2-isopropyl- -acetic acid

SYNS BENZYL ISOVALERATE (FCC) BENZYL-3-METHYLBUTANOATE BENZYL-3-METHYL BUTYRATE FEMA No. 2152 ISOPENTANOIC ACID, PHENYLMETHYL ESTER ISOPROPYL ACETIC ACID, BENZYL ESTER 3-METHYLBUTANOIC ACID, PHENYLETHYL ESTER... 

ISOPROPOXYPHENYL (METHYL)(T-BUTOXYSULFIN"YL)CARBAMATE see INE062 2-ISOPROPOXYPROPANE see IOZ750 ISOPROPYDRIN see DM 600 ISOPROPYLACETAAT (DUTCH) see INEIOO ISOPROPYLACETAT (GERMAN) see INEIOO ISOPROPYL ACETATE see INEIOO ISOPROPYL (ACETATE d) (FRENCH) see INEIOO ISOPROPYLACETIC ACID see ISUOOO ISOPROPYL ACETIC ACID, BENZYL ESTER see ISWOOO... 

II. Ordinary valerianic acid—DefpAfnfc acid—Phocenic acid— Isovaleric acid—Isopropyl acetic acid—Isobutylformie acid— Acidum valerianicum (Br.).—This acid exists in the oil of the porpoise, and in valerian root and in angelica root. It is formed during putrid fermentation or oxidation of albuminoid sub-.stances. It occurs in the urine and faeces in typhus, variola, and... 

Synonyms Benzyl 3-methyl butanoate Benzyl 3-methyl butyrate Isopentanoic acid, phenylmethyl ester Isopropyl acetic acid, benzyl ester Isovaleric acid, benzyl ester 3-Methylbutanoic acid, phenylethyl ester Empirical C12H16O2... 

Isopropylacetic acid. See Isovaleric acid Isopropyl acetic acid, benzyl ester. See Benzyl isovalerate... 

Wt % acetic acid. isopropyl Acetic acid, Isopropyl... 

Olefins add anhydrous acetic acid to give esters, usually of secondary or tertiary alcohols propjiene [115-07-1] yields isopropyl acetate [108-21-4], isobutjiene [115-11-7] gives tert-huty acetate [540-88-5]. Minute amounts of water inhibit the reaction. Unsaturated esters can be prepared by a combined oxidative esterification over a platinum group metal catalyst. Eor example, ethylene-air-acetic acid passed over a palladium—Hthium acetate catalyst yields vinyl acetate. 

Until World War 1 acetone was manufactured commercially by the dry distillation of calcium acetate from lime and pyroligneous acid (wood distillate) (9). During the war processes for acetic acid from acetylene and by fermentation supplanted the pyroligneous acid (10). In turn these methods were displaced by the process developed for the bacterial fermentation of carbohydrates (cornstarch and molasses) to acetone and alcohols (11). At one time Pubhcker Industries, Commercial Solvents, and National Distillers had combined biofermentation capacity of 22,700 metric tons of acetone per year. Biofermentation became noncompetitive around 1960 because of the economics of scale of the isopropyl alcohol dehydrogenation and cumene hydroperoxide processes. 

PMMA is not affected by most inorganic solutions, mineral oils, animal oils, low concentrations of alcohols paraffins, olefins, amines, alkyl monohahdes and ahphatic hydrocarbons and higher esters, ie, >10 carbon atoms. However, PMMA is attacked by lower esters, eg, ethyl acetate, isopropyl acetate aromatic hydrocarbons, eg, benzene, toluene, xylene phenols, eg, cresol, carboHc acid aryl hahdes, eg, chlorobenzene, bromobenzene ahphatic acids, eg, butyric acid, acetic acid alkyl polyhaHdes, eg, ethylene dichloride, methylene chloride high concentrations of alcohols, eg, methanol, ethanol 2-propanol and high concentrations of alkahes and oxidizing agents. 

AUyl acetate can be obtained by the vapoi-phase reaction of propylene and acetic acid over a supported Pd catalyst (eq. 20) (110). Reaction of acrylic acid and propylene yields isopropyl acrylate (eq. 21), and catalytic reaction with acetic acid produces isopropyl acetate (eq. 22) (110). 

