Propane-2,2-dicarboxylic acid

PROPANE DICARBOXYLIC ACID (110-94-1) Combustible solid. Dust forms explosive mixture with air. Aqueous solution is a strong organic acid. Reacts with oxidizers and strong bases. Incompatible with oxidizers, sulfuric acid, caustics, ammonia, aliphatic amines, alkanolamines, isocyanates, alkylene oxides, epichlorohydrin. 

Glutiurlc Add. Pentanedioic acid 1,3-propane-dicarboxylic acid. C5H 04 mol wt 132.11. C 45.45%, H 6.10%, O 48.44%. COOH(CHj)3COOH. Occurs in green sugar beets is found in water extracts of crude wool. Manuf from cydopentanone by oxidative ring fission with hot 50% nitric acid in the presence of vanadium pentoxide. Lab prepn by acid hydrolysis of trimethylene cyanide Marvel. 

Chlorophenylmaleic anhydride, 263 3- m-Chlorophenyl)-l, 2-propane-dicarboxylic acid, 201... 

A-Hydroxy-5-norbornene-2,3-dicarboxylic acid imide [21715-90-2] M 179.2, m 165-166", 166-169", pKesi-6 Dissolve in CHCI3, filter, evaporate and recrystallise from EtOAc. IR (nujol) 1695, 1710 and 1770 (C=0), and 3100 (OH) cm. 0-Acetyl derivative has m 113-114° (from EtOH) with IR bands at 1730, 1770 and 1815 cm only, and the 0-benzoyl derivative has m 143-144° (from propan-2-ol or C6H6). [Bauer and Miarka J Org Chem 24 1293 1959 Fujino et al. Chem Pharm Bull Jpn 22 1857 1974],... 

In addition several other materials have been reported by industrial companies, but have not at the time of writing been commercialised. These include the product of condensation of 2,2-bis-(p-aminocyclohexyl)propane (VI) (Figure 18.28) with a mixture of adipic and azelaic acid (Phillips Petroleum), a research material produced in the old German Democratic Republic obtained by melt condensation of /ranj -cyclohexane-l,4-dicarboxylic acid (VII) (Figure 18.28) and the two trimethylhexamethylenediamine isomers used in the manufacture of Trogamid T, and another amorphous material (Rilsan N by Ato Chimie). 

The procedure (with ethylene dibromide replacing trimetliyleiie dibromide) described for cycZobutanecarboxylic acid (previous Section) does not give satisfactory results when applied to the cyc propane analogue the yield of the cyclopropane-1 1-dicarboxylic acid is considerably lower and, furthermore, the decarboxylation of the latter gives a considerable proportion (about 30 per cent.) of butyrolactone ... 

An illustration of the tendency of alkane 1,2- and alkane-1,3-dicarboxylic acids to a ring closure during the reaction with sulfur tetrafluoride is the reaction of propane-1,2,3-tricarboxylie acid The corresponding six- and five-membered cyclic ethers are formed in a 1 4 ratio f211] (equation 106)... 

FIGURE 1.16 Isomers of cyclopropane-1,2-dicarboxylic acid, (a) is-l,2-Dicarboxycyclopropane (trans isomers) (b) Z-l,2-Dicarboxycyclopropane isomer, (meso isomer) (c) Molecular models of E- (trans-) 1,2-dimethylcyclo-propane shown in the tube representation. Rotation of the right hand structure about a vertical axis through the center of the cyclopropane will superimpose the two methyl groups. The methylene of the rotated structure will be in the back, rather than the front, and not superimposed, (d) A mirror plane through the methylene and the back carbon-carbon bond is a plane of symmetry. The two carboxyl groups appear not to reflect each other in the model shown but they can rotate freely and will reflect each other on an instantaneous basis. 

Monocarboxylic acids might be present in Murchison as free acids, esters or salts nothing is known about this aspect of the problem 38 They are relatively abundant in Murchison, more abundant than aminoacids and hydrocarbons. The relative concentration of propanoic acid with respect to propane is 205, while the ratio is 22 if propanoic acid is compared to glycine. So far, 17 dicarboxylic acids have been identified in Murchison. The lack of reference compounds precludes the identification of many others 24). 

The world-wide production of PA (excluding fibers) in 1997 was 1.6x10 t, with a 75 % use of casting processed materials. For food contact articles the following can be used as starting materials straight chain u -amino acids (C6-C12) and their lactams adipic acids, azelaic acids, sebacic acids, dodecane dicarboxylic acids and heptadecane-dicarboxylic acids salts with hexamethylenediamine isophthalic acid, bis(4-aminocy-clohexyl)-methane, 2,2-bis(4 -aminocyclohexyl)-propane, 3,3 -dimethyl-4,4 -diamino-dicyclohexyl-methane, terephthalic acid or its methylester, l,6-diamino-2,2,4-tri-methylhexane, 1,6-diamino-2,4,4-trimethylhexane, l-amino-3-amino-methyl-3,5,5-tri-methylhexane. 

The intramolecular Wurtz-type coupling of dihaloorganic compounds with use of metallic zinc is a classical synthetic route to cyclic compounds. For example, cyclopropane derivatives can be prepared from 1,3-dihalo-propanes (29, 189a, 248, 451), and cyclobutane derivatives from 1,4-dihalobutanes (71). These reactions presumably proceed via the intermediate formation of organozinc compounds. The reaction of diethylzinc with esters of a,a -dibrominated aliphatic dicarboxylic acids leads to the... 

Methylvinylpolysiloxane Polyamide formed by reacting a Cye dicarboxylic acid with l,3-di-4-piperdyl-propane and piperidine in the respective mole ratios of 1.00 0.90 0.20 5is (2-ethylhexyl) sebacate polyester Phenyldiethanolamine succinate polyester Sorbitol... 

Acylcyclopropanecarboxylic acids 15 are degraded by a Hunsdiecker reaction using red mercuric oxide and bromine to mixtures of trans- and cw-2-bromocyclopropyl alkanones in good to moderate yields. Similarly, 2-acetylcyclopropane-l,l-dicarboxylic acid and trans-cyclo-propane-l,2-dicarboxylic acid are transformed into 2-acetyl-l,l-dibromocyclopropane and /ran.j/c -l,2-dibromocyclopropane in 86.5 and 64% yield, respectively. ... 

A series of salts derived from alpha omega diamines, namely 1,3-propane- and 1,4-butane diamine, and various dicarboxylic acids was studied with the aim of extending ID PAD to 2D DPAD synthon. SXRD studies on 9 salts out of the 14 prepared revealed that none of the salts displayed the expected 2D DPAD synthon instead, 3D HBN was observed in these salts and consequently, only 2 salts were able to gel a few solvents [98]. 

Propylene glycol is often used as the diol. To a lesser extent, other glycols, like diethylene glycol, are also used for greater flexibility, or neopentyl glycol for a somewhat better thermal resistance. Bisphenol A (2,2 bis(4-hydroxyphenyl) propane) is used when better chemical resistance is needed. Use of mixed diols is conunon. Many unsafturated dicarboxylic acids can be used, but maleic (as an anhydride) or fumaric acids are the most common. Chloromaleic or chlorofumaric acids are also employed. 

Topanex 500H. See 1,5-Dioxaspiro [5.5] undecane 3,3-dicarboxylic acid, bis (2,2,6,6-tetramethyl-4-piperidinyl) ester Topanol 205. See 2,2-Bis [4-2-(3,5-di-t-butyl-4-hydroxyhydrocinnamoyloxy) ethoxyphenyl] propane... 

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