O-Phthalic acid

The concentration of o-phthalic acid in an organic solvent, such as n-butanol, may be determined by an acid-base titration using aqueous NaOH as the titrant. As the titrant is added, the o-phthalic acid is extracted into the aqueous... 

Some acids such as cinnamic, lactic, oxalic and quinaldic acid yield yellow zones. Maleic, fumaric and o-phthalic acids turn red in color, salicylic acid grey and 4-aminobenzoic acid bluish. 

Confirmation of this constitution was provided by Spath and Becke, > who identified 5-methoxy-3 4-methylenedioxy-o-phthalic acid as an oxidation product of anhalonine. The synthetic df-anhalonine was resolved by crystallisation of the f-tartrate from methyl alcohol, into f-anhalonine, m.p. 85-6°, — 56-3° (CHCI3) and its optical antipode,... 

Nitro-o-phthalic Acid. Pale yel prisms or plates from w mp dec 207—230°. Prepn and properties are given in Refs Rpfe- Oil /I a rtoci... 

Dinitro-o-phthalic Acid. Prisms from eth. mp 225—6°. Very sol in w, ale. eth insol in llgr, C disulfide and benz. Can be prepd by the oxidation of 5,7-dinitro-l,2,3,4-tetrahydro-naphthalene with 30% boiling nitric acid or by other methods given in the Refs. The barium salt, Cg H2 (N02)2 04. Ba is expl... 

Dinitro-o-phthalic Acid. Needles from eth, mp 200—202°. Easily sol in w, ale or eth. Can be prepd by heating 1,5-dinitronaphthalene with mixed nitric-sulfuric acid. Its barium salt (Refs 2 3) is expl... 

Hie most representative member of this class of polyesters is the low-molar-mass (M 1000-3000) hydroxy-terminated aliphatic poly(2,2/-oxydiethylene adipate) obtained by esterification between adipic acid and diethylene glycol. This oligomer is used as a macromonomer in the synthesis of polyurethane elastomers and flexible foams by reaction with diisocyanates (see Chapter 5). Hydroxy-terminated poly(f -caprolactonc) and copolyesters of various diols or polyols and diacids, such as o-phthalic acid or hydroxy acids, broaden the range of properties and applications of polyester polyols. 

Review of the toxicity of the esters of o-phthalic acid (phthalate esters). 

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 ... 

Note that in these three examples involving hydrogen peroxide, chromium trioxide and sodium nitrite, dangerous reactions have been described for carboxyiic acids (see on p.316-317). They all referred to the three following systems acetic acid-/hydrogen peroxide, acetic acid/chromium trioxide and o-phthalic acid/sodium nitrite. One can ask oneself whether the same reactions did not take place after the acetic and phthalic anhydride hydrolysis. 

Chromatography by ion exchange on a sulfonated poly(styrene-co-divinyl benzene) phase has been proposed as a replacement for titrimetry.57 Eluted by a dilute solution of a neutral salt such as sodium ethanesulfonate, the conductance of the protons can be measured in the absence of a suppressor from sub-millimolar to molar concentration. The response factors of mono-, di-, and trichloroacetic acid and of o-phthalic acid were large and essentially equivalent to ethanesulfonic acid, while the response factor of acetic acid was far smaller. A syringe pump has generated pressures as high as 72,000 psi (5000 bar) in a capillary column packed with 1 p particles, generating a fraction capacity of 300 peaks in 30 minutes.58... 

Nitrophenyl disulfide, b216 3-Nitro-o-phthalic acid, n31... 

The first examples of a homogeneous reduction of this type were reported in 1971. Cobalt carbonyl was found to reduce anhydrides such as acetic anhydride, succinic anhydride and propionic anhydride to mixtures of aldehydes and acids. However, scant experimental details were recorded [94]. In 1975, Lyons reported that [Ru(PPh3)3Cl2] catalyzes the reduction of succinic and phthalic anhydrides to the lactones y-bulyrolaclone and phthalide, respectively [95], The proposed reaction sequence for phthalic anhydride is shown in Scheme 15.15. Conversion of phthalic anhydride was complete in 21 h at 90 °C, but yielded an equal mixture of the lactone, phthalide (TON = 100 TOF 5) and o-phthalic acid, which is presumably formed by hydrolysis of the anhydride by water during lactoniza-tion. Neither acid or lactone were further hydrogenated to any extent using this catalyst system, under these conditions. 

Succinic anhydride is clearly hydrogenated more readily than the acid, as was the case with phthalic acid (Scheme 15.17), but faster absolute rates were observed in the hydrogenation of o-phthalic acid and phthalic anhydride to phtha-lide. In these reactions, the problem of anhydride hydrolysis is less significant as the acid can also be reduced to the same lactone product... 

Chemical/Physical. Benzyl butyl phthalate initially hydrolyzes to butyl hydrogen phthalate. This compound undergoes additional hydrolysis yielding o-phthalic acid, 1-butanol, and benzyl alcohol (Kollig, 1993). Gledhill et al. (1980) reported the hydrolysis half-life is >100 d. 

Chemical/Physical. Hydrolyzes in water to o-phthalic acid (via the intermediate 2-ethyl-hexyl hydrogen phthalate) and 2-ethylhexyl alcohol (Kollig, 1993 Wolfe et al., 1980). Although no pH value was given, the reported hydrolysis rate constant under alkaline conditions is 1,400/M-yr (Ellington et al., 1993 Kollig, 1993). A second-order rate constant of 1.1 x 10 /M-sec was reported for the hydrolysis bis(2-ethylhexyl) phthalate at 30 °C and pH 8 (Wolfe et al., 1980). 

Biological. In anaerobic sludge, di-/3-butyl phthalate degraded as follows mono-/3-butyl phthalate to o-phthalic acid to protocatechuic acid followed by ring cleavage and mineralization. 

Synonyms AI3 00329 Anozol 1,2-Benzenedicarboxylic acid, diethyl ester BRN 1912500 CCRIS 2675 DEP Diethyl-o-phthalate EINECS 201-550-6 EINECS 273-520-0 Estol 1550 Ethyl phthalate NCI-C60048 Neantine NSC 8905 Palatinol A Phthalic acid, diethyl ester o-Phthalic acid, diethyl ester Phthalic acid ethyl ester Phthalol Placidol E RCRA waste number U088 Solvanol Unimoll DA. 

Synonyms AI3-00262 Avolin 1,2-Benzenedicarboxylic acid, dimethyl ester BRN 1911460 C-11233 Caswell No. 380 CCRIS 2674 Dimethyl-1,2-benzenedicarboxylate Dimethylbenzene-o-dicarboxylate DMP EINECS 205-011-6 ENT 262 EPA pesticide chemical code 028002 Fermine Methyl phthalate Mipax NSC 15398 NTM Palatinol M Phthalic acid, dimethyl ester o-Phthalic acid, dimethyl ester Phthalic acid methyl ester o Phthalic acid, dimethyl ester RCRA waste number U102 Solvanom Solvarone. 

Biological. o-Phthalic acid was tentatively identified as the major degradation product of di-.n-octyl phthalate produced by the bacterium Serratia marcescens (Mathur and Rouatt, 1975). When di-.n-octyl phthalate was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, no degradation was observed after 7 d. In a 21-d period, however, gradual adaptation did occur, resulting in 94 and 93% losses at concentrations of 5 and 10 mg/L, respectively (Tabak et ah, 1981). In the presence of suspended natural populations from unpolluted aquatic systems, the second-order microbial transformation rate constant determined in the laboratory was reported to be 3.7 + 0.6 x lO L/organism-h (Steen, 1991). 

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