GB890082A - Compounds containing nickel in internal complex combination and their production - Google Patents
Compounds containing nickel in internal complex combination and their productionInfo
- Publication number
- GB890082A GB890082A GB2546358A GB2546358A GB890082A GB 890082 A GB890082 A GB 890082A GB 2546358 A GB2546358 A GB 2546358A GB 2546358 A GB2546358 A GB 2546358A GB 890082 A GB890082 A GB 890082A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nickel
- chelate
- phenol
- alcohol
- complexes
- 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title abstract 12
- 150000001875 compounds Chemical class 0.000 title abstract 10
- 229910052759 nickel Inorganic materials 0.000 title abstract 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 8
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 8
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 6
- 239000002738 chelating agent Substances 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 4
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 abstract 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 150000004683 dihydrates Chemical class 0.000 abstract 3
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 abstract 3
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 abstract 3
- 235000019353 potassium silicate Nutrition 0.000 abstract 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 abstract 3
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 2
- 229940105305 carbon monoxide Drugs 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000013522 chelant Substances 0.000 abstract 2
- KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 abstract 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 abstract 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 2
- 229940093858 ethyl acetoacetate Drugs 0.000 abstract 2
- 239000003292 glue Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 230000004048 modification Effects 0.000 abstract 2
- 238000012986 modification Methods 0.000 abstract 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- -1 C1-6 alkyl radical Chemical group 0.000 abstract 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000005662 Paraffin oil Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 238000004898 kneading Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- YXLVLOWNJCOOAU-ZCFIWIBFSA-N methyl (2r)-2-ethyl-3-oxobutanoate Chemical group CC[C@H](C(C)=O)C(=O)OC YXLVLOWNJCOOAU-ZCFIWIBFSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Nickel chelate compounds for use as catalysts in the polymerization of acetylene to cyclooctatetraene and the reaction of carbon monoxide with acetylene are prepared by reacting nickel hydroxide and/or nickel carbonate in the absence of a solvent with at least one organic chelate-forming compound, the reaction being carried on with intense mixing until the product is in the form of a paste, the product then being mixed with an inert binding agent such as glue or water-glass and pressed into tablet or string form. In a modification, part of the chelateforming compound is replaced by a substantially stoichiometric amount of a non-chelating alcohol or phenol. Specified chelate-forming compounds include b -diketones, b -acyl acetates, aminophenols and aromatic hydroxyaldehydes. The compounds replacing part of the chelating agents include aliphatic, cycloaliphatic and araliphatic alcohols, phenol and cresols. The complexes are normally obtained in the form of dihydrates which can be dehydrated in vacuo. In Example 4, nickel hydroxide is reacted with ethyl acetoacetate and the plastic product is mixed with a little water-glass, extruded into strings and dried.ALSO:Organic nickel chelate compounds are prepared by reacting nickel hydroxide and/or nickel carbonate in the absence of a solvent with at least one organic chelate-forming compound, the reaction being carried on with intense mixing until the product is in the form of a paste or is in finely-grained form. Complexes obtainable as above described and containing one gram atom of nickel combined with one mole each of two different organic chelate-forming compounds, and dihydrates of these complexes, are claimed per se. In a modification of the above process, part of the chelate-forming organic compound is replaced by a substantially stoichiometric amount of a non-chelating alcohol and/or phenol. The chelate-forming compounds contain two different or identical functional groups such as OH, CO, CHO, NH2 or COOR where R represents a C1-6 alkyl radical or a cycloalkyl or aryl radical, as in b -dicarbonyl compounds, aminophenols and aromatic hydroxy-aldehydes. The nickel reagent and the chelating agents are generally used in molar ratios of about 1 : 2 though a larger excess of the chelating agent may be used. When part of the chelating agent is replaced by an alcohol and/or phenol, the latter may be a mono- or di-hydric aliphatic, cycloaliphatic or araliphatic alcohol or phenol or a cresol, many being specified. Generally, the phenol and/or alcohol and the chelating agent are used in equimolar amounts, and the complexes contain one gram atom of nickel and one mole each of the chelating agent and other reactant. The reactions