GB858540A - Organo titanium compounds and a process for their manufacture - Google Patents
Organo titanium compounds and a process for their manufactureInfo
- Publication number
- GB858540A GB858540A GB12311/57A GB1231157A GB858540A GB 858540 A GB858540 A GB 858540A GB 12311/57 A GB12311/57 A GB 12311/57A GB 1231157 A GB1231157 A GB 1231157A GB 858540 A GB858540 A GB 858540A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclopentadienyl
- bis
- titanium
- compounds
- acid group
- 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
- -1 Organo titanium compounds Chemical class 0.000 title abstract 9
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000004411 aluminium Substances 0.000 abstract 2
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 abstract 2
- 125000002577 pseudohalo group Chemical group 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- RBQBNAVSUBXCGR-UHFFFAOYSA-M C1(C=CC=C1)[Ti](Cl)(CCC)C1C=CC=C1 Chemical compound C1(C=CC=C1)[Ti](Cl)(CCC)C1C=CC=C1 RBQBNAVSUBXCGR-UHFFFAOYSA-M 0.000 abstract 1
- KWHYMFNLYQLACB-UHFFFAOYSA-M CC[Ti](Cl)(C1C=CC=C1)C1C=CC=C1 Chemical compound CC[Ti](Cl)(C1C=CC=C1)C1C=CC=C1 KWHYMFNLYQLACB-UHFFFAOYSA-M 0.000 abstract 1
- JSEIGCXRVAGROG-UHFFFAOYSA-M C[Ti](Cl)(C1C=CC=C1)C1C=CC=C1 Chemical compound C[Ti](Cl)(C1C=CC=C1)C1C=CC=C1 JSEIGCXRVAGROG-UHFFFAOYSA-M 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical group [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 229910052790 beryllium Inorganic materials 0.000 abstract 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
- YNBJMIXWGPOBGE-UHFFFAOYSA-N carbanide;cyclopenta-1,3-diene;titanium(4+) Chemical compound [CH3-].[CH3-].[Ti+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 YNBJMIXWGPOBGE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- KSFCHHFBQJDGFF-UHFFFAOYSA-L cyclopenta-1,3-diene;dichlorotitanium Chemical compound Cl[Ti]Cl.C1C=CC=C1.C1C=CC=C1 KSFCHHFBQJDGFF-UHFFFAOYSA-L 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc 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
- C07F17/00—Metallocenes
-
- 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
- C07F7/28—Titanium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention comprises organo-titanium compounds of formula: <FORM:0858540/IV(b)/1> in which each R1 represents a cyclopentadienyl radical which may be substituted by one or more hydrocarbon radicals, R2 represents a saturated aliphatic hydrocarbon radical and Y is a saturated aliphatic hydrocarbon radical, an alkoxy group or a halogen atom (including pseudo-halogens) or another acid group. R2 may preferably contain 1 to 4 carbon atoms, and the other acid group may be sulphate or acetate. The preferred alkoxy groups are methoxy, ethoxy, propoxy and butoxy, and alkyl radicals such as ethylhexyl or dodecyl may be substituted into the alkoxy group. The compounds of the invention may be made by reacting a compound of formula (R1)2TiX2 where R2 is as above and X is halogen (or pseudo-halogen), alkoxy or another acid group, suitably in the presence of an inert diluent, with an alkyl of an alkali metal, alkaline earth metal, or of beryllium, magnesium, zinc or aluminium. Grignard compounds (magnesium alkyl halides) may also be used, as may aluminium sesquichlorides. Specified diluents include dimethyl, diethyl, dipropyl, diisopropyl and dibutyl ethers, tetrahydrofuran, dioxane, butane, pentane, hexane, heptane, octane, cyclohexane, cyclopentane, methylcylcohexane, methylcyclopentane, benzene fractions from petroleum or the Fischer-Tropsch synthesis, aromatic hydrocarbons such as benzene, toluene and xylene, amines such as trimethyl-, triethyl-and tripropylamine, and in some cases chlorinated hydrocarbons such as methylene chloride or chlorobenzene. The reaction is carried out under an atmosphere of nitrogen or other inert gas with the exclusion of moisture. Examples describe the preparation of (1) bis-(cyclopentadienyl) methyl titanium chloride, (2) bis (cyclopentadienyl) titanium dichloride, (3) bis (cyclopentadienyl) dimethyl titanium, (8) bis (cyclopentadienyl) n-propyl titanium chloride, (10) titanium bis (1-methyl-cyclopentadienyl) dimethyl and (11) bis (cyclopentadienyl) ethyl titanium chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF20038A DE1037446B (en) | 1956-04-13 | 1956-04-13 | Process for the production of organometallic titanium compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB858540A true GB858540A (en) | 1961-01-11 |
