The Laboratory of Chemical Extractives

Center for Applied Research and Technology Development – Natural Resource Research Institute

University of Minnesota, Duluth

Chemical Extractives Laboratory was created as the main research and development entity for the University of Minnesota Chemical Extractives Program, Natural Resources Research Institute. The main goal of our Laboratory is the development of value-added products based on natural products wastes (biomass wastes). Minnesota has vast amounts of different biomass wastes: paper-mill sludge, birch bark, paper-mill soap fraction, paper-mill black liquor, plant molasses, saw dust, hog wood, wood chips, willow bush shreds, potato-skin, dried distilled grains and solubles from the ethanol industry, numerous agricultural wastes. These waste-streams are all in the focus of Chemical Extractives Program. The Laboratory is devoted to the improvement of links between the University of Minnesota and the industries of the Upper Midwest and throughout the United States.

Being a part of Center of Applied Research and Technology Development (NRRI), the Laboratory is mostly concentrated on the Applied Chemistry of natural wastes until the value added products will meet market. Our six years R&D efforts on birch bark wastes are the best example of this approach. The new company NaturNorth, LLC was launched as a direct outgrowth from Chemical Extractives Program. This corporation formed in partnership between the University of Minnesota- Duluth, Minnesota Power, Inc. and Potlatch Corp.. NaturNorth was launched to obtain natural compounds from birch bark using patented processing technology development at NRRI. NaturNorth venture is the model for University to work with Industry, its economic development potential and the environmental sensitivity of using an industrial waste material. This venture reflects UMD's ongoing commitment to bring the University research into public arena.

Our current research efforts with paper mill sludge (paper mill plants), potato skin (the industry of potato processing), dried distilled grains and soluble, or DDGS (ethanol industry), plant molasses (the industry of wood board materials) are also on the way to commercialization.

Our knowledge and expertise in the technology of natural products processing is based on the specialized intellectual and equipment potential of the Chemical Extractives Laboratory. The intellectual potential of the Laboratory is represented by 8 Ph.D. in Chemistry, 9 MS in Chemical Engineering and 1 Senior Technician. The Laboratory facility and equipment allows deciding any all possible fundamental and applied tasks in the chemistry of natural products, organic chemistry, chemical and structural analysis of natural products, optimization of natural products processing, pilot scale development and samples preparation, chemical processes optimization, chemical modification of natural products into bioactive derivatives, broad consulting of the industrial partners from cosmetics, washing materials, nutraceuticals, pharmaceuticals, agro-chemicals, and many others.

The University of Minnesota has a unique flexible policy on different forms of partnership, which is economically attractable and practically simple. We are successfully working in tight cooperation with several large and small industrial partners, as well as our partners in the field of academics.

Dr. Pavel A. Krasutsky is a Director of Chemical Extractives Program at the University of Minnesota. His experience in the fundamental organic chemistry and specifically in the Chemistry of Natural Products is well documented in more than 150 publications and 25 patents.

/ Dr. Pavel Krasutsky – Director

Pavel Krasutsky is director of the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. He is an engineer in chemistry by training, and has a Ph.D. and doctor of science in organic chemistry. Pavel has 30 years of experience in organic chemistry research, which includes the following directions of organic chemistry: mechanisms of organic reactions, organic chemistry of cage structures, synthesis of biologically active compounds, synthesis and technology of insecticides, chemistry of natural products, and chemistry of chemical extractives. He has authored 150 papers for publication in national and international chemistry journals and has written 20 patents.
/ Dr. Oleksiy Kacharov – Research Associate

Oleksiy Kacharov is a research associate for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. He is an engineer in chemistry by training and has a Ph.D. in organic chemistry. Oleksiy has 10 years of experience in organic chemistry research and organic technology, which includes the following directions of organic chemistry: bio-organic chemistry and chemistry of natural products, asymmetric synthesis, catalytic organic chemistry, fluoro-organic chemistry, and chemistry of polymeric materials. He has authored 10 papers for publication in nationally and internationally recognized organic chemistry journals.
/ Dr. Liliya Kacharova – Research Associate

Liliya Kacharova is a research associate for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. She is a high school teacher in chemistry and biology by training and has a Ph.D. in bioorganic chemistry. Liliya has 8 years of experience in organic chemistry research and organic technology, which includes the following directions of organic chemistry: bio-organic chemistry and chemistry of natural products, synthesis of biologically active compounds, fine organic synthesis, catalytic organic chemistry, fluoro-organic chemistry, and chemistry of polymeric materials. She has authored 8 papers and thesis of conferences for publication in nationally and internationally recognized organic chemistry journals.
/ Dr. Andriy Khotkevych – Research Associate

