Methyl ether ketone

Mndzhoyan, O. L. and Gevorkyan, O. A., Derivatives of aminokelones. IX. Products of the Mannich reaction using methyl ether ketones, Ann. Khim. Zh.. 26, 220, 1973 Chem. 

Typically the selectivity is above 99%. The following impurities may be found higher alcohols, hydrocarbons and waxes, esters, di-methyl-ether, ketones. With these elements we may proceed with the flowsheet description. 

Acetic acid, acetone, acetonitrile, benzenerwater (1 1), chloroform, cyclohexanone, dichloroacetice acid, dichloromethane, N,N-dimethylacetamide, dimethyUormainide, dimethylsulfoxide, dioxane, ethanol, ethylene glycol monomethyl ether, formamide, formic acid, 2-hydroxyethyl methacrylate, isopropanol, methanol, 2-methoxyethanol, methyl ether ketone, morphloline, 2,2 -oxydiethanol, 1-penlanol, phenol, 1,2-propanediol, 1-propanol, propylene glycol, pyridine, letrahydrcrfuran, trielhyl phosphate, trifluoroacelic acid, trimelhyl phosphate, water ... 

The first study by the research team was very straightforward PTR-MS was simply employed to monitor the VOC emissions released from ground roasted coffee beans after water at a relatively low temperature of 18°C was added to produce the familiar aroma of coffee we are all familiar with [42]. The following volatile compounds were monitored acetaldehyde, acetone/propanal, methyl ether ketone/methylpropanal, ethyl formate/methyl acetate, acetic acid, methanol, 3-methylbutanal/furan, methyl furan, 5-methylfural, 2,3-butanedione/2-methylbutanal and furfural. 

With aldehydes, primary alcohols readily form acetals, RCH(OR )2. Acetone also forms acetals (often called ketals), (CH2)2C(OR)2, in an exothermic reaction, but the equiUbrium concentration is small at ambient temperature. However, the methyl acetal of acetone, 2,2-dimethoxypropane [77-76-9] was once made commercially by reaction with methanol at low temperature for use as a gasoline additive (5). Isopropenyl methyl ether [116-11-OJ, useful as a hydroxyl blocking agent in urethane and epoxy polymer chemistry (6), is obtained in good yield by thermal pyrolysis of 2,2-dimethoxypropane. With other primary, secondary, and tertiary alcohols, the equiUbrium is progressively less favorable to the formation of ketals, in that order. However, acetals of acetone with other primary and secondary alcohols, and of other ketones, can be made from 2,2-dimethoxypropane by transacetalation procedures (7,8). Because they hydroly2e extensively, ketals of primary and especially secondary alcohols are effective water scavengers. 

SAN resins show considerable resistance to solvents and are insoluble in carbon tetrachloride, ethyl alcohol, gasoline, and hydrocarbon solvents. They are swelled by solvents such as ben2ene, ether, and toluene. Polar solvents such as acetone, chloroform, dioxane, methyl ethyl ketone, and pyridine will dissolve SAN (14). The interactions of various solvents and SAN copolymers containing up to 52% acrylonitrile have been studied along with their thermodynamic parameters, ie, the second virial coefficient, free-energy parameter, expansion factor, and intrinsic viscosity (15). 

Actinide ions form complex ions with a large number of organic substances (12). Their extractabiUty by these substances varies from element to element and depends markedly on oxidation state. A number of important separation procedures are based on this property. Solvents that behave in this way are thbutyl phosphate, diethyl ether [60-29-7J, ketones such as diisopropyl ketone [565-80-5] or methyl isobutyl ketone [108-10-17, and several glycol ether type solvents such as diethyl CeUosolve [629-14-1] (ethylene glycol diethyl ether) or dibutyl Carbitol [112-73-2] (diethylene glycol dibutyl ether). 

