Synthesis of caprolactam from lysine

Details Synthesis of caprolactam from lysine Synthesis of caprolactam from lysine

2011-07-12

2011-07-12

Gulakowski, Randy (Department: 1766)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From carboxylic acid or derivative thereof

C540S528000, C540S533000

Reexamination Certificate

active

07977450

ABSTRACT:
In various embodiments, the present invention can involve a method of synthesizing α-amino-ε-caprolactam. The method can comprise heating a salt of L-lysine in a solvent comprising an alcohol. In other embodiments, the present invention can involve methods for synthesizing ε-caprolactam. The methods can comprise heating a salt of L-lysine in a solvent comprising an alcohol and deaminating the reaction product. In various embodiments, the invention can include methods of converting biomass into nylon 6. The methods can comprise heating L-lysine in a solvent comprising an alcohol to produce α-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 can include methods of making nylon 6. The methods can comprise synthesizing ε-caprolactam and then polymerizing, wherein the ε-caprolactam is derived from L-lysine.

REFERENCES:
patent: 2142007 (1938-12-01), Schlack
patent: 2241321 (1941-05-01), Schlack
patent: 2979439 (1961-04-01), Kinoshita et al.
patent: 3018273 (1962-01-01), Butler et al.
patent: 3625923 (1971-12-01), Roberts
patent: 3687810 (1972-08-01), Kurihara et al.
patent: 3707441 (1972-12-01), Shiio et al.
patent: 3862262 (1975-01-01), Hendrick et al.
patent: 3871960 (1975-03-01), Kubota et al.
patent: 3925325 (1975-12-01), Heimsch et al.
patent: 3965375 (1976-06-01), Bergman, Jr. et al.
patent: 4022683 (1977-05-01), Bludis et al.
patent: 4031164 (1977-06-01), Hedrick et al.
patent: 4034015 (1977-07-01), Hedrick et al.
patent: RE30371 (1980-08-01), Hedrick et al.
patent: 4223112 (1980-09-01), Hedrick et al.
patent: 4275157 (1981-06-01), Tosaka et al.
patent: 4368115 (1983-01-01), Chianelli et al.
patent: 4411997 (1983-10-01), Shimazaki et al.
patent: 4465790 (1984-08-01), Quayle
patent: 4520021 (1985-05-01), Harris et al.
patent: 4601829 (1986-07-01), Kaneko et al.
patent: 4615742 (1986-10-01), Wright
patent: 4617090 (1986-10-01), Chum et al.
patent: 4623623 (1986-11-01), Nakanishi et al.
patent: 4692520 (1987-09-01), Van Geenen et al.
patent: 4706903 (1987-11-01), Brink et al.
patent: 4716142 (1987-12-01), Laine et al.
patent: 4739064 (1988-04-01), Shaw
patent: 4740487 (1988-04-01), Matheson et al.
patent: 4752579 (1988-06-01), Arena et al.
patent: 4787939 (1988-11-01), Barker et al.
patent: 4826819 (1989-05-01), Vecchietti et al.
patent: 4861722 (1989-08-01), Sano et al.
patent: 4908312 (1990-03-01), Ozaki et al.
patent: 4954441 (1990-09-01), Katsumata et al.
patent: 4959452 (1990-09-01), Meyer et al.
patent: 4963486 (1990-10-01), Hang
patent: 5032664 (1991-07-01), Frauendorf et al.
patent: 5047332 (1991-09-01), Chahal
patent: 5177009 (1993-01-01), Kampen
patent: 5221357 (1993-06-01), Brink
patent: 5236831 (1993-08-01), Katsumata et al.
patent: 5250423 (1993-10-01), Murakami et al.
patent: 5252199 (1993-10-01), Singhal et al.
patent: 5258300 (1993-11-01), Glassman et al.
patent: 5278121 (1994-01-01), Singhal et al.
patent: 5409600 (1995-04-01), Weissman et al.
patent: 5628830 (1997-05-01), Brink
patent: 5639744 (1997-06-01), Marchi et al.
patent: 5650304 (1997-07-01), Ishii et al.
patent: 5798237 (1998-08-01), Picataggio et al.
patent: 5807870 (1998-09-01), Anderson et al.
patent: 5840358 (1998-11-01), Höfler et al.
patent: 5855767 (1999-01-01), Powers et al.
patent: 5868851 (1999-02-01), Lightner
patent: 6022419 (2000-02-01), Torget et al.
patent: 6096885 (2000-08-01), Dezube et al.
patent: 6162351 (2000-12-01), Sudhakar et al.
patent: 6228177 (2001-05-01), Torget
patent: 6267874 (2001-07-01), Iijima et al.
patent: 6379934 (2002-04-01), Tilg et al.
patent: 6403844 (2002-06-01), Zhang et al.
patent: 6504047 (2003-01-01), Knaup
patent: 6610530 (2003-08-01), Blank et al.
patent: 6620292 (2003-09-01), Wingerson
patent: 6670156 (2003-12-01), Möckel et al.
patent: 6692578 (2004-02-01), Schmidt et al.
patent: 7112312 (2006-09-01), Chou
patent: 2001/0056184 (2001-12-01), Noda et al.
patent: 2006/0258638 (2006-11-01), Olson et al.
