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Titanium isopropoxide

Titanium(IV) isopropoxide, also known as tetraisopropyl titanate, is an organotitanium compound with the chemical formula Ti(OCH(CH₃)₂)₄, consisting of a tetrahedral titanium(IV) center coordinated to four isopropoxide ligands.^[1] This moisture-sensitive, diamagnetic molecule appears as a water-white to pale-yellow liquid at room temperature, with a density of 0.971 g/cm³, a melting point around 20 °C, and a boiling point of 220 °C at standard pressure.^[1] It is highly reactive toward water, undergoing rapid hydrolysis to produce titanium dioxide and isopropanol, which underscores its utility as a versatile precursor in chemical synthesis.^[1] The compound is primarily synthesized through the exothermic reaction of titanium tetrachloride (TiCl₄) with isopropanol ((CH₃)₂CHOH), often requiring careful control to manage the release of hydrogen chloride gas and ensure high purity.^[2] This method yields the alkoxide in industrial quantities, making it commercially available for laboratory and manufacturing applications. In terms of safety, titanium(IV) isopropoxide is flammable (flash point approximately 40 °C) and poses risks of severe eye damage upon contact, with vapors heavier than air that can travel to ignition sources; it is classified as an irritant and requires handling under inert atmospheres to prevent decomposition.^[1] In materials science and organic chemistry, titanium(IV) isopropoxide plays a pivotal role as a source of titanium and oxygen atoms, particularly in sol-gel processes for fabricating titanium dioxide (TiO₂) nanoparticles, thin films, and coatings used in photocatalysis, solar cells, and protective layers.^[3] It also functions as a catalyst in transesterification and condensation reactions, and is a key component in the Sharpless epoxidation for the stereoselective synthesis of chiral epoxides from allylic alcohols.^[3] Additionally, its applications extend to the production of heat-resistant adhesives, glass treatments, and advanced nanomaterials like porous titanosilicates for ion-exchange in environmental remediation.^[1]

Chemical Identity

Formula and Structure

Titanium isopropoxide has the molecular formula \ce{Ti(OCH(CH3)2)4}, commonly abbreviated as \ce{Ti(OiPr)4} or \ce{Ti(OCHMe2)4}, corresponding to the empirical formula \ce{C12H28O4Ti}.^[1]^[4] The molecule features a central \ce{Ti(IV)} ion coordinated tetrahedrally by four isopropoxide ligands, each bound via an oxygen atom to the titanium center, resulting in a monomeric structure in the gas phase and non-polar solutions.^[5] This tetrahedral geometry arises from the steric demands of the bulky isopropoxide groups and the preference of \ce{Ti(IV)} for four-coordinate environments in alkoxides.^[6] The compound is diamagnetic due to the \ce{d^0} electronic configuration of \ce{Ti(IV)}, which lacks unpaired electrons.^[7] In structural representations, the Lewis structure depicts the titanium atom forming four \ce{Ti-O} single bonds, with each oxygen atom linked to an isopropyl group (\ce{-CH(CH3)2}), where the carbon-oxygen bonds are also single bonds and all atoms achieve octets except titanium, which follows the 18-electron rule loosely in coordination compounds.^[5] Three-dimensional models, such as those derived from energy minimization or X-ray diffraction analogs, illustrate the tetrahedral arrangement with the four oxygen atoms positioned at the vertices of a tetrahedron around the central titanium, and the isopropyl groups oriented to minimize steric repulsion.^[5] Key bond metrics include an average \ce{Ti-O} bond length of approximately 1.80 Å and \ce{O-Ti-O} bond angles near 109°, reflecting ideal tetrahedral symmetry, while \ce{C-O} bonds measure about 1.50 Å.^[5]^[6]

Nomenclature

Titanium isopropoxide is systematically named titanium(4+) tetrakis(propan-2-olate) according to IUPAC nomenclature, reflecting the tetravalent titanium cation coordinated to four propan-2-olate anions.^[1] An alternative IUPAC designation is titanium tetrakis(1-methylethoxide), where 1-methylethoxide denotes the isopropoxide ligand. Commonly, the compound is referred to as titanium tetraisopropoxide (TTIP), tetraisopropyl titanate, or titanium(IV) isopropoxide in chemical literature and commercial contexts.^[1] These names emphasize the four isopropoxy groups attached to the central titanium atom and are widely used for brevity in synthetic and materials science applications.^[3] In mid-20th century literature, particularly from the 1950s onward, titanium isopropoxide was predominantly described using early titanate nomenclature, such as tetraisopropyl titanate, reflecting the initial commercial and synthetic focus on alkyl titanates derived from titanium tetrachloride and alcohols.^[8] This naming convention evolved alongside advancements in organometallic chemistry, transitioning toward more precise coordination compound descriptors by the late 20th century.

