Ketones water solubility

Incompatibility Water soluble alcohols, ketones, heavy metals, quaternary detergents, cationic macromolecules Water soluble alcohols, ketones Water soluble alcohols, ketones, quaternary detergents, cationic macromolecules Water soluble alcohols, ketones, quaternary detergents, cationic macromolecules Water soluble alcohols, ketones, quaternary detergents, cationic macromolecules... 

The amine and the ketone are heated with azeotropic removal of the water formed, the carrier being benzene, toluene, xylene, or an excess of the ketone. Water-soluble amines and ketones, which cannot be treated in this way, are kept together at room temperature for 24 h after addition of concentrated hydrochloric acid (3 g per 5 moles of amine and ketone), after which the water produced is removed by solid sodium hydroxide and the organic phase is distilled. Very good yields of about 40 aliphatic ketimines were obtained by these two methods.886... 

Girard s reagents Quaternary ammonium salts of the type Me3NCH2CONHNH2 X which form water-soluble compounds with aldehydes and ketones, and are therefore separable from other neutral compounds the aldehyde or ketone may be subsequently regenerated after separation. 

Method 2. Dissolve 0-25 g. of 2 4-dinitrophenylhydrazine in a mixture of 42 ml. of concentrated hydrochloric acid and 50 ml. of water by warming on a water bath dilute the cold solution to 250 ml. with distilled water. This reagent is more suitable for water-soluble aldehydes and ketones since alcohol is absent. 

The yield can be raised to 28% if the Hofmann elimination is conducted in the presence of a water-soluble copper or iron compound (19). Further improvements up to 50% were reported when the elimination was carried out in the presence of ketone compounds (20). Further beneficial effects have been found with certain cosolvents, with reported yields of greater than 70% (8). 

The methyl ethyl ketazine forms an immiscible upper organic layer easily removed by decantation. The lower, aqueous phase, containing acetamide and sodium phosphate, is concentrated to remove water formed in the reaction and is then recycled to the reactor after a purge of water-soluble impurities. Organic by-products are separated from the ketazine layer by distillation. The purified ketazine is then hydrolyzed under pressure (0.2—1.5 MPa (2—15 atm)) to give aqueous hydrazine and methyl ethyl ketone overhead, which is recycled (122). The aqueous hydrazine is concentrated in a final distillation column. 

Solvent extraction techniques are useful in the quantitative analysis of niobium. The fluoro complexes are amenable to extraction by a wide variety of ketones. Some of the water-insoluble complexes with organic precipitants are extractable by organic solvents and colorimetry is performed on the extract. An example is the extraction of the niobium—oxine complex with chloroform (41). The extraction of the niobium—pyrocatechol violet complex with tridodecylethylammonium bromide and the extraction of niobium—pyrocatechol—sparteine complex with chloroform are examples of extractions of water-soluble complexes. Colorimetry is performed on the extract (42,43). Colorimetry may also be performed directly on the water-soluble complex, eg, using ascorbic acid and 5-nitrosahcyhc acid (44,45). 

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). 

Zinc chloride melts at 275°C, bods at 720°C, and is stable in the vapor phase up to 900°C. It is very hygroscopic, extremely water-soluble, and soluble in organic Hquids such as alcohols, esters, ketones, ethers, amides, and nitrides. Hydrates with 1, 1.5, 2.5, 3, and 4 molecules of water have been identified and great care must be exercised to avoid hydration of the anhydrous form. Aqueous solutions of zinc chloride are acidic (pH = 1.0 for 6 M) and, when partially neutralized, can form slightly soluble basic chlorides, eg, ZnCl2 4Zn(OH)2 [11073-22-6] and Zn(OH)Cl [14031-59-5]. Many other basic chlorides have been reported (58). 

Acid Dyes. These water-soluble anionic dyes ate appHed to nylon, wool, sUk, and modified acryHcs. They ate also used to some extent for paper, leather, food, and cosmetics. The original members of this class aU had one or mote sulfonic or catboxyHc acid groups in thein molecules. This characteristic probably gave the class its name. Chemically, the acid dyes consist of azo (including preformed metal complexes), anthraquiaone, and ttiaryHnethane compounds with a few azHie, xanthene, ketone imine, nitro, nitroso, and quHiophthalone compounds. 

