CA1123017A - Process for hydrogenating olefinic compounds - Google Patents

Process for hydrogenating olefinic compounds

Info

Publication number: CA1123017A
Authority: CA; Canada
Prior art keywords: hydrogenation; process according; carried out; olefin; solution
Prior art date: 1977-06-08
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

Application number

CA304,253A

Other languages

English (en)

French (fr)

Inventor

Salvatore Cucinella

Giovanni Dozzi

Alessandro Mazzei

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.)

Anic SpA

Original Assignee

Anic SpA

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.)

1977-06-08

Filing date

1978-05-29

Publication date

1982-05-04

1978-05-29 Application filed by Anic SpA filed Critical Anic SpA

1982-05-04 Application granted granted Critical

1982-05-04 Publication of CA1123017A publication Critical patent/CA1123017A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 17
238000000034 method Methods 0.000 title claims abstract description 15
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 42
239000003054 catalyst Substances 0.000 claims abstract description 26
229910052723 transition metal Inorganic materials 0.000 claims abstract description 12
150000003624 transition metals Chemical class 0.000 claims abstract description 12
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims abstract description 10
-1 hydride derivative of aluminium Chemical class 0.000 claims abstract description 8
125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
229910000091 aluminium hydride Inorganic materials 0.000 claims abstract description 6
239000002879 Lewis base Substances 0.000 claims abstract description 5
150000001412 amines Chemical class 0.000 claims abstract description 5
150000007527 lewis bases Chemical group 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 33
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 15
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 15
229920000642 polymer Polymers 0.000 claims description 12
239000004411 aluminium Substances 0.000 claims description 11
229910052782 aluminium Inorganic materials 0.000 claims description 11
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
229920001577 copolymer Polymers 0.000 claims description 5
150000001336 alkenes Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
229920001519 homopolymer Polymers 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 4
150000001993 dienes Chemical class 0.000 claims 2
150000001925 cycloalkenes Chemical class 0.000 claims 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
239000004711 α-olefin Substances 0.000 claims 1
150000001298 alcohols Chemical class 0.000 abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 61
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 19
230000000694 effects Effects 0.000 description 19
150000004678 hydrides Chemical class 0.000 description 19
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 18
239000000758 substrate Substances 0.000 description 17
229910001220 stainless steel Inorganic materials 0.000 description 11
239000010935 stainless steel Substances 0.000 description 11
235000010210 aluminium Nutrition 0.000 description 10
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 10
238000003760 magnetic stirring Methods 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
229910017052 cobalt Inorganic materials 0.000 description 9
239000010941 cobalt Substances 0.000 description 9
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 9
238000007792 addition Methods 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 8
239000000047 product Substances 0.000 description 8
239000007789 gas Substances 0.000 description 7
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
230000008901 benefit Effects 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
229910000831 Steel Inorganic materials 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 4
239000002815 homogeneous catalyst Substances 0.000 description 4
239000010959 steel Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
230000009850 completed effect Effects 0.000 description 3
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
229920000098 polyolefin Polymers 0.000 description 3
SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
101100379067 Caenorhabditis elegans anc-1 gene Proteins 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
239000005062 Polybutadiene Substances 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 2
239000013110 organic ligand Substances 0.000 description 2
229920002857 polybutadiene Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
IFVMAGPISVKRAR-UHFFFAOYSA-N 1-ethylcyclohexene Chemical compound CCC1=CCCCC1 IFVMAGPISVKRAR-UHFFFAOYSA-N 0.000 description 1
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
101100058670 Aeromonas hydrophila subsp. hydrophila (strain ATCC 7966 / DSM 30187 / BCRC 13018 / CCUG 14551 / JCM 1027 / KCTC 2358 / NCIMB 9240 / NCTC 8049) bsr gene Proteins 0.000 description 1
241000180579 Arca Species 0.000 description 1
238000010464 Blanc reaction Methods 0.000 description 1
229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
241000286904 Leptothecata Species 0.000 description 1
101100396971 Schizosaccharomyces pombe (strain 972 / ATCC 24843) ini1 gene Proteins 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
125000005234 alkyl aluminium group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000002506 iron compounds Chemical class 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000005291 magnetic effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
208000006379 syphilis Diseases 0.000 description 1
230000007704 transition Effects 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0252—Nitrogen containing compounds with a metal-nitrogen link, e.g. metal amides, metal guanidides
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
- 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
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
- 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
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C07C5/05—Partial hydrogenation
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
- 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
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/46—Titanium
- 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
- B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
- B01J2531/56—Vanadium
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Inorganic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA304,253A 1977-06-08 1978-05-29 Process for hydrogenating olefinic compounds Expired CA1123017A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT24468/77A IT1081825B (it)	1977-06-08	1977-06-08	Sistemi omogenei catalitici per la idrogenazione di substrati olefinici e relativi processi
IT24468A/77		1977-06-08

Publications (1)

Publication Number	Publication Date
CA1123017A true CA1123017A (en)	1982-05-04

Family

ID=11213641

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA304,253A Expired CA1123017A (en)	1977-06-08	1978-05-29	Process for hydrogenating olefinic compounds

Country Status (9)

