CS199043B1 - Process for the isolation of tetra/aryl/titanates - Google Patents
Process for the isolation of tetra/aryl/titanates Download PDFInfo
- Publication number
- CS199043B1 CS199043B1 CS47379A CS47379A CS199043B1 CS 199043 B1 CS199043 B1 CS 199043B1 CS 47379 A CS47379 A CS 47379A CS 47379 A CS47379 A CS 47379A CS 199043 B1 CS199043 B1 CS 199043B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- tetra
- aryl
- titanates
- isolation
- reaction mixture
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 238000002955 isolation Methods 0.000 title claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- AAFFTDXPYADISO-UHFFFAOYSA-N cyclohexyne Chemical compound C1CCC#CC1 AAFFTDXPYADISO-UHFFFAOYSA-N 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 238000006384 oligomerization reaction Methods 0.000 description 3
- -1 2-ethoxyphenyl Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález se týká způsobu izolace tetra(aryl)titanátů z reakční směsi obsahující volné hydroxylové skupiny.The invention relates to a process for the isolation of tetra (aryl) titanates from a reaction mixture containing free hydroxyl groups.
Čisté tetra(aryl)titanáty jsou zejména vhodné jako komponenta komplexních organokovových katalyzátorů, používaných k oiigomeracím a kooligomeracím olefinů a dienů.Pure tetra (aryl) titanates are particularly useful as a component of complex organometallic catalysts used for the oligomerization and co-oligomerization of olefins and dienes.
'ře'sx-a(aryl)titanáty vznikají reakcí chloridu titanlčitého s příslušným alkoholem v organickém rozpouštědle. Neutralizace vznikájíčího chlorovodíku, nutná pro substituci všech atomů chloru aryloxyskupinami se provádí plynným čpavkem, organickými zásadami nebo se vychází z alkoholátů sodných.The oxa (aryl) titanates are formed by reacting titanium tetrachloride with the appropriate alcohol in an organic solvent. Neutralization of the resulting hydrogen chloride required for the substitution of all chlorine atoms by aryloxy groups is carried out with gaseous ammonia, organic bases or starting from sodium alcoholates.
Dosud se čistý tetra(aryl)titanát získává z reakční směsi destilací za vysokého vakua. Tímto způsobem se však: získává čistý produkt velmi obtížně, většinou obsahuje zbytky fenolů. V případě (alkoxylfenyl)titanátů nelze vzhledem k bodu varu destilaci použít. Pro katalytické použití musí být připravený tetra(aryl)titanát dokonale zbaven výchozího alkoholu, nnbox již malé množství volných hydroxylů inhibuje oligomerační reakce.To date, pure tetra (aryl) titanate is obtained from the reaction mixture by high vacuum distillation. In this way, however, the pure product is very difficult to obtain, mostly containing phenol residues. In the case of (alkoxyphenyl) titanates, distillation cannot be used due to the boiling point. For catalytic use, the prepared tetra (aryl) titanate must be completely deprived of the starting alcohol, but a small amount of free hydroxyls already inhibits the oligomerization reactions.
199 043199 043
Uvedené nedostatky odstraňuje způsob izolace tetraíaryl)titanátů obecného vzorceThese drawbacks are overcome by a process for the isolation of tetraaryl) titanates of the general formula
kae H je alkoxylové skupina C-^ až Οθ, sí reakčni směsi obsahující volné hydroxylové skupiny podle vynálezu jehož podstata spočívá v tom, že se k reakčni směsi přidá organické rozpouštědlo, výhodně toluen, benzen, chlorbenzen, pentan, hexan, heptan, oktan nebo cyklohexan, načež ee směs nechá krystaliVýhodou způsobu podle vynálezu je, že se získává levně čistý tetraí aryDtitanát, vhodný zejména jako komponenta komplexního organ okov ovéh o katalyzátoru.kae H is an alkoxy group C 1 to C 6, a network of reaction mixtures containing free hydroxyl groups according to the invention, characterized in that an organic solvent, preferably toluene, benzene, chlorobenzene, pentane, hexane, heptane, octane or cyclohexane, whereupon the mixture is crystallized. An advantage of the process according to the invention is that cheaply pure tetra-aryl titanate is obtained, particularly suitable as a component of a complex organometallic catalyst.
