Carbonylation sebacic acid

An attractive alternative to building a world scale adipic acid plant is to construct a specialty smaller volume oxycarbonylation plant which is capable of exclusively producing the more valuable precursors for pelargonic and sebacic acid. Oxycarbonylation process conditions can be controlled to give methyl, 4-pentadienoate which is the product from butadiene mono-carbonylation(39,40). Methyl, 4-pentadienoate can react in a subsequent step with butadiene to give an unsaturated pelargonic acid precursor in high yield(41). Methyl, 4-pentadienoate... 

To understand how to control process conditions to give methyl, 4-pentadienoate, the reaction mechanism must be examined. (See Equation 2.). -palladium hydride elimination from 4 gives rise to trans and cis-methyl penta-, 4-dienoate which is the desired monocarbonylation intermediate for sebacic acid. The desired mono-carbonylation reaction is promoted by low carbon monoxide pressure ( 1000 psig) while high pressure (1800 psig) gives excellent 1,4-dicarbonylation product yield. The mono-carbonylation reaction is also facilitated by using a Lewis Acid as a co-catalyst and iodide as the preferred palladium counter-ion (Table III.). Chloride is the preferred palladium counter-ion for 1,4-dicarbonylation. 

A commercially attractive palladium catalyzed oxidative carbonylation route to adipic and sebacic acid has been developed which uses butadiene and the elements of synthesis gas as the raw... 

Fourier-Transform Raman Spectroscopy (FTR) was used to characterize a homologous series of aliphatic poly(anhydrides), poly(carboxyphenoxy)al-kanes, and copolymers of carboxyphenoxy propane (CPP) and sebacic acid. All anhydrides show two diagnostic carbonyl bands, the aliphatic polymers has the carbonyl pairing at 1803/1739 cm 1, and the aromatic polymers have the band pair at 1764 and 1712 cm -1. All the homo- and copolymers showed methylene bands due to deformation, stretching, rocking and twisting the spectra for the... 

The ester acids may also be converted to ester acid chlorides and then by reaction with sodium azide to ester azides. By these steps 3,4-dichloro-6-carbethoxypyrrole-2-carbonyl chloride" and sebacic ethyl ester chloride have been converted to the corresponding ester azides, which were then rearranged l-carbethoxyheneicosane-21-car-bonyl chloride has been converted to -aminobehenic acid in 66% yield. ... 

---