Heptane-4,4-dicarboxylic acid

Azelaic acid (AA), 1,9-nonanedioic acid or heptane-1,7-dicarboxylic acid, is used in manifold application areas. AA is offered in the pharmaceutical field for the treatment of acne and rosacea due to its antibacterial effect [1,2]. However, AA is much more widely applied as a monomer for the production of polymers such as alkyd resins, polyamides, and impact-proof polyesters or for the synthesis of plasticizers, lubricants, lithium complex greases, corrosion inhibitors, dielectric fluids, heat-transfer fluids, metal to glass fluxes, emulsion breakers, waxes, tobacco sheet plasticizers, hot-melt coatings and adhesives, water-soluble coating resins, hydraulic fluids, fungicides, insecticides, and so on [3-7]. 

Azelaic acid (nonanedioic acid, 1,7-heptane-dicarboxylic acid) n. HOOC(CH2)7COOH. A yellowish-white crystalline powder, derived from a fatty acid such as oleic acid by oxidation with ozone. It is an intermediate used in the production of plasticizers, polyamides and alkyd resins. Acid value, 595.5 mol wt, 188.2 mp, 106°C bp, 237°C/15mmHg. For plasticizers derived from azelaic acid. Merck Index (2001) 13th edn. Merck and Company Inc., Whitehouse Station, NJ. 

Numerous references to derivatives of 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid as defoliants, herbicides, fungicides, etc., are cited in index volumes of Chem. Ahstr. since Vol. 46 (1952). 

The diacylation of isopropenyl acetate with anhydrides of dicarboxylic acids is applicable for the synthesis of several other cyclic jS-triketones in moderate yield. - It has been used for the synthesis of 2-acetylcyclohexane-l,3-dione (40% yield), 2-acetyl-4-methylcyclopentane-l,3-dione (10% yield), 2-acetyl-4,4-dimethylcyclopentane-l,3-dione (10% yield), 2-acetyl-5,5-dimethylcyclohexane-l,3-dione (10% yield), 2-acetylcyclo-heptane-l,3-dione (12% yield) and 2-acetylindane-l,3-dione (26% yield). Maleic anhydrides under more drastic conditions give acetylcyclopent-4-ene-l,3-diones in yields from 5% to 12%. The corresponding acylation of the enol acetate of 2-butanone with succinic anhydride has been used to prepare 2-methylcyclopentane-l,3-dione, an important intermediate in steroid synthesis. - ... 

More drastic conditions of temperature, pressure and time gave carbon as the product from both aromatic and aliphatic compounds. This carbon is an activated char with decolorizing properties. Tars, tarry substances, the oxides of carbon, and the usual products of the oxidation of aromatic compounds (dicarboxylic acids) were all conspicuous by their absence. Benzotrifluoride oxidized to benzoyl fluoride. The aliphatic compounds cyclohexane, methycyclohexane, n-heptane, etc., could be oxidized to carbon and water. 

Bicyclo-[l, 2, 2]-heptane-2,3-diol Cyclopentane-1,3-dicarboxylic acid B [33]... 

Mercury(II) oxide together with a halogen is an early development of the classic Hunsdiecker reaction (bromodecarboxylation of a carboxylic acid silver salt, see below) which is still in use.20 22 A double Hunsdiecker reaction of cyclobutane-1,1-dicarboxylic acid with red mer-cury(ll) oxide in the presence of bromine gave 1,1-dibromocyclobutane (2) in 46% yield.21 However, a similar reaction performed on spiro[3.3]heptane-2-carboxylic acid afforded 2-bro-mospiro[3.3]heptane (3) in only 16% yield.22... 

Height equivalent per theoretical plate (H.E.T.P.), 95 n-Heptaldehyde, 251 n-Heptaldoxime, 348 n-Heptane, 238 1-Heptene, 240 n-Heptoic acid, 354, 356 n-Heptoic anhydride, 371, 374 n-Heptyl alcohol, 247, 251 n-Heptylamine, 413, 418 n-Heptyl chloride, 275 n-Heptyl iodide, 288 n-Hexacosane, 938, 941 Hexadecane-1 16-dicarboxylic acid, 938,940... 

Twenty-seven two-year-old scaleless hens were transported to Visalia, CA on October 1, 1979, housed in cages overnight with food and water provided ad lib, and exposed to field applications of DEF on October 2. Some birds were repeatedly treated over the next five days. The mature cotton fields (Diversified Farming Inc.) were sprayed from a ground vehicle that treated 8 rows simultaneously with DEF-6 (0.72 kg/l, 6 lb/gal Mobay Chemical Co.) at 0.37 gal/acre and Accelerate (amine salt of endothall (7-oxabicyclo (2.2.1) heptane-2,3-dicarboxylic acid, 0.06 kg/l, 0.5 lbs/gal) at 0.19 gal/acre in 25 gal water/acre. 

OXABICYCLO(2.2.1)HEPTANE-2,3-DICARBOXYLIC ACID. DISODIUM SALT... 