Synthesis

Laboratory Synthesis

Titanium isopropoxide, also known as titanium tetraisopropoxide, is commonly prepared in laboratory settings through the alcoholysis of titanium tetrachloride with isopropanol. The primary reaction involves the substitution of chloride ligands by isopropoxide groups, as represented by the equation:

\ce{TiCl4 + 4 (CH3)2CHOH -> Ti[(CH3)2CHO]4 + 4 HCl}

This process generates hydrogen chloride as a byproduct, which is typically neutralized using ammonia to form ammonium chloride precipitate.^[2]^[9] The reaction is conducted under strictly anhydrous conditions in an inert atmosphere, such as nitrogen, to prevent hydrolysis of the moisture-sensitive reagents. Titanium tetrachloride is slowly added to excess isopropanol (molar ratio of 1:4 to 1:8) at controlled temperatures, often below 0 °C initially, to manage the highly exothermic nature of the substitution and avoid side reactions. The mixture is stirred for several hours (typically 5–15 hours), followed by bubbling ammonia gas (0.1–0.2 L/min for 13–20 hours) to neutralize the HCl, with benzene or toluene sometimes added as a co-solvent to facilitate precipitation of ammonium chloride. The solid byproduct is then filtered under reduced pressure.^[9]^[10] Purification of the crude product involves fractional distillation under reduced pressure (typically 0.1–10 mmHg) to separate the volatile titanium isopropoxide (boiling point around 60–70 °C at reduced pressure) from unreacted alcohol and impurities, yielding a clear, colorless liquid. Laboratory-scale yields are generally 70–80% based on titanium tetrachloride, though optimized conditions can achieve over 99%.^[11]^[9] An alternative laboratory route employs transesterification, where titanium ethoxide reacts with isopropanol to exchange ethoxy groups for isopropoxy groups:

\ce{Ti(OCH2CH3)4 + 4 (CH3)2CHOH ⇌ Ti[(CH3)2CHO]4 + 4 CH3CH2OH}

This equilibrium-driven process is monitored spectroscopically and is useful for preparing mixed alkoxides or adjusting ligand properties in sol-gel applications, though it requires excess alcohol and heating to shift equilibrium toward the isopropoxide product.^[12]

Commercial Production

Titanium isopropoxide is manufactured industrially through the controlled reaction of high-purity titanium tetrachloride (TiCl₄) with isopropanol, a process adapted from laboratory methods but optimized for large-scale output using distillation under inert atmospheres to isolate the product and prevent hydrolysis.^[13]^[2] This exothermic reaction generates hydrogen chloride (HCl) as a primary byproduct, necessitating robust handling protocols including scrubbing systems and environmental controls to mitigate emissions and ensure compliance with regulations.^[2] In industrial settings, byproduct HCl is often recovered for reuse in downstream chemical processes, such as titanium dioxide production, enhancing overall process efficiency and reducing waste. Production facilities employ specialized equipment like corrosion-resistant reactors and distillation columns to manage the corrosive nature of intermediates, with operations typically conducted in batches or semi-continuous modes to achieve high yields.^[13] Leading global producers include Chinese companies such as Polygel, Zibo Riqi Chemical Co., Ltd., Jining Jianbang Chemical Co., Ltd., Shandong Harriton Chemical Co., Ltd., and Yixing Sunan Petrochemical Co., Ltd., which collectively dominate supply due to cost-effective manufacturing in Asia.^[14] Annual worldwide production is estimated at tens of thousands of metric tons, reflecting a market value of approximately $74 million in 2025 driven by demand in coatings and electronics sectors.^[15] Recent developments in the 2020s emphasize sustainability, with manufacturers adopting energy-efficient designs, recyclable materials, and explorations into bio-based alternatives to traditional solvents, aiming to lower environmental footprints as highlighted in industry analyses.^[16]^[17] These initiatives align with broader trends in green chemistry, including byproduct recycling to minimize waste in alkoxide synthesis.^[18]

