FR2478078A2 - Procede d'hydroformylation des olefines - Google Patents
Procede d'hydroformylation des olefines Download PDFInfo
- Publication number
- FR2478078A2 FR2478078A2 FR8005488A FR8005488A FR2478078A2 FR 2478078 A2 FR2478078 A2 FR 2478078A2 FR 8005488 A FR8005488 A FR 8005488A FR 8005488 A FR8005488 A FR 8005488A FR 2478078 A2 FR2478078 A2 FR 2478078A2
- Authority
- FR
- France
- Prior art keywords
- sep
- rhodium
- phosphine
- soln
- cpd
- 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.)
- Granted
Links
- 239000010948 rhodium Substances 0.000 title claims abstract description 20
- 229910052703 rhodium Inorganic materials 0.000 title claims abstract description 18
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 150000001336 alkenes Chemical class 0.000 title abstract description 5
- 238000007037 hydroformylation reaction Methods 0.000 title abstract description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000003003 phosphines Chemical class 0.000 title abstract description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 16
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 230000015556 catabolic process Effects 0.000 abstract description 4
- 238000006731 degradation reaction Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- -1 alkyl radical Chemical class 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- QOOQLKSEGVNYLA-UHFFFAOYSA-N 1-$l^{1}-oxidanylbutane Chemical compound CCCC[O] QOOQLKSEGVNYLA-UHFFFAOYSA-N 0.000 description 1
- SVNRDPVQDFIPSD-UHFFFAOYSA-N 3-phosphanylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(P)=C1 SVNRDPVQDFIPSD-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical group [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8005488A FR2478078A2 (fr) | 1980-03-12 | 1980-03-12 | Procede d'hydroformylation des olefines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8005488A FR2478078A2 (fr) | 1980-03-12 | 1980-03-12 | Procede d'hydroformylation des olefines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2478078A2 true FR2478078A2 (fr) | 1981-09-18 |
| FR2478078B2 FR2478078B2 (Direct) | 1982-05-07 |
Family
ID=9239575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8005488A Granted FR2478078A2 (fr) | 1980-03-12 | 1980-03-12 | Procede d'hydroformylation des olefines |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2478078A2 (Direct) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4510332A (en) * | 1982-03-12 | 1985-04-09 | Kuraray Company, Ltd. | Process for producing 1,9-nonanedial |
| US4578523A (en) * | 1985-05-29 | 1986-03-25 | Ruhrchemie Aktiengesellschaft | Process for the preparation of aldehydes |
| FR2571725A1 (fr) * | 1984-10-16 | 1986-04-18 | Rhone Poulenc Chim Base | Complexes rhodies, dinucleaires et hydrosolubles et leur utilisation comme catalyseur d'hydroformylation |
| US4633021A (en) * | 1985-11-29 | 1986-12-30 | National Distillers And Chemical Corporation | Olefin hydroformylation |
| US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
| US4795727A (en) * | 1986-05-13 | 1989-01-03 | Ruhrchemie Aktiengesellschaft | Rhodium catalysts and methods of preparation and use thereof |
| EP0226988A3 (en) * | 1985-12-24 | 1989-04-12 | Hoechst Aktiengesellschaft | Process for the preparation of aldehydes |
| US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5223648A (en) * | 1990-12-17 | 1993-06-29 | Hoechst Aktiengesellschaft | Process for producing aldehydes |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
-
1980
- 1980-03-12 FR FR8005488A patent/FR2478078A2/fr active Granted
