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Titanium isopropoxide

Titanium isopropoxide, also commonly referred to as titanium tetraisopropoxide or TTIP, is a chemical compound with the formula Ti{OCH(CH3)2}4. 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.[1][2]

Titanium isopropoxide
Names
IUPAC name
Titanium isopropoxide
Other names
Tetraisopropyl titanate
Titanium(IV) i-propoxide
Titanium tetraisopropoxide
Tetraisopropyl orthotitanate
Identifiers
  • 546-68-9 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:139496
ChemSpider
  • 21106214
ECHA InfoCard 100.008.100
EC Number
  • 208-909-6
  • 11026
UNII
  • 76NX7K235Y Y
UN number 1993
  • DTXSID5027196
  • Key: VXUYXOFXAQZZMF-UHFFFAOYSA-N
  • InChI=1S/4C3H7O.Ti/c4*1-3(2)4;/h4*3H,1-2H3;/q4*-1;+4
  • CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C
Properties
C12H28O4Ti
Molar mass 284.219 g·mol−1
Appearance colorless to light-yellow liquid
Density 0.96 g/cm3
Melting point 17 °C (63 °F; 290 K) approximation
Boiling point 232 °C (450 °F; 505 K)
Reacts to form TiO2
Solubility soluble in ethanol, ether, benzene, chloroform
1.46
Hazards
GHS labelling:
Danger
H226, H318, H319, H336
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
Lethal dose or concentration (LD, LC):
7600 mg/kg (rat, oral)
Related compounds
Other anions
Titanium methoxide; Titanium ethoxide; Titanium butoxide
Other cations
Aluminium isopropoxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

The structures of the titanium alkoxides are often complex. Crystalline titanium methoxide is tetrameric with the molecular formula Ti4(OCH3)16.[3] Alkoxides derived from bulkier alcohols such as isopropyl alcohol aggregate less. Titanium isopropoxide is mainly a monomer in nonpolar solvents.[4]

Preparation edit

It is prepared by treating titanium tetrachloride with isopropanol in presence of ammonia. Hydrogen chloride is formed as a coproduct:[4]: 19–20 

TiCl4 + 4 (CH3)2CHOH → Ti{OCH(CH3)2}4 + 4 HCl

Properties edit

Titanium isopropoxide reacts with water to deposit titanium dioxide:[5]

Ti{OCH(CH3)2}4 + 2 H2O → TiO2 + 4 (CH3)2CHOH

This reaction is employed in the sol-gel synthesis of TiO2-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.[5]

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)4.[6][7]

Naming edit

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: 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.

Applications edit

TTIP can be used as a precursor for ambient conditions vapour phase deposition such as infiltration into polymer thin films.[8]

References edit

  1. ^ Katsuki, T.; Sharpless, K. Barry (1980). "The first practical method for asymmetric epoxidation". J. Am. Chem. Soc. 102 (18): 5974. doi:10.1021/ja00538a077.
  2. ^ Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R. (1985). "Enantioselective Epoxidation Of Allylic Alcohols: (2s,3s)-3-propyloxiranemethanol". Org. Synth. 63: 66. doi:10.15227/orgsyn.063.0066.
  3. ^ Wright, D. A.; Williams, D. A. (1968). "The Crystal and Molecular Structure of Titanium Tetramethoxide". Acta Crystallographica B. 24 (8): 1107–1114. Bibcode:1968AcCrB..24.1107W. doi:10.1107/S0567740868003766.
  4. ^ a b Bradley, Donald Charlton; Mehrotra, Ram C.; Rothwell, Ian P.; Singh, A. (2001). Alkoxo and Aryloxo Derivatives of Metals. San Diego: Academic Press. ISBN 978-0-08-048832-5.
  5. ^ a b Hanaor, Dorian A. H.; Chironi, Ilkay; Karatchevtseva, Inna; Triani, Gerry; Sorrell, Charles C. (2012). "Single and Mixed Phase TiO2 Powders Prepared by Excess Hydrolysis of Titanium Alkoxide". Advances in Applied Ceramics. 111 (3): 149–158. arXiv:1410.8255. Bibcode:2012AdApC.111..149H. doi:10.1179/1743676111Y.0000000059. S2CID 98265180.
  6. ^ Zhao, S. H.; Samuel, O.; Kagan, H. B. (1987). "Asymmetric Oxidation of Sulfides Mediated by Chiral Titanium Complexes: Mechanistic and Synthetic Aspects". Tetrahedron. 43 (21): 5135–5144. doi:10.1016/S0040-4020(01)87689-4.
  7. ^ Zhao, S. H.; Samuel, O.; Kagan, H. B. (1990). "Enantioelective Oxidation of a Sulfide: (S)-(−)-Methyl p-Tolyl Sulfoxide". Organic Syntheses. 68: 49. doi:10.15227/orgsyn.068.0049; Collected Volumes, vol. 8, p. 464.
  8. ^ Giraud, Elsa C.; Mokarian-Tabari, Parvaneh; Toolan, Daniel T. W.; Arnold, Thomas; Smith, Andrew J.; Howse, Jonathan R.; Topham, Paul D.; Morris, Michael A. (2018-07-27). "Highly Ordered Titanium Dioxide Nanostructures via a Simple One-Step Vapor-Inclusion Method in Block Copolymer Films" (PDF). ACS Applied Nano Materials. 1 (7): 3426–3434. doi:10.1021/acsanm.8b00632. hdl:10468/11768. S2CID 139474500.

