GB858930A - Organotitanium acylates - Google Patents
Organotitanium acylatesInfo
- Publication number
- GB858930A GB858930A GB17190/59A GB1719059A GB858930A GB 858930 A GB858930 A GB 858930A GB 17190/59 A GB17190/59 A GB 17190/59A GB 1719059 A GB1719059 A GB 1719059A GB 858930 A GB858930 A GB 858930A
- Authority
- GB
- United Kingdom
- Prior art keywords
- titanium
- cyclopentadienyl
- trichloracetate
- compounds
- biscyclopentadienyl
- 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
- 150000001875 compounds Chemical class 0.000 abstract 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 4
- -1 hydroxyalkyl radical Chemical group 0.000 abstract 4
- 239000010936 titanium Substances 0.000 abstract 4
- 229910052719 titanium Inorganic materials 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- HPYIUKIBUJFXII-UHFFFAOYSA-N Cyclopentadienyl radical Chemical class [CH]1C=CC=C1 HPYIUKIBUJFXII-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical group CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 2
- 229910002661 O–Ti–O Inorganic materials 0.000 abstract 2
- 229910002655 O−Ti−O Inorganic materials 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 abstract 2
- SRKKQWSERFMTOX-UHFFFAOYSA-N cyclopentane;titanium Chemical compound [Ti].[CH]1C=CC=C1 SRKKQWSERFMTOX-UHFFFAOYSA-N 0.000 abstract 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 abstract 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 1
- YWYUHANJGLTEGU-UHFFFAOYSA-L C(CCCCCCCC=C/CCCCCCCC)(=O)[O-].C(CCCCCCCC=C/CCCCCCCC)(=O)[O-].[Ti+2] Chemical compound C(CCCCCCCC=C/CCCCCCCC)(=O)[O-].C(CCCCCCCC=C/CCCCCCCC)(=O)[O-].[Ti+2] YWYUHANJGLTEGU-UHFFFAOYSA-L 0.000 abstract 1
- WJOHJNULFHFXQL-UHFFFAOYSA-N C1=CC2=CC=CC=C2C1[Ti]C1C2=CC=CC=C2C=C1 Chemical compound C1=CC2=CC=CC=C2C1[Ti]C1C2=CC=CC=C2C=C1 WJOHJNULFHFXQL-UHFFFAOYSA-N 0.000 abstract 1
- JYMCZJMFORTKGZ-UHFFFAOYSA-L ClC(Cl)(Cl)C(=O)O[Ti]OC(=O)C(Cl)(Cl)Cl Chemical compound ClC(Cl)(Cl)C(=O)O[Ti]OC(=O)C(Cl)(Cl)Cl JYMCZJMFORTKGZ-UHFFFAOYSA-L 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000021360 Myristic acid Nutrition 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- LEYMZSJREMIJJS-UHFFFAOYSA-L [Cl-].ClCC(=O)[O-].[Ti+2] Chemical compound [Cl-].ClCC(=O)[O-].[Ti+2] LEYMZSJREMIJJS-UHFFFAOYSA-L 0.000 abstract 1
- APIDIPGVBRXKEJ-UHFFFAOYSA-N acetic acid titanium Chemical compound [Ti].CC(O)=O.CC(O)=O APIDIPGVBRXKEJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-M dichloroacetate Chemical compound [O-]C(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-M 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 1
- 150000004820 halides Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 150000002680 magnesium Chemical class 0.000 abstract 1
- VQIJOUISJHFMMQ-UHFFFAOYSA-L octadecanoate;titanium(2+) Chemical compound [Ti+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O VQIJOUISJHFMMQ-UHFFFAOYSA-L 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- 229940049964 oleate Drugs 0.000 abstract 1
- 235000021313 oleic acid Nutrition 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract 1
- 239000002685 polymerization catalyst Substances 0.000 abstract 1
- 239000004926 polymethyl methacrylate Substances 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
Compounds of formula RxTiXy (OOCR1)z where R represents a cyclopentadienyl or a substituted cyclopentadienyl radical bound to titanium by a carbon atom of the ring, X is a halogen or an alkoxy group, R1 is an alkyl, haloalkyl, mercaptoalkyl or hydroxyalkyl group, x is 1 or 2, y is 0, 1 or 2, z is 1 or 2 and (x+y+z) = 4 may be hydrolysed to give titanones characterized by a Ti-O-Ti-O skeleton or may be used as polymerization catalysts for unsaturated compounds. Examples 5 and 12 describe the production of hard films from cyclopentadienyl titanium dibutoxy trichloracetate and biscyclopentadienyl titanium dioleate respectively. Example 4 describes the production of polymethyl methacrylate using biscyclopentadienyl titanium di(trichloracetate) as catalyst, and Example 14 describes the production of