CA1338869C - Methode d'hydroformylation avec des catalyseurs au rhodium; separation du rhodium - Google Patents

Methode d'hydroformylation avec des catalyseurs au rhodium; separation du rhodium

Info

Publication number: CA1338869C
Authority: CA; Canada
Prior art keywords: carbon atoms; rhodium; alkyl; solubilizer; individually
Prior art date: 1984-03-26
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 - Fee Related

Application number

CA000537189A

Other languages

English (en)

Inventor

Boy Cornils

Werner Konkol

Helmut Bahrmann

Hanswilhelm Bach

Ernest Wiebus

Wolfgang Lipps

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date 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 date listed.)

1984-03-26

Filing date

1987-05-14

Publication date

1997-01-21

1984-03-26 Priority claimed from DE3411034A external-priority patent/DE3411034A1/de

1984-04-03 Priority claimed from DE19843412335 external-priority patent/DE3412335A1/de

1985-03-25 Priority claimed from CA000477406A external-priority patent/CA1245056A/fr

1987-05-14 Application filed by Hoechst AG filed Critical Hoechst AG

1997-01-21 Application granted granted Critical

1997-01-21 Publication of CA1338869C publication Critical patent/CA1338869C/fr

2014-01-21 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000010948 rhodium Substances 0.000 title claims abstract description 103
229910052703 rhodium Inorganic materials 0.000 title claims abstract description 98
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims abstract description 97
238000000034 method Methods 0.000 title claims abstract description 33
230000008569 process Effects 0.000 title claims abstract description 24
239000003054 catalyst Substances 0.000 title claims description 31
238000007037 hydroformylation reaction Methods 0.000 title claims description 30
238000000926 separation method Methods 0.000 title description 21
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 46
239000002904 solvent Substances 0.000 claims abstract description 33
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
-1 phosphine carboxylate Chemical class 0.000 claims abstract description 15
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 12
125000003118 aryl group Chemical group 0.000 claims abstract description 9
150000001299 aldehydes Chemical class 0.000 claims abstract description 8
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 8
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 6
239000007864 aqueous solution Substances 0.000 claims abstract description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims abstract description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims abstract description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
239000000243 solution Substances 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
150000001336 alkenes Chemical class 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical group O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical group CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
230000006872 improvement Effects 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
ORZMSMCZBZARKY-UHFFFAOYSA-N 1,3,2$l^{6}-benzodioxathiole 2,2-dioxide Chemical group C1=CC=C2OS(=O)(=O)OC2=C1 ORZMSMCZBZARKY-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
150000001805 chlorine compounds Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 claims 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000001421 myristyl 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])[H] 0.000 claims 1
FBUKVWPVBMHYJY-UHFFFAOYSA-N noncarboxylic acid Natural products CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims 1
125000000913 palmityl 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])[H] 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 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 claims 1
239000000203 mixture Substances 0.000 abstract description 24
239000008139 complexing agent Substances 0.000 abstract description 16
150000003839 salts Chemical class 0.000 abstract description 3
150000008055 alkyl aryl sulfonates Chemical class 0.000 abstract description 2
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 abstract description 2
150000008052 alkyl sulfonates Chemical class 0.000 abstract description 2
150000001412 amines Chemical class 0.000 abstract description 2
