GB882400A - Organic diphosphine nickel complexes - Google Patents
Organic diphosphine nickel complexesInfo
- Publication number
- GB882400A GB882400A GB2535958A GB2535958A GB882400A GB 882400 A GB882400 A GB 882400A GB 2535958 A GB2535958 A GB 2535958A GB 2535958 A GB2535958 A GB 2535958A GB 882400 A GB882400 A GB 882400A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nickel
- bis
- carbonyl
- diethyl
- phenylene bis
- Prior art date
- 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
Links
- VURFVHCLMJOLKN-UHFFFAOYSA-N Diphosphine Natural products PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 title abstract 3
- -1 diphosphine nickel complexes Chemical class 0.000 title abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 14
- 229910052759 nickel Inorganic materials 0.000 abstract 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 12
- 125000004437 phosphorous atom Chemical group 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 4
- 239000012298 atmosphere Substances 0.000 abstract 4
- WWXFZLVLAJUATK-UHFFFAOYSA-N (2-diethylphosphanylphenyl)-diethylphosphane Chemical compound CCP(CC)C1=CC=CC=C1P(CC)CC WWXFZLVLAJUATK-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 150000002815 nickel Chemical group 0.000 abstract 3
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 abstract 2
- KHMYIIPFUJCUEK-UHFFFAOYSA-N 1-diethylphosphanylethyl(diethyl)phosphane Chemical compound CCP(CC)C(C)P(CC)CC KHMYIIPFUJCUEK-UHFFFAOYSA-N 0.000 abstract 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- CHBDXRNMDNRJJC-UHFFFAOYSA-N 1,2,3-triphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CHBDXRNMDNRJJC-UHFFFAOYSA-N 0.000 abstract 1
- NCDREDLYLRUAQD-UHFFFAOYSA-N C(=O)=[Ni]=C=O.C1(=C(C=CC=C1)P(CC)CC)P(CC)CC Chemical compound C(=O)=[Ni]=C=O.C1(=C(C=CC=C1)P(CC)CC)P(CC)CC NCDREDLYLRUAQD-UHFFFAOYSA-N 0.000 abstract 1
- 101000621511 Potato virus M (strain German) RNA silencing suppressor Proteins 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- RUWYJYTWMNOYFM-UHFFFAOYSA-N [Ni].C1(=C(C=CC=C1)P(CC)CC)P(CC)CC Chemical compound [Ni].C1(=C(C=CC=C1)P(CC)CC)P(CC)CC RUWYJYTWMNOYFM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 238000005810 carbonylation reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
- 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
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- 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
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/12—Olefin polymerisation or copolymerisation
-
- 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
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- 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
-
- 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
- B01J31/20—Carbonyls
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises complex compounds of organic diphosphines as defined below and zerovalent nickel in which a nickel atom is attached to two tertiary phosphorus atoms and to two carbonyl groups or to four tertiary phosphorus atoms. The organic diphosphines are defined as aliphatic diphosphines having the general formula C2H4(PR2)2 and aromatic diphosphines having the general formula o-C6H4(PR12)2 wherein R is an alkyl or aryl radical and R1 is an alkyl radical. The complex compounds in which a nickel atom is attached to tertiary phosphorus atoms and to carbonyl groups may be obtained by reacting an aliphatic diphosphine or an o-phenylene bis-(dialkyl phosphine) with nickel carbonyl in an inert atmosphere and complexes having nickel atoms attached to four tertiary phosphorus atoms are obtained by heating in an inert atmosphere an o-phenylene bis-(dialkyl phosphine) with finely divided nickel or with one of the aromatic complex compounds in which a nickel atom is attached to tertiary phosphorus atoms and to carbonyl groups. It is preferred to use nitrogen as the inert atmosphere and methanol may be used as solvent for the nickel carbonyl. Examples are given for the production of (1) o-phenylene bis-(diethyl phosphine) dicarbonyl nickel by treating nickel carbonyl in methanol with o-phenylene bis-(diethyl phosphine) in a nitrogen atmosphere at 15 DEG C.; (2) di-o-phenylene bis (diethyl phosphine) nickel by heating a mixture of o-phenylene bis (diethyl phosphine) and the product of (1) for 2 hours at 150 DEG C. in a nitrogen atmosphere; (3) 1 : 2-bis (diethyl phosphino-) ethane dicarbonyl nickel by heating nickel carbonyl with 1 : 2-bis (diethyl phosphino) ethane in methanol solution under an atmosphere of nitrogen; (4) di o-phenylene bis (diethyl phosphine) nickel by reacting o-phenylene bis-(diethyl phosphine) with Raney nickel at 160 DEG C. for 8 hours in a nitrogen atmosphere, (5) 1 : 2-bis (diphenyl phosphino) ethane dicarbonyl nickel by reacting nickel carbonyl with 1 : 2-bis (diphenyl phosphino) ethane in benzene. The products are useful as catalysts in carbonylation reactions and in the polymerisation of acetylenes and olefines to yield cyclic hydrocarbons and examples are given for the production of triphenylbenzene compounds by polymerising phenyl acetylene in the presence of methanol using the products of Examples (1) and (5) respectively as catalyst. Specifications 859,391 and 859,741 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2535958A GB882400A (en) | 1958-08-07 | 1958-08-07 | Organic diphosphine nickel complexes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2535958A GB882400A (en) | 1958-08-07 | 1958-08-07 | Organic diphosphine nickel complexes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB882400A true GB882400A (en) | 1961-11-15 |
Family
ID=10226396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2535958A Expired GB882400A (en) | 1958-08-07 | 1958-08-07 | Organic diphosphine nickel complexes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB882400A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242171A (en) * | 1963-02-06 | 1966-03-22 | Du Pont | Complexes of organophosphorus fluorides with zerovalent transition metals |
| EP0220765A1 (en) * | 1985-10-15 | 1987-05-06 | Shell Internationale Researchmaatschappij B.V. | Novel copolymers of SO2 and ethene |
| US7700795B2 (en) * | 2003-10-30 | 2010-04-20 | Basf Aktiengesellschaft | Use of azeotropically dried nickel(ii) halogenides |
-
1958
- 1958-08-07 GB GB2535958A patent/GB882400A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242171A (en) * | 1963-02-06 | 1966-03-22 | Du Pont | Complexes of organophosphorus fluorides with zerovalent transition metals |
| EP0220765A1 (en) * | 1985-10-15 | 1987-05-06 | Shell Internationale Researchmaatschappij B.V. | Novel copolymers of SO2 and ethene |
| US7700795B2 (en) * | 2003-10-30 | 2010-04-20 | Basf Aktiengesellschaft | Use of azeotropically dried nickel(ii) halogenides |
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