Hydroxybenzaldehyde has an agreeable aromatic odor, but is not itself a fragrance. It is, however, a useful intermediate in the synthesis of fragrances. The methyl ether of -hydroxybenzaldehyde, ie, -anisaldehyde, is a commercially important fragrance. Anisaldehyde can be made in a simple one-step synthesis from hydroxybenzaldehyde and methyl chloride. Another important fragrance, 4-(p-hydroxyphenyl)butanone, commonly referred to as raspberry ketone, can be prepared from the reaction of -hydroxybenzaldehyde and acetone, followed by reduction (see Flavors and spices). 

Acetophenone. Acetophenone [98-86-2] (methyl phenyl ketone) is a colorless Hquid that forms laminar crystals at low temperature (mp 20°C). It has a characteristic sweet orange blossom odor, and is soluble in alcohols and ethers. It is found in nature in oil of casatoreum, obtained from beavers oil of labdanum, recovered from plants and in buds of balsam poplar. It can be prepared by the Friedel-Crafts reaction (qv) of acetyl chloride with benzene in the presence of aluminum chloride however, this route is of Htde commercial significance. 

The physical properties of finish removers vary considerably due to the diverse uses and requirements of the removers. Finish removers can be grouped by the principal ingredient of the formula, method of appHcation, method of removal, chemical base, viscosity, or hazardous classification. Except for method of apphcation, a paint remover formulation usually has one aspect of each group, by which it can be used for one or more appHcations. A Hst of the most common organic solvents used in finish removers has been compiled (3). Many are mentioned throughout this article others include ethyl lactate [97-64-3] propylene carbonate [108-32-7] furfural alcohol [98-01-1/, dimethyl formamide [68-12-2] tetrahydrofuran [109-99-9] methyl amyl ketone [110-43-0] dipropylene glycol methyl ether [34590-94-8] and Exxate 600, a trade name of Exxon Chemicals. 

Solvent Treatment. Solvent processes can be divided into two main categories, solvent extraction and solvent dewaxing. The solvent used in the extraction processes include propane and cresyHc acid, 2,2 -dichlorodiethyl ether, phenol (qv), furfural, sulfur dioxide, benzene, and nitrobenzene. In the dewaxing process (28), the principal solvents are benzene, methyl ethyl ketone, methyl isobutyl ketone, propane, petroleum naphtha, ethylene dichloride, methylene chloride, sulfur dioxide, and iV-methylpyrroHdinone. 

Many organic reagents have been used successfully in Pu separation processes. The reagents include tri- -butyl phosphate (TBP) methyl isobutyl ketone thenoyl ttifluoroacetone (TTA) ethers, eg, diethyl ether, di- -butyl ether, tetraethylene glycol dibutyl ether trdaurylamine (TT,A) trioctylamine (TOA) di- -butyl phosphate (DBP) hexyl-di(2-ethylhexyl) phosphate (HDEHP) and many others. Of these, TBP is by far the most widely used (30,95). 

Quinone Methides. The reaction between aldehydes and alkylphenols can also be base-cataly2ed. Under mild conditions, 2,6-DTBP reacts with formaldehyde in the presence of a base to produce the methylol derivative (22) which reacts further with base to eliminate a molecule of water and form a reactive intermediate, the quinone methide (23). Quinone methides undergo a broad array of transformations by way of addition reactions. These molecules ate conjugated homologues of vinyl ketones, but are more reactive because of the driving force associated with rearomatization after addition. An example of this type of addition is between the quinone methide and methanol to produce the substituted ben2yl methyl ether (24). 

Chemical. The use of isopropyl alcohol as a feedstock for the production of acetone is expected to remain stable, as the dominant process for acetone is cumene oxidation. Isopropyl alcohol is also consumed in the production of other chemicals such as methyl isobutyl ketone, methyl isobutyl carbinol [108-11-2] isopropjlamine, and isopropyl acetate. The use of diisopropyl ether as a fuel ether may become a significant oudet for isopropyl alcohol. 

A McMurry coupling of (176, X = O Y = /5H) provides ( )-9,ll-dehydroesterone methyl ether [1670-49-1] (177) in 56% yield. 9,11-Dehydroestrone methyl ether (177) can be converted to estrone methyl ether by stereoselective reduction of the C —double bond with triethyi silane in triduoroacetic acid. In turn, estrone methyl ether can be converted to estradiol methyl ether by sodium borohydride reduction of the C17 ketone (199,200). 

