Pelargonic acid

Therapeutic Function Fungicide Chemical Name Nonanoicacid Common Name — 

Structural Formula CH3(CH2)7COOH Chemical Abstracts Registry No. 112-05-0 

C7Hi5CH(C02H)2 + aC2H5OH C7Hi8CH(C02H)2------ C7H15CH2C02II + C02 

The entire mixture, including the precipitated sodium bromide, is transferred to a 12-I. flask together with a small 

The oil obtained in the preceding step is transferred to a 3-I. round-bottomed flask and heated under an air-cooled reflux condenser in an oil bath at about 1800. When the evolution of carbon dioxide has ceased (about two hours), the oil is decanted from a small amount of solid material. The solid residue on treatment with 200-300 cc. of concentrated hydrochloric acid gives an additional small quantity of oil which is added to the main portion, 

The crude pelargonic acid is distilled in a modified Claisen flask having a fractionating side arm, and the material boiling at i4o-i42°/i2 mm. (i88-i9o°/ioo mm.) is collected. The yield is 525-590 g. (66-75 per cent of the theoretical quantity). The melting point of the pure acid is 12-12.50. 

Commercial butyl alcohol was dried over solid potassium carbonate and distilled through a 90-cm. indented column. The portion boiling at 117-118° was used. 

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Pelargonic acid (n-Nonoic acid), CH3(CH2),COOH. Equip a 1-litre, three-necked flask with a reflux condenser, a mercury-sealed stirrer, a dropping funnel and a thermometer. Place 23 g. of sodium, cut in small pieces, in the flask, and add 500 ml. of anhydrous n-butyl alcohol (1) in two or three portions follow the experimental details given in Section 111,152 for the preparation of a solution of sodium ethoxide. When the sodium has reacted completely, allow the solution to cool to 70-80° and add 160 g. (152 ml.) of redistilled ethyl malonate rapidly and with stirring. Heat the solution to 80-90°, and place 182 5 g. (160 ml.) of n-heptyl bromide (compare experimental details in Section 111,37) in the dropping funnel. Add the bromide slowly at first until precipitation of sodium bromide commences, and subsequently at such a rate that the n-butyl alcohol refluxes gently. Reflux the mixture until it is neutral to moist litmus (about 1 hour). 

An additional small quantity of pelargonic acid may bo obtained by treating the solid residue with 60 ml. of concentrated hydrochloric acid. 

The by-product of this process, pelargonic acid [112-05-0] is also an item of commerce. The usual source of sebacic acid [111-20-6] for nylon-6,10 [9008-66-6] is also from a natural product, ticinoleic acid [141-22-0] (12-hydroxyoleic acid), isolated from castor oil [8001-79-4]. The acid reacts with excess sodium or potassium hydroxide at high temperatures (250—275°C) to produce sebacic acid and 2-octanol [123-96-6] (166) by cleavage at the 9,10-unsaturated position. The manufacture of dodecanedioic acid [693-23-2] for nylon-6,12 begins with the catalytic trimerization of butadiene to make cyclododecatriene [4904-61-4] followed by reduction to cyclododecane [294-62-2] (see Butadiene). The cyclododecane is oxidatively cleaved to dodecanedioic acid in a process similar to that used in adipic acid production. 

Nylon-13,13 and Nylon-13. The ingredients for nylon-13,13 [26796-68-9] [26796-70-3] and nylon-13 [14465-66-8], [26916-48-3] and their copolymers have become available in developmental quantities from a natural source, crambe and rapeseed oil (176). Emcic acid [112-86-7] is obtained in high yield approaching 50 wt % from the oil and oxidatively cleaved to produce the dicarboxyhc acid, brassyUc acid [505-55-2] and pelargonic acid ... 

The pelargonic acid by-product is already a useful item of commerce, making the overall process a commercial possibiUty. The 13-carbon polyamides appear to have many of the properties of nylon-11, nylon-12, or nylon-12,12 toughness, moisture resistance, dimensional stabiUty, increased resistance to hydrolysis, moderate melt point, and melt processibiUty. Thus, these nylons could be useful in similar markets, eg, automotive parts, coatings, fibers, or films. Properties for nylon-13,13 are = 56 (7 and = 183 (7 (179). 

Cleavage of an alkenoic acid can be carried out with permanganate, a permanganate—periodate mixture, periodate or with nitric acid, dichromate, ozone, or, if the unsaturation is first converted to a dihydroxy compound, lead tetraacetate (71,73). Oxidative ozonolysis is a process for the manufacture of azelaic acid [123-99-9] and pelargonic acid (74). 

