Titanium isopropoxide: Difference between revisions
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{{About|the chemical compound|the free trade agreement abbreviated as TTIP|Transatlantic Trade and Investment Partnership}} |
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| ImageFile = Ti(OiPr)4.png |
| ImageFile = Ti(OiPr)4.png |
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| ImageFile1 = Sample of Titanium isopropoxide 01.jpg |
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| ImageSize = |
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| IUPACName = Titanium isopropoxide |
| IUPACName = Titanium isopropoxide |
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| OtherNames = Tetraisopropyl titanate <br/>Titanium(IV) i-propoxide <br/> Titanium tetraisopropoxide <br/>Tetraisopropyl orthotitanate |
| OtherNames = Tetraisopropyl titanate <br/>Titanium(IV) ''i''-propoxide <br/> Titanium tetraisopropoxide <br/>Tetraisopropyl orthotitanate |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 546-68-9 |
| CASNo = 546-68-9 |
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| ChEBI = 139496 |
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| ChemSpiderID = 21106214 |
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| SMILES = |
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| EC_number = 208-909-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 76NX7K235Y |
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| Formula = C<sub>12</sub>H<sub>28</sub>O<sub>4</sub>Ti |
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| PubChem = 11026 |
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| MolarMass = 284.26 |
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| UNNumber = 1993 |
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| InChI = 1S/4C3H7O.Ti/c4*1-3(2)4;/h4*3H,1-2H3;/q4*-1;+4 |
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| StdInChIKey = VXUYXOFXAQZZMF-UHFFFAOYSA-N |
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| MeltingPt = 18–20 °C |
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| SMILES = CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C |
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| BoilingPt = 232 °C |
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| C = 12 | H = 28 | O = 4 | Ti = 1 |
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| MeltingPtC = 17 |
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| MeltingPt_notes = approximation |
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| BoilingPtC = 232 |
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| SolubleOther = soluble in [[ethanol]], [[diethyl ether|ether]], [[benzene]], [[chloroform]] |
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| RefractIndex = 1.46 |
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|Section5={{Chembox Hazards |
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| LD50 = 7600 mg/kg (rat, oral) |
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| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|226|318|319|336}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|303+361+353|304+340|305+351+338|310|312|337+313|370+378|403+233|403+235|405|501}} |
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}} |
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|Section6={{Chembox Related |
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| OtherAnions = [[Titanium methoxide]]; [[Titanium ethoxide]]; [[Titanium butoxide]] |
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| OtherCations = [[Aluminium isopropoxide]] |
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'''Titanium isopropoxide''' is a [[chemical compound]] with the [[chemical formula|formula]] Ti{OCH(CH<sub>3</sub>)<sub>2</sub>}<sub>4</sub>. This [[alkoxide]] of titanium(IV) is used in [[organic synthesis]] and [[materials science]]. |