patent: 748253 (1938-06-01), None
patent: 1067153 (1967-05-01), None
patent: 59-76063 (1984-04-01), None
patent: H03-17062 (1991-01-01), None
patent: 03-176474 (1991-07-01), None
patent: 2003/145933 (2003-05-01), None
patent: 2003-206276 (2003-07-01), None
patent: 2005/123669 (2005-12-01), None
patent: 2007/017610 (2007-02-01), None
patent: 2007/101867 (2007-09-01), None
patent: 2008/103366 (2008-08-01), None
Belyaev, A novel synthetic route to enantiomers of E-hydroxynorleucine and E-chloronorleucine from L- and D,L-lysine, Tetrahedron Lett. 36(3):439-440 (1995).
Blade-Font, Facile synthesis of γ-, δ-, and ε-lactams by cyclodehydration of ω-amino acids on alumina or silical gel, Tetrahedron Lett. 21:2443-2446 (1980).
Doldouras et al., A direct, selective, and general method for reductive deamination of primary amines, J. Am. Chem. Soc. 100:341-342 (1978).
Egorova et al., On the role of β hydrogen atoms in the hydrodenitrogenation of 2-methylpyridine and 2-methylpiperidine, J. Catalysis 206:263-271 (2002).
Eijsbouts et al., Periodic trends in the hydrodenitrogenation activity of carbon-supported transition metal sulfide catalysts, J. Catalysis 109:217-220 (1988).
Goto et al., Synthesis of 2-amino-β-caprolactam by cyclodehydration of lysine in subcritical water, J. Chem. Eng. of Japan 37(2):353-356 (2004).
Guttieri et al., Selective cleavage of carbon-nitrogen bonds with platinum, J. Org. Chem. 49:2875-2880 (1984).
Ho, Hydrodenitrogenation catalysis, Catal. Rev. Sci. Eng. 30(1):117-160 (1988).
Kamm et al., Biorefinery—Systems, Chem. Biochem. Eng. Q. 18(1):1-6 (2004).
Ledoux et al., Hydrodenitrogenation activity and selectivity of well-dispersed transition metal sulfides of the second row on activated carbon, J. Catalysis 115:580-590 (1989).
Metelkina et al., Reaction of metal alkoxides with lysine: substitution of alkoxide ligands vs. lactam formation, Monatshefte für Chemie 134:1065-1069 (2003).
Mochida et al., An overview of hydrodesulfurization and hydrodenitrogenation, Japan Pet. Inst. 47(3):145-163 (2004).
Pellegata et al., An improved sysnthesis of γ-, δ-, and ε-lactams, Synthesis, 614-616 (1978).
Ramamurthy et al., An improved synthesis of carbon-14 labelled carboxylic acids from carbon-14 labelled amino acids, J. Labelled Compd. Rad. 25(8):809-814 (1988).
Rota et al., Role of hydrogenolysis and nucleophilic substitution in hydrodenitrogenation over sulfided NiMo/γ- AI2O3 , J. Catalysis 202:195-199 (2001).
Rota et al., Stereochemistry of hydrodenitrogenation: the mechanism of elimination of the amino group from cyclohexylamines over sulfided Ni-Mo/γ-AI2O3 catalysts, J. Catalysis 200:389-399 (2001).
Thomsen et al., Manufacturing of stabilised brown juice for L-lysine production—from university lab scale over pilot scale to industrial production, Chem. Biochem. Eng. Q. 18(1):37-46 (2004).
Vit et al., Simultaneous hydrodenitrogenation of pyridine and hydrodesulfurization of thiophene over carbon-supported platinum metal sulfides, J. Catalysis 119:1-7 (1989).
Zhang et al., Aqueous-phase hydrogenation of lactic acid to porpylene glycol, Appl. Catal. A-Gen. 219:89-98 (2001).
Zhang et al., Kinetics of aqueous hydrogenation of lactic acid to propylene glycol, Ind. Eng. Chem. Res. 41:691-696 (2002).
Zhao et al., Investigation of the mechanism of the hydrodenitrogenation of n-hexylamines over sulfided NiMo/γ-AI2O3, J. Catalysis 221:441-454 (2004).
Zhao et al., Mechanisms of the hydrodenitrogenation of alkylamines with secondary and tertiary α-carbon atoms on sulfided NiMo/AI2O3, J. Catalysis 222:532-544 (2004).
Zhao, Mechanisms of hydrodenitrogenation of amines over sulfided NiMo, CoMo, and Mo supported on AI2O3, (doctoral dissertation; Swiss Federal Institute of Technology, Zurich), http://e-collection.ethbib.ethz.ch/ecol-pool/diss/fulltext/eth15555.pdf (2004).
Angelucci, Luciano, et al., “Synthesis and amnesia-reversal activity of a series of 7- and 5-membered 3-acylamino

Affiliated with

Also associated with

Rating

Synthesis of caprolactam from lysine does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of caprolactam from lysine, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of caprolactam from lysine will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2623232