Dibasic aliphatic acids

Hishida was unable to obtain any identifiable products when he attempted to extend this work to include the, monoesters of several aliphatic dibasic acids. However, definite products (269 and 270) were obtained using diethyl adipate and diethyl sebacate, respectively. A second product containing only one indole residue (271) was also obtained in the latter case. ... 

Monobasic carboxylic acids with an a-methyl group Esters of aliphatic dibasic carboxylic acids Cyclic sulfides... 

Esters of aliphatic dibasic carboxylic acids Aliphatic nitriles and dinitriles (see m/z 54)... 

Methyl esters of aliphatic dibasic carboxylic acids (-CH2C(0)0CH3) n-Butyl esters (loss of 04H9O)t... 

Polyamides from diamines and dibasic acids. The polyamides formed fi om aliphatic diamines (ethylene- to decamethylene-diamine) and aliphatic dibasic acids (oxalic to sebacic acid) possess the unusual property of forming strong fibres. By suitable treatment, the fibres may be obtained quite elastic and tough, and retain a high wet strength. These prpperties render them important from the commercial point of view polyamides of this type are called nylons . The Nylon of commerce (a 66 Nylon, nam after number of carbon atoms in the two components) is prepared by heating adipic acid and hexamethylenediamine in an autoclave ... 

The use of dibasic esters in this general condensation has also been studied in considerable detail. Much of this information has been disclosed in the form of patents. Two or more moles of biguanide react with esters of aliphatic dibasic acids 700) to yield diguanamines as expected. Insufficient biguanide gives rise to mixtures, said to consist of the polymethylene diguanamines and an o>-carbalkoxy-polymethyleneguanamine. 

Aminophenols from anilines, 35, 2 Anhydrides of aliphatic dibasic acids, Friedel-Crafts reaction with, 5, 5 Anion-assisted sigmatropic rearrangements, 43, 2 Anthracene homologs, synthesis of, 1, 6 Anti-Markownikoff hydration of alkenes, 13, 1... 

Depending on the identity, number and position of the acyl residues, these acids may be divided into the following groups mono-esters of caffeic, p-coumaric and ferulic acid di-, tri- and tetra-esters of caffeic acid [14,15] mixed di-esters of caffeic and ferulic acid or caffeic and sinapic acid [16] mixed esters of caffeic acid with dibasic aliphatic acids (e.g., oxalic, succinic) [17]. 

Plasticizers. Plasticizers are materials that soften and flexibilize inherently rigid, and even brittle polymers. Oiganic esters are widely used as plasticizers in polymers (97,98). These esters include the benzoats, phthalates, terephthalates, and trimellitates, and aliphatic dibasic acid esters. For example, triethylene glycol bis(2-ethylbutyrate) [95-08-9] is a plasticizer for poly (vinyl butyral) [63148-65-2], which is used in laminated safety glass (see Vinyl polymers, poly(vinyl acetals)). Di(2-ethylhexyl)phthalate [117-81-7] (DOP) is a preeminent plasticizer. Variation of acid and/or alcohol components) modifies the efficacy of the resultant ester as a plasticizer. In phthalate plasticizers, molecular sizes of the alcohol moiety can be varied from methyl to tridecyl to control permanence, compatibility, and efficiency branched (eg, 2-ethylhexyl, isodecyl) for rapid absorption and fusion linear (C6—Cl 1) for low temperature flexibility and low volatility and aromatic (benzyl) for solvating. Terephthalates are recognized for their migration resistance, and trimellitates for their low volatility in plasticizer applications. 

E. Berliner, The Friedel and Crafts Reaction with Aliphatic Dibasic Acid Anhydrides, Org. React. 1949, 5, 229-289. 

Phenol, btomobenzene, i-butylbenzene, and acenaphthene give keto acids in good yields. The reaction is applicable to other aliphatic dibasic acid anhydrides like glutaric anhydride, adipic poly anhydride, and maleic anhydride, furnishing w-aroyl acids. An excellent discussion including experimental conditions and procedures has been given. Optimum conditions for the reaction of naphthalene, biphenyl, and chlorobenzene with phthalic anhydride have been determined. The Corresponding keto acids are obtained in 90-98% yields. In this type of condensation, nitrobenzene is stated to be far superior to other solvents with respect to solvent power and ability to slow side reactions. ... 

M. P. Gupta. Can. J. Chem. 33, 1450-1 (1955). Crystal structure aliphatic dibasic acid, G4H40 2H20. 

Aliphatic dibasic acids, such as succinic, adipic, azelaic, and sebacic acids have also been used to make alkyd resins. Their linear and flexible chain structure lends higher flexibility and lower viscosity to the resin than the rigid aromatic rings of phthalic acids. 

Since 1935, when Carothers discovered the fiber-forming properties of polyamides, many chemists in the world have studied the synthesis of the raw materials for various polyamides, aliphatic diamines, aliphatic dibasic acids, caprolactam, and the w-amino fatty acids. The known synthetic routes to polyamides from w-amino fatty acids are as follows ... 

CH3OOC(CH2)nCOOCH3. An ester of a 13-carbon saturated aliphatic dibasic acid. Waxy, low-melting solid, made by an ozone oxidation process. Use Preparation of ethylene brassylate, a synthetic musk chemical intermediate. 

HOOCC10H20COOH. A 12-carbon, straight-chain, saturated aliphatic dibasic acid. 

Haworth phenanthrene synthesis. Acylation of aromatic compounds with aliphatic dibasic acid anhydrides to (i-aroylpropionic acids, reduction of the carbonyl group according to Clemmensen or Wolff-Kishner procedures, cyclization of the y-arylbutyric acid with 85% sulfuric acid, and conversion of the cyclic ketone to polycyclic hydroaromatic and subsequently to aromatic compounds. 

Table V. The Ionization Constants of Aliphatic Dibasic Acids and the Computation of Intergroup Distances...

The complexes are arranged according to the type of carboxylic acid they contain, from the simplest monobasic aliphatic acids to dibasic, aromatic and heterocyclic acids. With each acid, the full range of its complexes is explored, including those containing additional ligands and those in which the Uiacid ratio varies from that required for electroneutrality. 

The Friedel and Crafts Reaction with Aliphatic Dibasic Acid Anhydrides ... 

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