Properties

Physical Properties

Titanium isopropoxide is a colorless to pale yellow viscous liquid at room temperature. It has an odor resembling isopropyl alcohol.^[19]^[3]^[1] Its key physical properties include a molar mass of 284.22 g/mol, density of 0.971 g/cm³ at 20 °C, melting point of approximately 20 °C, boiling point of 220 °C at 760 mmHg, and refractive index of 1.46.^[1] The compound is miscible with common organic solvents such as ethanol, ether, benzene, and chloroform, but it is insoluble in water.^[20] Titanium isopropoxide has a low vapor pressure of approximately 0.1 mmHg at 20 °C and a flash point of approximately 40 °C, indicating its volatility and flammability under certain conditions.^[21]

Chemical Properties

Titanium isopropoxide undergoes rapid and exothermic hydrolysis upon exposure to water, following the general reaction Ti(OiPr)₄ + 2 H₂O → TiO₂ + 4 iPrOH, where iPr denotes the isopropoxide group, resulting in the formation of an insoluble titanium dioxide gel.^[22] This reactivity stems from the high affinity of the titanium(IV) center for oxygen-containing nucleophiles, making it highly moisture-sensitive and prone to decomposition in humid environments.^[23] As a strong Lewis acid, titanium isopropoxide features a coordinatively unsaturated Ti(IV) cation that readily coordinates with nucleophiles such as alcohols, amines, or carbonyl compounds, facilitating ligand exchange and complex formation.^[3] This property arises from the electron-deficient nature of the titanium atom in its tetrahedral coordination environment with isopropoxide ligands, enabling it to accept electron pairs and activate substrates in coordination chemistry applications.^[24] The compound exhibits air sensitivity, fuming upon contact with atmospheric moisture due to partial hydrolysis, and requires storage under inert conditions to maintain stability.^[1] It decomposes thermally above approximately 200°C, yielding titanium dioxide and volatile organic byproducts, with the onset of significant decomposition observed around 250°C.^[5] Spectroscopic characterization confirms its structure, with infrared (IR) spectroscopy showing characteristic Ti-O stretching bands around 550 cm^-1, indicative of the metal-oxygen bonds in the alkoxide framework.^[25] In ¹H nuclear magnetic resonance (NMR) spectra, the isopropoxide protons appear as a septet for the methine proton at approximately 4.0 ppm and doublets for the methyl protons at about 1.2 ppm due to coupling in the isopropoxy groups.^[26] ¹³C NMR further supports this, with signals at around 26 ppm for the methyl carbons and 76 ppm for the methine carbon.^[27]

