Neodecanoic acid

CARBOXYLICACIDS - BRANCHED-CHAINACIDS] pol5) Neodecanoic acid [26896-20-8]... 

Extraction by carboxyUc acids (qv) is carried out in a neutral or weaMy acidic medium. The most widely used carboxyUc acid is RR (CH2)CCOOH, where Rplus represents seven carbon atoms. Trade names are Versatic 10 (Shell Chemicals) and Neodecanoic acid (Exxon Chemicals). CarboxyUc acids can be used either in chloride or in nitrate media and have a better selectivity for light lanthanides than for heavy lanthanide separation. 

Highly Branched Acids. These acids, called neoacids, are produced from highly branched olefins, carbon monoxide, and an acid catalyst such as sulfuric acid, hydrogen fluoride, or boron trifluoride. 2,2,2-Trimethylacetic acid (pivaUc acid) is made from isobutylene and neodecanoic acid is produced from propylene trimer (see Carboxylic Acids, trialkylacetic acids). 

Branched-chain acids have a wide variety of industrial uses as paint driers (7), vinyl stabilizers (8), and cosmetic products (9). Cobalt and manganese salts of 2-ethyIhexanoic acid and neodecanoic acid are used as driers for paint, varnishes, and enamels litbium, magnesium, calcium, and aluminum salts of 2-ethyIhexanoic acid are used in the formation of greases and lubricants (see Driers and metallic soaps). Derivatives of isostearic acid have been used as pour point depressants in two-cycle engine oils, as textile lubricants, and in cosmetic formulations. Further industrial appHcations can be found (10). 

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. 

Physical Properties. The C q trialkylacetic acids, referred to as neodecanoic acid [26896-20-8] or as Versatic 10 [52627-73-3] are Hquids at room temperature. Typical physical properties for commercially available material are given in Table 2. These materials are typically mixtures of isomers, hence no stmctures are given throughout this section. 

Table 2. Physical Properties of Commercially Available Neodecanoic Acid ...

Chemical Properties. Like neopentanoic acid, neodecanoic acid, C2QH2QO2, undergoes reactions typical of carboxyHc acids. For example, neodecanoic acid is used to prepare acid chlorides, amides (76), and esters (7,11,77,78), and, like neopentanoic acid, is reduced to give alcohols and alkanes (21,24). One area of reaction chemistry that is different from the acids is the preparation of metal salts. Both neopentanoic acid and neodecanoic acid, like all carboxyHc acids, can form metal salts. However, in commercial appHcations, metal salt formation is much more important for neodecanoic acid than it is for neopentanoic acid. 

C0CI2 (aq) + 2Na(neodec) (org) Co(neodec)2 (org) + 2 NaCl (aq) where neodec = the anion of neodecanoic acid... 

In this method, a metal oxide or hydroxide is slurried in an organic solvent, neodecanoic acid is slowly added, and the mixture is refluxed to remove the water. Salts that are basic can be prepared by using less than stoichiometric amounts of acid. This method has been used in the preparation of metal salts of silver (80) and vanadium (81). The third method of preparation is similar to the fusion process, the difference is the use of finely divided metal as the starting material instead of the metal oxide or hydroxide. This method has been appHed to the preparation of cobalt neodecanoate (82). Salts of tin (83) and antimony (84) have been prepared by the fusion method, starting with lower carboxyHc acids, then replacing these acids with neodecanoic acid. 

Polymers, Resins, and Coatings. Peroxyesters of neodecanoic acid, such as / i -butylperoxyneodecanoate [26748-41-4] and a-cumyl peroxyneodecanoate [26748-47-0], constitute one of the most important uses for neodecanoic acid. These materials are used as free-radical initiators in the polymeri2ation of vinyl chloride (85), acrylates (86), ethylene (87), styrene [100-42-5] (87), and in the copolymeri2ation of vinyl chloride with other monomers, such as propylene [115-07-1] (88), or acrylates (89). The peroxyesters are also used as curing agents for resins (90). 

Metal salts of neodecanoic acid have also been used as catalysts in the preparation of polymers. For example, bismuth, calcium, barium, and 2kconium neodecanoates have been used as catalysts in the formation of polyurethane elastomers (91,92). Magnesium neodecanoate [57453-97-1] is one component of a catalyst system for the preparation of polyolefins (93) vanadium, cobalt, copper, or kon neodecanoates have been used as curing catalysts for conjugated-diene butyl elastomers (94). 

