Heteroatom-stabilized carbenes and precursors thereto as...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S215000, C548S316700, C558S080000

Reexamination Certificate

active

07053221

ABSTRACT:
A method is provided for carrying out depolymerization of a polymer containing electrophilic linkages in the presence of a catalyst and a nucleophilic reagent, wherein production of undesirable byproducts resulting from polymer degradation is minimized. The reaction can be carried out at a temperature of 80° C. or less, and generally involves the use of an organic, nonmetallic catalyst, thereby ensuring that the depolymerization product(s) are substantially free of metal contaminants. In an exemplary depolymerization method, the catalyst is a carbene compound such as an N-heterocyclic carbene, or is a precursor to a carbene compound. The method provides an important alternative to current recycling techniques such as those used in the degradation of polyesters, polyamides, and the like.

REFERENCES:
patent: 6080826 (2000-06-01), Grubbs et al.
patent: 6111121 (2000-08-01), Grubbs et al.
“DuPont™ Tyzor® Organic Titanates, Technical Note—Polyesterification Catalyst,” DuPont technical data sheet (2001).
“DuPont™ TYZOR® Organic Titanates, Technical Note—Transesterification,” DuPont technical data sheet (2001).
Bourissou et al. (2000), “Stable Carbenes,”Chemical Reviews100(1):39-91.
Mancini et al. (1999), “Recyclability of Pet from Virgin Resin,”Materials Research2(1):33-38.
Nadkarni (1999), “Polyester Waste Recycling: Sources, Processing Methods and End Uses,”International Fiber Journal14(3), printed from http://www.fiberjournal.com/issue/june99/polyester.html.
Nyce et al. (2002), “Expanding the Catalytic Activity of Nucleophilic N-Heterocyclic Carbenes for Transesterification Reactions,”Organic Letters4(21):3587-3590.
Sako et al. (1997), “Depolymerization of Polyethylene Terephthalate to Monomers with Supercritical Methanol,”Proc. of the 4thInternational Symposium on Supercritical Fluids, pp. 107-110 (abstract only).

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