Andriy Khotkevych is a research associate for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. He is an engineer in chemistry and has a Ph.D. in organic chemistry. Andriy has more than 15 years of experience in organic chemistry research, which includes the following directions of organic chemistry: organic chemistry of cage structures, mechanisms of organic reactions, synthesis and modification of natural products, and chemistry of chemical extractives. He has experience in industry development of chemical and pharmaceutical products and has authored 25 papers for publication in national and international chemistry journals.
/ Dr. Igor Kolomitsyn – Research Associate

Igor Kolomitsyn is a research associate for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. He is an engineer in chemistry by training, with a Ph.D. in organic chemistry. He has over 11 years of experience in organic chemistry research and organic technology, which includes the following directions of organic chemistry: organic chemistry of cage structures and terpenes, synthesis of biologically active compounds, synthesis and modification of natural products, chemistry of chemical extractives, chemistry of peracids and peresters, and mechanisms of organic reactions. He has authored 15 papers for publication in national and international organic chemistry journals and has two United States patents pending.
/ Oksana Kolomitsyna, MS – Research Associate

Oksana Kolomitsyn is a research associate for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. She has a Masters Degree in organic chemistry and chemical engineering. Oksana has 12 years of experience in organic chemistry research and organic technology, which includes the following directions of organic chemistry: organic chemistry of cage structures and terpenes, and synthesis of biologically active compounds, synthesis and modification of natural products, and chemistry of chemical extractives. She has authored 10 papers for publication in national and international organic chemistry journals and has two US patents pending (2005).
/ Dmytro Krasutskyy, MS – Research Associate

Dmytro Krasutskyy is a research fellow for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. He has a bachelor of science degree in organic chemistry and a master of science in organic chemistry and chemical technology engineering. He has seven years of experience in organic chemistry research, which includes the following directions of organic chemistry: organic chemistry of cage structures, synthesis, modification and separation of natural products, up-scaling procedures, and the technology of chemical extractives.
/ Dr. Nataliya Lyutenko – Research Associate

Nataliya Lyutenko is a research associate for the Chemical Extractives Program within the Forestry/Forest Product Division of the Center for Applied research and Technology Development. Dr. Lyutenko joined the Laboratory of Chemical Extractives in July of 2004. She is a High School Teacher of Chemistry and Biology and has a Ph.D. in bioorganic chemistry. Nataliya has 7 years of experience in organic chemistry research, which includes the following directions of organic chemistry: bioorganic chemistry and chemistry of natural products, fluoroorganic chemistry and heterocyclic chemistry. She has authored 3 papers for publication in nationally and internationally recognized organic chemistry journals.
/ Dr. Kalyan Munshi - Research Associate

Kalyan Munshi is a research associate for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. He has aBS in chemistry, MS chemical engineering and a Ph.D. in chemistry. Kalyan has 15 years of experience in chemistry of polymers and organic chemistry research, which includes the following directions of chemistry: antiviral polymeric drug design, synthesis of bioactive polymers, stereospecific higher alkene polymerization, chemistry of cage structures and triterpenes, and petrochemical syntheses. He has authored 15 papers for publication in nationally and internationally recognized journals and has participated in several international conferences.
/ Dr. Sergiy Yemets - Research Associate

Sergiy Yemets is a Research Associate for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. Dr. Yemets joined the Laboratory of Chemical Extractives in July of 2004. He has an MS degree in Chemistry and Natural Compounds Chemistry and Ph.D. in Organic Chemistry. Sergiy has 8 years of experience in Organic Chemistry research included the following directions, Chemistry of Heterocyclic Compounds, Chemistry of Sulfur and Fluorine Containing Organic Compounds, Chemistry of the Natural Compounds, Synthesis of the Biologically Active Compounds. He is the author and co-author of 8 papers published in international and national chemistry journals and he has one international patent.
/ Jonathan Lee, BA – Principal Lab Technician

Jonathan Lee is theprincipal laboratory technician for the Chemical Extractives Program within the Forestry/Forest Products Division of the Center for Applied Research and Technology Development. Jonathan receives the program's source materials, such as birch bark, from the lab's industrial partners and then processes them. His professional background in industrial safety comes from his years sailing with various fleets on the Great Lakes. Jonathan also has an academic background in technical writing and editing, which allows him to participate in information gathering and research duties for the lab.

