Chloride Adipic acid

Succinic acid reacts with urea in aqeous solution to give a 2 1 compound having mp 141°C (116,117), which has low solubiUty in water. A method for the recovery of succinic acid from the wastes from adipic acid manufacture is based on this reaction (118,119). The monoamide succinamic acid [638-32-4] NH2COCH2CH2COOH, is obtained from ammonia and the anhydride or by partial hydrolysis of succinknide. The diamide succinamide [110-14-3], (CH2C0NH2)2, nip 268—270°C, is obtained from succinyl chloride and ammonia or by partial hydrolysis of succinonitrile. Heating succinknide with a primary amine gives A/-alkylsucckiknides (eq. 9). 

Diesters. Many of the diester derivatives are commercially important. The diesters are important plasticizers, polymer intermediates, and synthetic lubricants. The diesters of azelaic and sebacic acids are useflil as monomeric plasticizing agents these perform weU at low temperatures and are less water-soluble and less volatile than are diesters of adipic acid. Azelate diesters, eg, di- -hexyl, di(2-ethylhexyl), and dibutyl, are useflil plasticizing agents for poly(vinyl chloride), synthetic mbbers, nitroceUulose, and other derivatized ceUuloses (104). The di-hexyl azelates and dibutyl sebacate are sanctioned by the U.S. Food and Dmg Administration for use in poly(vinyl chloride) films and in other plastics with direct contact to food. The di(2-ethylhexyl) and dibenzyl sebacates are also valuable plasticizers. Monomeric plasticizers have also been prepared from other diacids, notably dodecanedioic, brassyflc, and 8-eth5lhexadecanedioic (88), but these have not enjoyed the commercialization of the sebacic and azelaic diesters. 

A. Diethyl a,h-dibromoadipate. In a 3-1. three-necked flask (Note 1) fitted with a reflux condenser, a dropping funnel, and a mechanical stirrer are placed 1 kg. (6.85 moles) of adipic acid and 2 kg. (1220 ml., 16.8 moles) of thionyl chloride (Notes 2 and 3). The mixture is stirred and heated gently on the steam bath until solution is effected, and the evolution of hydrogen chloride (Note 4) ceases after about 3 hours. The excess thionyl chloride... 

Putrescine dihydrochloride has been prepared by the Hofmann degradation of adipamide 3.. s by the Curtius degradation of adipyl hydrazide through the urethane by the Curtius degradation of adipyl azide obtained from adipyl chloride and sodium azide by the Schmidt degradation of adipic acid with hydrogen azide by the reduction of succinonitrile, succinaldoxime, or 7-phthalimidobutyronitrile with sodium and from N-ben-zoyl-7-iodobutylamine ... 

Docosanedioic acid has been prepared by Wolff-Kishner reduction of 6,17-diketodocosanedioic acid, formed by reaction of the half-ester acid chloride of adipic acid with the a,co-cadmium derivative of decane (%26 overall yield).3 Reduction of Wolff-Kishner method, followed by simultaneous reduction and desulfurization with Raney nickel of the 2,5-bis(co-carboxyoctyl)thiophene pro-... 

Nylon 66 can be drawn from a dish containing two starting materials. The bottom layer is an aqueous solution of 1,6-hexanediamine, and the top layer is adipoyl chloride (a more reactive derivative of adipic acid). Nylon 66 forms at the interface between the two liquids. 

A recent report indicates that thiophenes (not benzothiophenes) may be formed from alkyl phenyl ketones by treatment with a slight excess of thionyl chloride in the cold.58 Propiophenone, for example, yields 3,4-dibenzoyl-thiophene (47). Adipic acid and related carboxylic acids yield thiophene derivatives upon treatment with thionyl chloride in the presence of pyridine.59... 

Dithioglyoollic Acid Oxalyl Chloride Nitrourea Nitramide Ethyl Orthoformate Fumaric Acid Glutaric Acid Adipic Acid Pimelic Acid... 

Chlorostannate ionic liquids have been used in hydroformylation reactions [23], Acidic [bmimjCl-SnCb and [l-butyl-4-methylpyridinium]Cl-SnCl2 were prepared from mixing the respective [cation]+ Cl with tin(II)chloride in a ratio of 100 104, much in the same way that the chloroaluminates are made (see Chapter 4). Both these chlorostannate ionic liquids melt below 25 °C. Addition of Pd(PPh3)2Cl2 to these chlorostannate ionic liquids leads to a reaction medium that catalyses the hydroformylation of alkenes such as methyl-3-pentenoate as shown in Scheme 8.9. The ionic liquid-palladium catalyst solution is more effective than the corresponding homogeneous dichloromethane-palladium catalyst solution. The product was readily separated from the ionic liquid by distillation under vacuum. This is an important reaction as it provides a clean route to adipic acid. 

