Phthalic anhydride, reaction with

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 1.5-hexadien-3-ol, 41, 50 Phthalic anhydride, reaction with L-phenylalanine to yield N-phthalyl-L-phenylalanine, 40, 82 Phthalic monoperacid, 42, 77 N-Phthalyl-i.-alanine, 40, 84 N-Phthalyl-/3-alanine, 40, 84 N-Phthalylglycine, 40, 84 N-Phthalyl-l-/5-phenylalanine, 40, 82... 

Starting material for the industrial synthesis is phthalide, which may be obtained by hydrogenation of phthalic anhydride. Reaction with o-cresol leads to the corresponding carboxyUc acid, which is converted via its acid chloride into the acyl cyanide. A Pinner reaction and treatment with methoxyamine finally give kresoxim-methyl. [59]... 

The transformation of arenes in the troposphere has been discussed in detail (Arey 1998). Their destruction can be mediated by reaction with hydroxyl radicals, and from naphthalene a wide range of compounds is produced, including 1- and 2-naphthols, 2-formylcinnamaldehyde, phthalic anhydride, and with less certainty 1,4-naphthoquinone and 2,3-epoxynaphthoquinone. Both 1- and 2-nitronaphthalene were formed through the intervention of NO2 (Bunce et al. 1997). Attention has also been directed to the composition of secondary organic aerosols from the photooxidation of monocyclic aromatic hydrocarbons in the presence of NO (Eorstner et al. 1997) the main products from a range of alkylated aromatics were 2,5-furandione and the 3-methyl and 3-ethyl congeners. 

The process. A typical process for phthalic anhydride starts with mixing hor q-xylene vapor with excess preheated air in a ratio of 20 1 air to o-xylene by weight. The gaseous mixture is then fed to a reactor consisting of tubes packed with vanadium pentoxide catalyst on a silica gel. The reaction takes place at 800—1000°F. Like most oxidation reactions, this one is exothermic, and the heat of reaction must be removed from the tubes to maintain the reaction temperature. 

Friedel-Crafts). (A., 291, 9 C. r., 119, 139.)—When the dichloride of phthalic anhydride reacts with the hydrocarbon, benzene, in presence of anhydrous aluminium chloride, phthalophenone (diphenylphthalide) is formed (see p. 107). With phthalic anhydride itself the reaction can be made to take the same or a different course. Using an excess of hydrocarbon, condensation and hydrolysis occur, and o-benzoyl-benzoic acid or its homologues are obtained according to the reacting hydrocarbon. Not only can the latter be varied, but derivatives of phthalic anhydride may be used, so that a great number of compounds can be synthesised in this way. 

Fischer 39 40> did not observe any effect of allyl alcohol on the copolymerization of allyl glycidyl ether with phthalic anhydride. Reaction rates were identical and indpendent of proton donor concentration. This finding indicates that the presence of... 

The agent employed in this reaction is usually an acid chloride or anhydride, catalyzed with aluminum chloride. Phthalic anhydride reacts with chlorobenzene to give p-chlorobenzoylbenzoic acid and, in a continuing action, the p-chlorobenzoy I be nzoic acid forms P-chloroanthraquinone. 

The major products from the reaction of arynes with thiophene and benzothiophene by addition and insertion are shown in Table 11. Benzyne from phthalic anhydride reacted with thiophene at 690° to give naphthalene and benzothiophene by 1,4-addition and loss of sulfur, and by 1,2-addition and loss of acetylene, respectively, as well as phenyl-thiophene by insertion (Fields and Meyerson, 1966d, 1967e) (Scheme 19). The ratio of naphthalene to benzothiophene was about 9 1, nearly the same preference for 1,4-over 1,2-addition as was inferred from the reaction of benzyne with dichlorobenzenes and pyridine at the same temperature, and again reflects the strong tendency of benzyne to act as a dienophile. 

Phthalic anhydride reacted with dibenzothiophene at 690° to give a 10% yield of addition and insertion products. Naphthobenzothiophene isomers, the addition products, were formed in a 2 1 ratio over phenyl-dibenzothiophene isomers, the insertion products—about the same ratio as was found in the reaction of benzyne with benzothiophene. The spectrum revealed no product of molecular weight 340, which would... 

The reaction of phthalic anhydrides 307 with trimethylsilyl azide affords l,3-benzoxazine-2,4-diones 308 in good yield (Scheme 168) <19950PP651, 1998JOC6797, CHEC-III(8.05.10)444>. 

Finally, the oopolymerization of a compound with two oxetano rings with another appropriate difunctional oompound has been used. Examples cited here are the reactions of. 2,6- oxaspiro[3.3]heptane with phthalic anhydride s with terphthaloyl chloride The latter polymer appeared to be croeslinkcd as it was insoluble in all solvents tosted and contained considerably less than the theomtjoaj amount of chlorine. 

