Butyl ester of fatty acid

BUTYL ESTERS OF FATTY ACIDS EXTRACTED FROM AGED BEVERAGE BRANDY [. o ... 

Synthesis of methyl and butyl esters of fatty acids through transesterification of triglycerides... 

Synonyms methyl ester of fatty acid butyl ester of fatty acid propyl ester of fatty acid glyceryl... 

Only a few natural sources of fatty alcohols were known at this time. Production on a technical scale could be first realized by the reduction of methyl or butyl esters of fatty acids with metallic sodium after the Bouveault-Blanc process. Nearly simultaneously, the high-pressure hydrogenation of fatty acids to the resulting alcohols was developed by Schrauth. Hence, fatty alcohols were soon available on the market in a price range that made it possible to produce fatty alcohol sulfates for use in detergents. 

The methyl, ethyl, propyl, Ao-propyl, -butyl, and iso-butyl esters of fatty acids are recommended. 

Ulberth, R, R.C. Cabernig, and F. Schrammel. Flame-Ionization Detector Response to Methyl, Ethyl, Propyl, and Butyl Esters of Fatty Acids,263—266 (1999). 

MethElute, Pierce Chemical Co.), or methanol/NA -dicyclohexylcarbodi-imide (Felder et ai, 1973) are to be recommended as a substitute for diazomethane. The dime thy Iformamide dialkyl acetals are particularly applicable to the preparation of methyl, ethyl, propyl and n-butyl esters of fatty acids. They have not, however, been studied extensively with a wide range of acids with multiple functional groups and care should be taken to examine their reactions with the pure acids of interest before application to biological extracts. With amino acids they form A -dimethylaminomethylene alkyl esters (Thenot and Horning, 1972), for example. 

Ethylcellulose is compatible with the following plasticizers dibutyl phthalate diethyl phthalate dibutyl sebacate triethyl citrate tributyl citrate acetylated monoglyceride acetyl tributyl citrate triacetin dimethyl phthalate benzyl benzoate butyl and glycol esters of fatty acids refined mineral oils oleic acid stearic acid ethyl alcohol stearyl alcohol castor oil corn oil and camphor. 

Esters constituted the largest family and included acetates (ethyl, propyl, isobutyl, butyl, isoamyl, and phenethyl), ethyl esters of fatty acids (propanoate, isobutanoate, butanoate, hexanoate, octanoate, 3-hydroxybutanoate, 3-hydroxyhexanoate and furcate), ethyl esters of organic acids (pyruvate, lactate, ethyl myristate, diethyl malate and, mono- and diethyl succinate) and various other esters, such as methyl butanoate, isobutyl lactate and phenylethyl octanoate. The acids quantified included isobutanoic, butanoic, hexanoic, octanoic, decanoic, lauiic and 3-methylbutanoic. The lactones included y-butyrolactone, pantolactone, y-decalactone and E- and Z-oak lactone and the terpenes included neral d-terpineol, P-dtronellol and Z-nerolidol. The aldehyde family comprised acetaldehyde, benzaldehyde, furfural, 5-methylfurfural and octanal, and the phenol family included eugenol, 4-ethylphenol and 4-ethylguaiacol. Finally, 1,1-diethoxyethane, acetoin, sotolon, 2, 3-butanedione, p-cymene and methionol were also determined. 

A limitation of external plasticizers of this kind is that they may eventually be lost by evaporation or by migration into the substrate, leaving an imperfect and brittle film. This limitation may be overcome by the use of copolymers and these are now widely used in surface coatings and other applications. Comonomers which may be employed for this purpose include butyl acrylate, 2-ethylhexyl acrylate, diethyl fumarate, diethyl maleate and vinyl esters of fatty acids (e.g. a branched Cio fatty acid). Typically, the copolymers contain 15-20% by weight of such comonomers. These copolymers are readily prepared by the emulsion polymerization techniques described previously for the homopolymer. 

In hot rolling of aluminum (down to a thickness of 1 cm), emulsions are in use that contain oil, anionic or nonionic emulsifiers and active rolling ingredients (fatty acid derivatives). Subsequent cold rolling (to a thickness of 0.5 mm) is accomplished with the aid of oils that contain 2-7% of - lauryl alcohol or 1-4% butyl ester of ->palmitic acid. Cold rolling of other metals requires oils that contain 10-15% fatty acids and EP-additives (- lubricants). 

