Decane-1,10-dicarboxylic acid

Decane-1 10-dicarboxylic acid from sebacic acid. Convert sebacic acid into the acid chloride by treatment with phosphorus penta-chloride (2 mols) and purify by distillation b.p. 146-143°/2 mm. the yield is almost quantitative. Dissolve the resulting sebacoyl chloride in anhydrous ether and add the solution slowly to an ethereal solution of excess of diazomethane (prepared from 50 g. of nitrosomethylurea) allow the mixture to stand overnight. Remove the ether and excess of diazomethane under reduced pressure the residual crystalline 1 8-bis-diazoacetyloctane weighs 19 -3 g. and melts at 91° after crystaUisation from benzene. 

Add, with stirring, a solution of 6 8 g. of the fiis-diazo ketone in 100 ml. of warm dioxan to a suspension of 7 0 g. of freshly precipitated silver oxide in 250 ml. of water containing 11 g. of sodium thiosulphate at 75°. A brisk evolution of nitrogen occurs after 1 5 hours at 75°, filter the liquid from the black silver residue. Acidify the almost colourless filtrate with nitric acid and extract the gelatinous precipitate with ether. Evaporate the dried ethereal extract the residue of crude decane-1 10-dicarboxylic acid weighs 4 -5 g. and melts at 116-117°. RecrystaUisation from 20 per cent, aqueous acetic acid raises the m.p. to 127-128°. 

Dodecane-l,10-dioic acid (decane-1,10-dicarboxylic acid) [693-23-2] M 230.3, m 129°, b 245°/10mm, pK ,t -4.8. Crystd from water, 75% or 95% EtOH (sol 10%), or glacial acetic acid. 

In 1978 Hiils (Mumcu et al ) described the properties of a block copolymer prepared by condensation of polytetramethylene ether glycol with laurin lactam and decane-1,10-dicarboxylic acid. The materials were introduced as XR3808 and X4006. The polyamide XR3808 is reported to have a specific gravity of 1.02, a yield stress of 24 MPa, a modulus of elasticity of 300 MPa and an elongation of break of 360%. The Swiss company Emser Werke also introduced similar... 

Alternatively, treat a solution of 3 9 g. of the 6is-diazo ketone in 50 ml. of warm dioxan with 15 ml. of 20 per cent, aqueous ammonia and 3 ml. of 10 per cent, aqueous silver nitrate under reflux in a 250 or 500 ml. flask on a water bath. Nitrogen is gently evolved for a few minutes, followed by a violent reaction and the production of a dark brown and op>aque mixture. Continue the heating for 30 minutes on the water bath and filter hot the diamide of decane-1 10-dicarboxylic acid is deposited on cooling. Filter this off and dry the yield is 3 -1 g., m.p. 182-184°, raised to 184-185° after recrystallisation from 25 per cent, aqueous acetic add. Hydrolyse the diamide (1 mol) by refluxing for 2-5 hours with ZN potassium hydroxide (4 mols) acidify and recrystallise the acid from 20 per cent, acetic acid. The yield of decane-1 10-dicarboxylic acid, m.p. 127-128°, is almost quantitative. 

FIGURE 1.9 Records of the minute electrical currents (downward deflections) that flow through single ligandgated ion channels in the junctional region of frog skeletal muscle. The currents arise from brief transitions of individual nicotinic receptors to an active (channel open) state in response to the presence of various agonists (ACh = acetylcholine SubCh = suberyldicholine DecCh = the dicholine ester of decan-1,10-dicarboxylic acid CCh = carbamylcholine). (From Colquhoun, D. and Sakmann, B., J. Physiol., 369,501-557, 1985. With permission.)... 

Dean and Stark apparatus, modified, 429 n-Decane, 237, 940 Decane-1 10-dicarboxylic acid, 904, 905... 

Rearrangement to acids is accomplished by adding a dioxane solution of diazoketone to a suspension of silver oxide in warm aqueous sodium thiosulfate solution. Examples include biphenyl-2-acetic acid (86%), ° 1-ace-naphthylacetic acid (64%), decane-1,10-dicarboxylic acid (72%), and o-bromophenylacetic acid (63%). ... 

Nylon-6,10 is prepared from the salt (melting point 170°C) of hexamethylenediamine and sebacic acid by a similar technique. Nylon-6,9 uses azelaic acid. Decane-1,10-dicarboxylic acid is used for nylon-6,12. 

CAS 693-23-2 EINECS/ELINCS 211-746-3 Synonyms DDDA Decamethylenedicarboxylic acid Decane-1,10-dicarboxylic acid 1,10-Decanedicarboxylic acid 1,10-Dicarboxydecane... 

Decanecarboxylic acid. See Undecanoic acid Decane-1,10-dicarboxylic acid 1,10-Decanedicarboxylic acid. See Cl2 dibasic acid Decanedioic acid. See Sebacic acid Decanedioic acid, bis (2-butoxyethyl) ester. See Dibutoxyethyl sebacate Decanedioic acid, bis (2-ethylhexyl) ester. See Dioctyl sebacate... 

Mumcu S, Burzin K, Feldmann R and Feinauer R (1978) Copolyetheramides from laurolactam, decane-1,10-dicarboxylic acid and a,w-dihydroxy(polytetrahydrofuran), Angew Makromol Chem 74 49-60. 

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