A1/zh active Application Filing
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029287A (en) | 1958-08-01 | 1962-04-10 | Hoffmann La Roche | Preparation of unsaturated ketones |
| US5113021A (en) | 1989-09-21 | 1992-05-12 | Givaudan Corporation | Process for the manufacture of a mixture of α- and β-irone |
| US6184420B1 (en) | 1997-09-10 | 2001-02-06 | Basf Aktiengesellschaft | Preparation of unsaturated ketones |
| US6380437B1 (en) | 1999-10-15 | 2002-04-30 | Degussa Ag | Process for the preparation of unsaturated 4,5-allene ketones, 3,5-diene ketones and the corresponding saturated ketones |
| US6586635B2 (en) | 2001-04-28 | 2003-07-01 | Degussa Ag | Process for the preparation of unsaturated ketones |
| CN100392045C (zh) | 2006-02-20 | 2008-06-04 | 周千淇 | 一种采用固定床气相酯化制备脂肪酸甲酯的方法 |
| WO2010046199A2 (en) | 2008-10-21 | 2010-04-29 | Dsm Ip Assets B.V. | Manufacture of gamma-delta-unsaturated ketones |
| CN101723828A (zh) | 2008-10-27 | 2010-06-09 | 谷长安 | 一种连续酯化制备己酸乙酯的方法 |
| CN204509222U (zh) | 2015-03-24 | 2015-07-29 | 浙江大学 | 一种具有焦油降解功能的u型固定床气化-催化反应装置 |
| CN105154239A (zh) | 2015-07-28 | 2015-12-16 | 宜春大海龟生命科学有限公司 | 一种植物油脱臭馏出物固定床连续酯化的方法 |
| CN106917163A (zh) | 2017-03-13 | 2017-07-04 | 中国科学院过程工程研究所 | 一种碳氢化合物裂解制备碳纤维的反应系统及其处理方法和用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020140414A1 (zh) | 2020-07-09 |
| CN109503342A (zh) | 2019-03-22 |
| DE112019002562T5 (de) | 2021-02-25 |
| CN109503342B (zh) | 2019-11-12 |
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| R020 | Patent grant now final |