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'''Titanium isopropoxide''', also commonly referred to as '''titanium tetraisopropoxide''' or '''TTIP''', is a [[chemical compound]] with the [[chemical formula|formula]] {{nowrap|Ti{OCH(CH<sub>3</sub>)<sub>2</sub>}<sub>4</sub>}}. This [[alkoxide]] of titanium(IV) is used in [[organic synthesis]] and [[materials science]]. It is a [[diamagnetic]] tetrahedral molecule. Titanium isopropoxide is a component of the [[Sharpless epoxidation]], a method for the synthesis of chiral epoxides.<ref name="Katsuki1980">{{Cite journal |last=Katsuki |first=T. |last2=Sharpless |first2=K. Barry |author-link2=K. Barry Sharpless |year=1980 |title=The first practical method for asymmetric epoxidation |journal=[[J. Am. Chem. Soc.]] |volume=102 |issue=18 |pages=5974 |doi=10.1021/ja00538a077}}</ref><ref>{{cite journal|author1=Hill, J. G.|author2=[[K. Barry Sharpless|Sharpless, K. B.]]|author3=Exon, C. M.|author4=Regenye, R.|journal=[[Org. Synth.]]|volume=63|pages=66|year=1985|doi=10.15227/orgsyn.063.0066| |
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title=Enantioselective Epoxidation Of Allylic Alcohols: (2s,3s)-3-propyloxiranemethanol}}</ref> |
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⚫ | The structures of the titanium alkoxides are often complex. |
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⚫ | The structures of the titanium alkoxides are often complex. Crystalline [[titanium methoxide]] is [[tetramer]]ic with the [[molecular formula]] {{nowrap|Ti<sub>4</sub>(OCH<sub>3</sub>)<sub>16</sub>}}.<ref>{{cite journal|last1 = Wright|first1 = D. A.|last2 = Williams|first2 = D. A.|title = The Crystal and Molecular Structure of Titanium Tetramethoxide|journal = [[Acta Crystallographica B]]|year = 1968|volume = 24|issue = 8|pages = 1107–1114|doi = 10.1107/S0567740868003766|doi-access = | bibcode=1968AcCrB..24.1107W }}</ref> Alkoxides derived from bulkier alcohols such as [[isopropyl alcohol]] aggregate less. Titanium isopropoxide is mainly a monomer in nonpolar solvents.<ref name="Bradley">{{Cite book |last=Bradley |first=Donald Charlton |author-link=Donald Charlton Bradley |title=Alkoxo and Aryloxo Derivatives of Metals |last2=Mehrotra |first2=Ram C. |author-link2=Ram Charan Mehrotra |last3=Rothwell |first3=Ian P. |last4=Singh |first4=A. |publisher=[[Academic Press]] |year=2001 |isbn=978-0-08-048832-5 |location=San Diego }}</ref> |
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==Preparation== |
==Preparation== |
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It is prepared by treating [[titanium tetrachloride]] with [[isopropanol]]. [[Hydrogen chloride]] is formed as a coproduct: |
It is prepared by treating [[titanium tetrachloride]] with [[isopropanol]] in presence of ammonia. [[Hydrogen chloride]] is formed as a coproduct:<ref name=Bradley/>{{rp|19-20}} |
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:[[Titanium tetrachloride|TiCl<sub>4</sub>]] |
:[[Titanium tetrachloride|TiCl<sub>4</sub>]] + 4 (CH<sub>3</sub>)<sub>2</sub>CHOH → Ti{OCH(CH<sub>3</sub>)<sub>2</sub>}<sub>4</sub> + 4 HCl |
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==Properties== |
==Properties== |
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Titanium isopropoxide reacts with water to deposit [[titanium dioxide]]:<ref name="hydro">{{cite journal|last1 = Hanaor|first1 = Dorian A. H.|last2 = Chironi|first2 = Ilkay|last3 = Karatchevtseva|first3 = Inna|last4 = Triani|first4 = Gerry|last5 = Sorrell|first5 = Charles C.|title = Single and Mixed Phase TiO<sub>2</sub> Powders Prepared by Excess Hydrolysis of Titanium Alkoxide|journal = [[Advances in Applied Ceramics]]|year = 2012|volume = 111|issue = 3|pages = 149–158|doi = 10.1179/1743676111Y.0000000059|url = https://www.researchgate.net/publication/235644645|arxiv = 1410.8255| bibcode=2012AdApC.111..149H | s2cid=98265180 }}</ref> |
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Titanium isopropoxide reacts with water to deposit [[titanium dioxide]]: |
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:Ti{OCH(CH<sub>3</sub>)<sub>2</sub>}<sub>4</sub> |
:Ti{OCH(CH<sub>3</sub>)<sub>2</sub>}<sub>4</sub> + 2 H<sub>2</sub>O → TiO<sub>2</sub> + 4 (CH<sub>3</sub>)<sub>2</sub>CHOH |
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This reaction is employed in the [[sol-gel]] synthesis of TiO<sub>2</sub>-based materials |
