GB1338237A - Hydroformylation process - Google Patents
Hydroformylation processInfo
- Publication number
- GB1338237A GB1338237A GB5962370A GB5962370A GB1338237A GB 1338237 A GB1338237 A GB 1338237A GB 5962370 A GB5962370 A GB 5962370A GB 5962370 A GB5962370 A GB 5962370A GB 1338237 A GB1338237 A GB 1338237A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon monoxide
- rhodium
- conducted
- triorganophosphorus ligand
- atom
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 4
- 238000007037 hydroformylation reaction Methods 0.000 title abstract 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 4
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000003446 ligand Substances 0.000 abstract 3
- 229910052703 rhodium Inorganic materials 0.000 abstract 3
- 239000010948 rhodium Substances 0.000 abstract 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 2
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004437 phosphorous atom Chemical group 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000006184 cosolvent Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 239000004711 α-olefin Substances 0.000 abstract 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
- C07C45/61—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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/44—Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88737069A | 1969-12-22 | 1969-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1338237A true GB1338237A (en) | 1973-11-21 |
Family
ID=25390999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5962370A Expired GB1338237A (en) | 1969-12-22 | 1970-12-16 | Hydroformylation process |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS511687B1 (ja) |
| BE (1) | BE760621A (ja) |
| CA (1) | CA918673A (ja) |
| DE (1) | DE2062703B2 (ja) |
| FR (1) | FR2074101A5 (ja) |
| GB (1) | GB1338237A (ja) |
| NL (1) | NL172646C (ja) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2715685A1 (de) * | 1976-04-08 | 1977-10-13 | Union Carbide Corp | Kontinuierliches verfahren zur herstellung von aldehyden durch hydroformylierung von alpha-olefinen |
| DE2730527A1 (de) * | 1976-07-07 | 1978-01-12 | Union Carbide Corp | Verfahren zur hydroformylierung eines alpha-olefins |
| US4143075A (en) * | 1976-08-12 | 1979-03-06 | Union Carbide Corporation | Control of condensation products in hydroformylation process |
| US4215077A (en) * | 1978-02-09 | 1980-07-29 | Kuraray Co., Ltd. | Hydroformylation of olefins |
| EP0017183A2 (en) * | 1979-03-28 | 1980-10-15 | Union Carbide Corporation | Hydroformylation medium, process of production thereof and process for producing aldehydes using the hydroformylation medium |
| US4242284A (en) * | 1978-07-27 | 1980-12-30 | Davy International (Oil & Chemicals) Limited | Process for recovery of rhodium values and triphenylphosphine from rhodium catalyzed hydroformylation medium |
| US4260828A (en) * | 1980-04-16 | 1981-04-07 | Union Carbide Corporation | Hydroformylation process |
| EP0028378A1 (en) * | 1979-10-26 | 1981-05-13 | Union Carbide Corporation | Improved hydroformylation process using stable rhodium catalyst |
| EP0031590A1 (en) * | 1979-12-28 | 1981-07-08 | Union Carbide Corporation | Rhodium catalyzed hydroformylation process |
| US4287370A (en) * | 1979-03-21 | 1981-09-01 | Davy Mckee (Oil & Chemicals) Limited | Hydroformylation process for the production of n-valeraldehyde |
| US4383125A (en) * | 1979-04-11 | 1983-05-10 | Davy Mckee (Oil & Chemicals) Limited | Aldehyde-ethers |
| US4482749A (en) * | 1982-06-11 | 1984-11-13 | Davy Mckee (London) Limited | Hydroformylation process |
