Tetracarboxylic acid

This tetra ethyl ester is difficult to hydrolyse the corresponding tetra-methyl ester can, however, be hydrolysed to give ethane tetracarboxylic acid, (HOOC)jCH CH(COOH)j. The latter readily loses 2 molecules of carbon dioxide (on being heated or even on boiling with water) to give succinic acid, HOOCCHjCHjCOOH. 

Polyimides (PI) are polycondensation products (1) prepared from derivatives of tetracarboxylic acids and primary diamines (1—5). Descriptions of self-polycondensation polymers (2) based on aminodicarboxylic acid derivatives are also found in the literature (6—9). 

Diesters of Tetracarboxylic Acids with Diamines. Dianhydrides react with alcohols at a moderate temperature, producing the tetracarboxyhc acid diesters. Ben2ophenonetetracarboxyhc acid diester (BTTA diester) is obtained from B I DA as a mixture of three positional isomers. Partiy because it is an isomeric mixture, the diester of BTTA is soluble in methanol at high concentrations. A state-of-the-art thermoset polyimide,... 

Acetylenedicaiboxylic esteis also react with phenyUiydioxylamines to give pyrroles (28), eg, N-phenylpyrrole-2,3,4,5-tetracarboxylic acid, tetramethyl ester [37802-39 ] (14). 

IH-Azepine 1-oxide, 1-methyl- C NMR, 7, 498 <770MR<9)333) 2H-Azepine-2-selenone, hexahydro-l-methyl- C NMR, 7, 498 <79AJC567> 3H-Azepine-2,3,5,7-tetracarboxylic acid, 4,6-diphenyl-, tetramethyl ester X-ray, 7, 494 <72CB982) 3H-Azepine-2,4,6,7-tetracarboxylic acid, 3,5-diphenyl-, tetramethyl ester X-ray, 7, 494 <72CB982>... 

H,5H-Pyrrolo[l,2-c]thiazole-6,7,8,9-tetracarboxylic acid, 3,5-etheno-5-methyl-, tetramethyl ester H NMR, 6, 977 (80JOC5396)... 

IndoIe-4,5,6,7-tetracarboxylic acid, l-aryl-3a,6-dihydro-esters... 

Pyrido[2,l-/][l,2,4]triazine-5,6,7,8-tetracarboxylic acid, 4,4a-biphenyl-l-p-tolyl-synthesis, 3, 428 Pyridotropylium cations... 

Naphthalene-1,8-dicarboxylic add, its nitro-substituted derivatives, and naphthalene-1,4,5,8 tetracarboxylic acid, on treatment with sulfur tetrafluoride at 0 C, undergo dehydration to form quantitatively the corresponding anhydrides [218, 221] Unsubstituted and mononitrated monoanhydndes react further at 200-250 °C to give derivatives of 1,1,3,3-tetrafluoro-l// naphtho[I,8 c,d]pyran Dinitronaphthalene-l,8-di-carboxyhc acid anhydndes and naphthalene 1,4,5,8 tetracarboxylic acid dianhydnde give the respective tetra- and octafluoroethers only in the presence of an excess of anhydrous hydrogen fluoride [221] (equabons 113 and 114)... 

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.

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). 

O. Ermer, L Lindenberg, Lorenz, "Double-diamond inclusion compounds of 2,6-dimethylideneadaman-tane-l,35,7-tetracarboxylic acid , Helv. Chim. Acta 1991, 74, 825-8277. 

R. J. Butcher, A. Bashir-Hashemi, R. Gilardi, Network hydrogen bonding the crystal and molecular structure of cubane-l,35,7-tetracarboxylic acid dihydrate , J. Chem. Cryst., 1997, 27, 99-107. 

Perylene pigments include the dianhydride and diimide of perylene tetracarboxylic acid along with derivatives of the diimide while perinone pigments are derived from naphthalene tetracarboxylic acid. 

The thermal requirements for pigments which are targeted for PETP melt extrusion are particularly severe. However, it is important to consider the individual conditions at the various stages of polymer coloration. Pigments, for instance, which are added during the so-called condensation process in a glycol dispersion prior to transesterification or condensation in the autoclave, are exposed to temperatures between 240 and 290°C for 5 to 6 hours [43]. These harsh conditions are only tolerated by very few polycyclic pigments, primarily by representatives of the quinacridone, copper phthalocyanine, naphthalenetetracarboxylic acid, and pery-lene tetracarboxylic acid series. 

Most pigments derived from vat dyes are structurally based on anthraquinone derivatives such as indanthrone, flavanthrone, pyranthrone, or dibromoan-thanthrone. There are other polycyclic pigments which may be used directly in the form in which they are manufactured. This includes derivatives of naphthalene and perylene tetracarboxylic acid, dioxazine (Carbazole Violet), and tetrachloro-thioindigo. Quinacridone pigments, which were first introduced in 1958, and recently DPP pigments have been added to the series. 

Perylene and perinone pigments are chemically related. The group of perylene pigments is derived from perylene-3,4,9,10-tetracarboxylic acid 67, while perinone pigments are derivatives of napthalene-l,4,5,8-tetracarboxylic acid 68 ... 

The primary starting material for the synthesis of perylene tetracarboxylic acid pigments is the dianhydride 71. It is prepared by fusing 1,8-naphthalene dicar-boxylic acid imide (naphthalic acid imide 69) with caustic alkali, for instance in sodium hydroxide/potassium hydroxide/sodium acetate at 190 to 220°C, followed by air oxidation of the molten reaction mixture or of the aqueous hydrolysate. The reaction initially affords the bisimide (peryldiimide) 70, which is subsequently hydrolyzed with concentrated sulfuric acid at 220°C to form the dianhydride ... 

A different route proceeds by alkali fusion of the corrspondingly substituted naphthalic acid imide. This pathway parallels the synthesis of perylene tetracarboxylic acid diimide 70 (Sec. 3.4.1.1). The method is particularly suited to aliphatic amines. 

Unsymmetrically substituted perylene pigments are a comparatively recent novelty. Selective protonation of the tetra sodium salt of perylene tetracarboxylic acid affords the monosodium salt of perylene tetracarboxylic monoanhydride in high yield. Stepwise reaction with amines produces unsymmetrically substituted perylene pigments [2],... 

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