Esterification is one of the most important reactions of fatty acids (25). Several types of esters are produced including those resulting from reaction with monohydric alcohols, polyhydric alcohols, ethylene or propylene oxide, and acetjiene or vinyl acetate. The principal monohydric alcohols used are methyl, ethyl, propyl, isopropyl, butyl, and isobutyl alcohols (26) (see Esterification Esters, organic). 

Iverson and Sheppard (1977) have compared the method above, substituting sodium butoxide for sodium methoxide to H2S04 and boron trifluoride-catalyzed butyrolyses. Butyl esters were used by these and other investigators to improve the resolution of short chain esters and to reduce their volatility. They recommend the boron trifluoride method for preparation of butyl esters of milk fatty acids, although the other catalysts gave satisfactory results. Analysis of methyl esters resulted in lower values for the short chain fatty acids. 

The number of fatty acids and related compounds in milk lipids grew from 16 in 1959 (Jenness and Patton, 1959) to 142 in 1967 (Jensen et al. 1967) to over 400 in 1983. However, there are only 10 fatty acids of quantitative importance. The amounts (weight percent) as butyl esters prepared by three methods of esterification were determined by Iverson and Sheppard (1977). Because of the widely differing molecular weights of the fatty acids (4 0-18 0), fatty acid compositions of ruminant milk fats are often presented as a mole percent. The nutritionist needs the data calculated in yet another manner weight of fatty acid/100 g or 100 ml of edible portion. Analyses of food fatty acids should always be accompanied by the fat content so that the actual weights of the fatty acids and be calculated. A compilation of this type was made by Posati et al. (1975). Since these analyses were done with methyl esters, the contents of 4 0 are low. Data from Feeley et al. (1975), obtained from careful analyses, are more reliable, and USDA Handbook 8-1 (Posati and Orr 1976) has data for many milk and dairy products. 

Iverson, J. L. and Sheppard, A. J. 1977. Butyl ester preparation for gas-liquid chromatographic determination of fatty acids in butter. J. Assn. Off. Anal. Chem. 60, 284-288. 

Fig. 20 RP-HPLC of n-butyl esters of long-chain fatty acids derived from sardine oil. Identified fatty acid n-butyl esters in order of their elution 1. C20 5a>3 2. 04 0 3. 06 la>7 4. C22 6 >3 5. 08 2 >6 6. 06 0 7. 08 I

Iverson, J.L. and Sheppard, A.J. (1986) Determination of fatty acids in butter fat using temperature-programmed gas chromatography of the butyl esters. Food Chem., 21, 223-234. 

Plasticizers. These materials are added to reduce the hardness of the compound and can reduce the viscosity of the uncured compound to facilitate processes such as mixing and extruding. The most common materials are petroleum-based oils, esters, and fatty acids. Critical properties of these materials are their compatibility with the rubber and their viscosity. Failure to obtain sufficient compatibility will cause the plasticizer to diffuse out of the compound. The oils are classified as aromatic, naphthenic, or paraffinic according to their components. Aromatic oils will be more compatible with styrene-butadiene rubber than paraffinic oils, whereas the inverse will be true for butyl rubber. The aromatic oils are dark colored and thus cannot be used where color is critical, as in the white sidewall of a tire. The naphthenic and paraffinic oils can be colorless and are referred to as nonstaining. 

Butyl ester of ethylene/MA copolymer (INCI). See Ethylene/MA copolymer, butyl ester Butyl ester of PVM/MA copolymer (INCI). See PVM/MA copolymer, butyl ester Butyl ester of tall oil fatty acids. See Butyl tall ate... 

CAS 67762-63-4 EINECS/ELINCS 267-028-5 Synonyms Butyl ester of tall oil fatty acids ... 

Definition n-Butyl ester of tall oil fatty acids Properties Sol. in hexane, toluene insol. in water, propylene glycol dens. 0.870 b.p. 201-216 C flash pt. > 109 C ref. index 1.4590 Toxicology May be harmful by inh., ing., or skin absorption may cause eye/skin irritation may be irritating to mucous membranes and upper respiratory tract TSCA listed Precaution Incompat. with strong oxidizing agents... 

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