TWI494299B - 具有多階段冷凝之醛製造方法 - Google Patents
具有多階段冷凝之醛製造方法 Download PDFInfo
- Publication number
- TWI494299B TWI494299B TW103104236A TW103104236A TWI494299B TW I494299 B TWI494299 B TW I494299B TW 103104236 A TW103104236 A TW 103104236A TW 103104236 A TW103104236 A TW 103104236A TW I494299 B TWI494299 B TW I494299B
- Authority
- TW
- Taiwan
- Prior art keywords
- liquid
- stream
- gas
- condenser
- stage
- Prior art date
Links
- 238000009833 condensation Methods 0.000 title description 16
- 230000005494 condensation Effects 0.000 title description 16
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- 239000007788 liquid Substances 0.000 claims description 198
- 150000001336 alkenes Chemical class 0.000 claims description 73
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 58
- 238000007037 hydroformylation reaction Methods 0.000 claims description 37
- 239000000047 product Substances 0.000 claims description 36
- 150000001299 aldehydes Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 32
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 238000003786 synthesis reaction Methods 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 14
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical group CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 5
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical group CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 239000007789 gas Substances 0.000 description 49
- 238000011084 recovery Methods 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000011017 operating method Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- -1 hydrogen olefin Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LGAQJENWWYGFSN-PLNGDYQASA-N (z)-4-methylpent-2-ene Chemical compound C\C=C/C(C)C LGAQJENWWYGFSN-PLNGDYQASA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UQMDOROEIVUWCP-UHFFFAOYSA-N [C].CCCCC=C Chemical compound [C].CCCCC=C UQMDOROEIVUWCP-UHFFFAOYSA-N 0.000 description 1
- FSHNFAOXXJLGJE-UHFFFAOYSA-N [Rh].[P] Chemical compound [Rh].[P] FSHNFAOXXJLGJE-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012360 testing method 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/002—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by condensation
-
- 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
- C07C45/505—Asymmetric hydroformylation
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361817506P | 2013-04-30 | 2013-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201441184A TW201441184A (zh) | 2014-11-01 |
| TWI494299B true TWI494299B (zh) | 2015-08-01 |
Family
ID=49622918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103104236A TWI494299B (zh) | 2013-04-30 | 2014-02-10 | 具有多階段冷凝之醛製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9340480B2 (enExample) |
| EP (1) | EP2991957B2 (enExample) |
| JP (1) | JP6357223B2 (enExample) |
| CN (1) | CN105164094B (enExample) |
| PL (1) | PL2991957T5 (enExample) |
| TW (1) | TWI494299B (enExample) |
| WO (1) | WO2014178912A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6357223B2 (ja) | 2013-04-30 | 2018-07-11 | オクシア・コーポレーション | 多段凝縮を用いるアルデヒド製造方法 |
| MX2018010980A (es) * | 2016-03-18 | 2018-11-15 | Dow Technology Investments Llc | Proceso de hidroformilacion. |
| CN120166986A (zh) * | 2023-10-16 | 2025-06-17 | 株式会社Lg化学 | 制备醛的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3379768A (en) * | 1965-06-01 | 1968-04-23 | Koppers Co Inc | Method of producing hydratropic aldehyde |
| CN1333201A (zh) * | 2000-07-14 | 2002-01-30 | 奥克森诺奥勒芬化学股份有限公司 | 羰基合成醛和/或醇的多级制备方法 |