This reaction is employed in the [[sol-gel]] synthesis of TiO<sub>2</sub>-based materials in the form of powders or thin films. Typically water is added in excess to a solution of the alkoxide in an alcohol. The composition, crystallinity and morphology of the inorganic product are determined by the presence of additives (e.g. [[acetic acid]]), the amount of water (hydrolysis ratio), and reaction conditions.<ref name="hydro"/> |
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The compound is also used as a catalyst in the preparation of certain cyclopropanes in the [[Kulinkovich reaction]]. [[Prochiral]] thioethers are oxidized enantioselectively using a catalyst derived from Ti(O-''i''-Pr)<sub>4</sub>.<ref>{{cite journal|first1 = S. H.|last1 = Zhao|first2 = O.|last2 = Samuel|first3 = H. B.|last3 = Kagan|authorlink3 = Henri B. Kagan|title = Asymmetric Oxidation of Sulfides Mediated by Chiral Titanium Complexes: Mechanistic and Synthetic Aspects|journal = [[Tetrahedron (journal)|Tetrahedron]]|volume = 43|issue = 21|year = 1987|pages = 5135–5144|doi = 10.1016/S0040-4020(01)87689-4}}</ref><ref>{{OrgSynth|first1 = S. H.|last1 = Zhao|first2 = O.|last2 = Samuel|first3 = H. B.|last3 = Kagan|authorlink3 = Henri B. Kagan|title = Enantioelective Oxidation of a Sulfide: (''S'')-(−)-Methyl ''p''-Tolyl Sulfoxide|collvol = 8|collvolpages = 464|year = 1990|volume = 68|pages = 49|prep = CV8P0464|doi = 10.15227/orgsyn.068.0049}}</ref> |
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==Naming== |
==Naming== |
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Titanium(IV) isopropoxide is a widely used item of commerce and has acquired many names in addition to those listed in the table. |
Titanium(IV) isopropoxide is a widely used item of commerce and has acquired many names in addition to those listed in the table. A sampling of the names include: |
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titanium(IV) i-propoxide, isopropyl titanate, tetraisopropyl titanate, tetraisopropyl orthotitanate, titanium tetraisopropylate, orthotitanic acid tetraisopropyl ester, Isopropyl titanate(IV), titanic acid tetraisopropyl ester, isopropyltitanate, titanium(IV) isopropoxide, titanium tetraisopropoxide, iso-propyl titanate, titanium tetraisopropanolate, tetraisopropoxytitanium(IV), tetraisopropanolatotitanium, tetrakis(isopropoxy) titanium, |
titanium(IV) ''i''-propoxide, isopropyl titanate, tetraisopropyl titanate, tetraisopropyl orthotitanate, titanium tetraisopropylate, orthotitanic acid tetraisopropyl ester, Isopropyl titanate(IV), titanic acid tetraisopropyl ester, isopropyltitanate, titanium(IV) isopropoxide, titanium tetraisopropoxide, ''iso''-propyl titanate, titanium tetraisopropanolate, tetraisopropoxytitanium(IV), tetraisopropanolatotitanium, tetrakis(isopropoxy) titanium, tetrakis(isopropanolato) titanium, titanic acid isopropyl ester, titanic acid tetraisopropyl ester, titanium isopropoxide, titanium isopropylate, tetrakis(1-methylethoxy)titanium. |
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== Applications == |
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TTIP can be used as a precursor for ambient conditions vapour phase deposition such as infiltration into polymer thin films.<ref>{{Cite journal|last1=Giraud|first1=Elsa C.|last2=Mokarian-Tabari|first2=Parvaneh|last3=Toolan|first3=Daniel T. W.|last4=Arnold|first4=Thomas|last5=Smith|first5=Andrew J.|last6=Howse|first6=Jonathan R.|last7=Topham|first7=Paul D.|last8=Morris|first8=Michael A.|date=2018-07-27|title=Highly Ordered Titanium Dioxide Nanostructures via a Simple One-Step Vapor-Inclusion Method in Block Copolymer Films|journal=ACS Applied Nano Materials|volume=1|issue=7|pages=3426–3434|doi=10.1021/acsanm.8b00632|hdl=10468/11768 |s2cid=139474500 |url=https://publications.aston.ac.uk/id/eprint/33637/1/acsanm.8b00632.pdf}}</ref> |
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==References== |
==References== |
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==External links== |
==External links== |
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[[lv:Titāna izopropoksīds]] |
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[[ |
[[Category:Titanium(IV) compounds]] |
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[[Category:Isopropyl compounds]] |
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[[zh:异丙醇钛]] |