108-21-4

Basic information

• Product Name: Isopropyl acetate
• Synonyms: 1-Methylethylethanoate;2-Methylethylethanoate;2-Propyl acetate;2-propylacetate;2-propylethanoate;Acetate d'isopropyle;acetated’isopropyle;acetated’isopropyle(french)
• CAS NO: 108-21-4
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 203-561-1
• Product Categories: Organics;Amber Glass Bottles;Carbon Steel Flex-Spout Cans;ReagentPlus(R) Solvent Grade Products;ReagentPlus(R)Semi-Bulk Solvents;ReagentPlus(R)Solvents;Solvent Bottles;Alpha Sort;Alphabetic;E-LAnalytical Standards;EstersAnalytical Standards;I;Volatiles/ Semivolatiles;I-N, Puriss p.a.Analytical Standards;Chemical Class;Nitriles;Puriss p.a.;Alphabetical Listings;Flavors and Fragrances;I-L;E-L, Puriss p.a. ACS;Analytical Reagents for General Use;Puriss p.a. ACS;Chemical Class;I-N;Amber Glass Bottles;Analytical Reagents;Analytical Reagents for General Use;Analytical Standards;Analytical/Chromatography;Puriss p.a.;Solvent Bottles;Solvent Packaging Options;Solvents;Organic synthesis
• Mol File: 108-21-4.mol
• Article Data: 110

Chemical Properties

• Melting Point: -73 °C
• Boiling Point: 88.8 °C
• Flash Point: 62 °F
• Appearance: Clear colorless/Liquid
• Density: 0.872 g/mL at 25 °C(lit.)
• Vapor Density: 3.5 (vs air)
• Vapor Pressure: 47 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.377(lit.)
• Storage Temp.: Flammables area
• Solubility: 1 M HCl: soluble50mg/mL, clear to slightly hazy, colorless
• Explosive Limit: 1.8%, 37°F
• Water Solubility: 2.90 g/100 mL
• Sensitive: Moisture Sensitive
• Stability: Stable. Flammable - note low flash point. Incompatible with strong oxidizing agents, strong acids, nitrates, alkali metals. May
• Merck: 14,5205
• BRN: 1740761
• CAS DataBase Reference: Isopropyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl acetate(108-21-4)
• EPA Substance Registry System: Isopropyl acetate(108-21-4)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38-67-66-36
• Safety Statements: 16-26-36-33-29
• RIDADR: UN 1220 3/PG 2
• WGK Germany: 1
• RTECS: AI4930000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 108-21-4(Hazardous Substances Data)

Usage

Chemical Properties

Isopropyl acetate is a colourless liquid with an intense, fruity odor. On dilution, it has a sweet apple-like flavor. Miscible with most organic solvents such as alcohols, ketones and ethers. 2.9% (w/w) soluble in water at 20°C. Synthesized by direct acetylation of isopropyl alcohol in the presence of various catalysts: concentrated H2S04, diethyl sulfate, chlorosulfonic acid, and boron trifluoride.

Physical properties

Clear, colorless liquid with an aromatic odor. Experimentally determined detection and recognition odor threshold concentrations were 2.1 mg/m3 (500 ppbv) and 3.8 mg/m3 (910 ppbv), respectively (Hellman and Small, 1974).

Occurrence

Reported found in pineapple, pear, cocoa, apple, banana, black currants, grapes, melons, strawberry, cheddar cheese, beer, white wine, red wine, cocoa, honey, soybean, yellow passion fruit, beans, plum brandy and nectarines

Uses

Isopropyl acetate is used as a solvent for nitrocellulose, plastics, oils, and fats, and as a flavoring agent. Isopropyl Acetate is a widely used chemical solvent in organic and industrial syntheses. Also used in the dissolution of gallstones. Environmental contaminants; Food contaminants.

Definition

ChEBI: Isopropyl acetate is a branched-chain saturated fatty acid anion that is the conjugate base of isovaleric acid; reported to improve ruminal fermentation and feed digestion in cattle.

