JP2013515058A - シンガス分圧を制御することによる、混合配位子ヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 - Google Patents
シンガス分圧を制御することによる、混合配位子ヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 Download PDFInfo
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- DTCCTIQRPGSLPT-UHFFFAOYSA-N beta-Aethyl-acrolein Natural products CCC=CC=O DTCCTIQRPGSLPT-UHFFFAOYSA-N 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- IEKXSSZASGLISC-UHFFFAOYSA-N but-3-enyl acetate Chemical compound CC(=O)OCCC=C IEKXSSZASGLISC-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011066 ex-situ storage Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UOGFCIYBLKSQHL-UHFFFAOYSA-N hex-5-en-3-ol Chemical compound CCC(O)CC=C UOGFCIYBLKSQHL-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- UZGCMRVEDHLBGY-UHFFFAOYSA-N oct-1-en-4-ol Chemical compound CCCCC(O)CC=C UZGCMRVEDHLBGY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005120 petroleum cracking Methods 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
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- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
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| US28911509P | 2009-12-22 | 2009-12-22 | |
| US61/289,115 | 2009-12-22 | ||
| PCT/US2010/060471 WO2011087688A1 (en) | 2009-12-22 | 2010-12-15 | Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the syngas partial pressure |
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| JP2015136747A Division JP6151743B2 (ja) | 2009-12-22 | 2015-07-08 | シンガス分圧を制御することによる、混合配位子ヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
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| JP2015136747A Active JP6151743B2 (ja) | 2009-12-22 | 2015-07-08 | シンガス分圧を制御することによる、混合配位子ヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
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| JP2015136747A Active JP6151743B2 (ja) | 2009-12-22 | 2015-07-08 | シンガス分圧を制御することによる、混合配位子ヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
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| Country | Link |
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| US (1) | US8598389B2 (enExample) |
| EP (2) | EP2516372B2 (enExample) |
| JP (2) | JP2013515058A (enExample) |
| KR (2) | KR101918054B1 (enExample) |
| CN (1) | CN102753511B (enExample) |
| CA (1) | CA2784943C (enExample) |
| ES (1) | ES2446722T5 (enExample) |
| MX (1) | MX365495B (enExample) |
| MY (1) | MY159684A (enExample) |
| PL (2) | PL2722325T5 (enExample) |
| RU (1) | RU2546110C2 (enExample) |
| TW (1) | TWI516470B (enExample) |
| WO (1) | WO2011087688A1 (enExample) |
| ZA (1) | ZA201204577B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013515061A (ja) * | 2009-12-22 | 2013-05-02 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 混合リガンドヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
| JP2015180694A (ja) * | 2009-12-22 | 2015-10-15 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | シンガス分圧を制御することによる、混合配位子ヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8664451B2 (en) † | 2009-12-22 | 2014-03-04 | Dow Technology Investments Llc | Controlling the normal:ISO aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure |
| CN102826967B (zh) * | 2011-06-17 | 2015-07-22 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化反应制备醛的方法 |
| WO2013181097A1 (en) * | 2012-06-01 | 2013-12-05 | Invista Technologies S.A.R.L. | Stabilized hydrocyanation ligand composition |
| WO2013181092A1 (en) * | 2012-06-01 | 2013-12-05 | Invista North America S.A.R.L. | Hydrolysis catalyst and process |
| MX360063B (es) * | 2012-08-29 | 2018-10-22 | Dow Technology Investments Llc | Proceso de preparacion de catalizador. |
| CN106256893A (zh) * | 2015-06-18 | 2016-12-28 | 中国石油化工股份有限公司 | 一种喷气燃料的制备方法 |
| CA3014177C (en) * | 2016-02-11 | 2023-12-12 | Dow Technology Investments Llc | Processes for converting olefins to alcohols, ethers, or combinations thereof |
| KR102073732B1 (ko) | 2016-07-08 | 2020-02-05 | 주식회사 엘지화학 | 하이드로포밀화 촉매, 이를 포함하는 촉매 조성물 및 이를 이용한 알데히드 제조방법 |
| KR102610473B1 (ko) * | 2018-10-16 | 2023-12-05 | 주식회사 엘지화학 | 알데히드의 제조방법 |
| US11976017B2 (en) | 2019-12-19 | 2024-05-07 | Dow Technology Investments Llc | Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms |
| US11370737B2 (en) * | 2020-09-25 | 2022-06-28 | Lyondell Chemical Technology, L.P. | Co-feeding ethylene with allyl alcohol in hydroformylation to make 1,4-butanediol and n-propanol |
| CN116478023B (zh) * | 2022-01-13 | 2025-03-14 | 中国科学院大连化学物理研究所 | 一种合成气直接转化合成多碳醛酮的方法 |
| CN114931961B (zh) * | 2022-06-10 | 2024-02-27 | 万华化学集团股份有限公司 | 一种氢甲酰化催化剂及其应用 |