150000001735 carboxylic acids Chemical class 0.000 abstract description 2
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
239000000047 product Substances 0.000 description 30
239000012074 organic phase Substances 0.000 description 18
238000000605 extraction Methods 0.000 description 13
239000012071 phase Substances 0.000 description 13
239000008346 aqueous phase Substances 0.000 description 12
230000000694 effects Effects 0.000 description 12
MYAJTCUQMQREFZ-UHFFFAOYSA-K tppts Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 MYAJTCUQMQREFZ-UHFFFAOYSA-K 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 8
239000007789 gas Substances 0.000 description 8
150000003003 phosphines Chemical class 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
239000011574 phosphorus Substances 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 6
238000011084 recovery Methods 0.000 description 6
238000004821 distillation Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
150000007942 carboxylates Chemical class 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000006555 catalytic reaction Methods 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
150000003283 rhodium Chemical class 0.000 description 3
150000003284 rhodium compounds Chemical class 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
150000004996 alkyl benzenes Chemical class 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
GHJOEPMHSNXADF-UHFFFAOYSA-N 1-aminoicosan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCC(O)CN GHJOEPMHSNXADF-UHFFFAOYSA-N 0.000 description 1
FFYRIXSGFSWFAQ-UHFFFAOYSA-N 1-dodecylpyridin-1-ium Chemical compound CCCCCCCCCCCC[N+]1=CC=CC=C1 FFYRIXSGFSWFAQ-UHFFFAOYSA-N 0.000 description 1
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
BMTDZORNBFQUEA-UHFFFAOYSA-K 2-ethylhexanoate;rhodium(3+) Chemical compound [Rh+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O BMTDZORNBFQUEA-UHFFFAOYSA-K 0.000 description 1
IXSXQWMXSQIKON-UHFFFAOYSA-N 2-heptadecyl-4,5-dihydro-1h-imidazole;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC1=NCC[NH2+]1 IXSXQWMXSQIKON-UHFFFAOYSA-N 0.000 description 1
AQPUIHIMPGOGQJ-UHFFFAOYSA-M 2-hydroxypropanoate;trimethyl(tetradecyl)azanium Chemical compound CC(O)C([O-])=O.CCCCCCCCCCCCCC[N+](C)(C)C AQPUIHIMPGOGQJ-UHFFFAOYSA-M 0.000 description 1
DDFNIWBATAORBX-UHFFFAOYSA-N 3-bis(3-sulfophenyl)phosphanylbenzenesulfonic acid;sodium Chemical compound [Na].[Na].[Na].OS(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S(O)(=O)=O)C=2C=C(C=CC=2)S(O)(=O)=O)=C1 DDFNIWBATAORBX-UHFFFAOYSA-N 0.000 description 1
BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
235000021360 Myristic acid Nutrition 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
CBXOEWNRYOSZTE-UHFFFAOYSA-N [Na].P Chemical compound [Na].P CBXOEWNRYOSZTE-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001869 cobalt compounds Chemical class 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
230000001351 cycling effect Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
XCCCPSSXVCKQLA-UHFFFAOYSA-L dodecyl(trimethyl)azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCCCCCCCCCC[N+](C)(C)C.CCCCCCCCCCCC[N+](C)(C)C XCCCPSSXVCKQLA-UHFFFAOYSA-L 0.000 description 1
VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
OEWKLERKHURFTB-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+](C)(C)C OEWKLERKHURFTB-UHFFFAOYSA-M 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000005528 methosulfate group Chemical group 0.000 description 1
VXBSKVAMQMBCCA-UHFFFAOYSA-M methyl sulfate;trimethyl(tetradecyl)azanium Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCC[N+](C)(C)C VXBSKVAMQMBCCA-UHFFFAOYSA-M 0.000 description 1
MNOIOAHRVYPSPE-UHFFFAOYSA-N n,n-diethyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(CC)CC MNOIOAHRVYPSPE-UHFFFAOYSA-N 0.000 description 1
KXLJCSQCKYGDKR-UHFFFAOYSA-N n,n-dimethyl-13-phenyltridecan-1-amine Chemical compound CN(C)CCCCCCCCCCCCCC1=CC=CC=C1 KXLJCSQCKYGDKR-UHFFFAOYSA-N 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
QYPWRPSMKLUGJZ-UHFFFAOYSA-N pyridin-1-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 QYPWRPSMKLUGJZ-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
GLFDLEXFOHUASB-UHFFFAOYSA-N trimethyl(tetradecyl)azanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)C GLFDLEXFOHUASB-UHFFFAOYSA-N 0.000 description 1
230000035899 viability Effects 0.000 description 1