Mechanical Equipment:

  • Centrifuges

-Bock Laundry Machine Co., Model #24BC, 1725 RPM

-IEC Centra CL3 (small)

-IEC Centra GP8R (large)

  • Filter

-Sparkler Mfg. Co., Model #8-6, 100 GPH capacity

  • Evaporator and Solvent Recycling

-Buchi Rotovapor R-135

-Buchi Vaccuum Controller B-720

-Brinkman Lauda WK 3200 (coolant regulator)

  • Dryer

-MS Blue M Electric Co. high capacity, high temperature dryer

-MS Blue M Electric Co. “Power-o-matic 60” ventilation/temperature regulator

-UniMac high-capacity, industrial mesh-barrel dryer

  • Material Processing

-U.S. Stoneware Jar Mill, Model #CV-87203

-U.S. Stoneware 6.2 liter ball-mill jar.

  • Extruder

-Wayne 3 HP, 1 inch extruder

-Consolidated Process Machinery, Lab Mill CL-5

-California Pellet Mill, 102-001-001

  • Screener

-Rotex Screeners, #3203

  • Dryer

-UniMac high-capacity, industrial mesh-barrel dryer

  • Big Press

-OilGear Servo Control Products

-Lloyd Controls, Inc.

  • Chipper/Shredder

-Yardman, # 246-648D401

-Unimount World Motor, #H17440A

  • Hammermill

-Hostile Duty High Efficiency Motor

-Jay-Bee Hammermill, #29141

-Delta Dust Collector, #50-182

  • 40-ton Press

-Arcan, #CP400

Chemical Apparatus and Lab Devices:

  • Buchi Rotovapor R-153 (Large)

-Buchi Vacuum Controller B-720

-Brinkman Lauda WK 3200

-Labconco Rotary Evaporator (Small, x 3)

-Buchi Vacubox B-177

-Buchi Vacuum Control V-800

  • 72 liter Distiller

-Glas-Col, Model #102B-0616700024

  • Super Critical Extractor

-Newport Scientific, Inc., Model #46-19360

  • Extraction Column

-Custom built for the ChemEx lab to exact specification

  • 50-liter chemical apparatus

-Glas-Col, Model #102B-0000200001

  • Autoclave

-2 l, 1900 psi, 350 oC

  • Moving Hood

-Isolated, ventilated pilot-scale work area, l x w x h = 30 x 8 x 15 ft

  • Chemical Hoods

-Two (2) 8 ft x 3 ft x 4 ft, ventilated chemical hoods

  • Drying Cabinet

-Large capacity materials and/or equipment drying hood

  • Refrigerators

-Standard Kenmore

-VWR by Devco, cold-storage

  • Vacuum Oven

-VWR Vacuum Oven, Model #1410

  • Disintegrator

-PowerGen 1800 D, Fisher Science

-Ultrasonic

-Virtis 475

Analytical Equipment:

  • HPLC

-Alltech 500 ELSD Evaporative Light-Scattering Detector

-Shimadzu SPD-M10A Diode Array Detector

-Shimadzu LC-10AT Liquid Chromatographer

-Shimadzu DGU-14A Degasser

  • GC/MS

-Hewlett-Packard 5970A Series Mass Selection Detector

-Hewlett-Packard 5890 Gas Chromatograph (x 3)

