Ethylhexanoic acid

Sta.nnous2-Ethylhexa.noa.te, Stannous 2-ethyIhexanoate, Sn(CgH 302)2 (sometimes referred to as stannous octanoate, mol wt 405.1, sp gr 1.26), is a clear, very light yellow, and somewhat viscous Hquid that is soluble in most organic solvents and in siHcone oils (166). It is prepared by the reaction of stannous chloride or oxide with 2-ethylhexanoic acid. 

Ethylhexanal, the reduced aldol condensation product of //-butyraldehyde, is converted into 2-ethylhexanoic acid [149-57-5] which is converted primarily into salts or metal soaps. These are used as paint driers and heat stabili2ers for poly(vinyl chloride). 

Butyric acid is made by air-oxidation of butyraldehyde, which is obtained by appHcation of the oxo synthesis to propylene. Isobutyric acid is made from isobutyraldehyde, a significant product in the synthesis of butyraldehyde (see Butyraldehydes). Butyraldehyde is also used to make 2-ethylhexanoic acid. 

Octoates were the next drier development. Because these driers are produced from synthetic 2-ethylhexanoic acid, the chemical composition can be controlled and uniformity assured. Also, other synthetic acids, eg, isononanoic and neodecanoic, became available and are used for metal soap production. Compared to naphthenic acid, these synthetic acids have high acid values, are more uniform, lighter in color, and do not have its characteristic odor. It is also possible to produce metal soaps with much higher metal content by using synthetic acids. 

Pd(Ph3P)4, 2-ethylhexanoic acid or barbituric acid (THF, 3 h, 93% yield). Tributylstannane can serve as an allyl scavenger. ... 

Figure 15.11 (a) Total ion clnomatogram of a Grob test mixture obtained on an Rtx-1701 column, and (b) re-injection of the entire clnomatogram on to an Rtx-5 column. Peak identification is as follows a, 2,3-butanediol b, decane c, undecane d, 1-octanol e, nonanal f, 2,6-dimethylphenol g, 2-ethylhexanoic acid h, 2,6-dimethylaniline i, decanoic acid methyl ester ], dicyclohexylamine k, undecanoic acid, methyl ester 1, dodecanoic acid, methyl ester. Adapted from Journal of High Resolution Chromatography, 21, M. J. Tomlinson and C. L. Wilkins, Evaluation of a semi-automated multidimensional gas chromatography-infrared-mass specti ometry system for initant analysis , pp. 347-354, 1998, with permission from Wiley-VCH. 

Figura 2.9 Dse of th Grob test Mixture to compare tbe activity of various glass surfaces coated with ov-ioi. Surface types A > Untreated pyrex glass, B pyrex glass deactivated by thermal degradation of Ceurbowax 20M, C < SCOT column, prepared with Silanox 101, D pyrex glass column coated with a layer of barium carbonate and deactivated as in (B), and E - untreated fused silica. Components are identified in Table 2.7 with ac - 2-ethylhexanoic acid. (Reproduced with permission from ref. 152. Copyright Elsevier Scientific Publishing Co.)...

In the reaction of heptafluorobutyrylimidazole with a carboxylic acid such as 2-ethylhexanoic acid, the imidazole group is exchanged quantitatively. 

This azole transfer has been used for expedient gas chromatographic determination of 2-ethylhexanoic acid.[34]... 

Ethylenimine, 30, 38 toxic properties of, 30, 40 Ethyl o-ethoxybenzoate, 32, 75 Ethyl formate, 32, 32 Ethyl glycidyl ether, 31, 3 2-Ethylhexanaldoxime, 32, 67 2-Ethylhexanamide, 32, 65 2-Ethylhexanoic acid, 32, 66 2-Ethylhexanonitrile, 32, 65 Ethylidene bromide, 32, 55 Ethyl iodide, 31, 34 Ethyl isodehydroacetate, 32, 76 Ethyl lactate, 31, 59, 60 5-ETHYL-2-METHYLPYRIDINE, 30, 41 Ethyl orthocarbonate, 32, 68 Ethyl orthoformate, 32, 5 Ethyl orthosilicate, 32, 5 Ethyl phenylazoacetoacetate, 32, 85 Ethyl phenylcyanoacetate, 30,43,80 Ethyl 0-phenyl-/3-cyanopropionate, 30, 84... 

These Rh-containing phases are mixed with NaOH and 2-ethylhexanoic acid and subsequently oxidized with air, H202, or other oxidizing agents. The Rh compounds in phase 1 and 2 are thus converted to Rh 2-ethylhexanoate and are extracted in a crossflow manner by means of 2-ethylhexanol. The recovery rate of rhodium is 97-98%. The residual water phase ends up in the fraction for external work-up as described above. 