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4510332A (en) * | 1982-03-12 | 1985-04-09 | Kuraray Company, Ltd. | Process for producing 1,9-nonanedial |
| US4778905A (en) * | 1984-10-16 | 1988-10-18 | Rhone-Poulenc Chimie De Base | Dinuclear and water-soluble rhodium complexes and hydroformylation catalysis therewith |
| FR2571725A1 (fr) * | 1984-10-16 | 1986-04-18 | Rhone Poulenc Chim Base | Complexes rhodies, dinucleaires et hydrosolubles et leur utilisation comme catalyseur d'hydroformylation |
| EP0179004A1 (fr) * | 1984-10-16 | 1986-04-23 | Rhone-Poulenc Chimie | Complexes rhodiés, dinucléaires et hydrosolubles et leur utilisation comme catalyseur d'hydroformylation |
| US4578523A (en) * | 1985-05-29 | 1986-03-25 | Ruhrchemie Aktiengesellschaft | Process for the preparation of aldehydes |
| US4633021A (en) * | 1985-11-29 | 1986-12-30 | National Distillers And Chemical Corporation | Olefin hydroformylation |
| FR2590892A1 (fr) * | 1985-11-29 | 1987-06-05 | Nat Distillers Chem Corp | Procede pour l'hydroformylation d'olefines pour la preparation d'aldehydes |
| EP0226988A3 (en) * | 1985-12-24 | 1989-04-12 | Hoechst Aktiengesellschaft | Process for the preparation of aldehydes |
| US4795727A (en) * | 1986-05-13 | 1989-01-03 | Ruhrchemie Aktiengesellschaft | Rhodium catalysts and methods of preparation and use thereof |
| US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
| US5223648A (en) * | 1990-12-17 | 1993-06-29 | Hoechst Aktiengesellschaft | Process for producing aldehydes |
| US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2478078B2 (Direct) | 1982-05-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2478078A2 (fr) | Procede d'hydroformylation des olefines | |
| FR2534903A1 (fr) | Procede d'hydroformylation | |
| FR2590892A1 (fr) | Procede pour l'hydroformylation d'olefines pour la preparation d'aldehydes | |
| JPS61501268A (ja) | 遷移金属錯体による触媒反応 | |
| JPH06126194A (ja) | オキソ合成の生成物の蒸留残留物からロジウムを回収する方法 | |
| EP0673355B1 (fr) | Procede de preparation d'octadienols | |
| JP7268602B2 (ja) | アルデヒドの製造方法及びアルコールの製造方法 | |
| JPS607941B2 (ja) | ロジウム錯体ヒドロホルミル化触媒の再活性化 | |
| JPH0356095B2 (Direct) | ||
| FR2741875A1 (fr) | Procede pour l'hydroformylation des composes olefiniques | |
| FR2511613A1 (fr) | Complexes organometalliques et leur utilisation comme catalyseurs homogenes | |
| EP0882698B1 (fr) | Procédé pour l'hydroformylation d'olefines | |
| FR2488884A1 (fr) | Procede pour la preparation d'acetaldehyde et d'ethanol | |
| JP7335417B2 (ja) | 触媒置換を伴う連続ヒドロホルミル化の方法 | |
| EP1106595B1 (fr) | Procédé amélioré d'hydroformylation au moyen d'un catalyseur à base de cobalt et/ou de rhodium mis en oeuvre en milieu biphasique | |
| EP0091385A1 (fr) | Procédé de préparation de p-hydroxybenzylnitriles ou p-hydroxybenzylamines | |
| EP1182187B1 (fr) | Procédé améloiré d'hydroformylation mettant en oeuvre un catalyseur à base de cobalt et/ou de rhodium dans un solvant ionique non aqueux | |
| JP7440865B2 (ja) | 銅電解液中の銀の回収方法 | |
| DE3108602A1 (de) | "verfahren zur herstellung von eine perfluorkohlenstoffgruppe enthaltenden aldehyden" | |
| CN115850041A (zh) | 一种烯烃氢甲酰化反应制备醛的方法、酚类抗氧化剂的用途和提高催化体系稳定性的方法 | |
| EP0526318B1 (fr) | Procédé pour la préparation d'alkylamines secondaires aliphatiques dissymétriques | |
| WO1984004299A1 (fr) | Systeme catalytique pour l'hydroformylation des olefines; procede d'hydroformylation | |
| JP7804281B2 (ja) | 銅電解液中の銀の回収方法 | |
| FR2473504A1 (fr) | Procede de preparation d'aldehydes a partir d'olefines par reaction d'hydroformylation en presence d'un catalyseur au cobalt | |
| EP0341124B1 (fr) | Procédé de préparation de dérivés fluorés fonctionnels |