Applications

Organic Synthesis

Titanium isopropoxide serves as a versatile reagent and catalyst in organic synthesis, particularly in reactions requiring Lewis acid activation or stereocontrol. Its ability to form coordination complexes with substrates enables selective transformations, including asymmetric epoxidations and cyclopropanations. These applications leverage its mild reactivity and compatibility with chiral ligands, contributing to the synthesis of complex molecules with high enantioselectivity.^[28] A prominent application is the Sharpless asymmetric epoxidation, developed in the early 1980s, which converts allylic alcohols to epoxy alcohols with excellent enantioselectivity. This reaction employs titanium isopropoxide as the key titanium source, combined with a chiral tartrate ester (such as diethyl tartrate) and tert-butyl hydroperoxide (TBHP) as the oxidant. The process, recognized in the 2001 Nobel Prize in Chemistry awarded to K. Barry Sharpless, achieves up to 96% enantiomeric excess for a wide range of allylic alcohols, directing the epoxide oxygen delivery to the face opposite the alcohol group through a directed mechanism.^[28]^[29] Another significant transformation is the Kulinkovich reaction, which generates substituted cyclopropanols from carboxylic esters and Grignard reagents. In this process, titanium isopropoxide facilitates the formation of a low-valent titanium species that promotes deoxygenation of the ester and subsequent cyclopropanation, typically yielding cis-disubstituted cyclopropanols in good yields (50-80%). First reported in 1989, the reaction is particularly useful for constructing strained rings in natural product synthesis, with variations extending to nitriles for aminocyclopropane preparation.^[30] Titanium isopropoxide also acts as a Lewis acid in reductive aminations, promoting imine formation from carbonyls and amines followed by reduction with sodium borohydride to afford secondary amines in high yields (often >90%). It enables regioselective ring opening of 2,3-epoxy alcohols with nucleophiles like amines or thiols, favoring attack at the less substituted carbon under mild conditions. Additionally, it catalyzes the selective oxidation of sulfides to sulfoxides using aqueous hydrogen peroxide, achieving chemoselectivity by preventing overoxidation to sulfones through controlled coordination.^[31]^[32]^[33] In these reactions, titanium isopropoxide enhances stereoselectivity via substrate coordination to the metal center, forming a rigid transition state that directs nucleophilic attack or oxygen transfer. This coordination mode, evident in both epoxidation and cyclopropanation mechanisms, minimizes non-selective pathways and amplifies chiral induction from ligands.^[29]^[30]

Materials Science

Titanium isopropoxide serves as a key precursor in the sol-gel process for synthesizing titanium dioxide (TiO₂) materials, where controlled hydrolysis and condensation reactions convert the alkoxide into TiO₂ gels, films, or nanoparticles. This method enables the production of high-purity, nanostructured TiO₂ with tunable properties, such as particle size and porosity, by adjusting parameters like pH, solvent, and temperature. The resulting TiO₂ gels and films find applications in photocatalysis, where they degrade organic pollutants under UV light due to the material's wide bandgap and high surface area, and in protective coatings that enhance corrosion resistance and optical clarity on substrates like glass and metals.^[34] In vapor phase deposition techniques, titanium isopropoxide acts as a volatile precursor for chemical vapor deposition (CVD) to fabricate TiO₂ thin films, offering precise control over film thickness and uniformity at relatively low temperatures. These films are integral to semiconductor devices, providing insulating layers with high dielectric constants, and to solar cells, where they function as electron transport layers that improve charge separation and device stability. For instance, atmospheric pressure CVD using titanium isopropoxide yields nanocrystalline TiO₂ films on substrates like fluorine-doped tin oxide, achieving enhanced photocatalytic and photovoltaic performance.^[35] Beyond these, titanium isopropoxide facilitates the synthesis of porous titanosilicates, such as Engelhard titanosilicate-4 (ETS-4), through hydrothermal methods involving hydrolysis with silica sources, resulting in microporous frameworks suitable for ion-exchange applications. These materials selectively sorb radioactive ions like cesium (Cs⁺) and strontium (Sr²⁺) from aqueous solutions, aiding in the cleanup of nuclear waste by leveraging their high selectivity and thermal stability. Additionally, titanium isopropoxide is employed in assembling heterosupermolecules, where sol-gel-derived TiO₂ nanocrystallites are linked to viologen acceptors via hydrogen bonding, enabling vectorial electron transfer upon photoexcitation for potential use in photoelectrochemical devices.^[36]^[37] Recent advancements in the 2020s highlight titanium isopropoxide's role in enhancing perovskite solar cells, where it forms compact TiO₂ layers via spin-coating, reducing recombination at interfaces and boosting power conversion efficiencies to over 17% through improved electron extraction. In antibacterial applications, hydrothermal synthesis using titanium isopropoxide produces TiO₂ nanostructures on titanium alloys, creating surfaces with sharp protrusions that reduce bacterial adhesion by up to 99% against Escherichia coli, attributed to mechanical disruption and photocatalytic reactive oxygen species generation under light.^[38]^[39]