Vynález je blíže vysvětlen v následujících příkladech.The invention is illustrated by the following examples.
.Příklad 1.Example 1
K vychladlé reakčni směsi obsahující 25 g tetraí2-etoxyfenylJtitanátu a zbytky iiesreagovaného 2-etoxyfenolu bylo přidáno 15 ml vysušeného benzenu. Vzniklý roztok byl přefiltrován a bylo přidáno 600 ml vysušeného n-pentanu. Směs byla po jedné hodině znovu zřiItrována.To the cooled reaction mixture containing 25 g of tetra-2-ethoxyphenyl titanate and the remainder of the unreacted 2-ethoxyphenol was added 15 ml of dried benzene. The resulting solution was filtered and 600 mL of dried n-pentane was added. The mixture was filtered again after one hour.
K pevnému podílu bylo přidáno 12 ml benzenu a po rozpuštění 600 ml n-pentanu. Směs byla zfiltrována.To the solid was added 12 mL of benzene and after dissolution of 600 mL of n-pentane. The mixture was filtered.
Tento postup byl znovu opakován.This procedure was repeated again.
Bylo získáno 18,6 g krystalického produktu,, který neobsahoval volné hydroxyly a Hopl být použit jako komponenta organokovového katalyzátoru.18.6 g of a crystalline product was obtained which did not contain free hydroxyls and Hopl was used as a component of an organometallic catalyst.
Příklad 2Example 2
Způsobem popsaným v příkladě 1 s tím, že místo benzenu bylo použito toluenu, bylo ř.í skáno 20,1 g tetraí2-etoxyfenyl)titanátu v uvedené čistotě.Using the procedure described in Example 1, except that toluene was used instead of benzene, 20.1 g of tetra (2-ethoxyphenyl) titanate were collected in the stated purity.
Iriklad 3Iriklad 3
Způsobem popsaným v příkladě 1 bylo z reakčni směsi obsahující 28,6 g tetra(-2-izoí.-yypoxyfenylJtitanátu získáno 23,2 g produktu, který neobsahoval volné hydroxyly a mohl kýý použit jako komponenta komplexního organokovového katalyzátoru.From the reaction mixture containing 28.6 g of tetra (-2-iso-yypoxyphenyl) titanate, 23.2 g of a product which was free of free hydroxyls could be used as a component of a complex organometallic catalyst as described in Example 1.
Způsobem popsaným v příkladě 1 s tím, že místo benzenu bylo použito toluenu, byloIn the manner described in Example 1, except that toluene was used instead of benzene
199 043 z reakční ®sšsi obsahující 22 g t®tra(2-fenoxy^!nyl)titanátu získáno 18 g produktu, který neobsahoval volné hydroxyly a mohl být použít jako komponenta komplexního organokovsvého katalyzátoru.199 043 of the reaction mixture containing 22 g of tert -butyl (2-phenoxyphenyl) titanate gave 18 g of a product which did not contain free hydroxyls and could be used as a component of a complex organometallic catalyst.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS47379A CS199043B1 (en) | 1979-01-22 | 1979-01-22 | Process for the isolation of tetra/aryl/titanates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS47379A CS199043B1 (en) | 1979-01-22 | 1979-01-22 | Process for the isolation of tetra/aryl/titanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199043B1 true CS199043B1 (en) | 1982-05-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS47379A CS199043B1 (en) | 1979-01-22 | 1979-01-22 | Process for the isolation of tetra/aryl/titanates |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS199043B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1323723A4 (en) * | 2000-10-05 | 2004-08-04 | Idemitsu Petrochemical Co | TRANSITION METAL COMPOUNDS, POLYMERIZATION CATALYSTS FOR OLEFINS, OLEFIN POLYMERS AND METHOD FOR THEIR PRODUCTION |
-
1979
- 1979-01-22 CS CS47379A patent/CS199043B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1323723A4 (en) * | 2000-10-05 | 2004-08-04 | Idemitsu Petrochemical Co | TRANSITION METAL COMPOUNDS, POLYMERIZATION CATALYSTS FOR OLEFINS, OLEFIN POLYMERS AND METHOD FOR THEIR PRODUCTION |
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