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Chemicals, Novel Cyanoethylation, Nitrile Hydrogenation Technologies

Overview:

Manufacturers of specialty amines would benefit from practicing new catalytic cyanoethylation and hydrogenation processes that improve selectivity to desired products through improved catalysts and processes. The patented cyanoethylation options include new cycloaliphatic amine compositions of matter and processes where water and acids are used as catalysts to produce derivatives of vicinal diamines. The patented nitrile hydrogenation options include the use of lithium hydroxide to promote hydrogenation over Raney cobalt to produce primary amines, and the use of bimetallic catalysts comprising nickel or cobalt with rhodium, ruthenium, or palladium to produce secondary amines, and the use of an organic halide to promote hydrogenation that produces tertiary amines more selectively.

Benefits:

  • Improved selectivity to 1°, 2° and 3° amines
  • Excellent reaction times
  • Reduced catalyst levels due to higher activity of the catalysts
  • Increased time of operation between catalyst regeneration
  • Selectivity towards 1° helps to avoid 2° formation
  • Eliminates need for ammonia and its associated problems
  • Good yield for new composition of matter product
  • Little or no unwanted by-products
  • Ability to immediately hydrogenate polynitriles to polyamines without separation and/or purification of the products
  • Ability to produce N-(2-cyanoethyl) and N,N’-di-(2-cyanoethyl) vicinal cycloaliphatic diamines in high selectivity
  • Avoids recovery problems by eliminating the need for inorganic or organic promoters
  • Water-insoluble product is easily removed from the reaction medium
  • Excellent reaction rates
  • Production of cyanoacetals with higher product selectivity
  • Increased reactor utilization through high unsaturated nitrile concentration
  • Production process under mild conditions and catalyst level
  • Hydrogenation of cyanoalkylaldehyde alkyl acetal feed in presence of reaction contaminants without purification
  • Higher reactor utilization with significantly reduced reaction time and improved selectivity during hydrogenation.
  • Reductive amination of wide range of fatty nitriles with primary or secondary amine
  • Increased selectivity to secondary or tertiary amine in a single step reaction
  • Higher reactor throughput with increased feed conversion to product
  • Lower operating cost through improved catalyst life

IP Table

Title

Priority Patent Docket No.

Cyanoethylation of Cycloaliphatic Vicinal Primary Diamines US 6,245,932
Synthesis of New Polynitriles from Cycloaliphatic Vicinal Primary Amines US 6,472,553
Hydrogenation of Nitriles to Produce Amines US 5,869,653
Hydrogenation of Nitriles to Tertiary Amines US 5,672,762
Hydrogenation of Nitriles to Produce Amines US 5,574,189
Disproportionation of Amines to Produce Secondary Amines US 5,567,847
Process for Hydrogenation of Cyanopropionaldehyde-containing Cyanopropionaldehyde Acetals US 5,847,220
Selective Reductive Amination of Nitriles US 6,248,925
Selective Reductive Amination of Nitriles US 6,399,830

Availability:

Licenses are being offered. Other methods of collaboration are open for discussion. Technical assistance support during technology transfer is offered.

Novel Cyanoethylation and Nitrile Hydrogenation Technologies
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