Of phthalic acid

Phthalein reaction. Fuse together carefully in a dry test-tube a few crystals of phthalic acid or of a phthalate and an equal quantity of ph tol moistened with 2 drops of cone. H2SO4. Cool, dissolve in water and add NaOH solution in excess the bright red colour of phenolphthalein in alkaline solution is produced. 

If the presence of phthalic acid is suspected, it may be readily removed by mixing with cold chloroform j phthalic anhydride dissolves readily, but the acid is insoluble. 

Physical and Chemical Properties. Tables 5, 6, and 7 bst some of the physical and chemical properties of phthabc acid and its anhydride. Table 5. Physical Constants of Phthalic Acid and Phthalic Anhydride... 

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

The extent to which intramolecular nucleophilic catalysis of the type depicted in mechanism I is important is a function of the leaving ability of the alkoxy group. This has been demonstrated by the study of the hydrolysis of a series of monoesters of phthalic acid ... 

Phthalic Acid. In the formation of phthalic acid by the oxidation of naphthalene with sulphuric acid, the mercuric, ul-... 

The two-step procedure includes formation of a N-substituted phthalimide 3, and its subsequent cleavage to the primary amine 5. Phthalimide (which can be obtained from reaction of phthalic acid with ammonia) shows NH-acidity, since the negative charge of the phthalimide anion (the conjugated base) is stabilized... 

A solution of 10 g (0.023 mole) of cholesteryl acetate (mp 112-114°) in ether (50 ml) is mixed with a solution containing 8.4 g (0.046 mole) of monoperphthalic acid (Chapter 17, Section II) in 250 ml of ether. The solution is maintained at reflux for 6 hours, following which the solvent is removed by distillation (steam bath). The residue is dried under vacuum and digested with 250 ml of dry chloroform. Filtration of the mixture gives 6.7 g of phthalic acid (87% recovery). The solvent is evaporated from the filtrate under reduced pressure and the residue is crystallized from 30 ml of methanol, giving 6.0 g (58% yield) of -cholesteryl oxide acetate. Recrystallization affords the pure product, mp 111-112°. Concentration of the filtrate yields 1.55 g (15% yield) of a-cholesteryl oxide acetate which has a mp of 101-103° after crystallization from ethanol. 

There was also obtained from the oil a second alcohol, which contains two double bonds, and is bicyclic. It is also a primary alcohol, but its characters have not been ascertained with accuracy. A mixture of bicyclic and tricyclic vetivenol isolated by means of phthalic acid had the following characters, from which those of bicyclic vetivenol may, to some extent, be deduced —... 

The detection of phthalic acid by fusion with resorcin has been found to be unreliable as a fluorescein reaction is frequently obtained with pure oils. 

Phthalocyanines have been synthesized with nearly all metals of the periodic table.77 Normally they are formed in a single-step reaction from available derivatives of phthalic acid, in particular phthalic acid (see Section 2.1.1.1.), phthalic anhydride (see Section 2.1.1.2.), phthalimide (see Section 2.1.1.3.), 2-cyanobenzamide (see Section 2.1.1.4.), phthalonitrile (see Section 2.1.1.5.), isoindolinediimine (see Section 2.1.1.6.), or 1,2-dibromobenzene (see Section 2.1.1.7.), usually in a high-boiling solvent or by heating the neat components.1 4... 

The formation of phthalocyanines can be formally regarded as cyclotetramerization of the appropriate substituted or unsubstituted derivatives of phthalic acid. It should be emphasized that mixtures of structural isomers are obtained if these derivatives are substituted as follows ... 

The final residue from the mother liquor is an oil which does not solidify in a freezing mixture, and appears to be a mixture of p- and w-tolylcarbinols. Only a trace of phthalic acid (phenolphthalein test) was obtained by oxidizing this oil with permanganate the portion of it which was more readily soluble in water yielded a phenylurethan which depressed the melting point of the phenylurethan of either />-tolylcarbinol or benzyl alcohol. 

Di- and mono-esters of phthalic acid, an ortho-dicarboxylic acid derivative of benzene. These compounds are widely used as industrial plasticizers to coat polyvinylchloride surfaces of plastics used in food packaging and medical devices (iv drip bags, blood storage bags, etc.) and are common environmental contaminants. Several phthalate mono-esters are peroxisome proliferator chemicals and can activate the peroxisome proliferator-activated receptor PPAR. 