| CN121194957A (zh) | 2023-06-26 | 2025-12-23 | 陶氏技术投资有限责任公司 | 控制加氢甲酰化工艺的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55127335A (en) * | 1979-03-21 | 1980-10-02 | Davy Mckee Oil & Chem | Hydroformylation for manufacturing nnvaleraldehyde |
| JPH06192158A (ja) * | 1992-09-25 | 1994-07-12 | Mitsubishi Kasei Corp | ヒドロホルミル化反応の制御方法 |
| WO2008115740A1 (en) * | 2007-03-20 | 2008-09-25 | Union Carbide Chemicals & Plastics Technology Llc | Hydroformylation process with improved control over product isomers |
| WO2008124468A1 (en) * | 2007-04-05 | 2008-10-16 | Dow Global Technologies Inc. | A calixarene bisphosphite ligand for use in hydroformylation processes |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3415906A (en) | 1964-05-29 | 1968-12-10 | Hooker Chemical Corp | Phosphite phospholane and phosphorinane compounds |
| US3527809A (en) | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| US4148830A (en) | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| US4247486A (en) | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
| US4169861A (en) | 1977-08-19 | 1979-10-02 | Celanese Corporation | Hydroformylation process |
| GB8334359D0 (en) | 1983-12-23 | 1984-02-01 | Davy Mckee Ltd | Process |
| US4599206A (en) | 1984-02-17 | 1986-07-08 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US5110990A (en) | 1984-03-30 | 1992-05-05 | Union Carbide Chemicals & Plastics Technology Corporation | Process for recovery of phosphorus ligand from vaporized aldehyde |
| US4567302A (en) | 1984-07-20 | 1986-01-28 | Angus Chemical | Polymeric quaternary ammonium salts possessing antimicrobial activity and methods for preparation and use thereof |
| US4737588A (en) | 1984-12-28 | 1988-04-12 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4748261A (en) † | 1985-09-05 | 1988-05-31 | Union Carbide Corporation | Bis-phosphite compounds |
| US4668651A (en) | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
| US4885401A (en) | 1985-09-05 | 1989-12-05 | Union Carbide Corporation | Bis-phosphite compounds |
| US4774361A (en) | 1986-05-20 | 1988-09-27 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
| RU2005713C1 (ru) * | 1987-01-06 | 1994-01-15 | Юнион Карбид Корпорейшн | Способ получения альдегидов c4-c5 |
| US4835299A (en) | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
| US5113022A (en) | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
| US5059710A (en) | 1988-08-05 | 1991-10-22 | Union Carbide Chemicals And Plastics Technology Corporation | Ionic phosphites and their use in homogeneous transition metal catalyzed processes |
| US4873213A (en) | 1988-08-12 | 1989-10-10 | Puckette Thomas A | Low pressure rhodium catalyzed hydroformylation of olefins |
| US5114473A (en) | 1988-08-25 | 1992-05-19 | Union Carbide Chemicals And Plastics Technology Corporation | Transition metal recovery |
| US5277532A (en) | 1989-07-31 | 1994-01-11 | Cefin S.P.A. | Mechanical acceleration device in can welding machines |
| US5210318A (en) | 1990-05-04 | 1993-05-11 | Union Carbide Chemicals & Plastics Technology Corporation | Catalysts and processes useful in producing 1,3-diols and/or 3-hydroxyldehydes |
| DE4026406A1 (de) † | 1990-08-21 | 1992-02-27 | Basf Ag | Rhodiumhydroformylierungskatalysatoren mit bis-phosphit-liganden |
| US5179055A (en) | 1990-09-24 | 1993-01-12 | New York University | Cationic rhodium bis(dioxaphosphorus heterocycle) complexes and their use in the branched product regioselective hydroformylation of olefins |
| US5102505A (en) | 1990-11-09 | 1992-04-07 | Union Carbide Chemicals & Plastics Technology Corporation | Mixed aldehyde product separation by distillation |
| TW213465B (enExample) † | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
| DE4204808A1 (de) | 1992-02-18 | 1993-08-19 | Basf Ag | Verfahren zur herstellung von (omega)-formylalkancarbonsaeureestern |
| US5312996A (en) † | 1992-06-29 | 1994-05-17 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process for producing 1,6-hexanedials |
| US5288918A (en) † | 1992-09-29 | 1994-02-22 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| US5364950A (en) | 1992-09-29 | 1994-11-15 | Union Carbide Chimicals & Plastics Technology Corporation | Process for stabilizing phosphite ligands in hydroformylation reaction mixtures |
| US5410091A (en) † | 1994-06-02 | 1995-04-25 | Quimica Oxal C.A. | Rhodium catalyzed oxo process in tubular reactor |
| US5744650A (en) † | 1995-12-06 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-Ligand complex catalyzed processes |
| EP0839787A1 (en) | 1996-11-04 | 1998-05-06 | Dsm N.V. | Process for the preparation of an aldehyde |
