Phthalic Acid effect

The effect of some organic acids on the exchange in perchlorate media has been investigated Fumaric , benzoic and o-phthalic acids have been shown to cause little or no alteration in the rate, whereas acetic, succinic, carbolic, oxalic and tartaric acids have an accelerating influence. The isotopic method ( Fe) and the 2,2 -dipyridyl separation have been used. The rate law observed was ... 

For the cydative cleavage step, it turned out that aprotic conditions were definitely superior to the use of protic media. Thus, employing N,N-dimethylformamide as solvent at somewhat elevated temperatures furnished the desired compounds in high yields and excellent purities. Having established the optimized conditions, various phthalic acids and amines were employed to prepare a set of phthalimides (Scheme 7.51). However, the nature of the amine was seen to have an effect on the outcome of the reaction. Benzyl derivatives furnished somewhat lower yields, probably due to the reduced activities of these amines. Aromatic amines could not be included in the study as auto-induced ring-closure occurred during the conversion of the polymer-bound phthalic acid. 

Bower RK, Haberman S, Minton PD. 1970. Teratogenic effects in the chick embryo caused by esters of phthalic acid. J Pharmacol Exp Ther 171 314-324. 

EPA. 1987a. Health and environmental effects profile for phthalic acid esters (PAEs). Cincinnati, OH ... 

EPA. 1987b. Health effects assessment for selected phthalic acid esters. Cincinnati, OH U.S. Environmental Protection Agency, Office of Research and Development. PB88-178934. 

Hinton RH, Mitchell FE, Mann A, et al. 1986. Effects of phthalic acid esters on the liver and thyroid. Environ Health Perspect 70 195-210. 

Korhonen A, Hemminki K, Vainio H. 1983a. Embryotoxic effects of phthalic acid derivatives, phosphates and aromatic oils used in the manufacturing of rubber on three day chicken embryos. Drug Chem Toxicol 6 191-207. 

Oishi S. 1990. Effects of phthalic acid esters on testicular mitochondrial functions in the rat. Arch Toxicol 64 143-147. 

Oishi S, Hiraga K. 1980. Testicular atrophy induced by phthalic acid esters Effect on testosterone and zinc concentrations. Toxicol Appl Pharmacol 53 35-41. 

Oishi S, Hiraga K. 1982. Effects of monoesters of 0-phthalic acid on serum lipid composition of rats. Toxicol Lett 14 79-84. 

Table 3 presents the experimental enthalpies of formation of polynitrobenzenes and Table 4 presents the calculated additivity values and DSEs for these same compounds. Enthalpy-of-formation values have been determined experimentally for all three dinitrobenzene isomers in the gaseous state. The enthalpy-of-formation difference between the meta and para isomers is indistinguishable from 0. Conventional wisdom suggests that the para isomer should be destabilized relative to the meta because of adjacent positive charges in key ionic or polar resonance structures. Thus it seems that electronic effects due to meta/para dinitro substituent position are small. This small enthalpy-of-formation difference is similar to that for the meta and para dicyano, difluoro and dichloro benzenes, but does not mimic the ca 22 kJ mol 1 difference for the phthalic acids with which the... 

Smdies of the thermal degradation of several aromatic acids have been reported. Phthalic acid (80), but not isophthalic acid (81) or terephthalic acid (82), decomposes via dehydration to its anhydride at 140-160 °C. However, (81) and (82) and benzoic acid are thermally stable below 200 °C. Dissociation constants of all 19 isomers of methyl-substimted benzoic acids (83) have been measured in methanol and DMSO. From the pA a values, the substiment effects of the methyl groups were calculated and tentatively divided into polar and steric effects. Also, in the case... 

Lamb JC, Chapin RE, Teague J, Lawton AD, Reel JR (1987) Reproductive effects of four phthalic acid esters in the mouse. Toxicol Appl Pharmacol 88 255-269... 

Thomas JA, Thomas MJ Biological effects of di-(2-ethylhexyl) phthalate and other phthalic acid esters. Crit Rev Toxicol 13 283-317, 1984... 

Phthalic anhydride is a direct but delayed irritant of the skin it is more severely irritating after contact with water, because of the pronounced effects of the phthalic acid that is formed. Prolonged or repeated exposure also may cause an allergic type of skin rash. Because phthalic anhydride is a known pulmonary and skin irritant, it is often difficult to differentiate between sensitization and irritation by clinical history. ... 

Young male Wistar rats were given 2000 mg/kg bw di(2-ethylhexyl) phthalate per day by gavage for periods of 3-21 days (Lake et al, 1975). Treatment caused increases in relative liver weight and in microsomal cytochrome P450 content. Ultra-structural examination revealed marked peroxisome proliferation and a dilation of the smooth and rough endoplasmic reticulum. Rats were also treated with mono(2-ethyl-hexyl) phthalate, 2-ethylhexanol and phthalic acid at doses equimolar to 2000 mg/kg bw per day di(2-ethylhexyl) phthalate for seven days. While phthalic acid had no effect, both mono(2-ethylhexyl) phthalate and 2-ethylhexanol increased relative liver weight and produced hepatic peroxisome proliferation. 

Thomas, J.A. Thomas, MJ. (1984) Biological effects of di-(2-ethylhexyl) phthalate and other phthalic acid esters. Crit. Rev. Toxicol., 13, 283-317 Thuren, A. (1986) Determination of phthalates in aquatic enviromnents. Bull, environ. Contam. Toxicol., 36, 33 0... 

During the appropriate tests phthalic anhydride was smoothly esterified with 2-ethylhexanol in the mole ratio 1 4. The reaction temperature rose to 200°C. after about 15 minutes, then rose slowly up to 210°C. till the end of the esterification. Table I shows the esterification time in hours after 99.9% conversion, while continuously removing the reaction water, according to the acid number relative to monooctyl phthalic acid. Furthermore, it indicates the ester colors according to the iodine scale in milligrams iodine/100 ml., whereby 1 mg. iodine/100 ml. can be more or less compared with a dye number of 120 APHA. Since, the values are obtained with the same starting materials, it is possible to compare the color numbers. They show that with the same times, the amphoteric catalysis achieves better colors than in the reaction course containing catalytically effective acids. 

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