Note The exothermic nitration of phthalic acid or phthalic anhydride by a fuming nitric acid-sulfuric acid mixt may give mixts of the potentially expl phthaloyl nitrates or nitrites or their nitro derivatives. Formation of these compds can be avoided if the nitrating mixt is... 

The flexibility of some plastics can be improved by the addition of small molecules called plasticizers. For example, pure PVC turns brittle and cracks too easily to make useful flexible plastic products. With an added plasticizer, however, PVC can be used to make seat covers for automobiles, raincoats, garden hoses, and other flexible plastic objects. Plasticizers must be liquids that mix readily with the pol Tner. In addition, they must have low volatility so that they do not escape rapidly from the plastic. Dioctylphthalate is a liquid plasticizer that is formed by condensing two alcohol molecules with one molecule of phthalic acid, as illustrated in Figure 13-10. 

Afring RP, BF Taylor (1981) Aerobic and anaerobic catabolism of phthalic acid by a nitrate-respiring bacterium. Arch Microbiol 130 101-104. 

Taylor BF, RW Curry, EF Corcoran (1981) Potential for biodegradation of phthalic acid esters in marine regions. Appl Environ Microbiol 42 590-595. 

The introduction of phthalic acid into sodium nitrite caused the medium to detonate. This was put down to the reaction below that leads to an unstable compound ... 

The independent preparation of potassium phthalimide (from a solution of phthalimide in absolute ethanol and potassium hydroxide in 75 per cent, ethanol) may be avoided in many cases by boiling phthalimide with the halide in the presence of anhydrous potassium carbonate. The N-substituted phthalimide (I) is frequently cleav with difficulty this is often facilitated by reaction with hydrazine hydrate to give an intermediate product, which is easily decomposed by hydrochloric acid to yield the insoluble hydrazide of phthalic acid (II) and the primary amine (III) ... 

Ejlertsson J, Alnervik M, Jonsson S, Svensson BH (1997) Influence of water solubility, side-chain structure on the degradation of phthalic acid esters under methanogenic conditions. Environ Sci Technol 31 2761-2764... 

Shelton DR, Boyd SA, Tiedje JM (1984) Anaerobic biodegradation of phthalic acid esters in sludge. Environ Sci Technol 18 93-97... 

Wang JL, Liu P, Shi HC, Qian Y (1997) Biodegradation of phthalic acid ester in soil by indigenous and introduced microorganisms. Chemosphere 35 1747-1754... 

Wang JL, Chen LJ, Shi HC, Qian Y (2000) Microbial degradation of phthalic acid esters under anaerobic digestion of sludge. Chemosphere 41 1245-1248... 

Amir S, Halidi M, Merlina G, Hamdi H, Jouraiphy A, Gharous ME, Revel JC (2005) Fate of phthalic acid esters during composting of both lagooning and activated sludges. Process Biochem 40 2183-2190... 

Losses of Phthalic Acid Esters and Polychlorinated Biphenyls... 

The important influence that sample container materials can have on seawater sample composition is illustrated next by two examples one concerning the storage of metal solutions in glass and plastic bottles, the other concerning the storage of solutions of phthalic acid esters and polychlorinated biphenyls in glass and plastic. 

Sullivan et al. [69] studied the loss of phthalic acid esters and chlorinated biphenyls from seawater whilst stored in glass containers. Equilibrium was essentially reached in 12 h at 25 °C. Labelled compounds were used in some of the studies. Table 1.10 shows that between 2.2 and 49.9% of the organic solutes were lost from the spiked solutions. 

Schwartz et al. [2] investigated the biodegradation of phthalic acid esters adsorbed in river sediments by repeated analysis of the sediment over a two-week period. The di-2-ethylhexyl phthalate content turned out to remain essentially constant (s.d., 5% n=10), irrespective of the absence or presence of a microbial inhibitor (500ppm of sodium azide or mercuric chloride added immediately after sampling) i.e. no marked biodegradation occurred. 

FIGURE 5.8 The molecular structures of phthalic acid and potassium hydrogen phthalate (KHP). 

For standardizing a base solution, primary standard grade potassium biphthalate is a popular choice. Also called potassium hydrogen phthalate, potassium acid phthalate, or simply KHP, it is the salt representing partially neutralized phthalic acid and is a monoprotic weak acid. The true formula is KHC8H404. Figure 5.8 shows the chemical structure of phthalic acid and KHP. The reaction with a base is as follows ... 

---