Preparation

Isopropyl acetate is prepared from propylene and anhydrous acetic acid in the presence of a catalyst . It may also be produced by direct acetylation of isopropyl alcohol in the presence of various catalysts; concentrated H2SO4, diethyl sulfate, chlorosulfonic acid and boron trifluoride.

Application

Isopropyl acetate is a solvent in chemical industry, especially for cellulose, plastics, waxes, resins, gums, paints, oil and fats. and also as flavoring agent. It is an active component of perfumes and printing inks. It is also employed as an extractant for the preparation of antibiotics, vitamins and hormones.

Aroma threshold values

Detection; 1.7 to 4.4 ppm

Taste threshold values

Taste characteristics at 60 ppm: ethereal, tutti-frutti, with a fruity apple and banana nuance

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 3728, 1974 DOI: 10.1021/jo00939a026

General Description

Isopropyl acetate appears as a clear colorless liquid. Flash point 40°F. Vapors are heavier than air. Contact with the material may irritate skin, eyes or mucous membranes. May be toxic by ingestion, inhalation and skin absorption. Used as a solvent.

Air & Water Reactions

Highly flammable. Less dense than water and slightly soluble in water.

Reactivity Profile

Isopropyl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Isopropyl acetate can react vigorously with nitrates, strong oxidizers, strong alkalis and strong acids. Isopropyl acetate may also attack some forms of rubber, plastics and coatings. .

Health Hazard

Isopropyl acetate is an irritant to the eyes,nose, and throat. Liquid irritates eyes but causes no serious injury; may cause dermatitis; no serious effects if swallowed. The acute toxicity in laboratory animals was low. Exposure to highconcentrations in air or ingestion can produce narcotic effects. A 4-hour exposure to aconcentration of 32,000 ppm in air was fatalto rats (ACGIH 1986). The oral LD50 valuein rats is in the range 6000 mg/kg.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Highlyflammable

Source

Identified among 139 volatile compounds identified in cantaloupe (Cucumis melo var. reticulates cv. Sol Real) using an automated rapid headspace solid phase microextraction method (Beaulieu and Grimm, 2001).

Environmental fate

Chemical/Physical. Hydrolyzes in water forming isopropyl alcohol and acetic acid (Morrison and Boyd, 1971). The estimated hydrolysis half-life at 25 °C and pH 7 is 8.4 yr (Mabey and Mill, 1978). At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 319 mg/L. The adsorbability of the carbon used was 137 mg/g carbon (Guisti et al., 1974).

Purification Methods

Wash the acetate with 50% aqueous K2CO3 (to remove acid), then with saturated aqueous CaCl2 (to remove any alcohol). Dry it with CaCl2 and fractionally distil it. [Beilstein 2 IV 141.]

InChI:InChI=1/C5H10O2/c1-4(2)7-5(3)6/h4H,1-3H3

Upstream product

• 64713-85-5 O-isopropyl selenoacetate 
• 187737-37-7 propene 
• 7637-07-2 boron trifluoride 
• 64-19-7 acetic acid 
• 79-20-9 acetic acid methyl ester 
• 67-63-0 isopropyl alcohol 
• 124-13-0 Octanal 
• 96-32-2 bromoacetic acid methyl ester 
• 7440-66-6 zinc 
• 30074-98-7 1-Acetyl-4(1H)-pyridinon 
• 563-80-4 3-methyl-butan-2-one 
• 75-36-5 acetyl chloride 
• 108-20-3 di-isopropyl ether 
• 67809-15-8 N-nitroso-N-propyl-acetamide 

