Anhydrides solubility

Lead(fl) ethanoate, Pb(02CCH3)2,3H20, sugar of lead. Soluble in water (ethanoic acid and ethanoic anhydride plus Pb304). 

Sydnones are neutral, highly crystalline, stable compounds, soluble in most organic solvents. N-Arylsydnones typically are obtained by treating N-nitroso-N-aryl-glycines with etha-noic anhydride. The parent glycine is regenerated when the sydnone is heated with dilute alkali. 

Although the acetylation of alcohols and amines by acetic anhydride is almost invariably carried out under anhydrous conditions owing to the ready hydrolysis of the anhydride, it has been shown by Chattaway (1931) that phenols, when dissolved in aqueous sodium hydroxide solution and shaken with acetic anhydride, undergo rapid and almost quantitative acetylation if ice is present to keep the temperature low throughout the reaction. The success of this method is due primarily to the acidic nature of the phenols, which enables them to form soluble sodium derivatives, capable of reacting with the acetic... 

Physical properties. Acetic anhydride, (CH3C0).20, is a colourless liquid with a sharp pungent odour, decomposed slowly by water, in which it is only slightly soluble. 

To distinguish these anhydrides from the corresponding acids, note that succinic anhydride (m.p. 120°) is almost insoluble in cold water, whereas succinic acid (m.p. 185 ) is readily soluble. Phthalic anhydride has m.p. 132° and phthalic acid has m.p. 196-199° with decomposition. Each of these anhydrides when heated with water hydrolyses to the corresponding acids. 

The alkylidene dimethone (dimedone) (I) upon boiling with glacial acetic acid, acetic anhydride, hydrochloric acid and other reagents frequently loses water and passes into a substituted octahydroxanthene or the anhydride (II), which often serves as another derivative. The derivatives (I) are soluble in dilute alkali and the resulting solutions give colourations with ferric chloride solution on the other hand, the anhydrides (II) are insoluble in dilute alkali and hence can easily be distinguished from the alkylidene dimedones (I). 

Derivatives with 3-nitrophthalic anhydride. 3-Nitrophthalic anhydride reacts with primary and secondary amines to yield nitro-phthalamic acids it does not react with tertiary amines. The phthalamic acid derived from a primary amine undergoes dehydration when heated to 145° to give a neutral A -substituted 3-nitrophthalimide. The phthalamic acid from a secondary amine is stable to heat and is, of course, soluble in alkali. The reagent therefore provides a method for distinguishing and separating a mixture of primary and secondary amines. 

Crystalline derivatives, suitable for identification and characterisation are dealt with in Section IV, 114, but the preparation of the following, largely liquid, derivatives will be described in the following Sections. When phenols are dissolved in aqueous sodium hydroxide solution and shaken with acetic anhydride, they undergo rapid and almost quantitative acetylation if the temperature is kept low throughout the reaction. This is because phenols form readily soluble sodium derivatives, which react with acetic anhydride before the latter undergoes appreciable hydrolysis, for example ... 

The solid appears to be a mixture of the complexes CH,COOH.BF, and 2CH COOH.BF,. The latter appears to be a liquid and is alone soluble in ethylene dichloride the former is a solid. The solid moiioocetic acid complex is obtained by saturating an ethylene dichloride solution of acetic acid with boron trifluoride, filtering and washing the precipitate with the solvent it is hygroscopic and should be protected from moisture. It may be used as required 0-75 mol is employed with 0-26 mol of ketone and 0 6 mol of anhydride. 

The nitration of phthalic anhydride with a mixture of concentrated sulphuric and nitric acids yields a mixture of 3-nitro- and 4 nitro phthalic acids these are readily separated by taking advantage of the greater solubility of the 4 nitro acid in water. Treatment of 3 nitrophtlialic acid with acetic anhydride gives 3 nitrophthahe anhydride. 

CO—C H,—CO—0—CHj—CHOH—CHj—OOC—CgH,—CO— These are comparatively soft materials and they are soluble in a number of organic solvents. Under more drastic conditions (200-220°) and with a larger proportion of phthahc anhydride, the secondary alcohol groups are esterified and the simple chains become cross-hnked three dimensional molecules of much higher molecular weight are formed ... 

The lower members of other homologous series of oxygen compounds— the acids, aldehydes, ketones, anhydrides, ethers and esters—have approximately the same limits of solubility as the alcohols and substitution and branching of the carbon chain has a similar influence. For the amines (primary, secondary and tertiary), the limit of solubility is about C whilst for the amides and nitriles it is about C4. 

It is convenient to consider the indiflferent or neutral oxygen derivatives of the hydrocarbons—(a) aldehydes and kelones, (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, i.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. 

The selection of solvents for quantitative work is not easy. Nitro-alkanes are sufficiently inert, but nitronium tetrafluoroborate is poorly soluble in them c. 0-3 %). Nitronium salts react rapidly with acetic anhydride, and less rapidly with acetic acid, A, A -dimethylformamide and acetonitrile, although the latter solvent can be used for nitration at low temperatures. Sulpholan was selected as the most suitable solvent ... 

It has long been known that, amongst organic solvents, acetic anhydride is particularly potent in nitration, and that reaction can be brought about under relatively mild conditions. For these reasons, and because aromatic compounds are easily soluble in mixtures of nitric acid and the solvent, these media have achieved considerable importance in quantitative studies of nitration. 