Oxidation is the first step for producing molecules with a very wide range of functional groups because oxygenated compounds are precursors to many other products. For example, alcohols may be converted to ethers, esters, alkenes, and, via nucleophilic substitution, to halogenated or amine products. Ketones and aldehydes may be used in condensation reactions to form new C-C double bonds, epoxides may be ring opened to form diols and polymers, and, finally, carboxylic acids are routinely converted to esters, amides, acid chlorides and acid anhydrides. Oxidation reactions are some of the largest scale industrial processes in synthetic chemistry, and the production of alcohols, ketones, aldehydes, epoxides and carboxylic acids is performed on a mammoth scale. For example, world production of ethylene oxide is estimated at 58 million tonnes, 2 million tonnes of adipic acid are made, mainly as a precursor in the synthesis of nylons, and 8 million tonnes of terephthalic acid are produced each year, mainly for the production of polyethylene terephthalate) [1]. 

Adipic acid Unknown s Amyl chloride Unknown 1... 

The condensation polymers are formed by repeated condensation reaction between two different bi-functional or tri-functional monomeric units. In these pol3nnerisation reactions, the elimination of small molecules such as water, alcohol, hydrogen chloride, etc. take place. The examples are terylene (dacron), nylon 6, 6, nylon 6, etc. For example, nylon 6, 6 is formed by the condensation of hexamethylene diamine with adipic acid. 

An oven-dried 100 ml flask with a side arm dosed with a septum is fitted with a magnetic stirring bar and a reflux condenser connected to a mercury bubbler. The flask is cooled to room temperature under nitrogen, charged with 4.36 g (0.025 mol) of adipic acid monoethyl ester followed by 12.5 ml of anhydrous tetrahydrofuran, and cooled to —18° by immersion in an ice-salt bath. Then 10.5 ml of 2.39 m (or 25 ml of 1 m) solution of borane in tetrahydrofuran (0.025 mol) is slowly added dropwise over a period of 19 minutes. The resulting clear reaction mixture is stirred well and the ice-salt bath is allowed to warm slowly to room temperature over a 16-hour period. The mixture is hydrolyzed with 15 ml of water at 0°. The aqueous phase is treated with 6 g of potassium carbonate (to decrease the solubility of the alcohol-ester in water), the tetrahydrofuran layer is separated and the aqueous layer is extracted three times with a total of 150 ml of ether. The combined ether extracts are washed with 30 ml of a saturated solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give 3.5 g (88%) of a colorless liquid which on distillation yields 2.98 g (75%) of ethyl 6-hydroxyhexanoate, b.p. 79°/0.7 mm. 

Recently, Monsanto has developed a carbonylation route(50) to prepare adipic acid from butenes. The process is based on dicarbonylation of 1, 4-dimethoxy- -butene with a palladium catalyst containing chloride ligands. This approach could achieve commercial potential if an economically viable 1,4-disubstituted -butene synthesis can be developed. A direct butene carbonylation rout to adipic acid is a desirable research target. 

Adipic acid can also polymerize with alcohols such as ethylene glycol to form polyesters, which can combine with isocyanates to form polyurethanes. Smaller esters of adipic acid produced with alcohols in the C-8 to C-10 range are called adipates. These are used as softeners in plastic (such as polyvinyl chloride) and as synthetic grease base oils. Adipic acid is also used in the food industry. Food grade adipic acid is prepared synthetically or extracted from beet juice as a natural source. It is used as a gelling agent, as an acidulant to provide tartness, and as a preservative. 

The ring may be cleaved hydrogenolytically. Halo acids afford 4-halobutanols or 1,4-dihalobutanes, depending on the reaction conditions. Acid chlorides in the presence of zinc chloride afford esters of 4-chlorobutanol, and LAH and aluminum chloride give butanol. Reaction with carbon monoxide and nickel tetracarbonyl affords adipic acid. 

Acrylic resins, activated carbon, adipic acid, alfalfa, alga powder, alumina, aluminium, ammonium chloride, animal feed, anthracite, asbestos... 

Adipic acid has been prepared by the following methods the action of silver1 or copper 2 on /3-iodopropionic acid the reduction of mucic add with phosphorus and iodine 3 the electrolysis of the potassium or sodium salts of monoethyl succinate 4 the condensation of ethylene chloride or bromide with malonic ester or cyanoacetic ester and subsequent hydrolysis 5 the oxidation of certain fractions of Baku petroleum 6 the oxidation of cyclohexanol or cyclohexanone with nitric acid 7 or potassium permanganate.8... 

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