Safety and Handling

Toxicity and Hazards

Titanium isopropoxide is classified under the Globally Harmonized System (GHS) as a flammable liquid (Category 3), causing serious eye damage/irritation (Category 2), and specific target organ toxicity (single exposure, Category 3) with narcotic effects, manifesting as drowsiness or dizziness. It is also acutely toxic if inhaled (Category 3 for vapors), with a signal word of "Warning" and associated hazard statements including H226 (flammable liquid and vapor), H319 (causes serious eye irritation), H335 (may cause respiratory irritation), and H336 (may cause drowsiness or dizziness).^[40]^[21] Toxicity data indicate low acute oral toxicity, with an LD₅₀ of 7460 mg/kg in rats and approximately 7500 mg/kg in male rats. Dermal toxicity is also low, with an LD₅₀ greater than 16 mL/kg in rabbits. Inhalation exposure shows higher risk, with an LC₅₀ of 7.78 mg/L over 4 hours in rats, potentially causing respiratory tract irritation, dizziness, headache, nausea, and in cases of aspiration, pulmonary edema. The compound irritates skin upon contact, though not classified as corrosive, and can cause serious eye irritation leading to redness, pain, and temporary vision impairment. Chronic exposure to titanium compounds, including this one, may result in titanium accumulation in the lungs, leading to scarring, chronic bronchitis, and impaired breathing.^[21]^[40]^[41]^[42] Primary exposure routes include inhalation of vapors, which irritate the respiratory tract and mucous membranes, and direct contact with skin or eyes, causing local irritation. Ingestion is less common but can lead to gastrointestinal discomfort. Environmentally, titanium isopropoxide exhibits low aquatic toxicity, with an EC₅₀ of 590 mg/L for Daphnia magna (48 hours) and greater than 820 mg/L for green algae (72 hours), and it is not classified as hazardous to the aquatic environment. Upon hydrolysis, it decomposes to non-toxic titanium dioxide and isopropanol, though releases should be minimized to prevent entry into waterways.^[40]^[43]

Storage and Disposal

Titanium isopropoxide should be stored in a cool, dry, well-ventilated area under an inert atmosphere such as nitrogen to prevent hydrolysis from moisture exposure.^[44]^[45] Containers must be tightly sealed and made of compatible materials like glass or PTFE, avoiding contact with metals that could react; storage away from water, oxidizing agents, heat sources, sparks, and open flames is essential to mitigate flammability risks.^[46]^[21] During handling, operations must occur in a fume hood or well-ventilated space to avoid inhalation of vapors, with personal protective equipment including nitrile or neoprene gloves, safety goggles or face shield, flame-retardant clothing, and a NIOSH-approved respirator for organic vapors if airborne concentrations exceed limits.^[21]^[44] Non-sparking tools and grounded equipment should be used to prevent static discharge ignition, and all transfers must avoid moisture contact due to the compound's sensitivity.^[45] For spills, evacuate the area, eliminate ignition sources, and absorb the liquid with dry inert materials like sand, lime, or soda ash before placing in sealed containers for disposal; ventilation is required post-cleanup, and contaminated areas should be washed with water if safe.^[46]^[44] Disposal requires incineration at a licensed facility equipped with afterburners and scrubbers, or transfer to an approved hazardous waste handler in accordance with local, national, and international regulations such as RCRA in the United States, where generators must classify the waste based on characteristics like flammability and reactivity.^[21]^[47] Prior to disposal, the compound may be hydrolyzed by controlled addition to water to produce titanium dioxide residue and isopropanol, with the organics incinerated and the TiO₂ treated as non-hazardous solid waste under RCRA guidelines unless contaminated.^[47] In the European Union, titanium isopropoxide is registered under REACH (EC 208-909-6) and must be disposed without release into the environment, complying with Directive 2008/98/EC on hazardous waste.^[1]^[48] To extend shelf life and prevent premature hydrolysis, stabilizers such as acetylacetone can be added to the solution, forming chelates that enhance stability by slowing gelation and maintaining reactivity for applications.^[49]

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Shall not be classified as hazardous to the aquatic environment. 12.2 Persistence and degradability. Data are not available. 12.3 Bioaccumulative potential.
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Wash contaminated clothing before reuse. Section 9 - Physical/Chemical Properties. Appearance. Physical State: Clear liquid. Color: Very faintly yellow.
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Flash Point: 46 deg C. Warning! Flammable liquid and vapor. May cause eye, skin, and respiratory tract irritation. May cause central nervous system.
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