Benzene-Tetracarboxylic Acids

A munber of organic compounds are suitable for use as tracers in a process for monitoring the flow of subterranean fluids. The following traces have been proposed benzene tetracarboxylic acid, methylbenzoic acid, naphthalenesulfonic acid, naphthalenedisulfonic acid, naphthalene-trisulfonic acid, alkyl benzene sulfonic acid, alkyl toluene sulfonic acid, alkyl xylene sulfonic acid, a-olefin sulfonic acid, salts of the foregoing acids, naphthalenediol, aniline, substituted aniline, pyridine, substituted pyridines [883]. 

Figure 17-11. Carbonic acids acetic acid, oxalic acid, malonic acid, maleic acid, succinic acid, adipic acid, benzoic acid, o-tolulic acid, and benzene tetracarboxylic acid.

Figure 6.4. The various carboxylic acids referred to in Section 6.7. Three different isomers of benzene tetracarboxylic acid are drawn in the first row. The penta- and hexacarboxylic acids are drawn in the second row.

One cannot resolve all the correlation functions from the experimental (thermodynamic) data. However, by processing the data in the same way that we processed the data as if they were strictly identical sites (see Section 5.9 and Appendix J), we obtain quantities that should be understood only in an average sense, as discussed in Appendix J. The results for benzene-tetracarboxylic acids are reported in Table 6.2. We recall the value of fcj = 1.58 x 10 for benzoic acid. We... 

Irradiation of electron deficient arenes in the presence of cis-l,2-diphenylcyclopropane leads to formation of the trans isomer by an electron transfer mechanism. The reaction occurs by way of the radical cation of the cyclopropane which isomerises prior to back electron transfer. It has now been examined using menthyl and bornyl esters of benzene tetracarboxylic acid as chiral electron transfer sensitisers. °° Slight excesses of one of the enantiomers of the trans-1,2-diphenylcyclopropane were observed. The dicyanoanthracene sensitised reactions of 1,1,2,3-tetra-arylcyclopropanes have been studied.Depending on the substituents present on the arene rings these compounds rearrange to 1,1,3,3-tetra-arylpropenes. The rearrangement occurs in a ring opened radical cation intermediate. 

Application of this technique to the identification of methyl esters of the organic acids obtained by the controlled oxidation of bituminous coal allowed the more volatile benzene carboxylic acid esters to be identified (Studier et al., 1978). These were esters of benzene tetracarboxylic acid, tere-phthalic acid, toluic acid, and benzoic acid. Decarboxylation of the total acid mixture was shown to afford benzene, toluene, Cj-benzenes (i.e., ethylbenzene or xylenes), Cj-benzenes, butylbenzenes, Cj-benzenes, Cybenzenes, naphthalene, methylnaphthalene, C2-naphthalene, biphenyl, methylbi-phenyl, C3-biphenyl, indane, methylindane, Cj-indane, phenanthrene, and fluorene. 

By using IR, Shafizadeh and co-workers have identified phthalic (1,2-benzene dicar-boxylic acid), isophthalic (1, 3), hemimellitic (1,2, 3), trimellitic (1, 2,4), prehnitic (1, 2,3,4), mellophanic (1,2,3,5), pyromellitic (1,2,4,5), benzene penta and hexa carboxylic acids [32]. Hemimellitic and trimellitic acids were formed approximately at 2 3 ratio and prehnitic, mellophanic and pyromellitic acid approximately at 2 1 1 ratio. At the lower HTTs, in addition to the above compounds, lower amounts of monohydroxy benzene dicarboxylic acid, monohydroxy benzene tricarboxylic acid, and monohydroxy benzene tetracarboxylic acid have been detected, as well. 

To improve rate performance, we have prep>ared cells containing a carbon layer on the current collector (CLC). This consists of a thin layer having a high concentration of conductive carbon material, situated between the activated carbon electrode layer and the current collector. We have foimd that a hydroxyalkylated chitosan (glycol-chitosan) derivative and 1,2,4,5-benzene-tetracarboxylic acid (pyromellitic acid) mixture acts as a thermally activated binder that adheres strongly to metal foil was very effective in improving the rate capability of EDLC cells. 

Perylenes (70) are diimides of perylene-3,4,9,10-tetracarboxylic acid, and may be prepared by reaction of the bis-anhydride of this acid, 89 (1 mol) with the appropriate amine (2 mol) in a high-boiling solvent as illustrated in Scheme 4.11. The synthesis of perinones 71 and 72 involves condensation of naphthalene-1,4,5,8-tetracarboxylic acid with benzene-1,2-diamine in refluxing acetic acid. This affords a mixture of the two isomers, which may be separated by a variety of methods, generally involving their differential solubility in acids and alkalis. 

Figure 12.15 Fixation of Cl Reactive Red 180 with various concentrations of potassium salts of tetracarboxylic acids [139]. K BTCA = Tetrapotassium butane-1,2,3,4-tetracarboxylate K B4CA = Tetrapotassium benzene-1,2,4,5-tetracarboxylate...

Binary molecular co-crystals of 2,5-bis(3-pyridyl)-l,3,4-oxadiazole and 2,5-bis-(4-pyridyl)-l,3,4-oxadiazole with benzene-1,3,5-tricarboxylic and benzene-1,2,4,5-tetracarboxylic acids were studied by X-ray and thermogravimetric analysis of mass loss <2005MI1247>. Dipole moments were used to study the flexoelectric effect in guest-host mixtures of 2,5-(4-pentylbenzene)-l,3,4-oxadiazole with commercial liquid crystal hosts <2005CM6354>. The luminescence properties of many other copolymers were also investigated (see Section 5.06.12.3). 

