Pyromucic acid

Pyromucic acid — see Furan-2-carboxylic acid Pyronaridine biological activity, 2, 625... 

Like the pentoses, mucic acid loses three molecules of water and is converted, as described on p. 386, into derivatives of furane with concentrated hydrochloric acid the product is furane-a d-dicarboxylic acid. Dry distillation yields furane-a-carboxylic or pyromucic acid. 

Furoic Acid or Pyromucic Acid (Brenz-schleimsaure in Ger), OCH CH—CH -CC02H mw 112.09, plates (w) or ndls (by subln), mp I33—4°(subln 100°), bp 230-2° sol in w, ale eth heat of combustion at const voi 494.4kcal/m. First observed in 1780 by Scheele in the dry distillation of H02C(CH0H)4C02H (mucic acid). Prepd from... 

B-formylacrylic acid and furan-2-carboxylic acid. Distd over an oil bath from 7% (w/w) Na2CO3 (added to neutralise acids, especially pyromucic acid). Redistd from 2% (w/w) Na2CO3, and then, finally fractionally distd under vacuum. It is stored in the dark. [Evans and Aylesworth lECAE 18 24 7926]. 

Furoic acid (furan-2-carboxylic acid, or pyromucic acid) is used as a bactericide, and the furoate esters are used as flavoring agents, as antibiotic and corticosteroid intermediates. It is obtained by the enzymatic or chemical/catalytic aerobial oxidation of furfural (2-furalaldehyde) the latter is the only unsaturated large-volume organic chemical prepared from carbohydrates today. D-Xylose and L-ara-binose, the pentoses contained in the xylan-rich portion of hemicelluloses from agricultural and forestry wastes, under the conditions used for hydrolysis undergo dehydration to furfural. 

Pyrogallol, t304 Pyromellitic acid, b26 Pyromellitic dianhydride, b27 Pyromucic acid, f42 Pyromucic aldehyde, f39... 

Although 2-furoic acid (pyromucic acid) was known to Scheele in 1780, furan was obtained only in 1870 by Limpricht. Furfural began to be produced commercially in the 1930s by the Quaker Oats Company and its subsidiary, the Miner Laboratory. It had been observed that oat husks (waste from breakfast cereals) afforded furfural on treatment with acids in about 10% yield, along with non-volatile cattle food. Among the many uses of furfural, one should mention (i) the manufacture of plastics based on the phenol-furfural-formaldehyde reaction, (ii) its use as selective solvent for aromatics in the petrochemical industry and oil refinement, and (iii) the separation of saturated from unsaturated fats (triglycerides) in the refinement of vegetable oils. Furfural can be recovered by steam distillation and recycled. 

FUROIC ACID, METHYL ESTER METHYL 2-FURANCARBOXYLATE METHYL 2-FUROATE METHYL PYROMUCATE PYROMUCIC ACID METHYL ESTER... 

I omucic Acid.—When mucic acid is heated three molecules of water and one of carbon dioxide are lost and a monobasic acid is obtained known as pyromucic acid, and this acid by loss of CO2 goes to furfuran thus proving it to be the acid derived from furfuran. The acid is also obtained by oxidizing furfural. The reactions and relationships are as follows ... 

Furfuryl Alcohol.—An alcohol, fnrfuryl alcohol, is also known obtained from the aldehyde by reduction. This reduction is brought about by treatment with alcoholic potassium hydroxide, one molecule of the aldehyde being reduced at the expense of a second molecule which is thereby oxidized to the acid. Thus one molecule of pyromucic acid and one of furfuryl alcohol are obtained from two molecules of furfural. 

Although little experimental data is available, numerous patents have been issued for the vapor phase catalytic oxidation of various other derivatives containing the benzene nucleus, as well as heterocyclic compounds Thus, fluorene (diphenyl methane) is oxidized to fluorenone with air in the presence of a catalyst containing iron vanadate or other suitable metal salt of the fifth or sixth group of the periodic system at a temperature of 360° to 400°.1,2 Maleic acid and anhydride are formed by the catalytic oxidation of compounds of the furan series, such as furan, furfural alcohol, furfural, methyl furfural, hydroxymethylfurfural, pyromucic acid or mixtures, with air over catalysts of molybdenum, vanadium, or other metals.133 Dimethyl benzaldehyde is formed by oxidizing pseudocumene with air at 550° C. in the presence of a tungsten oxide catalyst. Molybdenum, vanadium, or tantalum oxide catalysts may also be used to form aromatic aldehydes from o-, m-, or p-xylenes, mesitylene, p-cymene, or o-chlorotoluene by air oxidation. Times of contact of 0.3 to 0.4 seconds... 

Furancarboxylic acid, Jura n-2-carboxy lie acid, 2-furoic acid, furanoic acid, pyromucic acid, brenzschleimsaiire [88-14-2]... 

USE In the manufacture of furfural-phenol plastics such as Durite in solvent refining of petroleum oils in the prepn of pyromucic acid. As a solvent for nitrated cotton, cellulose acetate, and gums in the manuf of varnishes for accel -crating vulcanization as insecticide, fungicide, germicide as reagent in analytical chemistry. In the synthesis of furan derivatives. Caution Irritates mucous membranes and acts on CNS- Causes lacrimal ion, inflammation of eyes, irritation of throat, headache-... 

Beilstein Handbook Reference) AI3-16500 BRN 0110149 2-Carboxyfuran CCRIS 2157 EINECS 201-803-0 a-Furancarboxyllc acid 2-Furancarboxylic acid a-Furoic acid 2-Furoic acid Kyselina 2-furoova Kyselina pyrosiizova NSC 8842 Pyromucic acid. Preservative, bactericide, furcates for perfume and flavoring, fumigant, textile processing, chemical Intermediate. Needles mp o 133.5° sublimes at 130-140° bp = 231° Am = 247 nm (12300, MeOH) soluble in alcohol, ether, water. GreeffP.W. ... 

As in the case of <%-amino carboxylic acids, the zwitterions of N- and O-heterocyclic a-carboxylic acids can be decarboxylated thus <%-picolinic, thiazole-2-carboxylic, quinaldic, and chelidonic acid afford, respectively, pyridine, thiazole, quinoline, and 4-pyrone. Furan is best prepared by removal of carbon dioxide from pyromucic acid (2-furoic acid) by heat in early work this was effected by heating the acid in a sealed tube or with soda-lime, but Wilson19 has described a convenient method that involves only simple apparatus and affords the very good yields of 72-78% ... 

Potassium permanganate (diluted solution).Pyromucic acid... 

P3rromucic acid, C4H3O.COOH, is formed as the result of the oxidation of furfuraldehyde. As its name implies it is produced by the distillation of mucic acid, COOH(CHOH)4COOH. Pyromucic acid melts at 132° and sublimes readily. When heated at 275° in a sealed tube it loses carbon dioxide and is converted into furan it is sulphonated by fuming sulphuric acid. The unsaturation of the ring resembles that in the olefines it adds four bromine atoms and is oxidized by Baeyer s reagent. 

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