GIRARD SANDULESCU Reagent Reagents T and "P" (or separation ol aldehydes or Ketones by brming a water soluble hydraaide derivative. 

Potassium carbonate (anhydrous). Has a moderate efficiency and capacity, forming the dihydrate. Suitable for an initial drying of alcohols, bases, esters, ketones and nitriles by shaking with them, then filtering off. Also suitable for salting out water-soluble alcohols, amines and ketones. Unsuitable for acids, phenols, thiols and other acidic substances. 

In addition to its water solubility poly(vinyl pyrrolidone) is soluble in a very wide range of materials, including aliphatic halogenated hydrocarbons (methylene dichloride, chloroform), many monohydric and polyhdric alcohols (methanol, ethanol, ethylene glycol), some ketones (acetyl acetone) and lactones (a-butyrolactone), lower aliphatic acids (glacial acetic acid) and the nitro-paraffins. The polymer is also compatible with a wide range of other synthetic polymers, with gums and with plasticisers. 

Mention should also be made here of the extensive use of poly(vinyl alcohol) in potentially biodegradable applications. At appropriate hydroxyl contents these polymers will dissolve in water (see Chapter 14) and can apparently be conveniently washed away after use as a water-soluble packaging. Biodegradation does, however, appear to be slow and first requires an oxidative step involving enzymatic attack to a ketone such as polyenolketone, which then biodegrades more rapidly. 

An expedient and stereoselective synthesis of bicyclic ketone 30 exemplifies the utility and elegance of Corey s new catalytic system (see Scheme 8). Reaction of the (R)-tryptophan-derived oxazaboro-lidine 42 (5 mol %), 5-(benzyloxymethyl)-l,3-cyclopentadiene 26, and 2-bromoacrolein (43) at -78 °C in methylene chloride gives, after eight hours, diastereomeric adducts 44 in a yield of 83 % (95 5 exo.endo diastereoselectivity 96 4 enantioselectivity for the exo isomer). After reaction, the /V-tosyltryptophan can be recovered for reuse. The basic premise is that oxazaborolidine 42 induces the Diels-Alder reaction between intermediates 26 and 43 to proceed through a transition state geometry that maximizes attractive donor-acceptor interactions. Coordination of the dienophile at the face of boron that is cis to the 3-indolylmethyl substituent is thus favored.19d f Treatment of the 95 5 mixture of exo/endo diastereo-mers with 5 mol % aqueous AgNC>3 selectively converts the minor, but more reactive, endo aldehyde diastereomer into water-soluble... 

The isomerisation of aUylic alcohols to saturated ketones usually has a strong thermodynamic driving force. The ruthenium NHC complex 62 has been used to catalyse the isomerisation of allylic alcohol 59 which gives ketone 60 as the principal product along with some of the reduction product 61 [32]. The catalyst was water-soluble and the aqueous phase could be re-used for several runs (Scheme 11.15). NHC analogues of Crabtree s catalyst, [IrlPCyjKpyridineXcod)] PFg, were found to be less efficient for the isomerisation of allylic alcohols than... 

Ten Brink et al. (2000) have shown how biphasic systems, sometimes with the sparingly soluble alcohols as one phase and an aqueous phase as the other phase, benefit from the strategy for air oxidation to aldehydes/ketones by using water soluble Pd complex of bathophenanthroline disulphonate. This is a nice example of green technology. 

It is convenient to consider the indifferent or neutral oxygen derivatives of the hydrocarbons—(a) aldehydes and ketones, (b) esters and anhydrides, (c) alcohols and ethers— together. All of these, with the exception of the water-soluble members of low molecular weight, are soluble only in concentrated sulphuric acid, t.e., fall into Solubility Group V. The above classes of compounds must be tested for in the order in which they are listed, otherwise erroneous conclusions may be drawn from the reactions for functional groups about to be described. 

Examples of the components of the gelling composition are a water-soluble polymer such as polyacrylamide, an iron compound such as ferric acetyl-acetonate or ammonium ferric oxalate, and a ketone such as 2,4-pentanedione [1247]. The composition forms a temporary gel that is useful for the temporary plugging of a formation. The temporary gels that are formed will disappear after 6 months. 