The reaction of phthalic anhydrides 266 with methyl isocyanoacetate (267) in tetrahydrofuran in the presence of DBU gave a mixture of oxazole-4-carboxylates 268 and 269 (79CPB1373 79JAP(K)70285). Subsequently, products 268 and 269 were transformed into l-oxoisoquinoline-3-carboxylates in two steps. 

In a reaction similar to that of Ni(0) with phthalic anhydride [reaction (a)], when [Pt(COD)2] is treated with succinic anhydride in the presence of PCys, insertion of Pt(0) into one of the C—O bonds occurs to produce species of the type [Pt(COCH2CH2COO)(PCy3) ] (n = 1 or 2), from which the PCys ligand(s) may be displayed by dppe . Analogous reactions occur with [Ni(COD)2]. Oxidative addition of succinic anhydride to [Ni(COD)(bipy)] has been shown to occur by means of a second-order process . 

Under the preparation of fluorescein, it has already been mentioned that phthalic anhydride condenses with phenols in certain proportions, to form derivatives of anthraquinone. The reaction just effected takes place in accordance with the following equation ... 

Pyrazolin-5-ones can be readily acylated at C-4 with acid chlorides,110 esters1841 and anhydrides.1279 Very few reactions with acid chlorides and esters have been reported but the product is the ketone (XXI), as expected. Phthalic anhydride reacts with two moles... 

Partial oxidation of hydrocarbons employing mixed metal oxides as catalysts comprises an economically important class of reactions for the upgrading of base feed stocks [3]. An illustrative example of it is the partial oxidation of o-xylene and/or naphthalene to phthalic anhydride (PA) with a world production of 3.2 million metric tons per year, industrially carried out in shell and tube reactors using air as the oxidizing agent [4]. 

Benzyne (from pyrolysis of phthalic anhydride) reacts with thiophen at 690°C to give mainly naphthalene, benzo [b] thiophen (54), 2- and 3-phenyl-thiophens, and bithienyl.57 The bithienyl (probably the 2,2 -isomer) is also formed from thiophen alone under the same conditions. The phenylthiophens arise by insertion of benzyne into C—H bonds of thiophen. The source of naphthalene is most likely to be via a Diels-Alder reaction (Scheme 7, X = H), and Fields and Meyerson assume a mechanism involving initially 1,2-cyclo-addition of benzyne to a C—S bond of thiophen to account for the formation of 54 (Scheme 8).2,57,58 However, there is no evidence to support such a route, which seems unconvincing, not least because benzo [b]thiepin (53)... 

The transformation of arenes in the troposphere has been discussed in detail (Arey 1998). Destruction can be mediated by reaction with hydroxyl radicals, and from naphthalene, a wide range of compounds is produced, including 1- and 2-naphthols, 2-formylcinnamaldehyde, phthalic anhydride, and, with less certainty, 1,4-naphthoquinone and 2,3-epoxynaphthoquinone. Both... 

By using similar chemistry, aromatic polyester polyol structures are obtained by alkoxylation of the phthalic anhydride reaction product with glycerol (reaction 16.10). By the propoxylation of the reaction product of pyromellitic anhydride with DEG, tetrafunctional, highly viscous aromatic polyester polyols (16.11) are obtained. 

Equations (II) to (IX) illustrate basic methods of preparation, but many variations are used, particularly in industry, to obtain an economic yield. Phthalic acid, phthalamide, phthalimide, and phthalic anhydride, together with urea, are often used instead of phthalonitrile, and catalysts such as ammonium molybdate or zirconium tetrachloride may be employed (249, 251, 269). The reaction between phthalonitrile and metals (finely divided or acid-etched) is usually very vigorous at 250°-300°C, sufficient heat being generated to maintain the reaction temperature. This is an illustration of the ease with which the phthalocyanine skeleton is formed. Even more surprising are the observations that palladium black (118) and gold (189) will dissolve in molten phthalonitrile. Reaction (III) between phthalonitrile and a finely divided metal, metal hydride, oxide, or chloride is perhaps the most generally employed. For the unstable phthalocyanine complexes such as that of silver (11), the double decomposition reaction... 

Phthalic anhydride test n. Phthalic anhydride reacts with primary alcohols when the mixture is refluxed in benzene. Secondary alcohols react less readily, usually requiring a reaction temperature of 100-200° C, whereas the tertiary alcohols do not react. 

Figure 9.7 FTIR spectrum of MMT/ADA modified by the reaction with epichlorohydrine, maleic anhydride, and phthalic anhydride. Reproduced with permission from Polimery, ICRI.

---