Country	Link
JP (1)	JPS544292A (it)
BE (1)	BE867940A (it)
CA (1)	CA1123017A (it)
DE (1)	DE2825238A1 (it)
ES (1)	ES471144A1 (it)
FR (1)	FR2393608A1 (it)
GB (1)	GB1602145A (it)
IT (1)	IT1081825B (it)
NL (1)	NL7806253A (it)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58110466U (ja) *	1982-01-21	1983-07-27	株式会社学習研究社	回転印字器
GB2134909B (en) *	1983-01-20	1986-08-20	Asahi Chemical Ind	Catalytic hydrogenation of conjugated diene polymer
JPS6128507A (ja) *	1984-07-18	1986-02-08	Asahi Chem Ind Co Ltd	オレフイン性不飽和ポリマ−の水添方法
US4891456A (en) *	1987-07-06	1990-01-02	Nippon Oil Co., Ltd.	Method for preparing norbornene structure compound
EP0476737A3 (en) *	1990-08-27	1992-05-06	Shell Internationale Research Maatschappij B.V.	Block copolymer of polyalkylene and halogenated poly(vinyl aromatic)
DE102004022676A1 (de)	2004-05-07	2005-12-15	Bayer Ag	Hydrierte Copolymerisate aus nicht substituierten und substituierten konjugierten Dienen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1597517A (it) *	1968-09-05	1970-06-29
BE737574A (it) *	1968-09-05	1970-02-02
FR95896E (fr) *	1968-12-24	1971-11-12	Inst Francais Du Petrole	Nouveau catalyseur d'hydrogénation.

1977
- 1977-06-08 IT IT24468/77A patent/IT1081825B/it active
1978
- 1978-05-26 GB GB23598/78A patent/GB1602145A/en not_active Expired
- 1978-05-29 CA CA304,253A patent/CA1123017A/en not_active Expired
- 1978-06-06 ES ES471144A patent/ES471144A1/es not_active Expired
- 1978-06-07 FR FR787817090A patent/FR2393608A1/fr active Granted
- 1978-06-08 NL NL7806253A patent/NL7806253A/xx not_active Application Discontinuation
- 1978-06-08 BE BE188425A patent/BE867940A/xx unknown
- 1978-06-08 DE DE19782825238 patent/DE2825238A1/de not_active Ceased
- 1978-06-08 JP JP6840478A patent/JPS544292A/ja active Pending

Also Published As

Publication number	Publication date
NL7806253A (nl)	1978-12-12
GB1602145A (en)	1981-11-04
FR2393608A1 (fr)	1979-01-05
IT1081825B (it)	1985-05-21
BE867940A (fr)	1978-12-08
ES471144A1 (es)	1979-01-16
JPS544292A (en)	1979-01-12
DE2825238A1 (de)	1978-12-14
FR2393608B1 (it)	1982-04-02

Legal Events

Date	Code	Title	Description
1999-05-04	MKEX	Expiry

Publication	Publication Date	Title
Aracama et al.	1991	Synthesis, reactivity, molecular structure, and catalytic activity of the novel dichlorodihydridoosmium (IV) complexes OsH2Cl2 (PR3) 2 (PR3= Pi-Pr3, PMe-t-Bu2)
Bijpost et al.	1995	Early transition metal catalyzed-hydroboration of alkenes
US4424332A (en)	1984-01-03	Polymeric metal-amine complex compounds, processes for their preparation and use
US3412174A (en)	1968-11-19	Hydrogenation process employing a transition metal catalyst
Gomez et al.	1991	Stoichiometric model reactions in olefin hydroformylation by platinum-tin systems
Itatani et al.	1967	Homogeneous catalysis in the reactions of olefinic substances. 1a VII. Hydrogenation and isomerization of methyl linoleate with bis (triphenylphosphine) nickel halides1b
Esteruelas et al.	1989	The reduction of α, β-unsaturated ketones and cyclohexadienes catalyzed by mhcl (CO)(PiPr3) 2 (M= Ru, Os) complexes
CA1123017A (en)	1982-05-04	Process for hydrogenating olefinic compounds
US3562351A (en)	1971-02-09	Dimerization process
Choudary et al.	1987	Syntheses of interlamellar montmorillonitebipyridinepalladium (II) catalysts: the first examples of chelation in smectite clay
US3959239A (en)	1976-05-25	Use of nickel cyclooctadiene as a hydrogenation catalyst
Terasawa et al.	1979	Selective hydrogenation of acetylenes to olefins catalyzed by polymer-bound palladium (II) complexes
US3488400A (en)	1970-01-06	Hydrogenation process
Freeman et al.	1982	Triosmium clusters bonded to phosphine-functionalized supports: Catalysts for olefin isomerization
US3439054A (en)	1969-04-15	Metal carbonyl catalyst and hydrogenation process therefor
Grushin et al.	1991	Chemospecific, biphasic reduction of. alpha.,. beta.-unsaturated aldehydes and ketones catalyzed by rhodium complex (Cy3P) 2Rh (H) Cl2
Kroll	1969	Activity and selectivity of homogeneous Ziegler-type hydrogenation catalysts. I
Fusi et al.	1982	The homogeneous hydrogenation of carbon-carbon multiple bonds with heteronuclear platinum clusters
Dozzi et al.	1979	Hydrogenation catalysts from aluminium hydride derivatives and transition metal compounds
Pertici et al.	1984	(η6-Arene)(η4-cycloocta-1, 5-diene) ruthenium (0) complexes as homogeneous hydrogenation catalysts
KR20120115286A (ko)	2012-10-17	알파-올레핀 제조법
Kanai et al.	1980	Selective cis-Isomerization of 1-Pentene Catalyzed by Ni (I)-Triphenylphosphine Complexes
Nudel et al.	1984	Selective hydrogenation of 1, 3-butadiene over LaCoO3 perovskite
Raoult et al.	1992	Hydrogenation and isomerization of olefins with diphenylphosphinomethyl hydride zirconium,[Cp2ZrH (CH2PPh2)] n, a selective homogeneous catalyst
Pittman Jr et al.	1985	The catalytic activity of low oxidation state platinum-and palladium-containing mixed-metal clusters