CA1042009A - Catalyseurs de bis-diorganoorthophosphates de nickel - Google Patents

Catalyseurs de bis-diorganoorthophosphates de nickel

Info

Publication number: CA1042009A
Authority: CA; Canada
Prior art keywords: carbon atoms; catalyst; orthophosphate; nickel bis; reaction
Prior art date: 1973-11-16
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

CA294,366A

Other languages

English (en)

Inventor

Jeffrey G. Meyer

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.)

Anderson Development Co

Original Assignee

Anderson Development Co

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.)

1973-11-16

Filing date

1978-01-05

Publication date

1978-11-07

1974-11-14 Priority claimed from CA213,706A external-priority patent/CA1037963A/fr

1978-01-05 Application filed by Anderson Development Co filed Critical Anderson Development Co

1978-11-07 Application granted granted Critical

1978-11-07 Publication of CA1042009A publication Critical patent/CA1042009A/fr

Status Expired legal-status Critical Current

Links

PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 81
229910052759 nickel Inorganic materials 0.000 title claims abstract description 38
239000003054 catalyst Substances 0.000 title claims abstract description 29
239000000203 mixture Substances 0.000 title claims description 5
-1 alkyl aluminum halides Chemical class 0.000 claims abstract description 15
238000006384 oligomerization reaction Methods 0.000 claims abstract description 14
150000001336 alkenes Chemical class 0.000 claims abstract description 12
238000006243 chemical reaction Methods 0.000 claims description 29
239000000047 product Substances 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 9
125000001931 aliphatic group Chemical group 0.000 claims description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 5
150000002430 hydrocarbons Chemical class 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
230000002452 interceptive effect Effects 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000001033 ether group Chemical group 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 abstract description 17
229920000642 polymer Polymers 0.000 abstract description 3
230000015572 biosynthetic process Effects 0.000 abstract description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000178 monomer Substances 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 11
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
239000005977 Ethylene Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 9
239000007788 liquid Substances 0.000 description 9
238000007792 addition Methods 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
239000013638 trimer Substances 0.000 description 3
UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
YQHVEGTZGGQQMV-UHFFFAOYSA-N dicyclohexyl hydrogen phosphate Chemical compound C1CCCCC1OP(=O)(O)OC1CCCCC1 YQHVEGTZGGQQMV-UHFFFAOYSA-N 0.000 description 2
UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 2
MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000002560 nitrile group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical class CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 description 1
SBTXFPRXBNGIJM-UHFFFAOYSA-N 2-ethylhexyl 3-methylhexyl hydrogen phosphate Chemical compound CCCCC(CC)COP(O)(=O)OCCC(C)CCC SBTXFPRXBNGIJM-UHFFFAOYSA-N 0.000 description 1
YYTUUFMWKBIPEY-UHFFFAOYSA-N 3-ethenylcyclohexene Chemical compound C=CC1CCCC=C1 YYTUUFMWKBIPEY-UHFFFAOYSA-N 0.000 description 1
UJFJAMZCPFRYBW-UHFFFAOYSA-N 4-methylcyclooctene Chemical compound CC1CCCCC=CC1 UJFJAMZCPFRYBW-UHFFFAOYSA-N 0.000 description 1
MILSXGPCQQLZIA-UHFFFAOYSA-N 4-methylpentyl dihydrogen phosphate Chemical compound CC(C)CCCOP(O)(O)=O MILSXGPCQQLZIA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
GPBCXXQDAKRVAS-UHFFFAOYSA-N butyl propyl hydrogen phosphate Chemical compound CCCCOP(O)(=O)OCCC GPBCXXQDAKRVAS-UHFFFAOYSA-N 0.000 description 1
VPCAAUUIFCAFRZ-UHFFFAOYSA-N butylalumane Chemical compound CCCC[AlH2] VPCAAUUIFCAFRZ-UHFFFAOYSA-N 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
HYZXMVILOKSUKA-UHFFFAOYSA-K chloro(dimethyl)alumane;dichloro(methyl)alumane Chemical compound C[Al](C)Cl.C[Al](Cl)Cl HYZXMVILOKSUKA-UHFFFAOYSA-K 0.000 description 1
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
SWXUEJURRAEAMJ-UHFFFAOYSA-N dicyclobutyl hydrogen phosphate Chemical compound C1CCC1OP(=O)(O)OC1CCC1 SWXUEJURRAEAMJ-UHFFFAOYSA-N 0.000 description 1
POVJEPOYXLSCLY-UHFFFAOYSA-N dicyclopentyl hydrogen phosphate Chemical compound C1CCCC1OP(=O)(O)OC1CCCC1 POVJEPOYXLSCLY-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
239000000539 dimer Substances 0.000 description 1
HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000000727 fraction Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
YNEJOBWVBDEPOA-UHFFFAOYSA-N heptyl octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCC YNEJOBWVBDEPOA-UHFFFAOYSA-N 0.000 description 1
RYPKRALMXUUNKS-UHFFFAOYSA-N hex-2-ene Chemical class CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XWKFRUCQRXQQIF-UHFFFAOYSA-N hexyl pentyl hydrogen phosphate Chemical compound CCCCCCOP(O)(=O)OCCCCC XWKFRUCQRXQQIF-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000036647 reaction Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Landscapes

Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

CA294,366A 1973-11-16 1978-01-05 Catalyseurs de bis-diorganoorthophosphates de nickel Expired CA1042009A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US41639073A	1973-11-16	1973-11-16
CA213,706A CA1037963A (fr)	1973-11-16	1974-11-14	Synthese et emploi de bis-diorgano-orthophosphates de nickel

Publications (1)

Publication Number	Publication Date
CA1042009A true CA1042009A (fr)	1978-11-07

Family

ID=25667751

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA294,366A Expired CA1042009A (fr)	1973-11-16	1978-01-05	Catalyseurs de bis-diorganoorthophosphates de nickel
CA294,367A Expired CA1042008A (fr)	1973-11-16	1978-01-05	Catalyseurs de bis-diorganoorthophosphates de nickel

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA294,367A Expired CA1042008A (fr)	1973-11-16	1978-01-05	Catalyseurs de bis-diorganoorthophosphates de nickel

Country Status (1)

Country	Link
CA (2)	CA1042009A (fr)

1978
- 1978-01-05 CA CA294,366A patent/CA1042009A/fr not_active Expired
- 1978-01-05 CA CA294,367A patent/CA1042008A/fr not_active Expired

Also Published As

Publication number	Publication date
CA1042008A (fr)	1978-11-07

Publication	Publication Date	Title
US5496783A (en)	1996-03-05	Catalyst for the production of light alpha olefins by oligomerization of ethylene
US3379706A (en)	1968-04-23	pi-allyl metal compounds and their use as polymerization, including oligomerization, catalysts
US20110288308A1 (en)	2011-11-24	Process for dimerization of ethylene to but-1-ene using a composition comprising a titanium-based complex and an alkoxy ligand functionalized by a heteroatom
CA1084033A (fr)	1980-08-19	Augmentation de la granulometrie de copolymeres d'ethylene ou de polyethylene tels qu'ils sont formes
US20010023281A1 (en)	2001-09-20	Catalytic composition and a process for oligomerizing ethylene, in particular to 1-hexene
CA1183553A (fr)	1985-03-05	Obtention de produits a base d'olefines lineaires
US20110287927A1 (en)	2011-11-24	Process for oligomerization of olefins that uses a catalytic composition that comprises an organometallic complex that contains an alkoxy ligand that is functionalized by a heteroatom
US2387517A (en)	1945-10-23	Process for copolymerization
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US2985640A (en)	1961-05-23	Polymerization catalyst and process
CA1042009A (fr)	1978-11-07	Catalyseurs de bis-diorganoorthophosphates de nickel
EP0001186B1 (fr)	1981-08-12	Procédé de préparation de polyisobutène
US4111839A (en)	1978-09-05	Nickel bis-organo-orthosphosphate combination catalyst
US4642410A (en)	1987-02-10	Catalytic poly alpha-olefin process
US2905661A (en)	1959-09-22	Production of polymers from olefines
US3907849A (en)	1975-09-23	Chromium tris-diorgano-orthophosphates and their preparation
US3538171A (en)	1970-11-03	Process for the isomerization of 5-vinylbicyclo(2.2.1)hept-2-ene
US4359562A (en)	1982-11-16	Process for producing ethylene polymers and copolymers by means of a supported catalyst of a chromium-hydrocarbon complex on an inorganic oxide carrier
US3180837A (en)	1965-04-27	Polymerization catalyst containing polymeric diene-aluminum compounds
US3239497A (en)	1966-03-08	Method of preparing a polymerization catalyst for olefins and olefin polymers
US3255167A (en)	1966-06-07	Olefin polymerization in presence of a reduced titanium halide supported on gamma alumina and an organometallic compound
US3558519A (en)	1971-01-26	Aluminum nickel catalyst composition