| US4496769A (en) * | 1982-06-11 | 1985-01-29 | Davy Mckee (London) Limited | Process for the preparation of aldehydes by hydroformylation of olefins |
| US4496768A (en) * | 1982-06-11 | 1985-01-29 | Davy Mckee Limited | Process for the production of aldehydes by hydroformylation of alpha-olefins |
| US6756411B2 (en) | 1995-06-29 | 2004-06-29 | Sasol Technology (Proprietary) Limited | Process for producing oxygenated products |
| US6946580B2 (en) | 2001-05-30 | 2005-09-20 | Davy Process Technology Limited | Hydroformylation process with recycle of active rhodium catalyst |
| WO2013095766A1 (en) | 2011-12-20 | 2013-06-27 | Dow Technology Investments Llc | A hydroformylation process |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2351077A1 (fr) * | 1976-05-13 | 1977-12-09 | Celanese Corp | Procede perfectionne d'hydroformylation des olefines avec un catalyseur complexe au rhodium |
| ZA78147B (en) * | 1977-01-25 | 1978-11-29 | Union Carbide Corp | Improved hydroformylation process |
| ZA78146B (en) * | 1977-01-25 | 1978-12-27 | Union Carbide Corp | Improved hydroformylation process |
| DE2833538C2 (de) * | 1978-07-31 | 1984-09-20 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur Herstellung von α-methylverzweigten Aldehyden |
| EP1532094A1 (de) | 2002-08-31 | 2005-05-25 | Oxeno Olefinchemie GmbH | Verfahren zur hydroformylierung von olefinisch ungesättigten verbindungen, insbesondere olefinen in gegenwart cyclischer kohlensäureester |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2779795A (en) * | 1954-03-10 | 1957-01-29 | Gulf Research Development Co | Hydroformylation of olefins; temperature stabilization |
| US2790832A (en) * | 1954-03-29 | 1957-04-30 | Eastman Kodak Co | Directed isomer formation in the oxo reaction |
| DE1036839B (de) * | 1955-02-09 | 1958-08-21 | Chemische Verwertungsgesellsch | Verfahren zur Herstellung eines Katalysatorgemisches fuer die Oxo-Synthese durch Beladen von Kohlenoxyd oder Kohlenoxyd-Wasserstoff-Gemischen mit fluechtigen Kobaltcarbonylverbindungen |
| US2850541A (en) * | 1955-09-19 | 1958-09-02 | Standard Oil Co | Production of c5 alcohols by improved oxo process |
| FR1223381A (fr) * | 1958-12-17 | 1960-06-16 | Ets Kuhlmann | Perfectionnements au procédé de fabrication de composés oxygénés par synthèse oxo |
| BE606408A (ja) * | 1960-07-22 | |||
| US3239566A (en) * | 1960-07-22 | 1966-03-08 | Shell Oil Co | Hydroformylation of olefins |
| US3290379A (en) * | 1961-09-01 | 1966-12-06 | Diamond Alkali Co | Selective hydroformylation of olefinic compounds |
| US3310576A (en) * | 1963-02-05 | 1967-03-21 | Exxon Research Engineering Co | Hydroformylation catalyst and process relating thereto |
| DE1518236A1 (de) * | 1964-12-15 | 1972-06-08 | Johnson Matthey Co Ltd | Katalytische Verfahren |
| GB1138601A (en) * | 1964-12-15 | 1969-01-01 | Geoffrey Wilkinson | Improvements in catalytic reactions |
| US3452348A (en) * | 1965-06-29 | 1969-06-24 | Rca Corp | Conversion from self-clocking code to nrz code |
| US3487112A (en) * | 1967-04-27 | 1969-12-30 | Monsanto Co | Vapor phase hydroformylation process |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| GB1228947A (ja) * | 1967-10-12 | 1971-04-21 | ||
| CA1090823A (en) * | 1976-04-08 | 1980-12-02 | Everard A.V. Brewester | Cyclic hydroformylation process |
-
1970
- 1970-12-16 GB GB5962370A patent/GB1338237A/en not_active Expired
- 1970-12-16 CA CA100750A patent/CA918673A/en not_active Expired
- 1970-12-19 DE DE2062703A patent/DE2062703B2/de not_active Ceased