External links edit

titanium, isopropoxide, this, article, about, chemical, compound, free, trade, agreement, abbreviated, ttip, transatlantic, trade, investment, partnership, also, commonly, referred, titanium, tetraisopropoxide, ttip, chemical, compound, with, formula, this, al. This article is about the chemical compound For the free trade agreement abbreviated as TTIP see Transatlantic Trade and Investment Partnership Titanium isopropoxide also commonly referred to as titanium tetraisopropoxide or TTIP is a chemical compound with the formula Ti OCH CH3 2 4 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 1 2 Titanium isopropoxide Names IUPAC name Titanium isopropoxide Other names Tetraisopropyl titanate Titanium IV i propoxide Titanium tetraisopropoxide Tetraisopropyl orthotitanate Identifiers CAS Number 546 68 9 Y 3D model JSmol Interactive image ChEBI CHEBI 139496 ChemSpider 21106214 ECHA InfoCard 100 008 100 EC Number 208 909 6 PubChem CID 11026 UNII 76NX7K235Y Y UN number 1993 CompTox Dashboard EPA DTXSID5027196 InChI Key VXUYXOFXAQZZMF UHFFFAOYSA NInChI 1S 4C3H7O Ti c4 1 3 2 4 h4 3H 1 2H3 q4 1 4 SMILES CC C O Ti OC C C OC C C OC C C Properties Chemical formula C 12H 28O 4Ti Molar mass 284 219 g mol 1 Appearance colorless to light yellow liquid Density 0 96 g cm3 Melting point 17 C 63 F 290 K approximation Boiling point 232 C 450 F 505 K Solubility in water Reacts to form TiO2 Solubility soluble in ethanol ether benzene chloroform Refractive index nD 1 46 Hazards GHS labelling Pictograms Signal word Danger Hazard statements H226 H318 H319 H336 Precautionary statements P210 P233 P240 P241 P242 P243 P261 P264 P271 P280 P303 P361 P353 P304 P340 P305 P351 P338 P310 P312 P337 P313 P370 P378 P403 P233 P403 P235 P405 P501 Lethal dose or concentration LD LC LD50 median dose 7600 mg kg rat oral Related compounds Other anions Titanium methoxide Titanium ethoxide Titanium butoxide Other cations Aluminium isopropoxide Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references The structures of the titanium alkoxides are often complex Crystalline titanium methoxide is tetrameric with the molecular formula Ti4 OCH3 16 3 Alkoxides derived from bulkier alcohols such as isopropyl alcohol aggregate less Titanium isopropoxide is mainly a monomer in nonpolar solvents 4 Contents 1 Preparation 2 Properties 3 Naming 4 Applications 5 References 6 External linksPreparation editIt is prepared by treating titanium tetrachloride with isopropanol in presence of ammonia Hydrogen chloride is formed as a coproduct 4 19 20 TiCl4 4 CH3 2CHOH Ti OCH CH3 2 4 4 HClProperties editTitanium isopropoxide reacts with water to deposit titanium dioxide 5 Ti OCH CH3 2 4 2 H2O TiO2 4 CH3 2CHOH This reaction is employed in the sol gel synthesis of TiO2 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 5 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 4 6 7 Naming editTitanium 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 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 Applications editTTIP can be used as a precursor for ambient conditions vapour phase deposition such as infiltration into polymer thin films 8 References edit Katsuki T Sharpless K Barry 1980 The first practical method for asymmetric epoxidation J Am Chem Soc 102 18 5974 doi 10 1021 ja00538a077 Hill J G Sharpless K B Exon C M Regenye R 1985 Enantioselective Epoxidation Of Allylic Alcohols 2s 3s 3 propyloxiranemethanol Org Synth 63 66 doi 10 15227 orgsyn 063 0066 Wright D A Williams D A 1968 The Crystal and Molecular Structure of Titanium Tetramethoxide Acta Crystallographica B 24 8 1107 1114 Bibcode 1968AcCrB 24 1107W doi 10 1107 S0567740868003766 a b Bradley Donald Charlton Mehrotra Ram C Rothwell Ian P Singh A 2001 Alkoxo and Aryloxo Derivatives of Metals San Diego Academic Press ISBN 978 0 08 048832 5 a b Hanaor Dorian A H Chironi Ilkay Karatchevtseva Inna Triani Gerry Sorrell Charles C 2012 Single and Mixed Phase TiO2 Powders Prepared by Excess Hydrolysis of Titanium Alkoxide Advances in Applied Ceramics 111 3 149 158 arXiv 1410 8255 Bibcode 2012AdApC 111 149H doi 10 1179 1743676111Y 0000000059 S2CID 98265180 Zhao S H Samuel O Kagan H B 1987 Asymmetric Oxidation of Sulfides Mediated by Chiral Titanium Complexes Mechanistic and Synthetic Aspects Tetrahedron 43 21 5135 5144 doi 10 1016 S0040 4020 01 87689 4 Zhao S H Samuel O Kagan H B 1990 Enantioelective Oxidation of a Sulfide S Methyl p Tolyl Sulfoxide Organic Syntheses 68 49 doi 10 15227 orgsyn 068 0049 Collected Volumes vol 8 p 464 Giraud Elsa C Mokarian Tabari Parvaneh Toolan Daniel T W Arnold Thomas Smith Andrew J Howse Jonathan R Topham Paul D Morris Michael A 2018 07 27 Highly Ordered Titanium Dioxide Nanostructures via a Simple One Step Vapor Inclusion Method in Block Copolymer Films PDF ACS Applied Nano Materials 1 7 3426 3434 doi 10 1021 acsanm 8b00632 hdl 10468 11768 S2CID 139474500 External links edit Retrieved from https en wikipedia org w index php title Titanium isopropoxide amp oldid 1220029368, wikipedia, wiki, book, books, library,

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