Recently Togni et al. [19] focussed on the preparation of asymmetric dendrimer catalysts derived from ferrocenyl diphosphine ligands anchored to dendritic backbones constructed from benzene-1,3,5-tricarboxylic acid trichloride and adamantane-l,3,5,7-tetracarboxylic acid tetrachloride (e.g. 11, Scheme 11). In situ catalyst preparation by treatment of the dendritic ligands with [Rh(COD)2]BF4 afforded the cationic Rh-dendrimer, which was then used as a homogeneous catalyst in the hydrogenation reaction of, for example, dimethyl itaconate in MeOH. In all cases the measured enantioselectivity (98.0-98.7%) was nearly the same as observed for the ferrocenyl diphosphine (Josiphos) model compound (see Scheme 11). 

Figure 6.4 shows the structures of benzene-1,2,3,4- and 1,2,4,5- and 1,2,3,5-tetracarboxylic acids. The first is the analogue of the linear model discussed in Section 6.3. Here, we expect two different intrinsic binding constants, (for the... 

Benzene-1,2,3,4-tetracarboxylic acid Benzene-1,2,4,5-tetracarboxylic acid Benzene-1,2,3,5-tetracarboxylic acid Benzene-1,2,3,4,5-pentacarboxylic acid Benzene-1,2,3,4,5,6-hexacarboxylic acid... 

Kollner et al. (29) prepared a Josiphos derivative containing an amine functionality that was reacted with benzene-1,3,5-tricarboxylic acid trichloride (11) and adamantane-l,3,5,7-tetracarboxylic acid tetrachloride (12). The second generation of these two types of dendrimers (13 and 14) were synthesized convergently through esterification of benzene-1,3,5-tricarboxylic acid trichloride and adamantane-1,3,5,7-tetracarboxylic acid with a phenol bearing the Josiphos derivative in the 1,3 positions. The rhodium complexes of the dendrimers were used as chiral dendritic catalysts in the asymmetric hydrogenation of dimethyl itaconate in methanol (1 mol% catalyst, 1 bar H2 partial pressure). The enantioselectivities were only... 

Polyimides based on l-amino-3-phenoxy-5-(4-aminophenoxy)-benzene and snch dianhydrides as dianhydride of diphenyloxide-3,3 4,4 -tetracarboxylic acid, dianhydride A and dianhydride 6F are soluble in NMP, dimethylformamide (DMF), w-cresol, THF and chloroform. The polyimide based on benzophenone-3,3, 4,4 -tetracarboxylic acid dianhydride is partially soluble in w-cresol and NMP it is insoluble in chloroform, THF and DMF. Polypyromellitimide is insoluble in all the solvents tested. 

Oxidative homocoupling of aromatic and heteroaromatic rings proceeds with Pd(OAc)2 in AcOH. Biphenyl (165) is prepared by the oxidative coupling of benzene [104,105], The reaction is accelerated by the addition of perchloric acid. Biphenyl-tetracarboxylic acid (169), used for polyimide synthesis, is produced from dimethyl phthalate (168) commercially [106], Intramolecular coupling of the indole rings 170 is useful for the synthesis of staurosporine aglycone 171 [107]. 

The reaction of benzene-1,2,4,5-tetracarboxylic acid dihydrate with sulfur tetrafluoride leads to a mixture of l,2,4,5-tetrakis(tritluoromethyl)benzene (13), l,1.3,3-tetrafluoro-5,6-bis(tri-fluoromethyl)-l,3-dihydroisobenzofuran (14), and l,l,3,3,5,5,7,7-octafluoro-l,3,5,7-tetrahy-drobenzo[l,2-c 4,5-c ]difuran (15) in an 87 11.5 1.5 ratio. Treatment of the mixture with concentrated sulfuric acid results in quantitative hydrolysis of the fluorinated ethers to the corresponding carboxylic acids which could be removed from the fully trifluoroniethylated product by neutralization with aqueous potassium hydroxide. 

Plater M. J., Foreman M. R. St J., Howie R. A., Skakle J. M. S. and Slawin A. M. Z., Hydrothermal synthesis of polymeric metal carboxylates from benzene-1,2,4,5-tetracarboxylic acid and benzene-1,2,4-tricarboxylic acid, Inorg. Chim. Acta 315 (2001) pp. 126-132... 

A second strategy is to place mnltiple chiral Josiphos-type (329) units along the exterior of dendrimers, and snccessful apphcations for rhodium-catalyzed asynunetric hydrogenation ntUize cores composed of benzene-l,3,5-tricarboxyhc acid esters (381), adamantane-l,3,5,7-tetracarboxylic acid esters (382), and cyclophosphazenes see Phosphazenes) (383)." Enantioselectivities are excellent and these dendrimeric materials can be recovered by filtration throngh a nanofiltration membrane. 

The trimethoxyphenanthrene obtained by the degradation of isothebaine methyl ether is oxidized by nitric acid to benzene-1 2 3 4-tetracarboxylic acid [5]. (Compare the production of the same acid as final product of oxidation of 3 4 6-trimethoxyphenanthrene [9-10].)... 

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