Downstream Products

• 1515-76-0 1-acetoxy-1,3-butadiene 
• 77132-94-6 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-ylideneacetic acid isopropyl ester 4-oxide 
• 35219-73-9 2,2-bis-allyloxy-propane 
• 64-19-7 acetic acid 
• 187737-37-7 propene 
• 67-64-1 acetone 
• 542-08-5 isopropyl acetoacetate 
• 236742-98-6 (4S)-3-oxo-4,5-(N-triphenylmethylepimino)pentanoic acid isopropyl ester 
• 64-17-5 ethanol 
• 1859-09-2 ethanol-1,1-d2 
• 5440-69-7 N-isopropylbenzamide 
• 92520-13-3 N-(1-(4-methylphenyl)ethyl)acetamide 
• 36065-27-7 N-α-phenylethylacetamide 
• 1213668-79-1 (R)-1-(3,5-dimethylphenyl)-prop-2-en-1-amine 

Relevant articles and documents

Kinetics of the esterification of acetic acid with 2-propanol: Impact of different acidic cation exchange resins on reaction mechanism

The kinetics of the esterification of acetic acid with the secondary alcohol, 2-propanol, catalyzed by the cation exchange resins, Dowex 50Wx8-400, Amberlite IR-120, and Amberlyst 15 has been studied at temperatures of 303, 323, and 343 K; acid to alcohol molar ratios of 0.5, 1, and 2; and catalyst loadings of 20, 40, and 60 g/L. The equilibrium constant was experimentally determined, and the reaction was found to be mildly exothermic. External and internal diffusion limitations were absent under the implemented experimental conditions. Systems catalyzed by gel-type resins (Dowex 50Wx8-400 and Amberlite IR-120) exhibit some similarities in their reaction kinetics. Increase in reaction temperature, acid to alcohol ratio, and catalyst loading is found to enhance reaction kinetics for the three catalysts. The pseudohomogeneous (PH), Eley Rideal (ER), Langmuir Hinshelwood (LH), modified Langmuir Hinshelwood (ML), and Poepken (PP) models were found to predict reaction kinetics with mean relative errors of less than 5.4%. However, the ML model was found to be better for predicting reaction kinetics in the systems catalyzed by gel-type resins, while the PP model was better for the system catalyzed by the macroreticular catalyst, Amberlyst 15. The Eact for the forward reaction is found to be 57.0, 59.0, and 64.0 kJ/mole for the systems catalyzed by Dowex 50Wx8-400, Amberlite IR-120, and Amberlyst 15, respectively. For these three catalysts, the adsorption equilibrium constants of the components present in the system increase in the same order as do the solubility parameters of the component. Nonideality in the system is successfully accounted for by the UNIFAC model.

Acetylation of alcohols catalyzed by dodeca-tungsto(molybdo)phosphoric acid

Acetylation of primary, secondary, and tertiary alcohols was carried out in some refluxing alkyl acetates and in two carboxylic acids with the participation of catalytic amounts of H3PW12O 40, H3PMo12O40, and H 14P5W30O110 with good yields and high stereo(regio)specificity under mild reaction condition. H 3PW12O40 and H3PMo 12O40 have also shown excellent reactivity in the formylation of 1-butanol with ethyl formate at room temperature and in short reaction times. Heteropolyacid catalysts could be separated after a simple work up and reused for several times. Springer-Verlag 2006.

The heterogenation of melamine and its catalytic activity

The immobilization of melamine (Mela) onto silica extracted from rice husk ash (RHA) has been done via 3-chloropropyltriethoxysiline (CPTES). The resulting catalyst was designated as RHAPrMela. The melamine loading on the silica was found to be ca. 65.74%. The 29Si MAS NMR showed the presence of T2, T3, Q3 and Q4 silicon centers. The 13C MAS NMR showed that RHAPrMela had three chemical shifts at 14.83, 31.17 and 52.24 ppm, consistent with the three carbon atoms, and two chemical shifts at 161.52 and 169.67 ppm with double spinning side bands, indicating that the three carbon atoms in melamine ring are not equivalent in RHAPrMela. The catalytic potential of RHAPrMela was tested for the esterification of acetic acid with several alcohols. A conversion of 73% was achieved with 100% selectivity for the respective esters. The catalyst was easily regenerated and could be reused many times without loss of catalytic activity.

