Methyl myristate

Myristic acid from hexanoic acid and methyl hydrogen sebacate). Dissolve 23 -2 g. of redistilled hexanoic acid (re caproic acid), b.p. 204-6-205-5°/760 mm., and 21-6 g. of methyl hydrogen sebacate in 200 ml. of absolute methanol to which 0 13 g. of sodium has been added. Electrolyse at 2 0 amps., whilst maintaining the temperature between 30° and 40°, until the pH is about 8 0 (ca. 6 hours). Neutralise the contents of the electrolysis cell with a little acetic acid and distil off the methyl alcohol on a water bath. Dissolve the residue in 200 ml. of ether, wash with three 50 ml. portions of saturated sodium bicarbonate solution, once with water, dry with anhydrous magnesium sulphate, and distil with the aid of a fractionating column (see under Methyl hydrogen adipate). Collect the re-decane at 60°/10 mm. (3 0 g.), the methyl myristate at 158-160°/ 10 mm. (12 5g.) and dimethyl hexadecane-1 16-dicarboxylate at 215-230°/ 7 mm. (1 -5 g.)... 

Reflux a mixture of 7 3 g. of methyl myristate with a solution of 4 8 g. of sodium hydroxide in 200 ml. of 90 per cent, methanol for 2 hours, distil off the methanol on a water bath, dissolve the residue in 400 ml. of hot water, add 15 ml. of concentrated hydrochloric acid to the solution at 50° in order to precipitate the organic acid, and cool. Collect the acid by suction filtration, wash it with a little water and dry in a vacuum desiccator. The yield of myristic acid (tetradecanoic acid tetradecoic acid), m.p. 57-58°, is 5 9 g. 

Methyl myristate, m428 Methyl nicotinate, m412... 

Of the early references to the preparation of methyl myristate and methyl palmitate, few are of preparative value. Methyl myristate can be prepared by the fractional distillation of the methyl esters from ucuhuba fat4 and from cocoanut oil.5-6 Methyl palmitate can be prepared in a similar manner from cocoanut oil6 and from bayberry wax.7... 

J -Methylfobmaniude, ii, 66 -Methylglueoside, 99 Methyl myristate, 67 Methyl palmitate, 67 Methyl sulfate, 97 antidote, 97 Monel metal stirrer, 99 Monoferfhthalic acid, 70 Myristic acid, 69 Myrtle wax, 68... 

METHYL MYRISTATE AND METHYL PALMITATE AND THE CORRESPONDING ACIDS... 

The methyl myristate obtained (% 1.4353) showed a melting point of 19° when at equilibrium with the liquid. The methyl palmitate ( d 1.4391 when supercooled) gave a melting point of 29.5°. 

Myristic and palmitic acids can be obtained from their esters by the procedure in Org. Syn. Coll. Vol. 1, 371. From roo g. of methyl myristate is obtained 85-89 g. (90-95 per cent of the theoretical amount) of colorless myristic acid melting at 52-53°. From 100 g. of methyl palmitate is obtained 84-88 g. (90-95 per cent of the theoretical amount) of colorless palmitic acid melting at 62-63°. 

METHYL MYRISTATE (m.p. 18.39) Acetonitrile and Methanol Nine other solvents... 

Methyl myristate, m413 Methyl nicotinate, m404 4-Methyl-3-nitroanisole, m85... 

Two alternative syntheses of methyl myristate, and thence myristic acid, are described (Expt 5.131). In Method A hexanoic acid (2mol) is coupled with methyl hydrogen sebacate (1 mol), the products being methyl myristate, decane and dimethyl octadecanedioate. 

In Method B decanoic acid (2 mol) is coupled with methyl hydrogen adipate (1 mol) and the products are methyl myristate, octadecane and dimethyl sebacate. 

Fatty acid esters Ethyl acetate, methyl methacrylate, trimethylolpropane trimethacrylate, decyl methacrylate, 2-hydroxyethyl methacrylate, ethoxy ethyl acetate, methyl palmitate, ethyl palmitate, isopropyl palmitate, butyl palmitate, isobutyl palmitate, methyl margarate, butyl margarate, methyl stearate, ethyl stearate, butyl stearate, isobutyl stearate, methyl oleate, bis(2-ethylhexyl) adipate, bis(2-ethylhexyl) sebacate, methyl linoleate, methyl laurate, octyl laurate, methyl myristate, isobutyl myristate, butyl myristate, dihydroisopimaric add methyl ester... 

BP = benzophenone, MM = methyl myristate, DBS = dibutyl sebacate, TOA = trioctylamine, chbt = cyclohexylbutyrate, OAm = oleylamine, Et20 = diethylether. fcHI = hot injection method HU = heating-up method. 

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