Electrosynthesis

Selected Patents & Publications

Electrosynthesis Company, Inc. maintains the strictest level of confidentiality in all of its R&D efforts. For this reason, we do not publish a list of the R&D clients that we have collaborated with. However, on occasion we are encouraged to publish work funded by others. The following selected publications will give an indication of areas in which Electrosynthesis Company and its employees have contributed to the advancement of electrochemical technology.

Electrochemical Technology; Cells, Electrode Materials etc.

The status of electrochemical technology is extensively reviewed each year in the Journal of the Electrochemical Society. Dr. Ram Gopal compiled this report for 1993 and 1994:

  • Gibbons, D. W.; Gopal, R.; “Report of the Electrolytic Industries for the year 1993” In J. Electrochem. Soc. 1994, 414 (10), 2918-2933.
  • Fritts, S.; Gopal, R.; “Report of the Electrolytic Industries for the year 1994” In J. Electrochem. Soc.1993, 140 (11), 3337-3363.

There are very few books available that discuss the scale-up of electrochemical technology. Electrosynthesis – From Laboratory to Pilot to Production has proven to be a very popular compilation of successfully implemented technology.

  • Bockris, J. O’M.; Fletcher, S.; Gale, R. J.; Khan, S. U. M.; Kolb, D. M.; Mazur, D. J.; Uosaki, K.; Weinberg, N. L.; “Electrochemistry (1992-1995)” In Royal Society of Chemistry Annual Reports, 1996, 92 (C), 23-73.
  • Genders, J. D.; Pletcher, D.; Electrosynthesis-From Laboratory to Pilot to Production; Electrosynthesis: East Amherst, NY, 1990.

Research into electrode materials is always a “hot topic” in electrochemistry. Electrosynthesis Company has been the recipient of multiple awards from the National Science Foundation and Department of Defense to do research in this area.

  • Chandler, G. K.; Genders, J. D.; Pletcher, D.; “Electrodes Based on Noble Metals” In Platinum Metals Review, 1997, 41(2), 54-63.
  • Mazur, D. J.; Weinberg, N. L.; Bolster, M.; “Modified Carbons and Electrochemical Cells Containing the Same”; U. S. Patent 4 835 074, 1989.

Electroorganic Synthesis

Electrosynthetic methods are well known in their application to synthesis of pharmaceuticals and various organic intermediates. Among the books that have made a significant contribution to advancing this field are the Weissberger series edited by Norman Weinberg.

  • Electroorganic Synthesis: Festschrift In Honor of Manuel Baizer; Little, R. D.; Weinberg, N. L., Eds.; Marcel Dekker: New York, 1991.
  • Mazur, D. J.; Weinberg, N. L.; “Industrial Electroorganic Synthesis in the United States and Canada”;Kagaku to Kogyo: Japan, 1990, (43), 2002-2005.
  • Technique of Electroorganic Synthesis: Scale-Up, Part III; Tilak, E.V.; Weinberg, N.L., Eds.; Techniques of Chemistry Volume V; John Wiley & Sons: New York, 1982.
  • Technique of Electroorganic Synthesis Part II ; Weinberg, N.L., Ed.; Techniques of Chemistry Volume V; John Wiley & Sons: New York, 1975.
  • Technique of Electroorganic Synthesis Part 1; Weinberg, N.L., Ed.; Techniques of Chemistry Volume V; John Wiley & Sons: New York, 1974.

Electrosynthesis has become a valuable tool in the pharmaceutical industry. Electrosynthesis Company has collaborated with several companies in this area. Among those that have published some of our findings are Schering-Plough, Pfizer and Eli Lilly.

