E.I. Dupont De Nemours & Co. v. Synvina C.V.
904 F.3d 996
Fed. Cir.2018Background
- The ’921 patent (Synvina, formerly Furanix) claims a method to oxidize HMF or derivatives to FDCA using Co/Mn/Br catalysts in acetic acid at 140–200°C and O2 partial pressure (PO2) of 1–10 bar; dependent claims narrow catalyst, reactant, and temperature (e.g., 160–190°C).
- Prior art (WO 01/72732, RU-448177, and US 2008/0103318) taught oxidation of HMF/derivatives to FDCA with substantial overlap in solvents, catalysts, temperatures, and PO2 ranges (some references preferred acetic acid and Co/Mn/Br catalysts; one reported very high yields using different catalyst/solvent).
- DuPont petitioned for IPR and prevailed on institution of review for claims 1–5 and 7–9; the PTAB found DuPont failed to prove obviousness, relying in part on (1) no showing that temperature and PO2 were result-effective variables and (2) weak proof of unexpected results.
- DuPont appealed; Synvina challenged standing. The Federal Circuit held DuPont had Article III standing because DuPont/ADM operated a demonstration plant using overlapping conditions and Synvina refused a covenant not to sue.
- On the merits, the Federal Circuit reversed the Board: it held the Board applied the wrong legal standard for overlapping ranges and result-effective variables, found temperature and PO2 were result-effective, and concluded claims 1–5 and 7–9 would have been obvious in view of the prior art.
Issues
| Issue | DuPont's Argument | Synvina's Argument | Held |
|---|---|---|---|
| Standing to appeal IPR | DuPont faced a substantial risk of infringement liability because it built and operated a demonstration plant using overlapping claimed conditions and Synvina refused a covenant not to sue | No actual or imminent injury; only speculative future harm because no infringement suit was filed | DuPont has Article III standing (plant operations, competitive context, Synvina’s conduct gave realistic risk) — appeal proceeds |
| Burden-shifting/overlapping ranges | Overlapping prior-art ranges create a presumption of obviousness and shift the burden of production to the patentee to show teaching away or unexpected results | IPR precedents (Magnum Oil, Dynamic Drinkware) preclude applying the district-court overlapping-range burden-shifting framework in IPRs | The overlapping-range framework applies in IPRs; patentee must produce evidence (teaching away, criticality, unexpected results) once overlap is shown |
| Result-effective variables (temperature, PO2) | Temperature and PO2 were recognized in the prior art as affecting oxidation outcomes and thus are result-effective variables; optimizing them is routine | The Board correctly found DuPont failed to show they were result-effective | Court held the Board applied the wrong standard; substantial evidence supports that temperature and PO2 are result-effective variables |
| Obviousness of claims 1–5 and 7–9 | Prior art collectively disclosed same oxidation reaction, same solvent/catalyst and overlapping temperature/PO2 ranges; patentee failed to show teaching away, unexpected results commensurate in scope, or criticality | Objective indicia (reported high yields, long-felt need) support nonobviousness; Board’s factual findings support patentability | Claims 1–5 and 7–9 are obvious; Federal Circuit reversed the Board’s decision and held the claims would have been obvious |
Key Cases Cited
- In re Peterson, 315 F.3d 1325 (Fed. Cir. 2003) (overlapping ranges create prima facie obviousness)
- Ormco Corp. v. Align Technology, Inc., 463 F.3d 1299 (Fed. Cir. 2006) (overlap presumption can be rebutted by teaching away or unexpected results)
- Galderma Labs., L.P. v. Tolmar, Inc., 737 F.3d 731 (Fed. Cir. 2013) (burden of production shifts to patentee to show nonobviousness when claimed range falls within prior-art range)
- In re Aller, 220 F.2d 454 (CCPA 1955) (discovering optimization of known process variables normally obvious)
- In re Applied Materials, Inc., 692 F.3d 1289 (Fed. Cir. 2012) (variable is result-effective where prior art recognizes its effect; prior art need not disclose optimization method)
- Dynamic Drinkware, LLC v. National Graphics, Inc., 800 F.3d 1375 (Fed. Cir. 2015) (in IPR petitioner retains burden of persuasion; burden of production may shift in some contexts)
- In re Magnum Oil Tools Int’l, Ltd., 829 F.3d 1364 (Fed. Cir. 2016) (institution does not shift burden of persuasion to patentee; limited discussion of burden of production in IPR)
- Genetics Inst., LLC v. Novartis Vaccines & Diagnostics, Inc., 655 F.3d 1291 (Fed. Cir. 2011) (very broad prior-art disclosures may not invite routine optimization)
- In re Antonie, 559 F.2d 618 (CCPA 1977) (exception where prior art does not recognize a variable as affecting the result)
- In re Boesch, 617 F.2d 272 (CCPA 1980) (optimizing result-effective variables is ordinarily within skill of the art)