GB966860A - Organometallic compounds - Google Patents
Organometallic compoundsInfo
- Publication number
- GB966860A GB966860A GB38301/60A GB3830160A GB966860A GB 966860 A GB966860 A GB 966860A GB 38301/60 A GB38301/60 A GB 38301/60A GB 3830160 A GB3830160 A GB 3830160A GB 966860 A GB966860 A GB 966860A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclopentadienyl
- formula
- compounds
- hydrogen
- 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
- 150000002902 organometallic compounds Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 12
- -1 hydrocarbon radicals Chemical class 0.000 abstract 11
- 229930195733 hydrocarbon Natural products 0.000 abstract 9
- 239000004215 Carbon black (E152) Substances 0.000 abstract 8
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- TWKFYCJMKMVFCV-UHFFFAOYSA-N cyclopenta-1,3-diene;nickel Chemical compound [Ni].C=1C=C[CH-]C=1 TWKFYCJMKMVFCV-UHFFFAOYSA-N 0.000 abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 abstract 4
- 150000002430 hydrocarbons Chemical group 0.000 abstract 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 3
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 abstract 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000006079 antiknock agent Substances 0.000 abstract 2
- 239000012298 atmosphere Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 239000000446 fuel Substances 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 abstract 1
- QCRFSUNGWJPIIJ-UHFFFAOYSA-N C#C.C1(C=CC=C1)[Ni].C1(C=CC=C1)[Ni] Chemical group C#C.C1(C=CC=C1)[Ni].C1(C=CC=C1)[Ni] QCRFSUNGWJPIIJ-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052786 argon Inorganic materials 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 210000003298 dental enamel Anatomy 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 239000001307 helium Substances 0.000 abstract 1
- 229910052734 helium Inorganic materials 0.000 abstract 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000976 ink Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 238000007747 plating Methods 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002516 radical scavenger Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229920002545 silicone oil Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/06—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material
- C23C16/18—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of metallic material from metallo-organic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
- C10M2227/081—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds with a metal carbon bond belonging to a ring, e.g. ferocene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises organo metallic compounds of formula: QCCQ1.Cy(Ni)xCy1 wherein Q and Q1 are each hydrogen, C1-C10 univalent hydrocarbon radicals, or electron withdrawing groups, Cy and Cy1 are cyclopentadienyl hydrocarbon groups (as defined), x is 1 or 2 and when x is 2 and Q is hydrogen or phenyl, Q1 is an electron withdrawing group. Cy and Cy1 may be the same or different and are hydrocarbon groups of formulae: <FORM:0966860/C1/1> <FORM:0966860/C1/2> wherein the R1s are hydrogen or univalent hydrocarbon radicals, the complete radical preferably containing 5 to 13 carbon atoms. Typical electron withdrawing groups are specified. The above formula includes compounds of formula: QCCQ1.CyNiNiCy1 of structural formula: <FORM:0966860/C1/3> Suitable univalent hydrocarbon radicals may have polar substituents separated by at least two carbon atoms from the acetylenic bond; thus suitable acetylenic compounds are perhalo butynes, propargyl alcohol, ethynyl cyclohexanol, beta carboxy esters of the butynes, pentynes, hexynes and heptynes and 5-methoxy pentyne-1. Other compounds have the formula: QCCQ1.CyNiCy1 which may have the structure (in the case of dicyclopentadienyl nickeldimethyl butyndioate) <FORM:0966860/C1/4> These compounds may be hydrogenated at the double bond of the cyclopentadienyl ring attached to the acetylene compound. Both groups of compounds may be prepared by reacting a compound of formula CyNixCy1 with an acetylenic compound of formula QCCQ1 where Q,Q1,Cy,Cy1 and x are as above defined. If desired the resulting compound may be treated with ZCCZ1 where Z and Z1 are electron withdrawing groups. The reaction is carried out between -30 DEG and 110 DEG C., at a pressure from atmospheric to 10,000 psig (preferably to 250 psig) if desired in the presence of a solvent (which may be the acetylenic compound itself, or an ether, ester or silicone oil) and preferably under an inert blanket of nitrogen, helium or argon. Typical compounds prepared in the examples include bis(cyclopentadienyl nickel) acetylene; (v) bis (cyclopentadienyl nickel) propyne; (vi) bis(cyclopentadienyl nickel) hexyne-3, (x) bis(cyclopentadienyl nickel) phenyl acetylene; (xi) bis (cyclopentadienyl nickel) perfluorobutyne-2, (xiii) bis(cyclopentadienyl nickel) dimethyl acetylene dicarboxylate and (xiv) dicyclopentadienyl nickel-dimethyl-sym-butyndioate.ALSO:Cyclopentadienyl nickel acetylenic compounds of formula QCCQ1.Cy(Ni)xCy1 wherein Q and Q1 are each hydrogen, univalent C1-10 hydrocarbon radicals or electron withdrawing groups, Cy and Cy1 are cyclopentadienyl or indenyl groups which may be substituted by univalent hydrocarbon radicals, x is 1 or 2 and when x is 2 and Q is hydrogen or a phenyl radical, Q1 is an electron withdrawing group, may be added: (a) to paints, varnish, printing inks, oil enamels and drying oil synthetic resins to improve their drying characteristics; (b) as anti-knock agents to liquid hydrocarbon fuels, especially those in the gasoline boiling range. A specified additive is bis(cyclopentadienyl nickel) hexyne-3. The base fuel may contain all types of hydrocarbons, paraffins (straight and branched chain), olefins, cycloaliphatics and aromatics. Additionally there may be present an organolead anti-knock agent together with a conventional halohydrocarbon scavenger. Example XXI describes a gasoline composition containing tetraethyl lead, ethylene dichloride, ethylene dibromide and bis(cyclopentadienyl nickel)pentyne-1.ALSO:Cyclopentadienyl nickel acetylenic compounds of formula QCCQ1.Cy(Ni)xCy1 wherein Q and Q1 are each hydrogen, univalent C1-10 hydrocarbon radicals or electron withdrawing groups, Cy and Cy1 are cyclopentadienyl or indenyl groups which may be substituted by univalent hydrocarbon radicals, x is 1 or 2 and when x is 2 and Q is hydrogen or a phenyl group Q1 is an electron withdrawing group may be used in gas phase metal plating. They may be thermally decomposed in an atmosphere of a reducing gas such as hydrogen or a neutral atmosphere such as nitrogen to form metallic films on a substrate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB38301/60A GB966860A (en) | 1960-11-08 | 1960-11-08 | Organometallic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB38301/60A GB966860A (en) | 1960-11-08 | 1960-11-08 | Organometallic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB966860A true GB966860A (en) | 1964-08-19 |
Family
ID=10402562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38301/60A Expired GB966860A (en) | 1960-11-08 | 1960-11-08 | Organometallic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB966860A (en) |
-
1960
- 1960-11-08 GB GB38301/60A patent/GB966860A/en not_active Expired
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