Efficient Baeyer-Villiger electro-oxidation of ketones with molecular oxygen using an activated carbon fiber electrode in ionic liquid [bmim][OTf]

A new and efficient method for the synthesis of lactones and esters involving the application of an molecular oxygen-based electro-catalytic oxidation system and ionic liquid [bmim][OTf] as electrolyte has been developed. The reaction between various ketones with molecular oxygen proceeds in a three-electrode cell under constant current conditions in [bmim][OTf] at room temperature to give the corresponding esters and lactones in good to excellent isolated yield. Additionally, the possible mechanism of Baeyer-Villiger oxidation of ketones in the electro-catalytic system is proposed.

Chemical Conversions using Sheet Silicates: Facile Ester Synthesis by Direct Addition of Acids to Alkenes

Ethene and acetic acid react in the interlamellar regions of certain cation (e.g.Al3+)-exchanged montmorillonites to yield ethyl acetate as the sole product, and a variety of carboxylic acids readily add to C2-C8 alkenes at temperatures above 100 deg C to yield the corresponding esters in high and selective yields.

Hydroxide-promoted selective C(α)-C(β) bond activation of aliphatic ethers by rhodium(III) porphyrins

The selective aliphatic C(α)-C(β) bond activation (CCA) of ethers by rhodium(III) porphyrin halides in the presence of KOH was achieved to give Rh-C(β) alkyls up to 88% yield. The addition of H2O and a phase transfer agent Ph4PBr improved the homogeneity of the reaction mixture and significantly brought down the reaction temperature to 60 °C. At this mild temperature, the C(α) co-product was oxidized to the corresponding esters in up to 89% yield. KOH promotes the bond activation by transferring the hydroxyl group to rhodium porphyrin to generate the key intermediate RhIII(ttp)OH (ttp = 5,10,15,20-tetratolylporphyrinate dianion).

Homogeneous Metal-Complex Catalyst Systems in the Partial Oxidation of Propane with Oxygen

Abstract: The effect of copper compounds and phosphorus–molybdenum–vanadium heteropoly acids (HPAs) H5PMo10V2O40 and H7PMo8V4O40 used as cocatalysts in the cooxidation

Direct catalytic oxidation of lower alkanes in ionic liquid media

Immobilization of rhodium (palladium)-copper-chloride catalytic systems in ionic liquids as high-boiling-point solvents affects the distribution of propane oxidation products: the acetone yield increases and the yield of alcohols decreases. Propane is oxidized to acetone, bypassing the isopropanol formation step. Methane is oxidized under more severe conditions than propane, giving methyl trifluoroacetate as the main product. Mechanisms of action of the catalytic systems based on rhodium and palladium are close to each other and likely include oxo or peroxo complexes as intermediates.

A potential “green” organotin: Bis-(methylthiopropyl)tin dichloride, [MeS (CH2)3]2SnCl2

The tetravalent organotin compound [MeS(CH2)3]2SnCl2, 1, has been synthesized in high yield and structurally characterized as being hexa-coordinate at tin with two intramolecular Sn-S bonds. The specific structure has been shown by theoretical calculations to be the low energy geometric structure available, and the differences associated with the experimental and calculated Sn-S bond lengths ascribed to crystal packing issues. The intramolecular Sn-S bonding produces a benign organotin compound with respect to its interactions with human natural killer cells; however, this blocking of coordination sites at Sn does not reduce its capacity to act as an efficient esterification catalyst.

