CA1296327C - Procede pour la preparation de nouveaux catalyseurs d'hydrogenation au rhodium, et leur application - Google Patents

Procede pour la preparation de nouveaux catalyseurs d'hydrogenation au rhodium, et leur application

Info

Publication number: CA1296327C
Authority: CA; Canada
Prior art keywords: rhodium; hydrazine; process according; hydrogenation; fact
Prior art date: 1987-03-25
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

CA000539016A

Other languages

English (en)

Inventor

Philip Ronald Page

William Heggie

Ivan Villax

Indira Ghatak

Michael Barry Hursthouse

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.)

Plurichemie Anstalt

Original Assignee

Plurichemie Anstalt

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.)

1987-03-25

Filing date

1987-06-05

Publication date

1992-02-25

1987-03-25 Priority claimed from PT76061A external-priority patent/PT76061B1/pt

1987-06-05 Application filed by Plurichemie Anstalt filed Critical Plurichemie Anstalt

1992-02-25 Application granted granted Critical

1992-02-25 Publication of CA1296327C publication Critical patent/CA1296327C/fr

2009-02-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 33
238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 33
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims abstract description 26
238000000034 method Methods 0.000 title claims description 27
230000008569 process Effects 0.000 title claims description 23
239000010948 rhodium Substances 0.000 title claims description 21
238000002360 preparation method Methods 0.000 title claims description 18
229910052703 rhodium Inorganic materials 0.000 title claims description 18
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 72
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 61
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 24
239000002253 acid Substances 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 12
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 10
VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 claims abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
230000003197 catalytic effect Effects 0.000 claims description 18
239000011541 reaction mixture Substances 0.000 claims description 15
SULCFFJNLVZXGH-UHFFFAOYSA-N rhodium(3+);trinitrate;dihydrate Chemical compound O.O.[Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SULCFFJNLVZXGH-UHFFFAOYSA-N 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
239000012298 atmosphere Substances 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
230000035484 reaction time Effects 0.000 claims description 7
150000003283 rhodium Chemical class 0.000 claims description 7
239000000758 substrate Substances 0.000 claims description 7
238000002955 isolation Methods 0.000 claims description 4
239000012299 nitrogen atmosphere Substances 0.000 claims description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000004683 dihydrates Chemical class 0.000 claims description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims 2
150000004682 monohydrates Chemical class 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
SGKRLCUYIXIAHR-UHFFFAOYSA-N 2-carbamoyl-4-(dimethylazaniumyl)-5,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracen-1-olate Chemical compound C1=CC=C2C(C)C(C(O)C3C(C(O)=C(C(N)=O)C(=O)C3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-UHFFFAOYSA-N 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
238000011924 stereoselective hydrogenation Methods 0.000 claims 1
229960003722 doxycycline Drugs 0.000 abstract description 19
XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 abstract description 19
229940042016 methacycline Drugs 0.000 abstract description 17
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 5
MHIGBKBJSQVXNH-IWVLMIASSA-N methacycline Chemical compound C=C([C@H]1[C@@H]2O)C3=CC=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O MHIGBKBJSQVXNH-IWVLMIASSA-N 0.000 abstract 1
XIYOPDCBBDCGOE-IWVLMIASSA-N (4s,4ar,5s,5ar,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C=C1C2=CC=CC(O)=C2C(O)=C2[C@@H]1[C@H](O)[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O XIYOPDCBBDCGOE-IWVLMIASSA-N 0.000 description 17
239000001257 hydrogen Substances 0.000 description 13
229910052739 hydrogen Inorganic materials 0.000 description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
239000013078 crystal Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 9
235000013350 formula milk Nutrition 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 6
230000002829 reductive effect Effects 0.000 description 5
229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
239000003446 ligand Substances 0.000 description 4
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
SGKRLCUYIXIAHR-IPJAVASBSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-IPJAVASBSA-N 0.000 description 3
VZQARNDJLLWXGL-CCHMMTNSSA-N Methacycline hydrochloride Chemical compound Cl.C=C([C@H]1[C@@H]2O)C3=CC=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O VZQARNDJLLWXGL-CCHMMTNSSA-N 0.000 description 3
-1 benzenesulphonyl Chemical group 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
229940051860 methacycline hydrochloride Drugs 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
MEIQOILQMVIRKZ-UHFFFAOYSA-N O.O.[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[Rh+5].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-] Chemical compound O.O.[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[Rh+5].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-] MEIQOILQMVIRKZ-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
238000013480 data collection Methods 0.000 description 2
238000005695 dehalogenation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000007037 hydroformylation reaction Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000003003 phosphines Chemical group 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
241000243251 Hydra Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
GTTWFGPBBIBBJN-UHFFFAOYSA-N N(N)[Rh] Chemical class N(N)[Rh] GTTWFGPBBIBBJN-UHFFFAOYSA-N 0.000 description 1
VYCHTGDTIJOWLD-UHFFFAOYSA-N N(N)[Rh].P Chemical class N(N)[Rh].P VYCHTGDTIJOWLD-UHFFFAOYSA-N 0.000 description 1
XXIHDMCEEQEGED-UHFFFAOYSA-M N(N)[Rh]Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical class N(N)[Rh]Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 XXIHDMCEEQEGED-UHFFFAOYSA-M 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229910000074 antimony hydride Chemical group 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical group [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003060 catalysis inhibitor Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000005352 clarification Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
239000012634 fragment Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000007210 heterogeneous catalysis Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000007172 homogeneous catalysis Methods 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
230000002226 simultaneous effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical group [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1