| EP2220017A1 (de) * | 2007-12-20 | 2010-08-25 | Evonik Oxeno GmbH | Mehrstufiges kontinuierliches verfahren zur hydroformylierung von höheren olefinen oder olefingemischen |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4148830A (en) | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| EP0016285B2 (en) † | 1979-03-21 | 1986-03-05 | DAVY McKEE (LONDON) LIMITED | Process for the production of valeraldehydes by hydroformylation of butene-1 |
| DE3114147A1 (de) † | 1981-04-08 | 1982-10-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von aldehyden |
| DE3412336C2 (de) † | 1984-04-03 | 1994-03-31 | Hoechst Ag | Verfahren zur Hydroformylierung von Propylen |
| US4593127A (en) | 1985-01-11 | 1986-06-03 | Union Carbide Corporation | Hydroformylation process |
| US4640743A (en) | 1985-04-24 | 1987-02-03 | Shell Oil Company | Multi-stage condensation process |
| US4827043A (en) * | 1988-01-22 | 1989-05-02 | Eastman Kodak Company | Impurity removal from carbon monoxide and/or hydrogen-containing streams |
| JP2893902B2 (ja) | 1989-10-19 | 1999-05-24 | 三菱化学株式会社 | オレフィンのヒドロホルミル化法 |
| US5087763A (en) | 1990-11-09 | 1992-02-11 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| US5367106A (en) | 1993-09-20 | 1994-11-22 | Hoechst Celanese Corporation | Coupled secondary oxo reaction system |
| US5361589A (en) * | 1994-02-04 | 1994-11-08 | Air Products And Chemicals, Inc. | Precooling for ethylene recovery in dual demethanizer fractionation systems |
| JPH0899930A (ja) * | 1994-10-03 | 1996-04-16 | Mitsubishi Chem Corp | テレフタル酸の製造方法 |
| US5648553A (en) | 1994-12-09 | 1997-07-15 | Mitsubishi Chemical Corporation | Method for producing aldehydes |
| JP4080555B2 (ja) * | 1994-12-09 | 2008-04-23 | 三菱化学株式会社 | アルデヒド類の製造方法 |
| FR2735989B1 (fr) * | 1995-06-29 | 1997-08-14 | Rhone Poulenc Nutrition Animal | Procede et installation de purification d'un flux gazeux contenant de l'acroleine |
| JP2001342164A (ja) * | 2000-03-30 | 2001-12-11 | Mitsubishi Chemicals Corp | アルデヒド類の製造方法 |
| JP2001342162A (ja) * | 2000-03-30 | 2001-12-11 | Mitsubishi Chemicals Corp | アルデヒド類の製造法 |
| JP3864668B2 (ja) * | 2000-05-01 | 2007-01-10 | 三菱化学株式会社 | アルデヒド類の製造方法 |
| DE102008002187A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von C5-Aldehydgemischen mit hohem n-Pentanalanteil |
| CN202148269U (zh) | 2011-07-08 | 2012-02-22 | 南京荣欣化工有限公司 | 一种氢甲酰化反应中有机相的分离装置 |
| JP6357223B2 (ja) | 2013-04-30 | 2018-07-11 | オクシア・コーポレーション | 多段凝縮を用いるアルデヒド製造方法 |
-
2013
- 2013-11-11 JP JP2016511723A patent/JP6357223B2/ja active Active
- 2013-11-11 PL PL13793050T patent/PL2991957T5/pl unknown
- 2013-11-11 EP EP13793050.9A patent/EP2991957B2/en active Active
- 2013-11-11 CN CN201380076052.0A patent/CN105164094B/zh active Active
- 2013-11-11 US US14/782,694 patent/US9340480B2/en active Active
- 2013-11-11 WO PCT/US2013/069382 patent/WO2014178912A1/en not_active Ceased
-
2014
- 2014-02-10 TW TW103104236A patent/TWI494299B/zh active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3379768A (en) * | 1965-06-01 | 1968-04-23 | Koppers Co Inc | Method of producing hydratropic aldehyde |
| CN1333201A (zh) * | 2000-07-14 | 2002-01-30 | 奥克森诺奥勒芬化学股份有限公司 | 羰基合成醛和/或醇的多级制备方法 |
| EP2220017A1 (de) * | 2007-12-20 | 2010-08-25 | Evonik Oxeno GmbH | Mehrstufiges kontinuierliches verfahren zur hydroformylierung von höheren olefinen oder olefingemischen |
Also Published As
| Publication number | Publication date |
|---|---|
| US20160068460A1 (en) | 2016-03-10 |
| JP6357223B2 (ja) | 2018-07-11 |
| EP2991957B2 (en) | 2020-02-19 |
| TW201441184A (zh) | 2014-11-01 |
| WO2014178912A1 (en) | 2014-11-06 |
| JP2016520579A (ja) | 2016-07-14 |
| CN105164094A (zh) | 2015-12-16 |
| EP2991957A1 (en) | 2016-03-09 |
| US9340480B2 (en) | 2016-05-17 |
| EP2991957B1 (en) | 2017-04-26 |
| PL2991957T5 (pl) | 2020-08-10 |
| CN105164094B (zh) | 2016-10-12 |
| PL2991957T3 (pl) | 2017-08-31 |
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