The addition of TYZOR AA to larger quantities of water results in precipitation of the polytitanaoxane as a yellow soHd, which can be isolated and dried (92). The precipitation of this soHd can be prevented by diluting the TYZOR AA with an equal volume of 10% aqueous acetic acid and then 13 times the amount of a 1 1 mixture of isopropyl alcohol and water (93). 

Quarpel is an important combination of fluorochemical finish and resin-based extender developed by the U.S. Army Natick Laboratories for military use. This finish typicaUy contains 4—6 wt % commercial fluorochemical emulsion, 4—6 wt % resin-based repeUent emulsion, 0.1 wt % acetic acid, and 5 wt % isopropyl alcohol. If necessary, the formulation includes a catalyst to cross-link the resin-based component. Quarpel specifications demand exceUent initial water and oU repeUency and exceUent durabUity to washing and dry cleaning. 

Another method for direct precipitation of cellulose acetate powder suitable for extmsion into plastics is described (90). The reaction solution is precipitated with dilute aqueous acetic acid at 80—85°C in the presence of a coagulant such as isopropyl acetate. The resulting powder particles have a higher bulk density and absorb plasticizers more readily than powders obtained by the usual methods. 

Unsaturated Hydrocarbons. Olefins from ethylene through octene have been converted into esters via acid-catalyzed nucleophilic addition. With ethylene and propjiene, only a single ester is produced using acetic acid, ethyl acetate and isopropyl acetate, respectively. With the butylenes, two products are possible j -butyl esters result from 1- and 2-butylenes, whereas tert-huty esters are obtained from isobutjiene. The C5 olefins give rise to three j iC-amyl esters and one /-amyl ester. As the carbon chain is lengthened, the reactivity of the olefin with organic acids increases. 

Several examples of cost-effective liquid-hquid extraction processes include the recovery of acetic acid from water (Fig. 15-1), using ethyl ether or ethyl acetate as described by Brown [Chem. Eng. Prog., 59(10), 6.5 (1963)], or the recoveiy of phenolics from water as described by Lauer, Littlewood, and Butler [7/Steel Eng., 46(5), 99 (1969)] with butyl acetate, or with isopropyl ether as described by Wurm [Gliickauf, 12, 517 (1968)], or with methyl isobutyl ketone as described by Scheibel [ Liqmd-Liquid Extraction, in Periy Weiss-... 

Many carbamates have been used as protective groups. They are arranged in this chapter in order of increasing complexity of stmcture. The most useful compounds do not necessarily have the simplest stmctures, but are /-butyl (BOC), readily cleaved by acidic hydrolysis benzyl (Cbz or Z), cleaved by catalytic hy-drogenolysis 2,4-dichlorobenzyl, stable to the acid-catalyzed hydrolysis of benzyl and /-butyl carbamates 2-(biphenylyl)isopropyl, cleaved more easily than /-butyl carbamate by dilute acetic acid 9-fluorenylmethyl, cleaved by /3-elimination with base isonicotinyl, cleaved by reduction with zinc in acetic acid 1-adamantyl, readily cleaved by trifluoroacetic acid and ally], readily cleaved by Pd-catalyzed isomerisation. 

Cholesterol [57-88-5] M 386.7, m 148.9-149.4 , [a]D -35 (hexane). Crystd from ethyl acetate, EtOH or isopropyl ether/MeOH. [Hiromitsu and Kevan J Am Chem Soc 109 4501 I987. For extensive details of purification through the dibromide, see Fieser [J Am Chem SoclS 5421 1953] and Schwenk and Werthessen [Arch Biochem Biophys 40 334 7952], and by repeated crystn from acetic acid, see Fieser [J Am Chem Soc 75 4395 1953]. 

Isopropyl acetate [108-22-5] M 102.1, b 88.4 , d 0.873, n 1.3773. Washed with 50% aq K2CO3 (to remove acid), then with saturated aq CaCl2 (to remove any alcohol). Dried with CaCl2 and fractionally distd. 

Separated from retinol by column chromatography on water-deactivated alumina with hexane containing a very small percentage of acetone. Also chromatographed on TLC silica gel G, using pet ether/isopropyl ether/acetic acid/water (180 20 2 5) or pet ether/acetonitrile/acetic acid/water (190 10 1 15) to develop the chromatogram. Then recrystd from propylene at low temperature. 

Chemical Designations - Synonym Acetic acid, isopropyl ester 2-Propyl acetate Chemical Formula CH3COOCH(CH3)j. 