Carboxylation/Oxidation of Straight-Chain 1-Olefins. Selective carboxylation of a-olefins to predominately straight-chain aldehydes is realized through specific catalyst systems and by careful control of reaction conditions. The aldehyde produced is then air-oxidized to the acid using a Mn catalyst. Heptanoic acid [111-14-8] and pelargonic acid [112-05-0] are produced commercially in this manner. 

Rhodium catalyst is used to convert linear alpha-olefins to heptanoic and pelargonic acids (see Carboxylic acids, manufacture). These acids can also be made from the ozonolysis of oleic acid, as done by the Henkel Corp. Emery Group, or by steam cracking methyl ricinoleate, a by-product of the manufacture of nylon-11, an Atochem process in France (4). Neoacids are derived from isobutylene and nonene (4) (see Carboxylic acids, trialkylacetic acids). 

There has been only one major use for ozone today in the field of chemical synthesis the ozonation of oleic acid to produce azelaic acid. Oleic acid is obtained from either tallow, a by-product of meat-packing plants, or from tall oil, a byproduct of making paper from wood. Oleic acid is dissolved in about half its weight of pelargonic acid and is ozonized continuously in a reactor with approximately 2 percent ozone in oxygen it is oxidized for several hours. The pelargonic and azelaic acids are recovered by vacuum distillation. The acids are then esterified to yield a plasticizer for vinyl compounds or for the production of lubricants. Azelaic acid is also a starting material in the production of a nylon type of polymer. 

This explanation is probably applicable to the results recorded by Paesy, who found that with the homologous aliphatic acids the strength of the odour—as measured by the reciprocal of the smallest quantity that could be perceived—of formic acid is comparatively small, a maximum is reached with butyric acid and after diminution to the weak oenanthic acid, another maximum is reached with pelargonic acid, thereafter the odour diminishes very rapidly. 

In order to obtain information regarding the composition of these degradation products, aqueous extracts of the lead soaps of the linseed oil fatty acids were analysed, mainly by chromatography. The extracts contained formic acid 46%, azelaic acid 9% and pelargonic acid and its derivatives 27%, the remaining 18% consisting of a mixture of acetic, propionic, butyric, suberic, pimelic and adipic acids. It was shown that whereas the salts of formic acid were corrosive, those of azelaic and pelargonic acid were very efficient inhibitors. 

Barsky also used as a plasticizer, a compn prepd by heating a mixt of pelargonic acid 80, caprylic acid 15, and heptoic acid 5%, with a mixt of diethyleneglycol and triethyleneglycol in equal proportions... 

The rare example of synergistic action of a binary mixture of 1-naphthyl-A-phcnylaminc and phenol (1-naphthol, 2-(l,l-dimethylethyl)hydroquinone) on the initiated oxidation of cholesterol esters was evidenced by Vardanyan [34]. The mixture of two antioxidants was proved to terminate more chains than both inhibitors can do separately ( > /[xj). For example, 1-naphtol in a concentration of 5 x 10 5 mol L-1 creates the induction period t=170s, 1 -naphthyl-A-phenylamine in a concentration of 1.0 x 10-4 mol L 1 creates the induction period t = 400s, and together both antioxidants create the induction period r = 770 s (oxidation of ester of pelargonic acid cholesterol at 7= 348 K with AIBN as initiator). Hence, the ratio fs/ZfjXi was found equal to 2.78. The formation of an efficient intermediate inhibitor as a result of interaction of intermediate free radicals formed from phenol and amine was postulated. This inhibitor was proved to be produced by the interaction of oxidation products of phenol and amine. 

Palmitic acid, h34 Pelargonaldehyde, nl04 Pelargonic acid, n96 Pelargononitrile, n95 Pelargonoyl chloride, nl02 Pentaerythritol diformal, tl25 Pentalin, p7... 

Non-drying oil resins are soluble only in Aromatic hydrocarbons. They are used with amino resins for stoving finishes for appliances. Medium resins are used as plasticisers for cellulose nitrate. Along with natural oils several natural occurring and synthetic acid like resin (abiotic acid) pelargonic acid and isooctanoic acid are added to modify alkye resins. The alkyd resins are obtained by two processes, i.e., (1) Fatty Acid Process and (2) Alcoholysis process. 

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