Solubility in organic solvents

The solubility of the common bile acids and two common sodium salts in water and organic solvents are given in Table IV. Most of the values in Table IV have been extracted from the common references (27, 74). However, the values for the solubility of deoxycholic acid and cholic acid in water have been taken from the careful work of Ekwall et al. (121). In some cases 

Crude estimations of solubility carried out by the author at 25° 3°C. From Small et a . (2), 20 °C. 

Recently Bennet et al. (122) showed that the methyl ester of cholic acid forms small aggregates in relatively nonpolar organic solvents. These aggregates are made up of about four molecules of the methyl ester hydrogen bonded to one another through the hydroxyl groups and therefore might be considered as a form of reversed micelle. These derivatives do not form micelles in a more polar solvent, such as alcohol, but are present in true solution (122). 

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Insoluble in water, soluble in organic solvents b.p. — 15°C. Prepared by treating 1,4-dibromo-butane with metallic sodium. Reduced to n-butane by hydrogen at 200" C in presence of nickel catalysts. 

The lower members of the series are liquids soluble in water and volatile in steam. As the number of carbon atoms in the molecule increases, the m.p. and b.p. rise and the acids become less soluble in water and less volatile. The higher fatty acids are solids, insoluble in water and soluble in organic solvents. 

C. Insoluble in water, soluble in organic solvents. Flavone occurs naturally as dust on the flowers and leaves of primulas. It has been prepared from o-hydroxyacetophenone and benzaldehyde. 

While solid m.p. 95 -96 - C, soluble in organic solvents. An insecticide similar to chlordane. Used to control cotton boll weevil. 

The most common of the xanthophyll pigments, it is present in all green leaves, in blossoms and in various animal sources. It crystallizes in violet prisms with one molecule of methanol m.p. I93 C, soluble in organic solvents giving yellow solutions, li is related to a-carolene in the same way as zeaxanlhin is to /1-carolene. 

Substances are generally soluble in like solvents. Organic molecules in molecular solvents such as CCI4, C2H5OH, ether, propanone. Inorganic salts are often soluble in water and less soluble in organic solvents. 

Tin IV) chloride, SnCU, stannic chloride. M.p. — 33" C, b.p. 1I4°C. Colourless fuming liquid (Sn plus CI2) hydrolysed in water but forms SnCl4,5H20 and [SnCl p" from acid solutions, soluble in organic solvents. Used as a mordant. 

It is soluble in organic solvents (a characteristic of a covalent compound). but dissolves in water and can form hydrates (a characteristic of an ionic compound), hence the hydrated must be... 

Like bromine, iodine is soluble in organic solvents, for example chloroform, which can be used to extract it from an aqueous solution. The iodine imparts a characteristic purple colour to the organic layer this is used as a test for iodine (p. 349). NB Brown solutions are formed when iodine dissolves in ether, alcohol, and acetone. In chloroform and benzene a purple solution is formed, whilst a violet solution is produced in carbon disulphide and some hydrocarbons. These colours arise due to charge transfer (p. 60) to and from the iodine and the solvent organic molecules. 

Zincill) chloride. ZnCl2, is the only important halide—it is prepared by standard methods, but cannot be obtained directly by heating the hydrated salt. It has a crystal lattice in which each zinc is surrounded tetrahedrally by four chloride ions, but the low melting point and solubility in organic solvents indicate some covalent... 

The constant K is termed the distribution or partition coefficient. As a very rough approximation the distribution coefficient may be assumed equal to the ratio of the solubilities in the two solvents. Organic compounds are usually relatively more soluble in organic solvents than in water, hence they may be extracted from aqueous solutions. If electrolytes, e.g., sodium chloride, are added to the aqueous solution, the solubility of the organic substance is lowered, i.e., it will be salted out this will assist the extraction of the organic compound. 

When the nitrogen atom is substituted by a nitrophenacyl group, OH attack gives the betainic zwitterion (Scheme 13). which is soluble in organic solvents (32). The stability of the C-betainic or ylid structure has been explained as an effect of resonance of the negative charge in the molecule (33, 34). 