The phosphorodithioate is stable to heating at 100°, 80% acetic acid (1 h), dry or aqueous pyridine (days) and refluxing methanol, ethanol or isopropyl alcohol for Ih. 

A solution of 11.2 g of potassium permanganate in 100 ml of warm water was added drop-wise to a well stirred solution of 10 g of 2-(4-chlorophenyl)-3-methyl-4-metathiazanone in 50 ml of glacial acetic acid. The temperature was kept below 30°C with external cooling. An aqueous sodium bisulfite solution was then added to remove the manganese dioxide. The thick whitish oil which separated was taken up in chloroform and the extract was washed with water. Removal of the chloroform by distillation in vacuo yielded an oily residue which solidified. The solid was recrystallized from isopropyl alcohol to give 5 g of the product, 2-(4-chlorophenyl)-3-methyl-4-metathiazanone-1,1-dioxide, MP 116.2° to 118.6°C (corr.). 

A solution of 69g of sodium in 1,380 ccof absolute alcohol is mixed with 257.4 g of /3-methyl-thioethyl-d -methyl)-n-butvl-cyano-acetic acid ethyl ester and 114 g of thiourea and the whole mass boiled under reflux with stirring for six hours. After concentration under vacuum the residue is taken up in 1.5 liters of water and shaken up thrice, each time with 300 cc of ether. The aqueous alcoholic layer is stripped, under vacuum, of the dissolved ether and mixed with 300 cc of 30% acetic acid under stirring and ice cooling. The precipitated material is sucked off, washed with water, dried and recrystallized from isopropyl alcohol. The thus obtained j3-methvl-thioethyl-(1 -methyD-n-butyl-cyano-ecetyl thiourea forms yellowish green crystals having a melting point of 229°C to 230°C. 

This reaction mixture is kept between 0°C and -i-5°C for six hours, with agitation and under an inert atmosphere, then 5 cc of a 0.2N solution of acetic acid in toluene are added. The mixture is extracted with toluene, and the extracts are washed with water and evaporated to dryness. The residue is taken up in ethyl acetate, and then the solution Is evaporated to dryness in vacuo, yielding a resin which is dissolved in methylene chloride, and the solution passed through a column of 40 g of magnesium silicate. Elution is carried out first with methylene chloride, then with methylene chloride containing 0.5% of acetone, and 0.361 g Is thus recovered of a crude product, which is dissolved in 1.5 cc of isopropyl ether then hot methanol Is added and the mixture left at 0°C for one night. 

The trends of variation of the activation parameters are correlated with the solvation mechanism and dielectric behavior of the medium. Thus, AH, AG and A5 for the acidic resin-catalyzed hydrolysis of isopropyl acetate were calculated using the Wynne-Jones and Eyr-... 

About 50% of isopropanol use is to produce acetone. Other important synthetic uses are to produce esters of many acids, such as acetic (isopropyl acetate, solvent for cellulose nitrate), myristic, and oleic acids (used in lipsticks and lubricants). Isopropylpalmitate is used as an emulsifier for cosmetic materials. Isopropyl alcohol is a solvent for alkaloids, essential oils, and cellulose derivatives. 

Isopropyl acetate is produced by the catalytic vapor-phase addition of acetic acid to propylene. A high yield of the ester can be realized (about 99%) ... 

To a stirred solution of 0.74 g (4 mmol) of (S)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine in 20 mL of THF under a nitrogen atmosphere are added at — 70 °C, 2.6 mL (4 mmol, 1.55 N in hexane) of butyllithium and stirring is continued for 10 min. Then, a solution of 0.97 g (6 mmol) of methyl (/f)-3-phenylpropenoate in 10 mL of THF is added. After 2 3 h a solution of 0.24 g (4 mmol) of acetic acid in 2 mL of THF is added and the mixture is allowed to warm to 25 rC. The solvent is removed in vacuo, the residual product dissolved in 10 mL of diethyl ether, then shaken with 10 mL of water, and the water layer extracted twice with 10 mL of diethyl ether. The combined diethyl ether extracts are dried over MgS04 and the diethyl ether is evaporated. The crude product is purified by bulb-to-bulb distillation to give the adduct yield 1.28 g (92%). 

Acetaldehyde, acetone, isopropyl alcohol, ethyl acetate, methyl isobutyl ketone, toluene, butyl acetate, isobutyl alcohol, and acetic acid... 

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