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Acetic Anhydride as an Oxygen Donor in the Non-Hydrolytic Sol–Gel Synthesis of Mesoporous TiO2 with High Electrochemical Lithium Storage Performances

An original, halide-free non-hydrolytic sol–gel route to mesoporous anatase TiO2 with hierarchical porosity and high specific surface area is reported. This route is based on the reaction at 200 °C of titanium(IV) isopropoxide with acetic anhydride, in the absence of a catalyst or solvent. NMR spectroscopic studies indicate that this method provides an efficient, truly non-hydrolytic and aprotic route to TiO2. Formation of the oxide involves successive acetoxylation and condensation reactions, both with ester elimination. The resulting TiO2 materials were nanocrystalline, even before calcination. Small (about 10 nm) anatase nanocrystals spontaneously aggregated to form mesoporous micron-sized particles with high specific surface area (240 m2 g?1 before calcination). Evaluation of the lithium storage performances shows a high reversible specific capacity, particularly for the non-calcined sample with the highest specific surface area favouring pseudo-capacitive storage: 253 mAh g?1 at 0.1 C and 218 mAh g?1 at 1 C (C=336 mA g?1). This sample also shows good cyclability (92 % retention after 200 cycles at 336 mA g?1) with a high coulombic efficiency (99.8 %). Synthesis in the presence of a solvent (toluene or squalane) offers the possibility to tune the morphology and texture of the TiO2 nanomaterials.

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Substituent and Solvent Effects in the Kinetics of N-Alkylimidazole-Catalyzed Reaction of Acetic Anhydride with Isopropyl Alcohol

The overall rate of the N-alkylimidazole-catalyzed reaction of acetic anhydride with isopropyl alcohol is rather insensitive to solvent polarity.Of the nine solvents studied, N,N-dimethylformamide is the best for analytical use.A series of N-alkyl substituted imidazoles was investigated as catalysts in this reaction.The most effective catalyst was N-n-pentylimidazole, which is about 60percent more reactive than N-methylimidazole.

A Pyridine-Acetylene-Aniline Oligomer: Saccharide Recognition and Influence of this Recognition Array on the Activity as Acylation Catalyst

In order to create new functions of foldamer-type hosts, various kinds of recognition arrays are expected to be developed. Here, a pyridine-acetylene-aniline unit is presented as a new class of a saccharide recognition array. The conformational stabilities of this array were analyzed by DFT calculation, and suggested that a pyridine-acetylene-aniline oligomer tends to form a helical structure. An oligomer of this array was synthesized, and its association for octyl β-D-glucopyranoside was confirmed by 1H NMR measurements. UV/Vis, circular dichroism, and fluorescence titration experiments revealed its high affinity for octyl glycosides in apolar solvents (Ka=104 to 105 M?1). This oligomer was relatively stable under basic conditions, and therefore this array was expected to be applied to the derivatization of saccharides. A 4-(dialkylamino)pyridine attached pyridine-acetylene-aniline oligomer proved to catalyze the acylation of the octyl glucoside.

Synthesis, Characterisation, and Determination of Physical Properties of New Two-Protonic Acid Ionic Liquid and its Catalytic Application in the Esterification

A new ionic liquid was synthesised, and its chemical structure was elucidated by FT-IR, 1D NMR, 2D NMR, and mass analyses. Some physical properties, thermal behaviour, and thermal stability of this ionic liquid were investigated. The formation of a two-protonic acid salt namely 4,4′-trimethylene-N,N′-dipiperidinium sulfate instead of 4,4′-trimethylene-N,N′-dipiperidinium hydrogensulfate was evidenced by NMR analyses. The catalytic activity of this ionic liquid was demonstrated in the esterification reaction of n-butanol and glacial acetic acid under different conditions. The desired acetate was obtained in 62-88 % yield without using a Dean-Stark apparatus under optimal conditions of 10 mol-% of the ionic liquid, an alcohol to glacial acetic acid mole ratio of 1.3: 1.0, a temperature of 75-100°C, and a reaction time of 4 h. α-Tocopherol (α-TCP), a highly efficient form of vitamin E, was also treated with glacial acetic acid in the presence of the ionic liquid, and O-acetyl-α-tocopherol (Ac-TCP) was obtained in 88.4 % yield. The separation of esters was conducted during workup without the utilisation of high-cost column chromatography. The residue and ionic liquid were used in subsequent runs after the extraction of desired products. The ionic liquid exhibited high catalytic activity even after five runs with no significant change in its chemical structure and catalytic efficiency.