Phthalic acid, from oxidation

Phosphorus pentachloride, for conversion of pentaacetylgluconic add to add chloride, 41, 80 for oxidation of cycloheptatriene to tropylium fluoborate, 43, 101 with cyanoacetic acid, 41, 5 Phosphorus tribromide, reaction with l,5-hexadien-3-ol, 41, 50 Phthalic acids from thioimides, 44, 93 Phthalic anhydride, reaction with L-phenylalanine to yield N-phthaiyi-L-phenylalanine, 40, 82 Phthalic monoperacid, 42, 77 Phthaionic acid, 44, 63 N-Phthalyl-L-alanine, 40, 84 N-Phthalyl-0-alanine, 40, 84 N-Phthalylglydne, 40,84 N-Phthalyl-l-/3-phenylalanine, 40,82 PlMELIC ACID, (S-OXO-, DIETHYL ESTER, 42,41... 

Note that the high yield of phthalic acid was obtained from a mixture of extractives resulting from five different oxidation experiments. It is likely that some of these experiments gave much higher yields of phthalic acid than others. Therefore, the possible yield of phthalic acid from this alkali lignin is probably much higher than the 12.3% found in this combined sample. 

Phthalic acid from naphthalene. Naphthalene can be oxidized to phthalic... 

A study of the products which result from the nitration of ahzarin, shows that formula (I) is correct. In the two mononitro derivatives formed, the nitro group is in combination with the ring to which the hydroxyl groups are joined, since the two derivatives yield phthalic acid on oxidation. As a compound of the structure represented by formula (II) could not yield two such mononitro derivatives, the conclusion is drawn that the structure of alizarin is that indicated by formula (I). 

Homogeneous catalysts are used for many large-scale oxidation processes. Some of the most important large-scale oxidation processes are acetaldehyde from ethylene, adipic acid from cyclohexane, tere-phthalic acid from p-xylene, and propylene oxide (PO) from propylene. The mechanisms of these reactions are very different and can be broadly classified into three categories. 

Important derivatives are obtaiaed from PMBs by oxidation (see Phthalic acid and otherbenzenecarboxylic acids). For example, hemimellitene is oxidized to hemimellitic acid dihydrate [36362-97-7] or hemimellitic acid [569-51-7] which can be dehydrated to hemimellitic anhydride [3786-39-8]. 

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,... 

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. 

The following example illustrates in detail the preparation of amino benzoic acids from the hot reaction product obtained by the oxidation of a xylene and containing a mixture of salt, amide salt and diamide of a phthalic acid. 

Phosphine(s), chirality of, 314 Phosphite, DNA synthesis and, 1115 oxidation of, 1116 Phospholipid, 1066-1067 classification of, 1066 Phosphopantetheine, coenzyme A from. 817 structure of, 1127 Phosphoramidite, DNA synthesis and, 1115 Phosphoranc, 720 Phosphoric acid, pKa of, 51 Phosphoric acid anhydride, 1127 Phosphorus, hybridization of, 20 Phosphorus oxychloride, alcohol dehydration with. 620-622 Phosphorus tribromide, reaction with alcohols. 344. 618 Photochemical reaction, 1181 Photolithography, 505-506 resists for, 505-506 Photon, 419 energy- of. 420 Photosynthesis, 973-974 Phthalic acid, structure of, 753 Phthalimide, Gabriel amine synthesis and, 929... 

Besides the technical method starting from naphthalene, phthalic acid and its substituted derivatives can be prepared by oxidation of o-xylene to phthalic acid with potassium permanganate. This compound can be subsequently transformed via an anhydride, imide, and amide to a derivative of phthalonitrile, which is the more convenient starting material for several coordination compounds. The synthesis of the ferf-butyl-substituted dicarbonitrile, which is a very common starting material for highly soluble phthalocyanines, is shown below.97,105... 

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. 

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... 

This compound is obtained from phthalic acid and p-chlorophenol with sulfuric acid in the presence of boric acid. The intermediate product is quinizarin, which is sulfonated in oleum or with sodium hydrogen sulfite and oxidants to form 89 ... 

Introduction. The production of terephthalic acid (1,4-benzenedicarboxylic acid) has several interesting features. First, it is one of the examples of a homogeneous, radical-catalysed oxidation with the use of dioxygen and cobalt salt initiators. Secondly, it is an example of a catalyst/product separation involving a filtration of the product from the liquid that contains the catalyst. Crystallisation on such a huge scale is not very attractive, but the low solubility of phthalic acid in many solvents and the high boiling point do not allow any other solution. Theoretically, a solvent-solvent extraction would be an option, but we are not aware of a viable combination of solvents. 

Results of DEHP metabolism studies in vivo and in vitro, when considered together, suggest that the major route of metabolism for DEHP in fish consists of hydrolysis to the monoester. The monoester may then be conjugated with glucuronic acid, or further hydrolyzed to phthalic acid, or the remaining sidechain may be oxidized. This is similar to the reported pathway for DEHP metabolism in rats. In rats, dietary DEHP is to a large extent hydrolyzed to the monoester before absorption from the gut. When the monoester is administered orally, the urinary metabolites found are the same as those found after administration of DEHP (17). 

Until 1959, all the phthalic anhydride was made from coal tar naphthalene, the double-benzene ring compound also shown in Figure 18—3 was easily oxidized directly to phthalic acid. But with phthalic anhydride being only a small share of coal oil, and with the demand for phthalic anhydride escalating rapidly, coal tar became an inadequate source. The frantic search for an alternative route led to the development of the recovery process for ortho-xylene from refinery aromatics streams discussed in Chapter 3 and the... 

The direct reaction of [TCO4] in ethanolic solution with dppe and oxalic acid produces the red Tc" complex [Tc(ox)(dppe)2] (552). Attempts to prepare similar complexes with succinic acid, phthalic acid, or salicylic acid failed, or the complexes were stable in solution only. " Similarly, cationic complexes of Tc" are produced by reaction of the versatile precursor [TcO(OH)(dppe)2] (204) with various dithiocarbamates, which produces several complexes of general formula [Tc(dtc)(dppe)2] (553). For this reaction the reductant formamidine sulphinic acid (510) was required in an alkaline solution. The X-ray crystal structure of [Tc(S2CNMe2)(dppe)2] (554) shows a distorted octahedral geometry. Cyclic voltammetry reveals a reversible reduction wave Tc"/Tc couple at —0.53 V, and a reversible oxidation at +0.3 V for the Tc" /Tc" couple. The same compound (554) was also prepared from the thiourea precursor [TcO(tmtu)4] + (91).The reaction of this precursor in dmf in the presence of dppe produced a mixture of brown [TcO(dtc)(tmtu)2] and the Tc" complex (553). The first compound is probably an intermediate... 

Phthalic acid (1,2-benzene dicarboxylic acid), isophthalic acid (1,3-benzene dicarboxylic acid), and terephthalic acid (1,4-benzene dicarboxylic acid) are made by the selective oxidation of the corresponding xylenes. Terephthalic acid may also be produced from the oxidation of naphthalene and by the hydrolysis of terephthalonitrile. 

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