Production butyl-oleate

Butanol, which at one time was an unwanted by-product in the preparation of acetone, is now the most important product of the fermentation. The building of a large new factory in Puerto Rico using 10,000 tons of molasses per annum for its production is an indication of this importance. Butanol is probably still the best solvent for cellulose nitrate lacquers. Dibutyl phthalate is certainly the most widely used plasticizer for synthetic resins, and butyl oleate, tributyl citrate and dibutyl tartrate have also been described as plasticizers. Another important use of butanol is as a source of butadiene, which serves as an intermediate in the conversion of sucrose into a synthetic rubber. Although in recent years other methods have been described for the preparation of butanol (for example, from ethyl alcohol and from acetylene), yet the fermentation of carbohydrates is still the cheapest process. 

Lipases are being used in several reactions of synthesis for the production of valuable compounds. Biodegradable polymers, like butyl oleate and some polyesters, have been synthesized by esterification and transesterification reactions with lipases... 

The hydrogenation of an unsaturated ester to an unsaturated alcohol may be possible over zinc-chromium oxide as catalyst, although the catalyst is known to be much less active for the usual ester hydrogenations than copper-chromium oxide. Ethyl or butyl (eq. 10.25) oleates were hydrogenated to octadecenol in yields of over 60% with a zinc-chromium oxide at 280-300°C and 20 MPa H2.16 The butyl ester was much preferred to the ethyl ester, since it was difficult to separate the ethyl ester from the alcohol product because of their similar boiling points. 

In situ product separation by distillation offers applications in esterification (e.g., for ethyl acetate), trans-esterification (e.g., for butyl acetate), hydrolysis (e.g., for ethylene glycol, isopropyl alcohol), metathesis (e.g., for methyl oleate), etherification (e.g., for MTBE, ETBE, TAME), and alkylation reactions (e.g., for cumene). 

Octolite 628. See Dilauryl thiodipropionate Octolite 647. See 2,2,4-Trimethyl-1,2-dihydroquinoline polymer Octolite 682. See Styrenated diphenylamine Octolite WL. See p-Cresol/dicyclopentadiene butylated reaction product Octomer DBM. See Dibutyl maleate Octomer DIBM. See Diisobutyl maleate Octomer DIOM. See Diisooctyl maleate Octomer DOM. See Dioctyl maleate Octopirox . See Piroctone olamine Octopoi NB-47. See Sodium di-n-butyl dithiocarbamate Octopoi SBZ-20. See Sodium dibenzyidithiocarbamate Octopoi SDB-50. See Sodium di-n-butyl dithiocarbamate Octopoi SDE-25. See Sodium diethyidithiocarbamate Octopoi SDM-40. See Sodium dimethyidithiocarbamate Octosol 449. See Potassium oleate Octosol 474. See Steartrimonium chloride Octosol 562] Octosol 571. See Laurtrimonium chloride... 

From Porter etal. (1994) oxidation of methyl oleate in hexane solution inititated with di-tert-butyl hyponitrite products analysed as the hydroxyoctadecenoates by normal phase HPLC. Co-oxidation of oleate with tert-butyl hydroperoxide produced only the W-cis, 9-trans,10-transand 8-cis in a ratio of 1 1.2 for ll-cis 9-trans and i-cis 0-trans products. 

As with oleate and linoleate, some volatile decomposition compounds are formed from linolenate hydroperoxides that cannot be explained by the classical A and B cleavage mechanisms, including acetaldehyde, butanal, 2-butyl furan, methyl heptanoate, 4,5-epoxyhepta-2-enal, methyl nonanoate, methyl 8-oxooctanoate, and methyl lO-oxo-8-decenoate. Some of these minor volatile oxidation products can be attributed to further oxidation of unsaturated aldehydes. Other factors contribute to the complexity of volatile products formed from hydroperoxides, including temperature of oxidation, metal catalysts, stability of volatile products and competing secondary reactions including dimerization, cyclization, epoxidation and dihydroperoxidation (Section E). 

Butanol is used to produce plasticizer-type esters like phthalates, phosphates, sebacates, oleates, and stearates. Two important ester derivatives, n-butyl acetate and n-butyl acrylate, used in the coating are produced from n-butanol. Glycol ether derivatives like ethylene glycol monobutyl ether (EB) used in the coating industry is the product of the n-butanol reaction with ethylene oxide in the presence of an acidic catalyst. Other important derivatives of n-butanol include butyl amines and butyl esters used as herbicides, butyl xanthate ore flotation aids, butylated urea, and melamine-formaldehyde resins. 

FIGURE 4.41 Relation between volume of air in froth and solubility products of hydro-phobic precipitates, (a) Metal butyl xanthogenates at 5 x 10 M in 30 mg dm commercial frother solution, (b) Metal oleates at 2 X 10 M in 10 mg dm commercial frother solution. (From Dudenkov, S.V., Tsvet. Metally, 40, 18, 1967, reproduced by permission of Primary Sources.)... 

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