| US5892119A (en) | 1996-11-26 | 1999-04-06 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5874640A (en) | 1996-11-26 | 1999-02-23 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US6090987A (en) | 1998-07-06 | 2000-07-18 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| DE19954510A1 (de) † | 1999-11-12 | 2001-05-17 | Oxeno Olefinchemie Gmbh | Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Ligandenmischungen |
| US6294700B1 (en) | 2000-03-15 | 2001-09-25 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| ES2308230T3 (es) | 2003-10-21 | 2008-12-01 | Basf Se | Metodo para la produccion continua de aldehidos. |
| KR100596365B1 (ko) | 2004-06-12 | 2006-07-03 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
| KR100547587B1 (ko) | 2004-06-12 | 2006-01-31 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
| IN2007CN00473A (enExample) * | 2004-08-02 | 2007-08-24 | Union Carbide Chem Plastic | |
| DE102004055832A1 (de) † | 2004-11-19 | 2006-06-01 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
| US7615546B2 (en) † | 2005-08-19 | 2009-11-10 | Bioderm Research | Topical delivery system for phytosterols |
| ZA200804818B (en) † | 2005-12-15 | 2009-11-25 | Penn State Res Found | Tetraphosphorus ligands for catalytic hydroformylation and related reactions |
| US7586010B2 (en) | 2006-12-21 | 2009-09-08 | Eastman Chemical Company | Phosphonite-containing catalysts for hydroformylation processes |
| CN101293818B (zh) | 2007-04-28 | 2010-07-07 | 中国石油化工股份有限公司 | 混合丁烯氢甲酰化的两段反应方法 |
| CN101565353B (zh) | 2008-04-25 | 2013-01-02 | 中国石油化工股份有限公司 | 一种2-丙基庚醇的制备方法 |
| US7674937B2 (en) † | 2008-05-28 | 2010-03-09 | Eastman Chemical Company | Hydroformylation catalysts |
| CN102123978B (zh) † | 2008-08-19 | 2014-03-19 | 陶氏技术投资有限公司 | 用于改进对产物异构体的控制的使用对称的二亚磷酸酯配体的加氢甲酰化方法 |
| ES2446722T5 (es) * | 2009-12-22 | 2020-03-20 | Dow Technology Investments Llc | Control de la relación aldehído normal:isoaldehído en un proceso de hidroformilación de ligando mixto mediante el control de la presión parcial del gas de síntesis |
-
2010
- 2010-12-15 ES ES10795580T patent/ES2446722T5/es active Active
- 2010-12-15 JP JP2012546037A patent/JP2013515058A/ja not_active Withdrawn
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- 2010-12-15 EP EP10795580.9A patent/EP2516372B2/en active Active
- 2010-12-15 CN CN201080063170.4A patent/CN102753511B/zh active Active
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- 2010-12-15 PL PL13194944T patent/PL2722325T5/pl unknown
- 2010-12-15 EP EP13194944.8A patent/EP2722325B2/en not_active Not-in-force
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- 2010-12-15 WO PCT/US2010/060471 patent/WO2011087688A1/en not_active Ceased
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- 2010-12-15 MY MYPI2012002856A patent/MY159684A/en unknown
- 2010-12-15 MX MX2012007453A patent/MX365495B/es active IP Right Grant
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-
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- 2012-06-20 ZA ZA2012/04577A patent/ZA201204577B/en unknown
-
2015
- 2015-07-08 JP JP2015136747A patent/JP6151743B2/ja active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55127335A (en) * | 1979-03-21 | 1980-10-02 | Davy Mckee Oil & Chem | Hydroformylation for manufacturing nnvaleraldehyde |
| JPH06192158A (ja) * | 1992-09-25 | 1994-07-12 | Mitsubishi Kasei Corp | ヒドロホルミル化反応の制御方法 |
| WO2008115740A1 (en) * | 2007-03-20 | 2008-09-25 | Union Carbide Chemicals & Plastics Technology Llc | Hydroformylation process with improved control over product isomers |
| WO2008124468A1 (en) * | 2007-04-05 | 2008-10-16 | Dow Global Technologies Inc. | A calixarene bisphosphite ligand for use in hydroformylation processes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013515061A (ja) * | 2009-12-22 | 2013-05-02 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 混合リガンドヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
| JP2015180694A (ja) * | 2009-12-22 | 2015-10-15 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | シンガス分圧を制御することによる、混合配位子ヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
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| CA2784943A1 (en) | 2011-07-21 |
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| TWI516470B (zh) | 2016-01-11 |
| ES2446722T3 (es) | 2014-03-10 |
| MX2012007453A (es) | 2012-11-23 |
| KR101918054B1 (ko) | 2018-11-13 |
| PL2722325T3 (pl) | 2015-12-31 |
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| CN102753511A (zh) | 2012-10-24 |
| TW201129537A (en) | 2011-09-01 |
| CA2784943C (en) | 2016-09-06 |
| EP2722325B2 (en) | 2019-01-16 |
| EP2722325A1 (en) | 2014-04-23 |
| EP2516372B1 (en) | 2014-01-22 |
| JP6151743B2 (ja) | 2017-06-21 |
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