The metal salts of neodecanoic acid have found wide usage as driers for paints and inks (95,96). Metal neodecanoates that are used include silver (80), cobalt (82), and zirconium (79), along with lead, copper, manganese, and 2inc (see Driers and metallic soaps). 

Neodecanoic acid is also used as the carrier for metals in poly(vinyl chloride) heat stabilizers (qv). Metals used in this appHcation include barium, cadmium, and zinc. Tin as the neodecanoate salt has also been claimed as a heat stabilizer for maleic anhydride (97). 

Metal- Working and Hydraulic Fluids. In the preparation of fluids for metal-working and hydrauflcs, the trend has been to replace organic-based materials with aqueous-based materials. Neodecanoic acid has found apphcation in these newer fluids as a corrosion inhibitor and a viscosity improver. For example, neodecanoic acid is used in an aqueous hydrauflc fluid concentrate for corrosion inhibition and improved antiwear properties (101), in the preparation of a thickened aqueous hydrauflc fluid to reduce viscosity loss (102), and in a water-soluble metal working oil to reduce corrosion (103). In a similar vein, neodecanoic acid has been used in antifreeze concentrates for corrosion inhibition (104). 

Metal Extraction. As with other carboxyhc acids, neodecanoic acid can be used in the solvent extraction of metal ions from aqueous solutions. Recent appHcations include the extraction of zinc from river water for deterrnination by atomic absorption spectrophotometry (105), the coextraction of metals such as nickel, cobalt, and copper with iron (106), and the recovery of copper from ammoniacal leaching solutions (107). 

Fuels and Lubricants. Rare-earth neodecanoates have been claimed as additives for diesel fuels that reduce the precipitation of particles and gum (108). Neodecanoic acid has also been used in the preparation of ashless detergent additives for fuels and lubricants that reduce engine deposits in internal combustion engines (109). 

Miscellaneous Applications. Polyamides, prepared from polyamines and neodecanoic acid, are used as wash-cycle antistatic agents (qv)... 

Salts of neodecanoic acid have been used in the preparation of supported catalysts, such as silver neodecanoate for the preparation of ethylene oxide catalysts (119), and the nickel soap in the preparation of a hydrogenation catalyst (120). Metal neodecanoates, such as magnesium, lead, calcium, and zinc, are used to improve the adherence of plasticized poly(vinyl butyral) sheet to safety glass in car windshields (121). Platinum complexes using neodecanoic acid have been studied for antitumor activity (122). Neodecanoic acid and its esters are used in cosmetics as emoUients, emulsifiers, and solubilizers (77,123,124). Zinc or copper salts of neoacids are used as preservatives for wood (125). 

Glycidyl and Vinyl Esters. Glycidyl neodecanoate [26761-45-5] sold commercially as GLYDEXXN-10 (Exxon) or as CarduraElO (Shell), is prepared by the reaction of neodecanoic acid and epichl orohydrin under alkaline conditions, followed by purification. Physical properties of the commercially available material are given in Table 3. The material is a mobile Hquid monomer with a mild odor and is used primarily in coatings. Eor example, it is used as an intermediate for the production of a range of alkyd resins (qv) and acryHcs, and as a reactive diluent for epoxy resins (qv). 

Vinyl neodecanoate [26544-09-2] is prepared by the reaction of neodecanoic acid and acetjiene in the presence of a catalyst such as zinc neodecanoate. Physical properties of the commercially available material, VeoVa 10 from Shell, are given in Table 4. The material is a mobile Hquid with a typical mild ester odor used in a number of areas, primarily in coatings, but also in constmction, adhesives, cosmetics, and a number of misceUaneous areas. Copolymerization of vinyl neodecanoate with vinyl acetate gives coating materials with exceUent performance on alkaline substrates and in exterior weathering conditions. 

A monomeric (and anhydrous) neodecanoate (= NDH) was obtained from the ligand exchange reaction between hydrated neodymium(III) acetate Nd(0Ac)3(H20)6 and neodecanoic acid (Scheme 14). The coordination sphere of the large neodymium cation is saturated by an additional molecule of neodecanoic acid, as evidenced by MALDI-TOF mass spec-... 

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