- 1970-12-21 FR FR7046050A patent/FR2074101A5/fr not_active Expired
- 1970-12-21 BE BE760621A patent/BE760621A/xx not_active IP Right Cessation
- 1970-12-21 NL NLAANVRAGE7018585,A patent/NL172646C/xx not_active IP Right Cessation
- 1970-12-21 JP JP45114312A patent/JPS511687B1/ja active Pending
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2360544A1 (fr) * | 1976-04-08 | 1978-03-03 | Union Carbide Corp | Procede de preparation continue d'aldehydes par hydroformylation |
| DE2715685A1 (de) * | 1976-04-08 | 1977-10-13 | Union Carbide Corp | Kontinuierliches verfahren zur herstellung von aldehyden durch hydroformylierung von alpha-olefinen |
| DE2730527A1 (de) * | 1976-07-07 | 1978-01-12 | Union Carbide Corp | Verfahren zur hydroformylierung eines alpha-olefins |
| US4143075A (en) * | 1976-08-12 | 1979-03-06 | Union Carbide Corporation | Control of condensation products in hydroformylation process |
| US4215077A (en) * | 1978-02-09 | 1980-07-29 | Kuraray Co., Ltd. | Hydroformylation of olefins |
| US4242284A (en) * | 1978-07-27 | 1980-12-30 | Davy International (Oil & Chemicals) Limited | Process for recovery of rhodium values and triphenylphosphine from rhodium catalyzed hydroformylation medium |
| US4287370A (en) * | 1979-03-21 | 1981-09-01 | Davy Mckee (Oil & Chemicals) Limited | Hydroformylation process for the production of n-valeraldehyde |
| EP0017183A2 (en) * | 1979-03-28 | 1980-10-15 | Union Carbide Corporation | Hydroformylation medium, process of production thereof and process for producing aldehydes using the hydroformylation medium |
| EP0017183A3 (en) * | 1979-03-28 | 1981-01-07 | Union Carbide Corporation | Hydroformylation medium, process of production thereof and process for producing aldehydes using the hydroformylation medium |
| US4383125A (en) * | 1979-04-11 | 1983-05-10 | Davy Mckee (Oil & Chemicals) Limited | Aldehyde-ethers |
| EP0028378A1 (en) * | 1979-10-26 | 1981-05-13 | Union Carbide Corporation | Improved hydroformylation process using stable rhodium catalyst |
| EP0031590A1 (en) * | 1979-12-28 | 1981-07-08 | Union Carbide Corporation | Rhodium catalyzed hydroformylation process |
| US4260828A (en) * | 1980-04-16 | 1981-04-07 | Union Carbide Corporation | Hydroformylation process |
| US4482749A (en) * | 1982-06-11 | 1984-11-13 | Davy Mckee (London) Limited | Hydroformylation process |
| US4496769A (en) * | 1982-06-11 | 1985-01-29 | Davy Mckee (London) Limited | Process for the preparation of aldehydes by hydroformylation of olefins |
| US4496768A (en) * | 1982-06-11 | 1985-01-29 | Davy Mckee Limited | Process for the production of aldehydes by hydroformylation of alpha-olefins |
| US6756411B2 (en) | 1995-06-29 | 2004-06-29 | Sasol Technology (Proprietary) Limited | Process for producing oxygenated products |
| US6946580B2 (en) | 2001-05-30 | 2005-09-20 | Davy Process Technology Limited | Hydroformylation process with recycle of active rhodium catalyst |
| WO2013095766A1 (en) | 2011-12-20 | 2013-06-27 | Dow Technology Investments Llc | A hydroformylation process |
| US9067876B2 (en) | 2011-12-20 | 2015-06-30 | Dow Technology Investments Llc | Hydroformylation process |
Also Published As
| Publication number | Publication date |
|---|---|
| NL172646C (nl) | 1983-10-03 |
| NL172646B (nl) | 1983-05-02 |
| FR2074101A5 (ja) | 1971-10-01 |
| CA918673A (en) | 1973-01-09 |
| JPS511687B1 (ja) | 1976-01-20 |
| DE2062703A1 (de) | 1971-07-01 |
| BE760621A (fr) | 1971-06-21 |
| NL7018585A (ja) | 1971-06-24 |
| DE2062703B2 (de) | 1981-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |