Ethane-1,2-dicarboxylic acid

Succinic acid (ethane-1,2-dicarboxylic acid) is also known as amber acid with an International Union of Pure and Applied Chemistry name of butanedioic acid. It is a dicarboxylic acid (saturated) with the chemical formula of HO2C (CH2)2C02H, and its chemical structure is illustrated in Fig. 9.3. The acid and its esters occur in nature in amber, spring water, meteorites, vegetables, and fruit and animal tissues. The production methods generally include the biochemical and chemical oxidation of fats and alcoholic fermentation. In its pure form, succinic acid occurs as colorless triclinic prisms (a-form) and monoclinic prisms (p-form) (Fumagalli, 2007). Some of the significant properties of succinic acid are summarized in Table 9.2. 

Succinic acid, ethane dicarboxylic acid HOOC-... 

Free radical mechanisms have been proposed for this reaction [61, 72], and 4,4 -biplien y I dicarboxylic acid, 2,4, 5 - hi phenyltricarboxy I ic acid, and l,2-bis(4-carboxyphenyl)ethane have been detected as side products [72], The formation of chromophores is also enhanced by the presence of oxygen, as discussed below in Section 2.7. 

We have been working on the preparation of novel LCPs from substituted HQs and substituted l,2-bis(phenoxy)ethane-4,4/-dicarboxylic acids (PECs) [18], and substituted HQs and 4,4-diphenyldicarboxylic acid (BB) [19-21],... 

On the other hand, the moduli of as-spun fibers of polyarylates from Cl-HQ and l,2-bis(2-chlorophenoxy)ethane-4,4/-dicarboxylic acid (Cl-PEC) (Cl-HQ/ Cl-PEC), and Me-HQ and Cl-PEC (Me-HQ/Cl-PEC), were higher than those of Cl-HQ/PEC and Me-HQ/PEC. The reason for the higher moduli seemed to be the increased rigidity of the polymer chain caused by the restricted rotation of the ether linkage of Cl-PEC as a result of the steric hindrance of the Cl atoms. However, the moduli of polyarylates from fBu-HQ and Cl-PEC (fBu-HQ/Cl-PEC), and Ph-HQ and Cl-PEC (Ph-HQ/Cl-PEC), were lower than those of fBu-HQ/PEC and Ph-HQ/PEC, because the Cl atoms on the PEC units prevent... 

Polyarylates derived from various substituted HQs and l,2-bis(methoxy-phenoxy) ethane-4,4/-dicarboxylic acid or l,2-bis(2,6-dichlorophenoxy)ethane-4,4 -dicarboxylic acid exhibited low moduli because of the lack of liquid crystallinity resulting from the steric hindrance of the substituents on the PEC units. 

We can obtain different polymers with different properties if we carry out condensation polymerisation reactions between other monomer molecules. For example, if we react ethane- 1,2-diol with benzene-1,4-dicarboxylic acid, then we produce a polymer called Terylene. 

Oxalyl chloride, (C0CI)2, is the double acid chloride of oxalic acid, or ethane-1,2-dioic acid, the toxic dicarboxylic acid found in rhubarb leaves. 

Much the same act can be carried out with dicarboxylic acids and diols. The most famous example is the polymer of ethylene glycol (ethane-1,2-diol) and terephthalic acid, which can be made simply by melting the two components together so that water is lost in the esterification reaction. The mecha-... 

Preparation of (R)-l involves the chlorination of (R)-l,l-bina-phthyl-2,2-dicarboxylic acid with scc-BuLi and hexachloro-ethane. Condensation of the resulting dichorinated product with 3-chloro-2-chloromethyl-l-propene, followed by oxidative cleavage of the olefin moiety with ruthenium trichlorde affords (R)-l in modest yields. 

It has long been known that molecules do not rotate freely. In 1891, Bischoff proposed that ethane preferred a staggered conformation and that restricted rotation occurred in substituted ethanes.l" Christie and Kenner first demonstrated restricted rotation in 1922 by resolving 2,2 -dinitrophenyl-6,6 -dicarboxylic acid into optically active isomers.l" Pitzer showed that the calculated and observed entropies for ethane were identical if restricted rotation was considered.l" " The phenomenon of restricted rotation appears to be ubiquitous and has stimulated intense interest and research. 

Polyester can be made by reacting a diol (ethane-1,2-diol) with a dicarboxylic acids (benzene-1,4-dicarboxylicacid), nHO-CH2CH2-OH + n IlOOC-CJf-(OOH -> (-O-CHdl -O-OC -C H -CO-)n + n H2O Polyester makes reasonable fibres, it is quite inflexible so it does not crease easily but for clothing it is usually combined with cotton for comfort. The plastic is not light-sensitive, so it is often used for net curtains. Film, bottles and other moulded products are made from polyester. 

The products of the reaction between alkyldiphenylphosphines and hexachloro-ethane in the presence of a tertiary amine are the ylide (88) and the a-chloro-alkylphosphine (89), which are interchangeable, constitutional isomers that interconvert via an intramolecular reversible 1,2-chlorine shift from phosphorus to carbon. Application of the triphenylphosphine-hexachloroethane reagent for the self-condensation polymerization of / -aminobenzoic acid has been studied in detail. Related reactions between dicarboxylic acids and diamines, conducted in the presence of pyridine, involve the cationic phosphorane (90) as a key intermediate. Replacement of hexachloroethane by hexabromoethane or... 

At first,we studied the effect of the chemical structure of polymer chain on the stability of liquid crystalline state.The liquid crystalline state of polyether-esters derived from substituted hydroquinone and substituted 1,2-bis(phenoxy) ethane-4,4 -dicarboxylic acid could be controled by the... 

Okada M., Tachikawa K., Aoi K., Biodegradable polymers based on renewable resources. 111. Copolyesters composed of l,4 3,6-dianhydro-D-glucitol, l,l-bis(5-carboxy-2-furyl)ethane and aliphatic dicarboxylic acid units, J. App. Polym. Sci., 74,1999, 3342-3350. 

It was back in 1902 when Ludwig Wolff (1875-1919), a professor of analytical chemistry at the University of Jena, discovered the thermal rearrangement of ethyl 2-diazo-3-oxobutyrate in water to produce ethane-1,1-dicarboxylic acid, a reaction that has since been named after him Although it is now over 100 years old, the Wolff rearrangement is still alive and well, with prominent applications in modern synthetic organic chemistry. The main applications of the... 

For example, the method for production of aromatic polyketones by means of Friedel-Craft polycondensation of bis (arylsilanes) with chlorides of aromatic dicarboxylic acids (isophthaloyl-,terephthaloyl-,4,4 -oxydibenzoylchloride) at 20 °C in environment of dissolvent (1,2-dichlor-ethane) in the presence of aluminum chloride is proposed in Ref [331], The polyketones have the intrinsic viscosity more than 0.37 deciliter/gram (at 30 °C, in concentrated H SO ), glass transition temperature is 120-231 °C and melting point lies within 246-367 °C. The polyketones start decomposing at a temperature of 400 °C, the temperature of 10% loss of mass is 480-530 °C. 

Aromatic polyesters were investigated to examine their suitability as a toughening agent for epoxy, and found to be effective for a highly crosslinked system. Liquid rubber is less efficient in toughening a highly crosslinked system. lijima and co-workers [132, 133] synthesised a series of polyesters by the reaction of 1,2 ethane diol and aromatic dicarboxylic acid. The latter and the derivatives contained pthalic anhydride. 

Ethane dicarboxylic add see Succinic acid. Ethanoic add see Acetic acid. 

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