  • Bernasconi, E.; Genders, D; Lee, J.; Longoni, D.; Martin, C. R.; Menon, V.; Roletto, J.; Sogli, L.; Walker, D.; Zappi, G.; Zelenay, P.; Zhang, H.; “Ceftibuten: Development of a Commercial Process Based on Cephalosporin C. Part II. Process for the Manufacture of 3-Exomethylene-7(R)-glutaroylaminocepham-4-carboxylic Acid 1(S)-Oxide,” Organic Process Research and Development,2002, 6, 158-168.
  • Chai, D.; Genders, D; Weinberg, N.; Zappi, G.; Bernasconi, E.; Lee, J.; Roletto, J.; Sogli, L.; Walker, D.; Martin, C. R.; Menon, V.; Zelenay, P.; Zhang, H.; “Ceftibuten: Development of a Commercial Process Based on Cephalosporin C. Part IV. Pilot-Plant Scale Electrochemical Reduction of 3-Acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic Acid 1(S)-Oxide” Organic Process Research and Development, 2002, 6, 178-183.
  • Bernasconi, E.; Chai, D.; Genders, J. D.; Lee, J.; Martin, C. R.; Menon, V.; Roletto, J.; Sogli, L; Walker, D.; Weinberg, N. L.; Zappi, G. D.; Zelenay, P.; Zhang, H.; “Pilot Plant Scale-Up of a Pharmaceutical Intermediate” In the 12th International Forum on Electrolysis in the Chemical Industry; Electrosynthesis: Lancaster, NY, 1998.
  • Genders, J. D.; Pletcher, D.; “Electrosynthesis – ; A Tool for the Pharmaceutical Industry Today?” InChemistry and Industry, September 1996, 682-686.
  • Dunn, P.; Kendall, P. M.; Mazur, D. J.; Murtiashaw, C. W.; Pexxullo, S. L.; Zung, J. B.; “Electrochemical Deacetoxylation: Synthesis of 11-Ketotigogenin” In J. Org. Chem. 1996, 61, 405.
  • Kendall, P. M.; Mazur, D. J.; Schmidt, C. R.;“Electrosynthesis of Ketal-protected Glyceraldehyde” In the 7th Internationational Forum on Electrolysis in the Chemical Industry; Electrosynthesis: Lancaster, NY, 1993.

Electrosynthesis Company, Inc. has also been developing novel electrosynthetic methods for producing fine chemicals. A good example is a method for electrochemically producing the free base of Cysteine. In this approach the starting material cystine is dissolved in ammonium hydroxide to form a conductive ammonium salt. At the end of the electrolysis the ammonium hydroxide is simply evaporated to leave the pure product.

  • Genders, J. D.; Weinberg, N. L.; Zawodzinski, C.; “The Direct Electrosynthesis of L. Cysteine Free Base”  in Electroorganic Synthesis: Festschrift In Honor of Manuel Baizer; Little, R. D.; Weinberg, N. L., Eds.; Marcel Dekker: New York, 1991.

Electrosynthesis Company has been a long term partner with DFI Corp. developing novel technology for a range of polyols used as low calorie sweetness.

  • Stapley, J. A.; Genders, J. D.; “Methods for the electrolytic decarboxylation of sugars” U.S. Patent 9,702,047 (2017)
  • Stapley; J. A., Genders, J. D.; Atherton, D. M.; Kendall, P. M.; “Methods for the electrolytic production of xylo-pent-1,5-diose” U.S. Patent 9,169,571 (2015)

Inorganic Electrosynthesis

The chlor-alkali industry is one of the world’s largest chemical process, the economics of which rely on the balance for the demand of caustic soda and chlorine. Since these are not always the same, Electrosynthesis Company and others have investigated processes for the production of caustic soda without the co-production of chlorine (see Watts New, “Electrochemical Salt Splitting“). One such process was developed under funding from the National Science Foundation and in collaboration with Chemetics International.

  • Genders, J. D.; Pletcher, D.; Spiegel, E.; Weinberg, N. L.; “Electrochemical Methods for the Purification of Alkali Metal Hydroxides Without the Co-Production of Chlorine”; U. S. Patent 5 246 551, 1993.

Hydrogen Iodide is a valuable product used in the manufacture of a number of high purity iodine compounds. Electrosynthesis Company, in collaboration with Benham Electrosynthesis, has developed an electrochemical method that produces HI of a higher purity.

  • Genders, J. D.; Hartsough, D. M.; Weinberg, N. L.; “Methods of Producing Hydrogen Iodide Electrochemically”; U. S. Patent 5 520 793, 1996.

Electrosynthesis Company has worked with Chemical Products Corporation to develop an electrochemical process for the production of high purity alkaline earth metal hydroxides.

  • Maudlin, L. B.; Adams, C.; Randolph, D. R.; Mazur, D. J.; Genders J. D.; Chai, D. M.; “Process for the Production of Alkaline Earth Hydroxide”, U. S. Patent 6 375 825, 2002.

