CA1042008A - Catalyseurs de bis-diorganoorthophosphates de nickel - Google Patents

Catalyseurs de bis-diorganoorthophosphates de nickel

Info

Publication number: CA1042008A
Authority: CA; Canada
Prior art keywords: carbon atoms; orthophosphate; catalyst; diorgano; nickel bis
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

CA294,367A

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 CA1042008A publication Critical patent/CA1042008A/fr

Status Expired legal-status Critical Current

Links

PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 68
229910052759 nickel Inorganic materials 0.000 title claims abstract description 34
239000003054 catalyst Substances 0.000 title claims abstract description 25
239000000203 mixture Substances 0.000 title claims description 7
-1 alkyl aluminum halides Chemical class 0.000 claims abstract description 12
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052720 vanadium Inorganic materials 0.000 claims abstract description 6
238000006243 chemical reaction Methods 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 16
239000000047 product Substances 0.000 claims description 16
238000006116 polymerization reaction Methods 0.000 claims description 14
150000001336 alkenes Chemical class 0.000 claims description 12
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 6
150000002430 hydrocarbons Chemical class 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
239000004215 Carbon black (E152) Substances 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 compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
230000002452 interceptive effect Effects 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 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
239000007795 chemical reaction product Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000001033 ether group Chemical group 0.000 claims 1
239000000178 monomer Substances 0.000 abstract description 9
229920000642 polymer Polymers 0.000 abstract description 9
239000000306 component Substances 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
229940045605 vanadium Drugs 0.000 description 3
UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-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
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000001450 anions Chemical class 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
239000011521 glass Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
150000002816 nickel compounds Chemical class 0.000 description 2
125000002560 nitrile group Chemical group 0.000 description 2
238000006384 oligomerization reaction Methods 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 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
NSFOUAOLESMNKQ-UHFFFAOYSA-N 2-methylpentyl pentyl hydrogen phosphate Chemical compound CCCCCOP(O)(=O)OCC(C)CCC NSFOUAOLESMNKQ-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
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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
125000003118 aryl group Chemical group 0.000 description 1
230000003190 augmentative effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UUKHERKOYFZUQO-UHFFFAOYSA-N bis(4-methylpentyl) hydrogen phosphate Chemical compound CC(C)CCCOP(O)(=O)OCCCC(C)C UUKHERKOYFZUQO-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 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
FMGOGHOQORLKJD-UHFFFAOYSA-N butyl tert-butyl hydrogen phosphate Chemical compound CCCCOP(O)(=O)OC(C)(C)C FMGOGHOQORLKJD-UHFFFAOYSA-N 0.000 description 1
QQHRHLXGCZWTDK-UHFFFAOYSA-L butylaluminum(2+);dibromide Chemical compound [Br-].[Br-].CCCC[Al+2] QQHRHLXGCZWTDK-UHFFFAOYSA-L 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 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
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000007334 copolymerization reaction Methods 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
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 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
238000004508 fractional distillation Methods 0.000 description 1
239000007789 gas Substances 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
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
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 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
239000007788 liquid Substances 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
150000007522 mineralic acids Chemical class 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
150000002815 nickel Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003606 oligomerizing effect Effects 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 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
238000002360 preparation method Methods 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
239000011541 reaction mixture Substances 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
238000001228 spectrum 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
150000003682 vanadium compounds Chemical class 0.000 description 1

Landscapes

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

CA294,367A 1973-11-16 1978-01-05 Catalyseurs de bis-diorganoorthophosphates de nickel Expired CA1042008A (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
CA1042008A true CA1042008A (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 Before (1)

Application Number	Title	Priority Date	Filing Date
CA294,366A Expired CA1042009A (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
CA1042009A (fr)	1978-11-07

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