are suitably carried out in a kneading machine or in a bucket type drier, suitable forms of both being described, and at temperatures from about 0 DEG C. to 90 DEG C. The product is generally first formed as a paste which subsequently becomes a pulverulent mass; a small amount of paraffin oil may be present to prevent dust formation. The product is also normally obtained as a hydrate which may be dehydrated in vacuo. Plastic products may be pressed into desired shapes, e.g. tablets suitably after admixture with a binding agent, e.g. glue or water glass and then dried. The complexes may be used as catalysts for the polymerization of acetylene to cyclo-octatetraene and for carbonmonoxide/acetylene reactions. Examples describe the preparation of complexes from nickel carbonate and/or nickel hydroxide and (1) methylethyl or tert.-butyl aceto acetate, (2) ethyl benzoyl acetate, (3) benzoyl acetone, (4) dibenzoyl methane, (5) salicyl aldehyde, (6) o-aminophenol, (7) a mixture of methyl or ethyl aceto acetate and acetyl acetone, (8) a mixture of acetyl acetone and either benzoyl acetone, dibenzoyl methane, salicyl aldehyde or o-aminophenol, (9) acetyl acetone and methanol, ethanol, propanol, butanol, amyl alcohol, benzyl alcohol, phenol or p-cresol, and (10) acetyl acetone, the products generally being dihydrates sometimes rendered anhydrous by drying.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB45641A DE1044801B (en) | 1957-08-10 | 1957-08-10 | Process for the production of nickel acetylacetonate |
DEB0048948 | 1958-05-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB890082A true GB890082A (en) | 1962-02-28 |
Family
ID=25965217
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2546358A Expired GB890082A (en) | 1957-08-10 | 1958-08-08 | Compounds containing nickel in internal complex combination and their production |
Country Status (4)
Country | Link |
---|---|
CH (1) | CH380710A (en) |
DE (2) | DE1044801B (en) |
FR (1) | FR1213503A (en) |
GB (1) | GB890082A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4147556A (en) * | 1972-01-12 | 1979-04-03 | Ppg Industries, Inc. | Nonflammable beta diketonate composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10297840B8 (en) * | 2002-12-23 | 2012-02-02 | Council Of Scientific And Industrial Research | Process for the preparation of metal acetylacetonates |
-
0
- DE DENDAT1071693D patent/DE1071693B/en active Pending
-
1957
- 1957-08-10 DE DEB45641A patent/DE1044801B/en active Pending
-
1958
- 1958-07-28 CH CH6232858A patent/CH380710A/en unknown
- 1958-08-08 GB GB2546358A patent/GB890082A/en not_active Expired
- 1958-08-11 FR FR1213503D patent/FR1213503A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4147556A (en) * | 1972-01-12 | 1979-04-03 | Ppg Industries, Inc. | Nonflammable beta diketonate composition |
Also Published As
Publication number | Publication date |
---|---|
FR1213503A (en) | 1960-04-01 |
DE1044801B (en) | 1958-11-27 |
CH380710A (en) | 1964-08-15 |
DE1071693B (en) | 1959-12-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1534902A (en) | Process for the preparation of arylene sulphide polymers | |
Cohen et al. | Azo-bis-diphenylmethane and the Decomposition of Aliphatic Azo Compounds. The Diphenylmethyl Radical1 | |
ZM5875A1 (en) | Process for the synthesis of alkyl-terbutyl ethers starting from a primary alcohol and isobutylene in presence of butadiene | |
Brook et al. | Cleavage of Hexaphenyldisilane by Sodium and Lithium | |
GB890082A (en) | Compounds containing nickel in internal complex combination and their production | |
US3775483A (en) | Process for producing a mono-condensation product of an alkylene oxide and a mercaptan | |
Kwiatek et al. | Protonation of organocyanocobaltate (III) complexes: A new synthesis of nitriles | |
ES347030A1 (en) | Process for the continuous preparation of vinyl acetate | |
US3133951A (en) | Process for the production of esters and carboxylates of alkyl boric acids | |
GB1330808A (en) | Process for the preparation of carotenoid compounds | |
GB1174331A (en) | A process for the preparation of Mono- and Polyacetoacetic Acid Esters | |
US2944084A (en) | Sodium tetraethylboron | |
Tsuzuki et al. | Novel conversion of diphenylcarbodiimide by sodium naphthalene | |
US3152156A (en) | Tri-n-butyl-t-butylperoxy stannane | |
ES408730A1 (en) | Novel chemical compounds and processes for preparing same | |
US3135786A (en) | Organoboron esters | |
GB1047109A (en) | Aromatic ether-alcohols | |
ES430903A1 (en) | Process for preparing *11oxoo22phenyl halophenyu or thienyll22mehyll 6*77dichlorooindanyloxy*acetate | |
ES445322A1 (en) | Process for preparing p-isobutyl-phenylacetic acid derivatives | |
US3109858A (en) | Unsymmetrical organoboron dicarboxylic acids and process for their synthesis | |
ES348340A1 (en) | Process for the preparation of n-hydroxyimidothiocarboxylic acid esters | |
US2680098A (en) | Silicon compounds | |
US2540267A (en) | Esters of acetoethyl-malonic acids and process | |
Allred et al. | Decomposition of azo compounds via cationic intermediates. Elucidation of the mechanism of ionization and nitrogen elimination | |
US3538135A (en) | Process for preparing stabilized forms of trialkynyl aluminums |