CN105777509A - 一种基于膦功能化聚醚吡啶盐离子液体的烯烃两相氢甲酰化高选择性制备正构醛的方法 - Google Patents
一种基于膦功能化聚醚吡啶盐离子液体的烯烃两相氢甲酰化高选择性制备正构醛的方法 Download PDFInfo
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- CN105777509A CN105777509A CN201610164775.1A CN201610164775A CN105777509A CN 105777509 A CN105777509 A CN 105777509A CN 201610164775 A CN201610164775 A CN 201610164775A CN 105777509 A CN105777509 A CN 105777509A
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- Prior art keywords
- phase
- ionic liquid
- alkene
- rhodium catalyst
- polyethers
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims abstract description 57
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 44
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 44
- 229920000570 polyether Polymers 0.000 title claims abstract description 33
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000007788 liquid Substances 0.000 title abstract description 20
- 239000004721 Polyphenylene oxide Substances 0.000 title abstract 4
- 239000010948 rhodium Substances 0.000 claims abstract description 79
- 238000006243 chemical reaction Methods 0.000 claims abstract description 65
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 65
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000003054 catalyst Substances 0.000 claims abstract description 62
- 239000000758 substrate Substances 0.000 claims abstract description 13
- 239000012071 phase Substances 0.000 claims description 89
- 239000002608 ionic liquid Substances 0.000 claims description 83
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical group [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 claims description 53
- 239000012074 organic phase Substances 0.000 claims description 37
- 230000015572 biosynthetic process Effects 0.000 claims description 25
- 238000003786 synthesis reaction Methods 0.000 claims description 25
- 238000007306 functionalization reaction Methods 0.000 claims description 23
- 238000006555 catalytic reaction Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 230000035484 reaction time Effects 0.000 claims description 13
- 239000012298 atmosphere Substances 0.000 claims description 12
- 238000011084 recovery Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- -1 C6-C12Alkane Chemical compound 0.000 claims description 4
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005466 alkylenyl group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 claims description 4
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 2
- 230000002051 biphasic effect Effects 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 abstract description 15
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000005191 phase separation Methods 0.000 abstract 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 110
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 55
- 239000007789 gas Substances 0.000 description 41
- 238000004587 chromatography analysis Methods 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- 238000002512 chemotherapy Methods 0.000 description 14
- 239000011734 sodium Substances 0.000 description 12
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 229910001220 stainless steel Inorganic materials 0.000 description 10
- 239000010935 stainless steel Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 4
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical group CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 3
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 0 *(*1)*1C1C=C**1 Chemical compound *(*1)*1C1C=C**1 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 2
- 238000007172 homogeneous catalysis Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
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CN201610164775.1A CN105777509B (zh) | 2016-03-19 | 2016-03-19 | 一种基于膦功能化聚醚吡啶盐离子液体的烯烃两相氢甲酰化高选择性制备正构醛的方法 |
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CN201610164775.1A CN105777509B (zh) | 2016-03-19 | 2016-03-19 | 一种基于膦功能化聚醚吡啶盐离子液体的烯烃两相氢甲酰化高选择性制备正构醛的方法 |
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CN105777509A true CN105777509A (zh) | 2016-07-20 |
CN105777509B CN105777509B (zh) | 2018-10-12 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102260147A (zh) * | 2011-06-01 | 2011-11-30 | 中国科学院过程工程研究所 | 一种在离子液体溶剂中烯烃氢甲酰化反应的方法 |
CN103483381A (zh) * | 2013-08-22 | 2014-01-01 | 青岛科技大学 | 一类膦功能化离子液体的制备及其在氢甲酰化反应中的应用 |
CN103570514A (zh) * | 2013-10-07 | 2014-02-12 | 青岛科技大学 | 一种均相催化-两相分离烯烃氢甲酰化的方法 |
CN105001260A (zh) * | 2015-05-16 | 2015-10-28 | 青岛科技大学 | 一类膦功能化聚醚吗啉盐离子液体及其在烯烃氢甲酰化反应中的应用 |
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2016
- 2016-03-19 CN CN201610164775.1A patent/CN105777509B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102260147A (zh) * | 2011-06-01 | 2011-11-30 | 中国科学院过程工程研究所 | 一种在离子液体溶剂中烯烃氢甲酰化反应的方法 |
CN103483381A (zh) * | 2013-08-22 | 2014-01-01 | 青岛科技大学 | 一类膦功能化离子液体的制备及其在氢甲酰化反应中的应用 |
CN103570514A (zh) * | 2013-10-07 | 2014-02-12 | 青岛科技大学 | 一种均相催化-两相分离烯烃氢甲酰化的方法 |
CN105001260A (zh) * | 2015-05-16 | 2015-10-28 | 青岛科技大学 | 一类膦功能化聚醚吗啉盐离子液体及其在烯烃氢甲酰化反应中的应用 |
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