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Diimide hydrogenation of emulsified unsaturated polymers

[Category : - Organic Chemistry]
[Viewed 321 times]

The diimide hydrogenation of unsaturated elastomers in latex utilizing hydrazine and hydrogen peroxide or oxygen, is a metal-catalyzed process. Copper ion has been found to be the most superior catalyst for this reaction, requiring an extremely low concentration for optimal results. Generated diimide efficiently hydrogenates the polymer olefinic unsaturation while generating water and nitrogen as byproducts. With a falling hydrazine concentration during the hydrogenation process however, a competing copper-catalyzed process capable of generating hydroxyl, superoxide and/or copper-oxyl radicals becomes increasingly competitive. The ability of these radical species to abstract hydrogen from the polymer backbone to generate polymeric radicals, ultimately results in crosslinking that occurs concurrently with hydrogenation. The concept of an OH radical inactivating ligand (OIL) complexed with copper is demonstrated to ameliorate the crosslinking reaction.

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This technology is useful for the hydrogenation of commercially available rubber latexes SBR (styrene butadiene rubber), PBD (polybutadiene rubber) and especially NBR (nitrile butadiene rubber). NBR latex can be converted into high value HNBR latex/rubber with greatly reduced or trace crosslinking with a thorough understanding of side reactions and the catalytic system. Although HNBR latex is currently a commercial product via a latex diimide reduction method, the latex rubber particles suffer from excessive crosslinking (gelation) making the dry rubber derived from it unprocessable. Commercial processable HNBR rubber is currently prepared by the costly conventional hydrogenation of an NBR rubber cement. Detailed comparison of the latex and solution hydrogenation methods show an ~50% cost reduction for the latex method. Current estimates for the global HNBR rubber market in 2023 range from 14-16 billion dollars. The high cost of HNBR rubber has limited its use and is a restraining factor that continues to restrict its market growth.

Patent publications:

US 11827723

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danek111 (United States)

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