polystyrene using as catalyst biscyclopentadienyl titanium diglycollate.ALSO:The invention comprises compounds of formula: RxTiXy(OOCR1)z where R represents a cyclopentadienyl or substituted cyclopentadienyl radical bound to titanium by a Ti-C bond, the carbon atom of said bond being a member of said radical, X is a halogen atom or an alkoxy group, R1 is an alkyl, haloalkyl, mercaptoalkyl or hydroxyalkyl radical, x is 1 or 2, y is 0, 1 or 2, z is 1 or 2 and (x+y+z)=4. The cyclopentadienyl radical may be alkyl-substituted or may contain fused rings as in indenyl and fluorenyl. R1 may contain 1 to 18 carbon atoms, corresponding to acetic, propionic, butyric, lauric, myristic, oleic and stearic acids, as well as being derived from acids such as chloracetic, dichloracetic, trichloracetic, thioglycollic, mercaptopropionic and glycollic acids. They may be prepared by reacting compounds of formula Rn TiXm where R and X are as above, n is 1 or 2 and m is 2 or 3, at least one X being halogen, and an alkali metal salt or alkaline earth metal (including magnesium) salt of the acid corresponding to the acylate group desired. The reaction may be carried out in a solvent such as tetrahydrofuran, dimethylformamide, acetone and dimethylsulphoxide, and in the absence of air and moisture. When the compound Rn TiXm is a mixed halide-alkoxide, the halide atom only is replaced by the acylate group giving an alkoxide acylate. The compounds of the invention may be used as polymerisation catalysts and may be hydrolysed to give titanones having Ti-O-Ti-O chains (see Group IV(a)). In the examples there are prepared (1) biscyclopentadienyl titanium diacetate, (2) di (monochloracetate, (3) di (dichloracetate), (4) di(trichloracetate) (5) cyclopentadienyl titanium dibutoxy trichloracetate, (6) biscyclopentadienyl titanium monochloracetate chloride, (7) di-indenyltitanium di (trichloracetate), (8) biscyclopentadienyl titanium dithioglycollate, (11) biscyclopentadienyl titanium distearate, (12) di-oleate, and (14) diglycollate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US858930XA | 1958-05-21 | 1958-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB858930A true GB858930A (en) | 1961-01-18 |
Family
ID=22194669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17190/59A Expired GB858930A (en) | 1958-05-21 | 1959-05-20 | Organotitanium acylates |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE578869A (en) |
| DE (1) | DE1096359B (en) |
| FR (1) | FR1227570A (en) |
| GB (1) | GB858930A (en) |
| LU (1) | LU37207A1 (en) |
| NL (1) | NL239398A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242081A (en) * | 1963-04-30 | 1966-03-22 | Monsanto Res Corp | Lubricating compositions |
| US3305498A (en) * | 1963-02-18 | 1967-02-21 | Nat Lead Co | Process for making particle-polymer compositions |
| US3505369A (en) * | 1967-12-26 | 1970-04-07 | Gulf Research Development Co | Bis(cyclopentadienyl) compounds of titanium |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2139119T3 (en) * | 1995-07-12 | 2000-02-01 | Witco Gmbh | PROCEDURE FOR THE PREPARATION OF CYCLOPENTADIENYL-TITANIUM-TRIALCOXI DERIVATIVES. |
-
0
- BE BE578869D patent/BE578869A/xx unknown
- LU LU37207D patent/LU37207A1/xx unknown
- NL NL239398D patent/NL239398A/xx unknown
-
1959
- 1959-05-20 FR FR795107A patent/FR1227570A/en not_active Expired
- 1959-05-20 GB GB17190/59A patent/GB858930A/en not_active Expired
- 1959-05-21 DE DEN16745A patent/DE1096359B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3305498A (en) * | 1963-02-18 | 1967-02-21 | Nat Lead Co | Process for making particle-polymer compositions |
| US3242081A (en) * | 1963-04-30 | 1966-03-22 | Monsanto Res Corp | Lubricating compositions |
| US3505369A (en) * | 1967-12-26 | 1970-04-07 | Gulf Research Development Co | Bis(cyclopentadienyl) compounds of titanium |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1227570A (en) | 1960-08-22 |
| BE578869A (en) | |
| LU37207A1 (en) | |
| NL239398A (en) | |
| DE1096359B (en) | 1961-01-05 |
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