Unusual dibasic acid spurs new research - C&EN Global Enterprise

Nov 6, 2010 - Publication Date: September 07, 1959 ... Inc., is one of the most intriguing materials to come out of the fatty acid field in quite some...
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s p e c t r o p h o f o m e f r i c a n a l y s i s d o e s n ' t tell the c o m p l e t e story of t h e u n i q u e a n d s t i l l e l u s i v e structure of d i m e r a c i d .

Unusual dibasic acid spurs n e w research Dimer acid, in constantly increasing production by Emery Industries, Inc., is one of the most intriguing materials to come out of the fatty acid field in quite some time. Already, dimer acid has inspired over 160 use patents in the realms of resins, polymers and polyesters. And, according to industry experts, these achievements just barely scratch the surface of the potential represented by dinner's unique structure, surprisingly low cost and ready availability. Empol 1022 is Emery's "standard" mixture of dimer and trimer acid, approximately 75% and 25% respectively. Although these proportions seem to meet most needs, other combinations within the limits of 95% dimer and 85% trimer are available on a development basis. Because of its 36 carbon atom structure, the molecular weight of 578 for dimer acid is very high compared to the range of 116 to 200 for the more common dibasic acids (maleic, phthalic, adipic, azelaic, s e b a e i c ) . Furthermore, contrary to what might be expected from its high molecular weight and the solid n a t u r e of o t h e r d i b a s i c s , d i m e r is a liquid. This combination of high molecular weight and liquid nature makes dimer acid an intriguing dibasic acid for new product research. Dinner's sister product, trimer acid, is even more a chemical anomaly. With three acid groups, 54 carbons and a molecular weight of about 845, trimer is

certainly a commercial rarity. And from the standpoint of research, the three acid groups suggest investigations in polymeric type reactions to form three dimension polymers of high bulk. Though the structure of the dibasic acid in Empol 1022 has not been definitely established, this formula represents its general nature. R1

HOOC-R-CH

R2

CH-R3-COOH

The shaded area represents an undetermined linkage which could be as simple as a single carbon-to-carbon bond or as complex as a cyclic structure. The R groups are probably straight-chain hydrocarbons, not necessarily of the same chain length. One or more of t h e s e groups may contain unsaturation. However, this unsaturation appears to be inhibited as indicated by the slower rate, or by the incompleteness of such reactions as hydrogénation, sulfation, a n d maleic anhydride condensations. And, this very inactivity makes dimer very stable and resistant to high temperatures. Thus far the greatest commercial utilization of Empol 1022 to date is based on reactions of the1 carboxyl groups as in most common dibasic acids. For example, in polyesters, polyamides, epoxy finishes, urethanes, elastomers, foams, alkyds and related products, the ability of dibasic acids to form polymeric products is of

prime importance. And, because of its unusual structure, dimer opens up unlimited opportunities to create entirely new materials; some of which will meet an existing need readily, and others, for which utility may have to be developed. Combined with alcohols and polyols, dimer produces interesting esters that may find use as plasticizers and hydraulic fluid additives. Since most of these are oily in nature, the potential of dimer esters in the lubrication and hyd r a u l i c fluid area w o u l d seem to b e limited only by the number of polyols available. In general, the utility of these esters is broadened by their high temperature stability, a property inherited from the dimer acid itself. Because dimer acid will react much the same as monobasic acids, such as oleic and stearic, it enlarges the possibilities for unique soaps, metallic soaps and condensation products. These areas of utility are but a few of the many that are showing increased research activity in dimer and trimer acids not only because of their unusual chemical structure but also because of an attractive price, in tankcars Empol 1022 sells for 26c per pound as compared to the approximate carload price of 69c for sebaeic, 40c for azelaic, 32c for adipic. Its liquid nature also permits the cost-reducing advantages of bulk storage and handling. Emery Industries will furnish samples on request. And, for additional information, you can write for the Emeryfacts titled "Empol 1022" and Technical Bulletin 412 containing abstracts of use patents. Write Emery Industries, Dept. 0.9. Carew Tower, Cincinnati 2, Ohio.