August 8, 2011

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The following patent record is from the CAplusSM database.

CAPLUS COPYRIGHT 2011 ACS

Patent Number: US 7977450
Title: Synthesis of caprolactam from lysine
Inventor(s): Frost, John W.
Patent Assignee(s): Board of Trustees of Michigan State University, USA
Source: PCT Int. Appl., 28 pp. CODEN: PIXXD2
Language: English

Abstract:
In various embodiments, the present invention involves a method of synthesizing a-amino-ε-caprolactam. The method comprises heating a salt of L-lysine in a solvent comprising an alc. In other embodiments, the present invention involves methods for synthesizing ε-caprolactam. The methods comprise heating a salt of L-lysine in a solvent comprising an alc. and deaminating the reaction product. In various embodiments, the invention includes methods of converting biomass into nylon 6. The methods comprise heating L-lysine in a solvent comprising an alc. to produce a-amino-ε-caprolactam, deaminating to produce ε-caprolactam and polymerizing into nylon 6, wherein the L-lysine is derived from the biomass. In other embodiments, the present invention includes methods of making nylon 6. The methods comprise synthesizing ε-caprolactam and then polymerizing, wherein the ε-caprolactam is derived from L-lysine. Thus, heating a mixture of L-lysine HCl salt and NaOH in hexanol with removal of water gave, after workup and treatment with HCl, a-amino-ε-caprolactam HCl salt in 75% yield. A mixture of a-amino-ε-caprolactam, KOH, and NH2OSO3H was heated at 70 degrees C to 75 degrees C to give ε-caprolactam in 75% yield.

View the full-text U.S. patent from USPTO.

 

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