SuIfona.tlon, Sulfonation is a common reaction with dialkyl sulfates, either by slow decomposition on heating with the release of SO or by attack at the sulfur end of the O—S bond (63). Reaction products are usually the dimethyl ether, methanol, sulfonic acid, and methyl sulfonates, corresponding to both routes. Reactive aromatics are commonly those with higher reactivity to electrophilic substitution at temperatures > 100° C. Tn phenylamine, diphenylmethylamine, anisole, and diphenyl ether exhibit ring sulfonation at 150—160°C, 140°C, 155—160°C, and 180—190°C, respectively, but diphenyl ketone and benzyl methyl ether do not react up to 190°C. Diphenyl amine methylates and then sulfonates. Catalysis of sulfonation of anthraquinone by dimethyl sulfate occurs with thaHium(III) oxide or mercury(II) oxide at 170°C. Alkyl interchange also gives sulfation. 

Anhydrous stannous chloride, a water-soluble white soHd, is the most economical source of stannous tin and is especially important in redox and plating reactions. Preparation of the anhydrous salt may be by direct reaction of chlorine and molten tin, heating tin in hydrogen chloride gas, or reducing stannic chloride solution with tin metal, followed by dehydration. It is soluble in a number of organic solvents (g/100 g solvent at 23°C) acetone 42.7, ethyl alcohol 54.4, methyl isobutyl carbinol 10.45, isopropyl alcohol 9.61, methyl ethyl ketone 9.43 isoamyl acetate 3.76, diethyl ether 0.49, and mineral spirits 0.03 it is insoluble in petroleum naphtha and xylene (2). 

In the initial thiocyanate-complex Hquid—Hquid extraction process (42,43), the thiocyanate complexes of hafnium and zirconium were extracted with ether from a dilute sulfuric acid solution of zirconium and hafnium to obtain hafnium. This process was modified in 1949—1950 by an Oak Ridge team and is stiH used in the United States. A solution of thiocyanic acid in methyl isobutyl ketone (MIBK) is used to extract hafnium preferentially from a concentrated zirconium—hafnium oxide chloride solution which also contains thiocyanic acid. The separated metals are recovered by precipitation as basic zirconium sulfate and hydrous hafnium oxide, respectively, and calcined to the oxide (44,45). This process is used by Teledyne Wah Chang Albany Corporation and Western Zirconium Division of Westinghouse, and was used by Carbomndum Metals Company, Reactive Metals Inc., AMAX Specialty Metals, Toyo Zirconium in Japan, and Pechiney Ugine Kuhlmann in France. 

Rapid, simple, quaUtative methods suitable for determining the presence of benzene in the workplace or surroundings have been utilized since the 1930s. Many early tests offered methods for detection of aromatics but were not specific for benzene. A straightforward test allowing selective detection of benzene involves nitration of a sample to y -dinitrobenzene and reaction of the resultant ether extract with an ethanoHc solution of sodium hydroxide and methyl ethyl ketone (2-butanone), followed by the addition of acetic acid to eliminate interferences from toluene and xylenes. Benzene imparts a persistent red color to the solution (87). The method is claimed to be sensitive to concentrations as low as 0.27 ppm benzene from 10 mL air samples. 

Cya.nideExcha.nge, Acetone cyanohydrin and methyl isobutyl ketone cyanohydrin [4131 -68-4] dissolved in an organic solvent, such as diethyl ether or methyl isobutyl ketone, undergo cyanide exchange with aqueous cyanide ion to yield a significant cyanide carbon isotope separation. The two-phase system yields cyanohydrin enriched in carbon-13 and aqueous cyanide depleted in carbon-13. Fquilibrium is obtained in seconds. 

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-... 

Water with aniline, benzene, benzyl alcohol, carbon disulfide, carbon tetrachloride, chloroform, cyclohexane, cyclohexanol, cyclohexanone, diethyl ether, ethyl acetate, isoamyl alcohol, methyl ethyl ketone, nitromethane, tributyl phosphate or toluene. 

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