Organic Chemistry Expert: Isocyanates, Amines, Hydrogenation, Catalysis, Synthesis, and Mechanisms

Expertise

• Isocyanates, esp. Isophorone Diisocyanate (IPDI), Hexamethylene Diisocyanate (HDI), bis(isocyanatocyclohexyl)methane (H12MDI), Toluene Diisocyanate (TDI), and bis(isocyanato-phenyl)methane (MDI) - synthesis, and impurities identification.
• Amines, esp. Isophorone Diamine (IPDA), bis(aminocyclohexylmethane (H12MDA), and bis(aminophenyl)methane (MDA) - optimization, impurities, and identification.
• Catalytic hydrogenation, esp. hydrogenation of MDA to H12MDA.
• Epoxidation, esp. propylene oxide - synthesis and catalysis.
• New product development: Generate revenue, problem solving, and cost reduction.
• General organic synthesis and mechanisms.

Experience

Independent Contractor, Present

LyondellBasell/Lyondell Chemical Co, ARCO Chemical Co., Newtown Square, PA, 1997 - 2008

• As Research Advisor and Senior Scientist supervised technicians.
• Coordinated ARCO's and Lyondell's efforts in joint Dow/Dupont/Olin processes for preparation of isophoronediisocyanate.
• Monitored quality of DuPont's isophoronediamine and assisted DuPont's quality control by the synthesis of authentic samples of several impurities and by-products.
• Initiated investigation to use acetone by-product streams in making isophorone.
• Recommended successful process changes resulting in reducing levels of impurities in hexamethylenediisocyanate by preparation of authentic samples of known and suspected by-products.
• Carried out successful synthesis of TDI Allophanates and TDI Biuret optimizing viscosity.
• Prepared novel catalysts which were successfully utilized in pilot plant runs for the epoxidation of propylene to propylene oxide.
• Prepared prepolymers with excellent gloss and hardness in moisture-cured coatings.

Olin Corporation, Cheshire, CT, 1990 - 1997

• As Consulting Scientist and Senior Research Scientist supervised chemists and technicians.
• Developed low-cost, new catalyst system for hydrogenation of ring amines at medium pressures; successfully implemented in continuous pilot plant process for preparation of bis(aminocyclohexyl)-methane (H12MDA), precursor to bis(isocyanatocyclohexyl)methane (H12MDI). This system can be utilized for hydrogenation of other compounds.
• Coordinated successful research and development and pilot plant efforts to produce high yield bis(aminocyclohexyl)-methane (H12MDA) containing negligible amounts of catalyst poisons following identification of impurities.
• Coordinated Olin's efforts in joint Dow/Dupont/Olin processes for preparation of isophoronediisocyanate.
• Contributed to Olin's isophoronenitrile/isophoronediamine/isophoronediisocyanate market development team as technical representative.
• Developed annual savings of $145,000 by solving cause of catalyst poisoning at DuPont's isophoronediamine plant and increasing catalyst life.
• Developed lab procedure and coordinated pilot plant run that successfully isolated purified isophoronenitrile, the Dow product in the isophoronediisocyanate process.
• Developed proprietary use of bis(aldimines) as reactive diluents for use in low VOC coatings.
• Identified and developed several workable approaches to water dispersible isocyanates that are non-infringing, proprietary, and outside of any TSCA issues.
• Postulated and demonstrated feasibility of two-step approach to obtain desired isomer ratio in new Olin nitration process for dinitrotoluene (DNT) after pilot plant produced unacceptable isomer ratio.
• Postulated correct structures and causes for formation of bimolecular impurities in reduction of DNT into toluenediamine (TDA), allowing for better monitoring of catalyst life.
• Showed feasibility of carrying out phosgenation of hexamethylenediamine at elevated temperatures, decreasing reaction time while keeping impurity level low.
• Developed lab procedures to lower levels of isocyanide dichlorides (DCI), acidity, and hydrolyzable chlorides in isocyanates resulting in higher quality plant product.
• Coordinated technical issues among plant, plant QC, research and development, analytical, and business groups, helping to develop trust and teamwork. Early problems resolved and multi-product isocyanate plant running smoothly.

Upjohn Company, North Haven, CT, 1972 - 1990

• Started as Research Chemist; progressed to Senior Scientist and Project Leader; supervised chemists.
• Increased annual sales by $50,000 of an existing product, 2-ethylhexyl p-(N,N-dimethylamino)-benzoate by proposing and developing new use.
• Optimized lab conditions for catalytic hydrogenation of o-chloronitrobenzene to dichlorohydrazo-benzene (precursor to dichlorobenzidine) replacing an environmentally "unfriendly" process resulting in a savings of over $100,000 annually by eliminating an iron sludge waste residue.
• Led initiative that resulted in new process utilizing acidic clay catalysis for formation of MDA with varying isomer compositions. Using this technology, developed first MDI-based flexible foams, successfully commercialized by Dow Chemical, successor company to Upjohn's urethanes business.
• Discovered secondary mechanistic pathways in formation of MDA and analogs, via ipso proto-dealkylation and ipso alkylation-dealkylation; allowed for better understanding of isomer.

Honors & Publications

Academic and Professional Affiliations

• Member, ACS; Organic Division, ACS
• Former member, Catalysis Club of Philadelphia
• Former chairman, New Haven, CT Section, ACS
• Former chairman, Connecticut and Massachusetts sections of the ACS Centennial Committee
• Member, ACS; Organic Division, ACS
• Former member, Catalysis Club of Philadelphia
• Former chairman, New Haven, CT Section, ACS
• Former chairman, Connecticut and Massachusetts sections of the ACS Centennial Committee.

Research

• Postdoctoral research, Yale University, Biosynthesis of vitamin B12: synthesis of known and suspected precursors with 13C labels.
• "Synthesis and Reactions of ą,ą-bis(diazo) Ketones."
• "Synthesis and Stereochemistry of 2-Substituted-1,2,3,4-tetrahydroquinoxalines."

Awards

• Granted the Lyondell Research Award, for novel catalysts which were successfully utilized in pilot plant runs for the epoxidation of propylene to propylene oxide.
• Served on "Manufacturing Excellence Standards" and "Impediments to Innovation" Committees which decreased red tape and streamlined communication; member of Internal Education Committee.
• Granted the "Olin Technology Award", for developing a novel, medium pressure process for the catalytic hydrogenation of bis(aminophenyl)methane (MDA) into bis(aminocyclohexyl)methane (H12MDA).
• Granted the "Olin Technology Award", for identifying and resolving a serious problem of decreasing catalyst life in the isophoronediamine (IPDA) commercial plant.
• Granted the "Donald S. Gilmore Research Award," for advances in the understanding of the chemistry of bis(aminophenyl)methane (MDA).

Publications and Patents

• Presented three seminars at LyondellBasell/Lyondell Chemical Co./ARCO Chemical Co. on special topics in organic chemistry.
• Presented two seminars at Olin Colloquia on Catalytic Hydrogenation.
• Selected as Discussion Leader, International Conference of Radiation Curing, "Photoinitiators."
• Selected as Discussion Leader, American Chemical Society (ACS) Short Course in "Modern Organic Synthesis."
• Presented seminars at Upjohn on 1H and 13C-nmr spectroscopy.
• Author and Co-Author of numerous articles in American Chemistry and Organic Chemical Journals.
• Inventor and Co-Inventor of 14 U.S. Patents.

Education

• Ph.D. Organic Chemistry, University of Wisconsin, Madison, WI
• M.S. Organic Chemistry, University of Miami, Coral Gables, FL
• B.S. Chemistry, (Magna cum Laude), University of Miami, Coral Gables, FL