The diazonium salts precursors can be aniline, o- and p-toluidine, o-and p-anisidine, o- and p-phenetidine. or 3-naphthy]amine. The resulting formazans are crystalline and inlensel> colored. They are soluble in organic solvents, giving a red-violet coloration that darkens to blue. Dehydrogeneration gives the corresponding tetrazolium salts, which are isolated as perbromides (Scheme 51. Table X-13). 

Cellulosics. CeUulosic adhesives are obtained by modification of cellulose [9004-34-6] (qv) which comes from cotton linters and wood pulp. Cellulose can be nitrated to provide cellulose nitrate [9004-70-0] which is soluble in organic solvents. When cellulose nitrate is dissolved in amyl acetate [628-63-7] for example, a general purpose solvent-based adhesive which is both waterproof and flexible is formed. Cellulose esterification leads to materials such as cellulose acetate [9004-35-7], which has been used as a pressure-sensitive adhesive tape backing. Cellulose can also be ethoxylated, providing hydroxyethylceUulose which is useful as a thickening agent for poly(vinyl acetate) emulsion adhesives. Etherification leads to materials such as methylceUulose [9004-67-5] which are soluble in water and can be modified with glyceral [56-81-5] to produce adhesives used as wallpaper paste (see Cellulose esters Cellulose ethers). 

In general, the reactions of the perfluoro acids are similar to those of the hydrocarbon acids. Salts are formed with the ease expected of strong acids. The metal salts are all water soluble and much more soluble in organic solvents than the salts of the corresponding hydrocarbon acids. Esterification takes place readily with primary and secondary alcohols. Acid anhydrides can be prepared by distillation of the acids from phosphoms pentoxide. The amides are readily prepared by the ammonolysis of the acid haUdes, anhydrides, or esters and can be dehydrated to the corresponding nitriles (31). 

Dicofol [54532-36-4] l,l-bis(/)-chlorophenyl)-2,2,2-trichloroethanol, R = Cl (139), is a white crystalline soHd (mp 79°C). This compound is insoluble in water and soluble in organic solvents, and in the presence of alkaU forms the inactive/),/) -dichloroben2ophenone and chloroform. Dicofol is a long-lasting acaricide and is active against all stages of mites. The rat oral LD qS are 809, 684 mg/kg. 

Bl cetyl. Biacetyl [431-03-8] (2,3-butanedione) is a greenish yeUow liquid with a quinone odor. Biacetyl occurs naturally in bay oil and is readily soluble in organic solvents. It is a constituent of many food aromas, eg, butter, and is commonly used to flavor margarine. Flavor-grade biacetyl was available at 20.40/kg in July 1993, and is used as an odorant for coffee, vinegar, tobacco, and in perfumes. 

Diketones. y-Diketones contain two carbonyl groups separated by two carbon atoms. With the exception of 2,5-hexanedione which is a high boiling Hquid, 1,4-diketones ate low melting white soHds with only faint odors. Lower members are soluble in organic solvents and water. Properties of representative 1,4-diketones are shown in Table 14. 

Naphthenic acids are viscous hquids, with phenohc and sulfur impurities present that are largely responsible for their characteristic odor. Their colors range from pale yeUow to dark amber. An odor develops upon storage of the refined acids. Naphthenic acids have wide boiling point ranges at high temperatures (250—350°C). They are completely soluble in organic solvents and oils but are insoluble (<50 mg/L) in water. Commercial naphthenic acids are available in... 

Metal-free, chloroaluminum phthalocyanine [14154-42-8] vanadyl phthalocyanine [13930-88-6], or magnesium phthalocyanines are sufficiently soluble in organic solvents and show enough bleachable absorption at 694.3 nm to serve as repeated Q-switching elements for mby lasers (qv) (180). Phthalocyanines have been used in other lasers as weU (181). 

Other double alkoxides are more covalent, distillable, and often mote soluble in organic solvents. 

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