 

Membrane Research 

Ion permeable membranes are an essential part of many electrochemical cells. Moreover, they are used extensively for electrochemical separation processes such as electrodialysis and salt splitting. Electrosynthesis Company has been working with several groups including the National Science Foundation and National Institute of Standards and Technology through an ATP NIST award with Eastman Chemical and Genencor International.

  • Genders, J. D.; Gopal, R.; Hartsough, D. M.; Kendall, P. M.; Long, W. J.; Mazur, D. J.; Zappi, G. D.;“Electrodialysis Methods for Recovery and Purification of Gluconic Acid Derivitives”, U. S. Patent 6 187 570 B1, 2001.
  • Genders, J. D.; Hartsough, D. M.; “Electrochemical Method for Recovery of Ascorbic Acid”; U. S. Patent 6 004 445, 1999.
  • Davis, T.; Genders, J. D.; Pletcher, D.; A First Course in Ion Permeable Membranes ; Electrochemical Consultancy: England, 1997.
  • Genders, J. D.; Thompson, J.; “Process for Producing Sodium Hydroxide and Ammonium Sulfate from Sodium Sulfate”; U. S. Patent 5 098 532, 1992.
  • Genders, J. D.; George, E. L.; Pletcher, D.; “A Study of the Transport of Formaldehyde and Ethlene Glycol Through Ion Permeable Membranes in Electrolytic Cells” In J. Electrochem. Soc. 1996, 143 (1), 175-178.

 

Environmental Electrochemistry

It is well known that electrochemistry offers a unique approach to both cleaner processing and remediation or recycle of waste streams.

  • Electrochemistry For a Cleaner Environment; Genders, J. D.; Weinberg, N. L., Eds.; Electrosynthesis: East Amherst, New York, 1992.

The destruction of nitrates in a variety of waste streams can be achieved electrochemically. One area where we have been particularly active is in the destruction of nitrate in radioactive waste streams present at many of the DOE facilities. Electrosynthesis Company has been the recipient of several contracts from Westinghouse Savannah River Company for the destruction of such streams.

  • Lilga, M. A.; Orth, R. J.; Sukamto, J. P. H.; Rassat, S. D.; Genders, J. D.; “Cesium Separation Using Electrically Switched Ion Exchange” In Separation and Purification Technology 2001, 24, 451-466.
  • Genders, J. D.; Chai, D.; Hobbs, D. T.; “Durability Testing for the Recovery of Sodium Hydroxide from Alkaline Waste Solutions” In J. Appl. Electrochem. 2000, 30 (1) 13-19.
  • Genders, J. D.; Hartsough, D.; Hobbs, D. T.; “Electrochemical Reduction of Nitrates and Nitrites in Alkaline Nuclear Waste Solutions” In J. Appl. Electrochem. 1996, 26 (1), 1-9.
  • Hartsough, D. M.; Hobbs, D. T.; Genders, J. D.; “Electrochemical Treatment of Radioactive Wastes at the Savannah River Site” In the 4th International Fourm on Electrolysis in the Chemical Industry; Electrosynthesis: Lancaster, NY, 1990.

The destruction of organics in wastewater continues to be an area of interest to many companies. Electrosynthesis Company has been involved in the development of cell technologies in this field.

The electrochemical destruction of organic acids by converting them into combustible fuels is an attractive approach to the treatment of a waste stream. This approach was developed at Electrosynthesis Company in collaboration with DuPont Specialty Chemicals.

  • Genders, J. D.; Harstough, D.; Super, J.; “Electrochemical Destruction of Organic Acids”; The Electrochemical Society Extended Abstracts, 1994. Vol. 94-1, Abstract 761.

Electrosynthesis Company also successfully accomplished the electrochemical destruction of PCBs while working with Sandpiper.

  • Aurnou, E. A.; Liolios, E. A.; Kendall, P. M.; Mazur , D. J.; Weinberg, N. L.; “High Surface Area Electrode for PCB Destruction”; The Electrochemical Society Extended Abstracts, 1987. Vol. 87-2, Abstract 1857.
  • Mazur, D. J.; Weinberg, N. L.; “Methods for Electrochemical Reduction of Halogenated Organic Compounds”; U. S. Patent 4 702 804, 1987.

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