Family
ID=7089537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12311/57A Expired GB858540A (en) | 1956-04-13 | 1957-04-15 | Organo titanium compounds and a process for their manufacture |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3104249A (en) |
| DE (1) | DE1037446B (en) |
| GB (1) | GB858540A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7010659A (en) * | 1969-07-17 | 1971-01-19 | ||
| US5523435A (en) * | 1994-05-13 | 1996-06-04 | Witco Gmbh | Process for the synthesis of monomethylmetallocenes and dimethylmetallocenes and their solutions specifically for use in the polymerization of olefins |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041361B1 (en) * | 1980-06-02 | 1985-07-31 | Hercules Incorporated | Preparation of block copolymers using dimethyl-bis(methylcyclopentadienyl)titanium |
| US4937299A (en) * | 1983-06-06 | 1990-06-26 | Exxon Research & Engineering Company | Process and catalyst for producing reactor blend polyolefins |
| US5324800A (en) * | 1983-06-06 | 1994-06-28 | Exxon Chemical Patents Inc. | Process and catalyst for polyolefin density and molecular weight control |
| US6013743A (en) * | 1985-12-24 | 2000-01-11 | Mitsui Chemicals Inc. | Process for polymerization of alpha-olefins |
| US5641843A (en) * | 1985-12-24 | 1997-06-24 | Mitsui Petrochemical Industries, Ltd. | Process for polymerization of alpha-olefins |
| US5700750A (en) * | 1985-12-26 | 1997-12-23 | Mitsui Petrochemical Industries, Ltd. | Process for polymerization of alpha-olefins |
| US5654248A (en) * | 1986-08-26 | 1997-08-05 | Mitsui Petrochemical Industries, Ltd. | Catalyst for polymerizing alpha-olefins and process for polymerization |
| KR920001353B1 (en) * | 1986-08-26 | 1992-02-11 | 미쓰이 세끼유 가가꾸 고오교오 가부시끼가이샤 | Catalyst for polymerizing alpha-olefin and polymerization process |
| US5700749A (en) * | 1986-09-24 | 1997-12-23 | Mitsui Petrochemical Industries, Ltd. | Process for polymerizing olefins |
| US4882039A (en) * | 1986-12-04 | 1989-11-21 | Mobil Oil Corporation | Catalytic cracking of hydrocarbons with oxygen promoted alkali metal zeolite cracking catalyst |
| US5003019A (en) * | 1987-03-02 | 1991-03-26 | Mitsui Petrochemical Industries, Ltd. | Cyclo-olefinic random copolymer, olefinic random copolymer, and process for producing cyclo-olefinic random copolymers |
| EP0500944B1 (en) * | 1990-07-24 | 1998-10-07 | Mitsui Chemicals, Inc. | Catalyst for alpha-olefin polymerization and production of poly-alpha-olefin therewith |
| ES2166465T3 (en) * | 1995-09-07 | 2002-04-16 | Merck & Co Inc | PROCEDURE FOR THE PREPARATION OF DIMETHYLTITANOCENE. |
| US5849975A (en) * | 1997-01-07 | 1998-12-15 | Chevron U.S.A. Inc. | Process for isomerization of normal olefin |
| US6153551A (en) * | 1997-07-14 | 2000-11-28 | Mobil Oil Corporation | Preparation of supported catalyst using trialkylaluminum-metallocene contact products |
| WO2000024723A1 (en) | 1998-10-28 | 2000-05-04 | Merck & Co., Inc. | Stabilization of the reagent dimethyl titanocene |
| WO2012097146A1 (en) | 2011-01-14 | 2012-07-19 | W. R. Grace & Co.-Conn. | Process of making modified metallocene catalyst, catalyst produced and use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2356476A (en) * | 1941-06-28 | 1944-08-22 | Shappirio Sol | Motor fuels |
| US2818416A (en) * | 1952-12-10 | 1957-12-31 | Ethyl Corp | Cyclomatic compounds |
| GB785760A (en) * | 1953-09-23 | 1957-11-06 | Union Carbide Corp | Process for the production of cyclopentadiene compounds of transition elements |
| BE551283A (en) * | 1955-09-27 |
-
1956
- 1956-04-13 DE DEF20038A patent/DE1037446B/en active Pending
-
1957
- 1957-04-12 US US652381A patent/US3104249A/en not_active Expired - Lifetime
- 1957-04-15 GB GB12311/57A patent/GB858540A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7010659A (en) * | 1969-07-17 | 1971-01-19 | ||
| US5523435A (en) * | 1994-05-13 | 1996-06-04 | Witco Gmbh | Process for the synthesis of monomethylmetallocenes and dimethylmetallocenes and their solutions specifically for use in the polymerization of olefins |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1037446B (en) | 1958-08-28 |
| US3104249A (en) | 1963-09-17 |
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