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Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000537189A 1984-03-26 1987-05-14 Methode d'hydroformylation avec des catalyseurs au rhodium; separation du rhodium Expired - Fee Related CA1338869C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DE3411034A DE3411034A1 (de)	1984-03-26	1984-03-26	Verfahren zur rueckgewinnung von rhodium aus reaktionsprodukten der oxosynthese
DEP3411034.8		1984-03-26
DE19843412335 DE3412335A1 (de)	1984-04-03	1984-04-03	Verfahren zur herstellung von aldehyden
DEP3412335.0		1984-04-03
CA000477406A CA1245056A (fr)	1984-03-26	1985-03-25	Hydroformylation sur catalyseur au rhodium, et extraction dudit rhodium

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000477406A Division CA1245056A (fr)	1984-03-26	1985-03-25	Hydroformylation sur catalyseur au rhodium, et extraction dudit rhodium

Publications (1)

Publication Number	Publication Date
CA1338869C true CA1338869C (fr)	1997-01-21

Family

ID=27167503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000537189A Expired - Fee Related CA1338869C (fr)	1984-03-26	1987-05-14	Methode d'hydroformylation avec des catalyseurs au rhodium; separation du rhodium

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CA (1)	CA1338869C (fr)

1987
- 1987-05-14 CA CA000537189A patent/CA1338869C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2002-01-21	MKLA	Lapsed

Publication	Publication Date	Title
US5091350A (en)	1992-02-25	Process for hydroformylation with rhodium catalysts and the separation of rhodium therefrom
US4740626A (en)	1988-04-26	Process for the preparation of aldehydes
EP0019296B1 (fr)	1983-05-04	Procédé pour éliminer les triorganophosphines d'une composition liquide
CA1243687A (fr)	1988-10-25	Preparation d'aldehydes
SU1757458A3 (ru)	1992-08-23	Способ получени масл ного альдегида
US4242284A (en)	1980-12-30	Process for recovery of rhodium values and triphenylphosphine from rhodium catalyzed hydroformylation medium
KR890002153B1 (ko)	1989-06-21	옥소(oxo)합성의 반응 생성물로부터 로듐을 회수하는 방법
KR890003783B1 (ko)	1989-10-04	알데히드의 제조방법
US4731485A (en)	1988-03-15	Process for hydroformylation with rhodium catalysts and the separation of rhodium therefrom
HU204249B (en)	1991-12-30	Process for producing aldehydes withcatalytic hydroformilizing olephines
CA1292246C (fr)	1991-11-19	Methode de preparation d'aldehydes
JP2981328B2 (ja)	1999-11-22	アルデヒド類の製造方法
CA1257878A (fr)	1989-07-25	Methode de preparation de nonadecanediols
JPH0544935B2 (fr)	1993-07-07
TWI378915B (en)	2012-12-11	Process for the hydroformylation of olefinically unsaturated compounds
AU653073B2 (en)	1994-09-15	Process for reactivation of water-soluble hydroformylation catalysts
AU653072B2 (en)	1994-09-15	Process for recovering rhodium from the reaction products of the oxo synthesis
CA2027514C (fr)	1996-09-24	Procede de recuperation du rhodium a partir des residus de distillation des produits de l'oxo-synthese
US5294415A (en)	1994-03-15	Process for the separation and recovery of rhodium from the products of the oxo synthesis
CA1245056A (fr)	1988-11-22	Hydroformylation sur catalyseur au rhodium, et extraction dudit rhodium
JP2002516300A (ja)	2002-06-04	マイクロエマルジョンの状態に於ける触媒作用下でのオレフィンのハイドロフォルミル化の方法
Trzeciak et al.	2000	The new organometallic rhodium–iron homogeneous catalytic system for hydroformylation
US5741941A (en)	1998-04-21	Process for preparing aldehydes
JP2001516639A (ja)	2001-10-02	ヒドロホルミル化によってアルデヒドを製造する方法
JPS6072844A (ja)	1985-04-24	極性官能基含有ホルミルノルボルナンの製造方法