-Hewlett-Packard 5890 Gas Chromatograph

-Hewlet-Packard 5988A Gas Chromatograph

  • FTIR

-Matson Genesis II FTIR

  • NMR

-Varian Unity Inova 300

Publications

  1. Krasutsky, P.A., Kolomitsyn, I.V., Kiprof, P., Carlson, R.M., Sydorenko, N.A. and Fokin, A.A. A Double Consecutive Criegee Rearrangement Using TFPAA: One Step Conversions of Homoadamantane to Oxahomoadamantanes., J. Org. Chem., 2001, 66, 1701-17007.
  2. Krasutsky, P.A., Kolomitsyn, I.V., Kiprof, P., Carlson, R.M. and Fokin, A.A. Observation of a Stable Carbocation in a Consecutive Criegee Rearrangement with Trifluoroperacetic Acid. , J. Org. Chem., 2000, 65 (13) 3926-3933.
  3. Kolomitsin, I.V.; Sidorenko, N. A.; Krasutsky, P.A.; Yurchenko, A. G.; Fokin, A.A., Oxidative Fragmentation of Tetrahydrodicyclopentadiene skeleton. Russ. J. Org. Chem., 2000, 36(3), 438-439.
  4. Pavel A. Krasutsky; Igor V. Kolomitsyn; and Robert M. Carlson. A Novel Catalytic Pathway for Perfluoroacyl Peroxide Synthesis. Org. Letters, 2001, 3, 19, 2997-2999.
  5. Krasutsky, P.A., Kolomitsyn, I.V., Kiprof, P., Carlson, R.M., Sydorenko, N.A. and Fokin, A.A. A Double Consecutive Criegee Rearrangement Using TFPAA: One Step Conversions of Homoadamantane to Oxahomoadamantanes., J. Org. Chem., 2001, 66, 1701-1707.
  6. Krasutsky, P.A., Kolomitsyn, I.V., Kiprof, P., Carlson, R.M. and Fokin, A.A. Observation of a Stable Carbocation in a Consecutive Criegee Rearrangement with Trifluoroperacetic Acid. , J. Org. Chem., 2000, 65 (13) 3926-3933.
  7. Kolomitsin, I.V.; Sidorenko, N. A.; Krasutsky, P.A.; Yurchenko, A. G.; Fokin, A.A., Oxidative Fragmentation of Tetrahydrodicyclopentadiene skeleton. Russ. J. Org. Chem., 2000, 36(3), 438-439.
  8. Pavel A. Krasutsky; Igor V. Kolomitsyn; and Robert M. Carlson. A Novel Catalytic Pathway for Perfluoroacyl Peroxide Synthesis. Org. Letters, 2001, 3, 19, 2997-2999.
  9. Pavel A. Krasutsky; Igor V. Kolomitsyn; Evgenij M. Botov; Robert M. Carlson; Irina G. Semenova; Andrey A. Fokin. Heterolytic decarboxylation involving acyltrifluoroacetyl peroxide intermediates. Tetrahedron Letters, 2002, 43, 8687-8691.

Patents

  1. Carlson, R. M.; Krasutsky, P. A.; Karim, M. R. Use of Betulin and Analogs Thereof to Treat Herpes Virus Infection. U.S. 5,750,578, May 12, 1998.
  2. Carlson, R. M.; Krasutsky, P. A.; Karim, M. R. Use of Betulin and Analogs Thereof to Treat Herpes Virus Infection. PCT/US 9802445, Nov 11, 1998.
  3. Krasutsky, P. A.; Carlson, R. M.; Kolomitsyn, I. M.; Edwardson, C.; Nesterenko, V. V. Birch Bark Processing and Isolation of Natural Products from Birch Bark. U.S. 09/938,173, Aug 23, 2001.
  4. Krasutsky, P. A.; Carlson, R. M.; Kolomitsyn, I. M.; Edwardson, C.; Nesterenko, V. V. Birch Bark Processing and Isolation of Natural Products from Birch Bark , PCT/US00/21829 Aug 10, 2000.
  5. Pavel A. Krasutsky; Robert M. Carlson; Vitaliy V. Nesterenko. Method for Manufacturing of Betulinic Acid. U.S. Patent, Aug 7, 2001, 6,271,405 B1.
  6. Pavel A. Krasutsky; Robert M. Carlson; Vitaliy V. Nesterenko. Method for Manufacturing of Betulinic Acid. PCT/US01/00991, Jan. 11, 2001.
  7. Krasutsky, P. A.; Carlson, R. M.; Karim, M. R. Triterpenes Having Antibacterial Activity. US/Docket 1339 005, patent application serial no. 09/969,556, Sep 29, 2000.
  8. Krasutsky, P. A.; Nesterenko, V. V., Process for Extracting Compounds from Plants. US/Docket 13339.001 PRV, patent application serial no. 60/236,578, Sep 29, 2000.
  9. Krasutsky, P. A.; Avilov, D., Triterpene Quaternary Salts as New Cationic Surfactants. US/Docket1339 006 PRV, provisional patent application, Jan 10, 2002.
  10. Krasutsky, P. A.; Nesterenko, V. V., Process for Extracting Compounds from Plants. PCT/Docket 13339 001 WO1, patent application serial no. 01/30756, Sep 29, 2000.
  11. Krasutsky, P. A.; Carlson, R. M.; Karim, M. R. Triterpenes Having Human Antifungal and Antiyeast Activity. US/Docket 1339.002, patent application serial no. 60/236,578, Sep 29, 2000.
  12. Krasutsky, P. A.; Avilov, D. V. Triterpene Quaternary Salts as New Cationic Surfactants. PCT/ Docket 1339 010 WO, provisional patent application, January 10, 2002.
  13. Krasutsky, P. A.; Kolomitsyn, I.V.; Carlson, R. M.; Wang Hong. In Situ Production of Bis(perfluporoacyl)-, (or Aroyl) Peroxides in the Corresponding Perfluorocarboxylic Acids. U.S. Patent Application Serial No. 10 / 163,840