IE60598B1 - Process of preparation of a new catalyst containing rhodium and its application - Google Patents

Process of preparation of a new catalyst containing rhodium and its application

Info

Publication number: IE60598B1
Authority: IE; Ireland
Prior art keywords: hydrogenation; hydrazine; process according; compound; rhodium
Prior art date: 1987-03-25

Application number

IE161087A

Other languages

English (en)

Other versions

IE871610L (en

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

1987-06-18

Publication date

1994-07-27

1987-06-18 Application filed by Plurichemie Anstalt filed Critical Plurichemie Anstalt

1988-09-25 Publication of IE871610L publication Critical patent/IE871610L/xx

1994-07-27 Publication of IE60598B1 publication Critical patent/IE60598B1/en

Links

239000003054 catalyst Substances 0.000 title claims abstract description 25
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims abstract description 14
238000000034 method Methods 0.000 title claims description 21
239000010948 rhodium Substances 0.000 title claims description 18
229910052703 rhodium Inorganic materials 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 11
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 32
150000001875 compounds Chemical class 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
239000011541 reaction mixture Substances 0.000 claims description 12
239000012298 atmosphere Substances 0.000 claims description 8
230000003197 catalytic effect Effects 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
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 claims description 7
239000013078 crystal Substances 0.000 claims description 6
238000002955 isolation Methods 0.000 claims description 5
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 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
230000000707 stereoselective effect Effects 0.000 claims description 3
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
150000004682 monohydrates Chemical class 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
229960003722 doxycycline Drugs 0.000 abstract description 13
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 10
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 description 8
229940042016 methacycline Drugs 0.000 abstract description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 4
SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,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-AKNGSSGZSA-N 0.000 abstract 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 abstract 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 16
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 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
229910000073 phosphorus hydride Inorganic materials 0.000 description 8
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
101100438156 Arabidopsis thaliana CAD7 gene Proteins 0.000 description 1
101150071647 CAD4 gene Proteins 0.000 description 1
101100322652 Catharanthus roseus ADH13 gene Proteins 0.000 description 1
101100087088 Catharanthus roseus Redox1 gene Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
LONQTZORWVBHMK-UHFFFAOYSA-N [N].NN Chemical group [N].NN LONQTZORWVBHMK-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000004458 analytical method Methods 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
125000004429 atom Chemical group 0.000 description 1
239000003060 catalysis inhibitor Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000013480 data collection Methods 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011521 glass Substances 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
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
150000003283 rhodium Chemical class 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical group [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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)

IE161087A 1987-03-25 1987-06-18 Process of preparation of a new catalyst containing rhodium and its application IE60598B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PT7430387		1987-03-25

Publications (2)

Publication Number	Publication Date
IE871610L IE871610L (en)	1988-09-25
IE60598B1 true IE60598B1 (en)	1994-07-27

Family

ID=20083055

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE161087A IE60598B1 (en)	1987-03-25	1987-06-18	Process of preparation of a new catalyst containing rhodium and its application

Country Status (8)

Country	Link
AT (1)	ATE63312T1 (de)
AU (1)	AU595606B2 (de)
CA (1)	CA1338107C (de)
DE (1)	DE3769977D1 (de)
HK (1)	HK81191A (de)
IE (1)	IE60598B1 (de)
NZ (1)	NZ220506A (de)
ZA (1)	ZA873543B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3771705D1 (de) *	1987-03-25	1991-08-29	Plurichemie Anstalt	Rhodiumhydrierungskatalysatoren.
ATE63312T1 (de) *	1987-03-25	1991-05-15	Plurichemie Anstalt	Rhodium enthaltende hydrierungskatalysatoren.
EP0391005B1 (de) *	1989-04-03	1991-10-16	Ranbaxy Laboratories, Ltd.	Verfahren zur Herstellung von alpha-6-Deoxytetracyclinen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT79774A (en) *	1984-12-28	1985-01-01	Joao Emerico Villax	Process to prepare rhodium catalysts and applications thereof
US4500458A (en) *	1982-01-19	1985-02-19	Plurichemie Anstalt	Process for the preparation of α-6-deoxytetracyclines
ATE63312T1 (de) *	1987-03-25	1991-05-15	Plurichemie Anstalt	Rhodium enthaltende hydrierungskatalysatoren.

1987
- 1987-05-14 AT AT87304278T patent/ATE63312T1/de not_active IP Right Cessation
- 1987-05-14 DE DE8787304278T patent/DE3769977D1/de not_active Expired - Fee Related
- 1987-05-18 ZA ZA873543A patent/ZA873543B/xx unknown
- 1987-05-27 AU AU73432/87A patent/AU595606B2/en not_active Ceased
- 1987-05-29 NZ NZ220506A patent/NZ220506A/xx unknown
- 1987-06-05 CA CA000539015A patent/CA1338107C/en not_active Expired - Lifetime
- 1987-06-18 IE IE161087A patent/IE60598B1/en not_active IP Right Cessation
1991
- 1991-10-17 HK HK811/91A patent/HK81191A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE63312T1 (de)	1991-05-15
AU595606B2 (en)	1990-04-05
ZA873543B (en)	1988-11-30
HK81191A (en)	1991-10-25
NZ220506A (en)	1989-09-27
CA1338107C (en)	1996-03-05
IE871610L (en)	1988-09-25
DE3769977D1 (de)	1991-06-13
AU7343287A (en)	1988-09-29

Legal Events

Date	Code	Title	Description
2007-03-21	MM4A	Patent lapsed

Publication	Publication Date	Title
Roembke et al.	2004	Application of (phosphine) gold (I) carboxylates, sulfonates and related compounds as highly efficient catalysts for the hydration of alkynes
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EP0283616B1 (de)	1991-07-24	Rhodiumhydrierungskatalysatoren
EP0283615B1 (de)	1991-05-08	Rhodium enthaltende Hydrierungskatalysatoren
IE41554B1 (en)	1980-01-30	Preperation of 6-deoxy-5-hydroxytetracycline
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IE60599B1 (en)	1994-07-27	Rhodium hydrogenation catalysts
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JPH04504412A (ja)	1992-08-06	α―６―デオキシテトラサイクリン類の製造法
EP0631814A1 (de)	1995-01-04	Ru-Sn-HETEROPOLYNUKLEARKOMPLEX UND VERFAHREN ZUR HERSTELLUNG VON ESSIGSÄURE ODER METHYLACETAT DURCH SEINE VERWENDUNG
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