Fig. 14.8. Chromatogram and mass spectrum showing typical GC/MS data. The mass spectrum shown was obtained from the peak indicated with the arrow. Peak identification ldecane, 2 = 1-octanol, 3 = 2,6-dimethylphenol, 4 = 2-ethylhexanoic acid, 5 = 2,3-dimethylaniline, 6 = dodecane, 7 = decanoic acid, methyl ester, 8 = dicyclohexyl amine, 9 = undecanoic acid, methyl ester, 10-dodecanoic acid, methyl ester.

A number of organic compounds, such as N, N-dimethylaniline-present in amoxycillin trihydrate cephalexin cloxacillin sodium dicloxacillin sodium 2-ethylhexanoic acid-in amoxycillin sodium 4-chlorophenol-in clofibrate acetone and butanol-in daunorubacin hydrochloride cineole limonene ratio-in dementholised mint oil etc ... 

The hyperbranched polyesteramides described above can also easily be functionalized by esterification with various mono carboxylic acids like acetic acid, benzoic acid, 2-ethylhexanoic acid, stearic acid, (un)satuxated fatty acids, or (meth)acrylic acid. With the exception of the latter mentioned acids, which give highly temperature sensitive products, the synthesis of these functionalized hyperbranched polyesteramides can be performed in two different ways ... 

Figure 20. Simultaneous enantiomer separation of various classes of compounds ( Schurig test mixture 184) on CP-Cyclodextrin-/3-2,3,6-M-19 (permethylatcd /3-cyclodextrin in OV-1701) [25 m x 0.25 mm (i.d.) column, 70°C for 5 min followed by 3cC/miu, 0.65 bar hydrogen]143. 1+2 2,6,6-trimethylbicy-clo[3.1.1]hept-2-ene (x-pinene), 3 ( + )-(lJR)-//ms-2,6,6-trimethylbicyclo[3.1. l]heptane (pinane), 4 (-)-(lS )-fra/M-pinanc. 5 (-)-(lS)-fw-pinane, 6 ( + )-(l/J)-cw-pinane, 7 + 8 2,3-butancdiol. 9 meso-2,3-butanediol, 10 + 11 tetrahydro-5-methyl-2-furanone (y-valerolactone). 12 + 13 1-phenylethanaminc. 14 + 15 1-phenylethanol, 16 + 17 2-ethylhexanoic acid.

The 2-ethylhexanamide was prepared in 86-88% yield from technical 2-ethylhexanoic acid (Carbide and Carbon Chemicals Corporation) by a method similar to that described previously,2 except that the crude amide was filtered directly from the reaction mixture, washed well with water, and dried. The resulting product, which melted at 99-101°, was used without further purification. If the pure amide is desired, this product may be recrystallized (with 83-90% recovery) from 50% ethanol. For 100 g. of amide, 2 1. of 50% ethanol is used, and the hot solution is decolorized with charcoal. The product thus obtained is in the form of white needles which melt at 102-103°. 

CH2 CH.OOC.CH(C2H5).C4H9 mw 170.25 liq, sp gr 0.8751 at 20/20° fr p -90°, bp 185.2°, fl p 165°F insol in w. It can be prepd from acetylene, 2-ethylhexanoic acid, zinc oxide and Raney nickel heated under pressure. Used in polymers and emulsi-fying paints... 

Di(2-ethylhexyl) phthalate-induced hepatic peroxisome proliferation in rodents is not due to the parent diester per se, but rather to its metabolites. With mono(2-ethyl-hexyl) phthalate, the two proximate peroxisome proliferators were found to be the (co-l)-hydroxy (IX) and keto (VI) metabolites, while for 2-ethylhexanol the proximate peroxisome proliferator was 2-ethylhexanoic acid (Mitchell et al., 1985 Elcombe Mitchell, 1986 Cornu etal, 1992 Lewis Lake, 1993). 

Peroxisome proliferators have also been shown to induce replicative DNA synthesis in cultured rodent hepatocytes (lARC, 1995). In contrast, several peroxisome proliferators have failed to induce replicative DNA s mthesis in human hepatocyte cultures (Doull et al., 1999). Hepatocytes were isolated from male Wistar-derived rats and from three human liver samples (liver transplantation donors) and treated with 2-ethylhexanoic acid and some other peroxisome proliferators for 72 h (Elcombe et al, 1996). While 2-ethylhexanoic acid induced replicative DNA s5mthesis in cultured rat hepatocytes, no effect was observed in human hepatocytes. Hepatocytes were isolated from male Fischer 344 rats and three humans and treated in culture with 250-2000 pM mono(2-ethylhexyl) phthalate (Hasmall et al, 1999). Increased peroxisomal (O-oxi-dation (at 250-750 pM), replicative DNA s mthesis (at 500-1000 pM), and inhibition of apoptosis (at 250-1000 pM) were observed in rat hepatocytes. None of these parameters was affected by mono(2-ethylhexyl) phthalate in human hepatocytes. 

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