Versatic acid

Versatic acid Versatic Acids Versa TL Versed... 

Trialkylacetic acids have been produced commercially siace the early 1960s, ia the United States by Exxon and ia Europe by Shell, and have been marketed as neo acids (Exxon) or as Versatic Acids (Shell). The principal commercial products are the acid and the C q acid (neodecanoic acid, or Versatic 10), although smaller quantities of other carbon numbers, such as C, C, and C, are also produced. 

Fig. 2. Flow sheet of Shell Versatic Acid unit (33).

Low-molecular-weight extractants can generally be expected to have uneconomic solubilities in most systems, but where high salt concentrations prevail, the solubility may be substantially lower and may be economic. This has been shown to be true for naphthenic and Versatic acids, which have high solubilities in water but appear to be economically useful when used in high ammonium sulfate liquors, such as those produced in the Sherritt-Gordon process for the extraction of cobalt and separation from nickel [12]. 

Problems associated with this flow sheet include cross contamination of the organic phases and aqueous solubility losses of the Versatic acid. 

Both carboxylic (e.g., Versatic acid) and organophosphorus acids have been used commercially to extract the lanthanides. The extraction follows the formation of the metal-extractant complex [Eq. (11.21)] and so depends on the pH of the feed. 

Versatic acid vinyl esters Vinyl ethers N-Vinylpyrrolidone Vinyl chloride Vinylidene chloride Semicrystalline polymers (2)... 

Versatic acid has been used in Japan to recover indium and gallium from solutions obtained from the leaching of bauxites, zinc minerals, coal ash and flue dusts.40 41-63 Extraction is carried out at a pH value of 2.5 to 4.0 some coextraction of tin(II), iron(III) and aluminum(III) occurs if these metals are present. In the extraction of indium(III) by n-hexanoic acid,64 the predominant species in the organic phase was found to be InA3(HA)3 whereas in the extraction by n-decanoic acid65 the existence of trimeric (InA3-HA)3 and hexameric [InA2(OH)]g species was also postulated. 

Moyer, B.A., McDowell, W.J., Ontko, R.J., Bryan, S.A., Case, G.N. Complexation of strontium in the synergistic extraction system dicyclohexano-18-crown-6, versatic acid, carbon tetrachloride. Solvent Extr. Ion Exch. (1986), 4(1), 83-93. 

Distribution data for the extraction of Ni2+ by Versatic acid (Table 1) are consistent with a generalized reaction, [73, 74]... 

M-hexane or hexyl hexaisobutyl alumoxane high-impact polystyrene hexamethylphosphoric acid triamide versatic acid... 

Quirk et al. studied the impact of excess versatic acid [191]. According to this study an excess of versatic acid nexcess acid/ Nd > 0.22 reduces monomer conversion at a fixed polymerization time (1 h) and leads to an increase in Mw as well as PDI and has no effect on cis- 1,4-contents (Table 17). 

Table 17 Influence of excess versatic acid in the BD polymerization with the catalyst system NdV/DIBAH/EASC [191], reprinted with permission from Elsevier...

These studies on the influence of water and carboxylic acids show that Nd-based catalyst systems are relatively robust to water and excess versatic acid. From an industrial point of view this is an extremely important aspect. 

In large-scale production the presence of impurities cannot be avoided. Impurities are brought into the system as byproducts of the raw materials monomers, solvents, catalyst components, additives etc. The presence of impurities in monomers and solvents is mainly due to insufficient removal of moisture in their recycling. The most important byproducts of Nd carboxy-lates (dissolved in an organic solvent) are Nd compounds such as Nd oxide, Nd hydroxide, carboxylic acids, e.g. versatic acid which can be present in NdV, and water. The impact of some of these relevant impurities is mainly available from scientific reports. The according literature is summarized in Sect. 2.1.8. 

HV = versatic acid NdV HV is equivalent with NdHV4 in literature given by Kwag et al. NdV HV is also referred to as NDV4 = NdHV4... 

Tihe use of Versatic acids as the base material to manufacture alkyd resins was described a few years ago (2, 4, 5, 6, 7, 12, 15, 16, 17). These acids are prepared by the acid-catalyzed reaction between olefins, carbon monoxide, and water. Owing to rearrangements in the intermediate carbonium ion, they are nearly all trialkylacetic acids, of which one alkyl group is invariably methyl. 

They include vinyl acetate homopolymers and all copolymers in which vinyl acetate is the major constituent (50% or greater). The major PVAc copolymers are vinyl acetate-ethylene (VAE) and vinyl acetate-acrylic ester (vinyl acrylic). Vinyl acetate-versatic acid (vinyl versatate) and vinyl acetate- maleate are major PVAc copolymer emulsions used. 

Propa, Propanoic acid Buta, butanoic acid Penta, pentanoic acid Hexa, hexanoic acid Hepta, heptanoic acid Octa, octanoic acid Nona, nonanoic acid Deca, decanoic acid Pal, palmitic acid St, stearic acid Piva, trimethylacetic acid Vers, Versatic acid a-BrHexa, a-bromohexanoic acid x-BrSt, a-bromostearic acid Me2(OH)Hexa, 2,5-dimethyl-2-hydroxyhexanoic acid a,a -DAC, a,a -dialkylcarboxylic acid Naph, naphthenic acid cy-PA, cyclopentylacetic acid cy-Hexa, cyclohexanecarhoxylic acid C7-C mix, C7-C9 mixture CB, chlorobenzene cy-Hexn, cyclohexane 1,2-DCE, 1,2-dichloro-ethane (i-Pr)2CO, diisopropyl ketone i-amOAc, isoamyl acetate i-amOH, isoamyl alcohol MIBK, 4-methyl-2-pentanone NB, nitrobenzene n-Hexn, n-hexane PE, petroleum ether TCB, 1,2,4-trichlorobenzene. 

Alternative processes include the vinyl esters cf "Versatic acid" (shell Chemicals), with vinyl acetate and acrylamide (49 49 2), which are added gradually after conversion to a pre-emulsion, to an anionic surfactant solution containing a persulfate. Transt parent waterproof films are formed. 

Nakamura, S., Ohashi, S., and Akiba, K., Permeation behaviour of europium through versatic acid liquid membrane. Sep. Sci. Tech., 1992, 27 741-752. 

Koch carbonylations use strong acid catalysts to react olefins with carbon monoxide and water to form branched isomers of carboxylic acids. Neo acids produced by Exxon Chemical and Versatic acids produced by Shell Chemical are examples of commercial processes utilizing Koch carbonylation chemistry [9]. 

Exxon is the only producer of neo acids in the United States and Shell is the sole producer in Western Europe. Shell markets neo acids under the trade name Versatic Acids. 

Shell produces C, to C, carboxylic acids marketed under the trade name Versatic acids. Exxon carbonylates propylene oligomers to produce neo acids. The derivatives and markets for these products are described in this chapter under the section on oxo chemicals. 

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