Classifications

- 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
- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- 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
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium

Landscapes

Chemical & Material Sciences (AREA)
Inorganic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000539016A 1987-03-25 1987-06-05 Procede pour la preparation de nouveaux catalyseurs d'hydrogenation au rhodium, et leur application Expired - Fee Related CA1296327C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PT76061A PT76061B1 (pt)	1982-12-30	1987-03-25	Process for preparing the new catalysers of rhodium of hydrogenation and its application
PT76.061		1987-05-25

Publications (1)

Publication Number	Publication Date
CA1296327C true CA1296327C (fr)	1992-02-25

Family

ID=20083241

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000539016A Expired - Fee Related CA1296327C (fr)	1987-03-25	1987-06-05	Procede pour la preparation de nouveaux catalyseurs d'hydrogenation au rhodium, et leur application

Country Status (12)

Country	Link
AU (1)	AU595319B2 (fr)
CA (1)	CA1296327C (fr)
DE (1)	DE3771705D1 (fr)
FI (1)	FI86305C (fr)
GR (1)	GR3002372T3 (fr)
HK (1)	HK101191A (fr)
HU (1)	HU200150B (fr)
IE (1)	IE60599B1 (fr)
IL (1)	IL84196A (fr)
NO (1)	NO169342C (fr)
NZ (1)	NZ220505A (fr)
ZA (1)	ZA873545B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE68476T1 (de) *	1989-04-03	1991-11-15	Ranbaxy Lab Ltd	Verfahren zur herstellung von alpha-6deoxytetracyclinen.
EP1157740A3 (fr)	2000-05-18	2002-02-27	Haldor Topsoe A/S	Solution contentant du rhodium

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3444198A (en) *	1967-02-13	1969-05-13	Pfizer & Co C	Process for producing alpha-6-deoxytetracyclines
US4550096A (en) *	1982-01-19	1985-10-29	Plurichemie Anstalt	Homogeneous catalytic system comprising rhodium, hydrazine and phosphine and a process for the preparation of same
DE3769977D1 (de) *	1987-03-25	1991-06-13	Plurichemie Anstalt	Rhodium enthaltende hydrierungskatalysatoren.

1987
- 1987-05-14 DE DE8787304279T patent/DE3771705D1/de not_active Expired - Fee Related
- 1987-05-18 ZA ZA873545A patent/ZA873545B/xx unknown
- 1987-05-27 AU AU73431/87A patent/AU595319B2/en not_active Ceased
- 1987-05-29 NZ NZ220505A patent/NZ220505A/xx unknown
- 1987-06-05 CA CA000539016A patent/CA1296327C/fr not_active Expired - Fee Related
- 1987-06-18 IE IE161187A patent/IE60599B1/en not_active IP Right Cessation
- 1987-10-18 IL IL84196A patent/IL84196A/xx not_active IP Right Cessation
- 1987-11-23 FI FI875168A patent/FI86305C/fi not_active IP Right Cessation
1988
- 1988-03-23 HU HU881489A patent/HU200150B/hu not_active IP Right Cessation
- 1988-03-24 NO NO881313A patent/NO169342C/no unknown
1991
- 1991-07-25 GR GR91400972T patent/GR3002372T3/el unknown
- 1991-12-12 HK HK1011/91A patent/HK101191A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
HK101191A (en)	1991-12-20
GR3002372T3 (en)	1992-12-30
HU200150B (en)	1990-04-28
DE3771705D1 (de)	1991-08-29
FI875168L (fi)	1988-09-26
IE871611L (en)	1988-09-25
ZA873545B (en)	1988-11-30
IL84196A0 (en)	1988-03-31
NZ220505A (en)	1989-07-27
NO881313D0 (no)	1988-03-24
AU595319B2 (en)	1990-03-29
FI86305C (fi)	1992-08-10
FI86305B (fi)	1992-04-30
HUT47065A (en)	1989-01-30
AU7343187A (en)	1988-09-29
IL84196A (en)	1991-08-16
IE60599B1 (en)	1994-07-27
NO169342C (no)	1992-06-10
NO169342B (no)	1992-03-02
NO881313L (no)	1988-09-26
FI875168A0 (fi)	1987-11-23

Legal Events

Date	Code	Title	Description
2007-02-26	MKLA	Lapsed

Publication	Publication Date	Title
JPS6045938B2 (ja)	1985-10-12	シュウ酸ジエステルの水素添加触媒の製造法
EP0086046B1 (fr)	1987-06-24	Procédé pour la préparation de alpha-6-DEOXYTETRACYCLINES
JPH064545B2 (ja)	1994-01-19	シクロオレフインの製造方法
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CA1296327C (fr)	1992-02-25	Procede pour la preparation de nouveaux catalyseurs d'hydrogenation au rhodium, et leur application
IE41554B1 (en)	1980-01-30	Preperation of 6-deoxy-5-hydroxytetracycline
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EP0283615B1 (fr)	1991-05-08	Catalyseurs d'hydrogénation contenant du Rhodium
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