SYNS AQUATHOL 3,6-ENDOOXOHEXAHYDRO-PHTHALIC ACID ENDOTHALL ENDOTHAL TECHNICAL 3,6-ENDOXOHEXAHYDROPHTHALIC ACID 3,6-endo-EPOXY-l,2-CYCLOHEXANEDI-CARBOXYLIC ACID HEXAHYDRO-3,6-endo-OXYPHTHALIC ACID HYDOUT HYDROTHAD47 7-OXABICYCLO(2.2,l)HEPTANE-2,3-DICARBOXYLIC ACID RCRA WASTE NUMBER P088 TRI-ENDOTHAL... 

Other agents [e.g., acylcamitine, azone (1-dodecylazacyclo-heptan-2-one), dicarboxylic acids and enamine]... 

Decarboxylation of bicyclo[4.1.0]heptane-7,7-dicarboxylic acid (16) affords exo- and endo-hi-cyclo[4.1.0]heptane-7-carboxylic acid (17) in a relatively poor yield together with cyclohex-2-eneacetic acid (18). ... 

Addition of hydrochloric acid to tetracyclo[3.2.0.0 . 0 ]heptane-2,3-dicarboxylic acid (17) in dioxane gave a mixture of the two epimeric exo-5-chlorotricyclo[2.2.1.0 ]heptane-2,3-di-carboxylic acids 18 and 19 as the result of an inversion of configuration at... 

Tetracyclo[3.2.0.0 . 0 ]heptane-l,5-dicarboxylic acid (2) reacted readily with bromine to give the product 3 in which one of the three-membered rings was opened and the other retained." ... 

Azelaic acid (1,9-nonanedioic acid, heptane-l,7-dicarboxylic acid) [123-99-9] M 188.2, m... 

Dunlop J, Eliasof S, Stack G et al (2003) WAY-855 (3-amino-tricyclo[2.2.1.02.6]heptane-l, 3-dicarboxylic acid) a novel, EAAT2-preferring, nonsubstrate inhibitor of high-affinity glutamate uptake. Br J Pharmacol 140 839-846... 

The combination reagent was used for selective cleavage of 1 -methyl-7-oxabi-cyclo[2.2.1]heptane-2,3-dicarboxylic acids.3 Thus the ether (1), obtained by reaction of 2-methylfurane with maleic anhydride followed by hydrogenation, when warmed with the reagents afforded (2) and the product of hydrolysis (3). Both reagents are necessary for the cleavage. 

Azelaic acid (1,9-nonanedioic acid, heptane-l,7-dicarboxylic acid) [123-99-9] M 188.2, m 105-106 , b 225 /10mm, 256 /50mm, pK 4.53, pK 5.33. Reciystallise it from H2O (charcoal) or thiophene-free benzene. The acid can be dried by azeotropic distillation with toluene, the residual toluene solution is then cooled and filtered, and the precipitate is dried in a vacuum oven. It has been purified by zone refining or by sublimation onto a cold finger at 10 torr. It distils above 360 with partial formation of the anhydride. The dimethyl ester has in -3.9° and b 140°/8mm. [Hill McEwen Org Synth Coll Vol II 53 1943, Beilstein 2 IV 2055.]... 

Synonyms Dipotassium 7-oxabicyclo [2.2.1] heptane-2,3-dicarboxylate Endothall dipotassium salt 7-Endothall, dipotassium salt 7-Oxabicyclo (2.2.1) heptane-2,3-dicarboxylic acid, dipotassium salt Classification Dicarboxylic acid-disalt Empirical CsHaOs 2K Properties M.w. 262.36 Toxicology TSCA listed Uses Herbicide... 

Synonyms Endothall, mono (N,N-dimethylcocoamine) salt Mono (N,N-dimethyl alkyl amine) endothall Oxabicycio (2.2.1) heptane-2,3-dicarboxylic acid, compd. with N,N-dimethylcocoamine (1 1)... 

Endoxohexahydrophthalic acid, disodium salt 7-Oxabicyclo (2.2.1) heptane-2,3-dicarboxylic acid, disodium salt... 

Azelaic Acid (n-Heptane-l 1-dicarboxylic acid, lepargylic acid)... 

Hydroxy-l-methylcyclohexane-l,2-dicarboxylic acid 1,4-lactone, T40.3 Bicyclo[3.2.l]heptane-3,3-dicarboxylic acid, A 31.6... 

Synonyms Accelerate Aquathol Des-i-cate 3,Jo-Epoxy-1,2-cyclohexane-dicarbox-ylic acid Endothal 3,6-Endooxohexahydrophthalic acid 3,6-Epoxy cyclohexane-1,2-dicarboxylic acid Hydout Hydrothal Hydrothal-47 Hydrothal-191 7-Oxabicy-clo[2.2.1]heptane-2,3-dicarboxylic acid Pennout RCRA waste number P088 Ripenthal Triendothal. 

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