2- Butyl acetate

Butyl acetate (BYOO-til AS-uh-tate) exists in three isomeric forms. Isomers are two or more forms of a chemical compound with the same molecular formula, but different structural formulas and different chemical and physical properties. Their names and synonyms are as follows n-butyl acetate is known as butyl ester, or butyl ethanoate -butyl acetate is called i-methylpropyl ester and acetic acid -butyl ester and ferf-butyl acetate is known by 1,1,-dimethylethyl ester or acetic acid, ferf-butyl ester. The expanded chemical formulas for the forms are slightly different n-butyl acetate, CH3C00CH2CH2CH2CH3 -butyl acetate, CH3COOCH(CH3)(C2H5) and ferf-butyl acetate, CH3C00C(CH3)3. 

About 100,000 kilograms (250,000 pounds) of the n-butyl isomer, the most popular, is produced each year in the United States. By far the most common use of the compound (and the isomers) is as an industrial solvent, with about 90 percent of total output going for this use. 

Butyl acetate. Red atoms are oxygen white atoms are hydrogen and black atoms are carbon. Gray sticks indicate double bonds, publishers 

All three isomers of butyl acetate are made by reacting acetic acid (CH3COOH) with the appropriate butyl alcohol (n-butyl alcohol, -butyl alcohol, or tert-butyl alcohol, respectively). 

The primary use of all three isomers of butyl acetate is as a solvent in the production of lacquers and paints photographic film resins and coatings for furniture, fixtures, containers, and automobiles. Since the 1990s, these compounds have been substituted for other solvents that are considered hazardous environmental pollutants. 

of glacial acetic acid, and reflux for 10 hours. Isolate the ester as forn-butyl acetate. B.p. 110-112. Yield 35 g. 

Iso-Propyl acetate. Use 40 g. (61 ml.) of tso-propyl alcohol, 160 g. of glacial acetic acid and 2 g. of concentrated sulphuric acid. Reflux for 18 hours. Proceed as for n-propyl acetate. B.p. 87-88°. Yield 31 g. 

Ethyl n-butyrate. Use a mixture of 88 g. (92 ml.) of n-butyric acid, 23 g. (29 ml.) of ethanol and 9 g. (5 ml.) of concentrated sulphuric acid. Reflux for 14 hours. Pour into excess of water, wash several times with water, followed by saturated sodium bicarbonate solution until all the acid is removed, and finally with water. Dry with anhydrous magnesium sulphate, and distil. The ethyl w-butyrate passes over at 119-5-120-5°. Yield 40 g. An improved yield can be obtained by distilling the reaction mixture through an efficient fractionating column untU the temperature rises to 125°, and purifying the crude ester as detailed above under methyl acetate. 

Method A. Fit a 1-htre three-necked flask with a mercury-sealed stirrer, a reflux condenser, and a dropping funnel. Place 57 g. (73-5 ml.) of dry erl.-butyl alcohol (1), 101 g. (106 ml.) of A.R. dimethylaniline and 100 ml. of anhydrous ether in the flask, set the stirrer in motion, and 

Submitted by Robert H. Baker and Frederick G. Bordiveix. Checked by R. L. Shriner and Fred W. Neumann. 

After removal of the drying agent, the ester is fractionally distilled through an efficient fractionating column (Note 2). A fore-run of 21-37 g. is collected up to a temperature of 95°. The pure ester distils between 95° and 96° and amounts to 129-148 g. (53-60%) (Note 3). 

Eastman Kodak Company s best grade of tert.-butyl alcohol and the Practical grade of acetic anhydride are satisfactory. If these are not available, the alcohol should be dried over quicklime and distilled, and the acetic anhydride should be redistilled also. 

