DE3723713A1 - Alkoholfreie orthoester des zirkoniums und hafniums und verfahren zu deren herstellung - Google Patents
Alkoholfreie orthoester des zirkoniums und hafniums und verfahren zu deren herstellungInfo
- Publication number
- DE3723713A1 DE3723713A1 DE19873723713 DE3723713A DE3723713A1 DE 3723713 A1 DE3723713 A1 DE 3723713A1 DE 19873723713 DE19873723713 DE 19873723713 DE 3723713 A DE3723713 A DE 3723713A DE 3723713 A1 DE3723713 A1 DE 3723713A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alcohol
- melting point
- zirconate
- tetra
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 13
- 150000002905 orthoesters Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 7
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 title 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 21
- -1 hafnium orthoesters Chemical class 0.000 claims description 17
- 229910052726 zirconium Inorganic materials 0.000 claims description 16
- 229910001507 metal halide Inorganic materials 0.000 claims description 15
- 150000005309 metal halides Chemical class 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052735 hafnium Inorganic materials 0.000 claims description 9
- 238000006386 neutralization reaction Methods 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims 6
- 230000008018 melting Effects 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 239000012433 hydrogen halide Substances 0.000 description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910007932 ZrCl4 Inorganic materials 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 4
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910003865 HfCl4 Inorganic materials 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000002362 hafnium Chemical class 0.000 description 2
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 241000723368 Conium Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873723713 DE3723713A1 (de) | 1987-07-17 | 1987-07-17 | Alkoholfreie orthoester des zirkoniums und hafniums und verfahren zu deren herstellung |
| DE3889388T DE3889388D1 (de) | 1987-07-17 | 1988-05-21 | Alkoholfreie Orthoester des Zirkoniums und Hafniums und Verfahren zu deren Herstellung. |
| EP88108189A EP0299171B1 (de) | 1987-07-17 | 1988-05-21 | Alkoholfreie Orthoester des Zirkoniums und Hafniums und Verfahren zu deren Herstellung |
| US07/217,643 US4891439A (en) | 1987-07-17 | 1988-07-12 | Alcohol-free orthoesters of zirconium and hafnium and method for the preparation thereof |
| JP63177266A JPS6434992A (en) | 1987-07-17 | 1988-07-18 | Alcohol-free ortho ester of zirconium and hafnium and manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873723713 DE3723713A1 (de) | 1987-07-17 | 1987-07-17 | Alkoholfreie orthoester des zirkoniums und hafniums und verfahren zu deren herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3723713A1 true DE3723713A1 (de) | 1989-01-26 |
| DE3723713C2 DE3723713C2 (en, 2012) | 1989-10-12 |
Family
ID=6331811
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873723713 Granted DE3723713A1 (de) | 1987-07-17 | 1987-07-17 | Alkoholfreie orthoester des zirkoniums und hafniums und verfahren zu deren herstellung |
| DE3889388T Expired - Fee Related DE3889388D1 (de) | 1987-07-17 | 1988-05-21 | Alkoholfreie Orthoester des Zirkoniums und Hafniums und Verfahren zu deren Herstellung. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3889388T Expired - Fee Related DE3889388D1 (de) | 1987-07-17 | 1988-05-21 | Alkoholfreie Orthoester des Zirkoniums und Hafniums und Verfahren zu deren Herstellung. |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4891439A (en, 2012) |
| EP (1) | EP0299171B1 (en, 2012) |
| JP (1) | JPS6434992A (en, 2012) |
| DE (2) | DE3723713A1 (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012201629A (ja) * | 2011-03-25 | 2012-10-22 | Ube Industries Ltd | 高純度ジルコニウムアルコキシド原料及びその製造方法、並びに当該原料の分析方法 |
| JP2012201630A (ja) * | 2011-03-25 | 2012-10-22 | Ube Industries Ltd | 金属テトラ（１−アルキルイソブチルアルコキシド）の製造方法 |
| CN103554145A (zh) * | 2013-10-09 | 2014-02-05 | 烟台宏泰达化工有限责任公司 | 一种纳米氧化锆前躯体的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB997892A (en) * | 1963-06-18 | 1965-07-14 | British Titan Products | Production of alkyl titanates |
| DE2138691A1 (de) * | 1970-08-11 | 1972-02-17 | CIBA Geigy AG, Basel (Schweiz) | Verfahren zur Herstellung von tertiär Butylaten |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4442309A (en) * | 1960-09-14 | 1984-04-10 | Exxon Reserch And Engineering Co. | Preparation of linear olefin products |
| FR2088583A5 (en, 2012) * | 1970-04-17 | 1972-01-07 | Thann Mulhouse Prod Chim | |
| FR2088582A5 (en, 2012) * | 1970-04-17 | 1972-01-07 | Thann Mulhouse Prod Chim | |
| US3754011A (en) * | 1970-10-28 | 1973-08-21 | M Hoch | Method for the preparation of zirconium,hafnium and thorium alkoxides |
| DE2220101C3 (de) * | 1972-04-25 | 1975-03-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Umsetzung halogenhaltiger Substanzen mit Verbindungen, die reaktionsfähire Wasserstoffatome enthalten |
| JPS5433553A (en) * | 1977-08-04 | 1979-03-12 | Tokuyama Soda Co Ltd | Polyolefin composition |
| US4434312A (en) * | 1978-03-02 | 1984-02-28 | Exxon Research And Engineering Co. | Preparation of linear olefin products |
| DE3522904A1 (de) * | 1985-06-27 | 1987-01-08 | Dynamit Nobel Ag | Verfahren zur herstellung von orthoestern des titans, zirkons oder hafniums |
-
1987
- 1987-07-17 DE DE19873723713 patent/DE3723713A1/de active Granted
-
1988
- 1988-05-21 EP EP88108189A patent/EP0299171B1/de not_active Expired - Lifetime
- 1988-05-21 DE DE3889388T patent/DE3889388D1/de not_active Expired - Fee Related
- 1988-07-12 US US07/217,643 patent/US4891439A/en not_active Expired - Fee Related
- 1988-07-18 JP JP63177266A patent/JPS6434992A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB997892A (en) * | 1963-06-18 | 1965-07-14 | British Titan Products | Production of alkyl titanates |
| DE2138691A1 (de) * | 1970-08-11 | 1972-02-17 | CIBA Geigy AG, Basel (Schweiz) | Verfahren zur Herstellung von tertiär Butylaten |
Non-Patent Citations (3)
| Title |
|---|
| C.A. Vol.105, 1986, 26611 = JP 85258132 * |
| Encyclopedia of chemical technology, Kirk-Othmer, Vol.24, S.809, 1984 * |
| Inorg. Chem. Vol.10, No.10, 1971, S.2143-2146 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0299171A3 (de) | 1991-03-06 |
| EP0299171A2 (de) | 1989-01-18 |
| DE3723713C2 (en, 2012) | 1989-10-12 |
| JPS6434992A (en) | 1989-02-06 |
| US4891439A (en) | 1990-01-02 |
| DE3889388D1 (de) | 1994-06-09 |
| EP0299171B1 (de) | 1994-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8127 | New person/name/address of the applicant |
Owner name: HUELS AG, 4370 MARL, DE |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: E.I. DU PONT DE NEMOURS AND COMPANY, WILMINGTON, D |
|
| 8339 | Ceased/non-payment of the annual fee |