Scheme 9.20 Ru-catalysed reductions of ketones with water-soluble analogues of Noyori s and Knochel s ligands.

Alkyne-nitrile cyclotrimerization is a powerful synthetic methodology for the synthesis of complex heterocyclic aromatic molecules.118 Recently, Fatland et al. developed an aqueous alkyne-nitrile cyclotrimerization of one nitrile with two alkynes for the synthesis of highly functionalized pyridines by a water-soluble cobalt catalyst (Eq. 4.62). The reaction was chemospecific and several different functional groups such as unprotected alcohols, ketones, and amines were compatible with the reaction.119 In addition, photocatalyzed [2+2+2] alkyne or alkyne-nitrile cyclotrimerization in water120 and cyclotrimerization in supercritical H2O110121 have been reported in recent years. 

Recently, great advancement has been made in the use of air and oxygen as the oxidant for the oxidation of alcohols in aqueous media. Both transition-metal catalysts and organocatalysts have been developed. Complexes of various transition-metals such as cobalt,31 copper [Cu(I) and Cu(II)],32 Fe(III),33 Co/Mn/Br-system,34 Ru(III and IV),35 and V0P04 2H20,36 have been used to catalyze aerobic oxidations of alcohols. Cu(I) complex-based catalytic aerobic oxidations provide a model of copper(I)-containing oxidase in nature.37 Palladium complexes such as water-soluble Pd-bathophenanthroline are selective catalysts for aerobic oxidation of a wide range of alcohols to aldehydes, ketones, and carboxylic acids in a biphasic... 

The water-soluble calix[n]arenes 6.3 (n = 4, 6 and 8) containing trimethylammonium groups act as efficient inverse phase-transfer catalysts in the nucleophilic substitution reaction of alkyl and arylalkyl halides with nucleophiles in water (Eq. 6.19).40 In the presence of various surfactants (cationic, zwitterionic and anionic), the reactions of different halides and ketones show that the amount of ketone alkylation is much higher and that the reactions are faster in the presence than in the absence of surfactant aggregates.41 The hydrolysis of the halide is minimized in the presence of cationic or zwitterionic surfactants. 

The use of chiral ruthenium catalysts can hydrogenate ketones asymmetrically in water. The introduction of surfactants into a water-soluble Ru(II)-catalyzed asymmetric transfer hydrogenation of ketones led to an increase of the catalytic activity and reusability compared to the catalytic systems without surfactants.8 Water-soluble chiral ruthenium complexes with a (i-cyclodextrin unit can catalyze the reduction of aliphatic ketones with high enantiomeric excess and in good-to-excellent yields in the presence of sodium formate (Eq. 8.3).9 The high level of enantioselectivity observed was attributed to the preorganization of the substrates in the hydrophobic cavity of (t-cyclodextrin. 

One of the exciting results to come out of heterogeneous catalysis research since the early 1980s is the discovery and development of catalysts that employ hydrogen peroxide to selectively oxidize organic compounds at low temperatures in the liquid phase. These catalysts are based on titanium, and the important discovery was a way to isolate titanium in framework locations of the inner cavities of zeolites (molecular sieves). Thus, mild oxidations may be run in water or water-soluble solvents. Practicing organic chemists now have a way to catalytically oxidize benzene to phenols alkanes to alcohols and ketones primary alcohols to aldehydes, acids, esters, and acetals secondary alcohols to ketones primary amines to oximes secondary amines to hydroxyl-amines and tertiary amines to amine oxides. 

It has been reported that the sonochemical reduction of Au(III) reduction in an aqueous solution is strongly affected by the types and concentration of organic additives. Nagata et al. reported that organic additives with an appropriate hydro-phobic property enhance the rate of Au(III) reduction. For example, alcohols, ketones, surfactants and water-soluble polymers act as accelerators for the reduction of Au(III) under ultrasonic irradiation [24]. Grieser and coworkers [25] also reported the effects of alcohol additives on the reduction of Au(III). They suggested that the rate of the sonochemical reduction of Au(III) is related to the Gibbs surface excess concentration of the alcohol additives. 

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