The fractionating column may be a 16-plate Stedman column or a 30-cm. Carborundum-packed column.1 

In a 2-1. flask equipped with a reflux condenser, mercury-sealed stirrer, and a dropping funnel are placed 147 ml. (114 g., 1.5 moles) of ter/.-butyl alcohol (Note 1), 212 ml. (202 g., 1.67 moles) of dimethylaniline, and 200 ml. of dry ether. The solution is heated to refluxing, and 113 ml. (124 g., 1.58 moles) of acetyl chloride is run into the stirred solution at such a rate that moderate refluxing continues after the source of heat is removed. When approximately two-thirds of the acetyl chloride has been added, dimethylaniline hydrochloride begins to crystallize and the mixture refluxes very vigorously. An ice bath is applied immediately, and, after refluxing ceases, the remainder of the acetyl chloride is added. Finally, the mixture is heated for 1 hour on a water bath. The mixture is cooled to room tempera- 

Hydrocarbons, pp 261-212. New York, Elsevier Science Pub, 1987 9. Moore AF Final report on the safety assessment of isobutane, isopentane, -butane, and propane, y Coll Toxicol 1 127-142, 1982 

Synonyms Butyl ethanoate acetic acid, butyl ester 

Solvent for nitrocellulose, oils, fats, resins, waxes, and camphor manufacture of lacquer and plastics 

Toxicology. -Butyl acetate causes irritation of mucous membranes and the eyes at high concentrations it causes narcosis in animals, and it is expected that severe exposure will cause the same effect in humans. 

In humans, -butyl acetate affected the throat at 200 ppm severe throat irritation occurred at 3 00 ppm, and the majority of the subjects also complained of eye and nose irritation. Only slight eye and pulmonary irritation (as determined by lung function tests) were observed in volunteers exposed to 1400 mg/m for 20 minutes or 700mg/m for 4 hours.  

Neither cool flames nor a region of negative temperature coefficient have been observed, and it appears that at 220 °C this ester pyrolyses rather than combusts [97]. 

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M-Butyl formate. Ethyl iso-butyrate IsO -butyl acetate Ethyl butyrate -Propyl propionate Iso-amyl formate, -But> l acetate Iso-propyl butyrate Iso-butyl propionate n-Propyl -butyrate -Butyl propionate Iso-butyl isobutyrate Ethyl lactate Iso-butyl butyrate Cycloheicyl formate -Butyl -butyrate Iso-propyl lactate. Cyclohexyl acetate Diethyl oxalate Di-iao-propyl oxalate... 

Hydrolysis (or saponification) of n-butyl acetate. Boil 4-5 g. of n-butyl acetate (Section 111,95) with 50 ml. of 10 per cent, sodium hydroxide solution under reflux until the odour of the ester can no longer be detected (about 1 hour). Set the condenser for downward distiUation and coUect the first 10 ml. of distillate. Saturate it with potassium carbonate, aUow to stand for 5 minutes, and withdraw all the Uquid into a small pipette or dropper pipette. AUow the lower layer of carbonate solution to run slowly into a test-tube, and place the upper layer into a small test-tube or weighing bottle. Dry the alcohol with about one quarter of its buUr of anhydrous potassium carbonate. Remove the alcohol with a dropper pipette and divide it into two parts use one portion for the determination of the b.p. by the Siwoloboff method (Section 11,12) and convert the other portion into the 3 5-dinitrobenzoate (Section III, 27) and determine the m.p. 

Successful results have been obtained (Renfrew and Chaney, 1946) with ethyl formate methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl and iso-amyl acetat ethyleneglycol diacetate ethyl monochloro- and trichloro-acetates methyl, n-propyl, n-octyl and n-dodecyl propionates ethyl butyrate n-butyl and n-amyl valerates ethyl laurate ethyl lactate ethyl acetoacetate diethyl carbonate dimethyl and diethyl oxalates diethyl malonate diethyl adipate di-n-butyl tartrate ethyl phenylacetate methyl and ethyl benzoates methyl and ethyl salicylates diethyl and di-n-butyl phthalates. The method fails for vinyl acetate, ieri.-butyl acetate, n-octadecyl propionate, ethyl and >i-butyl stearate, phenyl, benzyl- and guaicol-acetate, methyl and ethyl cinnamate, diethyl sulphate and ethyl p-aminobenzoate. 

Esters. re-Butyl acetate Ethyl acetate Ethyl benzoate. 

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