Characteristics of the system as nitrating reagents Wibaut, who introduced the competitive method for determining reactivities (his experiments with toluene, benzene and chlorobenzene were performed under heterogeneous conditions and were not successful), pointed out that solutions of nitric acid in acetic anhydride are useful in making comparisons of reactivities because aromatic compounds are soluble in them. ... 

A series of water-soluble fiber-reactive xanthene dyes has been prepared from the reaction of ben2oxanthenedicatboxylic acid anhydride disulfonic acid with, for example, 3-aminophenyl-P-hydtoxyethyl sulfone to yield dyes, with high brilliance and good fastness properties for dyeing of or printing on leather, wool, sHk, or ceUulosic fibers (53). 

Potassium acetate, mbidium acetate, and cesium acetate are very soluble ia anhydride ia contrast to the only slightly soluble sodium salt. Barium forms the only soluble alkaline earth acetate. Heavy metal acetates are poorly soluble. 

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). 

Bisa.codyl, 4,4 -(2-PyridyLmethylene)bisphenol diacetate [603-50-9] (Dulcolax) (9) is a white to off-white crystalline powder ia which particles of 50 p.m dia predominate. It is very soluble ia water, freely soluble ia chloroform and alcohol, soluble ia methanol and ben2ene, and slightly soluble ia diethyl ether. Bisacodyl may be prepared from 2-pyridine-carboxaldehyde by condensation with phenol and the aid of a dehydrant such as sulfuric acid. The resulting 4,4 -(pyridyLmethylene)diphenol is esterified by treatment with acetic anhydride and anhydrous sodium acetate. Crystallisation is from ethanol. 

Phenolphthalein. Alophen, Ex-Lax, Feen-a-Miat, Modane, and Phenolax are trade names for phenolphthaleia [77-09-8] (3,3-bis(4-hydroxyphen5l)-l-(3ff)-l isobensofuranone) (10). It is a white or faintiy yellowish white crystalline powder, odorless and stable ia air, and practically iasoluble ia water one gram is soluble ia 15 mL alcohol and 100 mL diethyl ether. Phenolphthaleia may be prepared by mixing phenol, phthaHc anhydride, and sulfuric acid, and heating at 120°C for 10—12 h. The product is extracted with boiling water, then the residue dissolved ia dilute sodium hydroxide solution, filtered, and precipitated with acid. 

Norethindrone may be recrystakhed from ethyl acetate (111). It is soluble in acetone, chloroform, dioxane, ethanol, and pyridine slightly soluble in ether, and insoluble in water (112,113). Its crystal stmcture has been reported (114), and extensive analytical and spectral data have been compiled (115). Norethindrone acetate can be recrystakhed from methylene chloride/hexane (111). It is soluble in acetone, chloroform, dioxane, ethanol, and ether, and insoluble in water (112). Data for identification have been reported (113). The preparation of norethindrone (28) has been described (see Fig. 5). Norethindrone acetate (80) is prepared by the acylation of norethindrone. Norethindrone esters have been described ie, norethindrone, an appropriate acid, and trifiuoroacetic anhydride have been shown to provide a wide variety of norethindrone esters including the acetate (80) and enanthate (81) (116). 

A polyester-type fluorescent resin matrix (22) is made by heating trimellitic anhydride, propylene glycol, and phthaUc anhydride with catalytic amounts of sulfuric acid. Addition of Rhodamine BDC gives a bright bluish red fluorescent pigment soluble in DME and methanol. It has a softening point of 118°C. Exceptional heat resistance and color brilliance are claimed for products of this type, which are useful for coloring plastics. 

Table 2. Solubility of Maleic Anhydride, Maleic Acid, and Fnmaric Acid, g/100 g Solntion ...

Aqueous ring-opening metathesis polymerization (ROMP) was first described in 1989 (90) and it has been appHed to maleic anhydride (91). Furan [110-00-9] reacts in a Diels-Alder reaction with maleic anhydride to give exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3—dicarboxylate anhydride [6118-51 -0] (24). The condensed product is treated with a soluble mthenium(Ill) [7440-18-8] catalyst in water to give upon acidification the polymer (25). Several apphcations for this new copolymer have been suggested (91). 

The general sales specification under which maleic anhydride is sold ia the United States specifies a white fused mass or briquettes of 99.5% minimum assay and 52.5°C minimum crystallisation poiat. The melt color specification is 20 APHA maximum with a maximum APHA color of 40 after two hours of heating at 140°C. Four grams of maleic anhydride ia 10 milliliters of water are to be completely soluble. The resulting solution is to be colodess. The acidity resulting from maleic acid is allowed to be a maximum of 0.2%. 

Nickel Arsenate. Nickel arsenate [7784-48-7] Ni2(As0 2 8H20, is a yellowish green powder, density 4.98 g/cm. It is highly iasoluble ia water but is soluble ia acids, and decomposes on heating to form As20 and nickel oxide. Nickel arsenate is formed by the reaction of a water solution of arsenic anhydride and nickel carbonate. Nickel arsenate is a selective hydrogenation catalyst for iaedible fats and oils (59). 

Table 7. Solubilities of Phthalic Acid and Phthalic Anhydride ...

Table 31. Solubilities of Trimellitic Acid and Trimellitic Anhydride at 25°C ...

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