Chad Friesen

Chad 07 small

Professor of Chemistry
Trinity Western University
7600 Glover Road
Langley, BC V2Y 1Y1
phone: (604) 513-2121 ext 3220
fax: (604) 513-2018
email: chad.friesen@twu.ca

Professional Background

Full Professor of Chemistry (August 2010-present)
Department of Chemistry, Trinity Western University, Langley, BC, V2Y 1Y1 Canada.

Associate Professor of Chemistry (August 2005-2010)
Department of Chemistry, Trinity Western University, Langley, BC, V2Y 1Y1 Canada

Assistant Professor of Chemistry (August 2000-2005)
Department of Chemistry, Trinity Western University, Langley, BC, V2Y 1Y1 Canada

Adjunct Professor of Chemistry (November 2004-present)
Department of Chemistry, Simon Fraser University, 8888 University Drive Burnaby, B.C. V5A 1S6, Canada

Visiting Scientist (April -June 2001, September 2006 - August 2007)
E.I. du Pont de Nemours and Co., Inc., Jackson Laboratory, Chambers Works, Deepwater, NJ, 08023 USA.,E. I. du Pont de Nemours, Experimental Station, Bldg. 402, Rm. 433C, Rt 141 Henry & Clay Works, Wilmington, DE, 19880-0402, USA

Graduate Council Research Fellow (August 1999-July 2000)
Department of Chemistry, The University of Alabama, Tuscaloosa, AL, 35487 USA

DuPont R&D Chemist, Limited Service Employee (June 1998-May 1999)
E.I. du Pont de Nemours and Co., Inc., Jackson Laboratory, Chambers Works, Deepwater, NJ, 08023 USA.

Education

Ph.D. in Chemistry, May 2000
The University of Alabama, Tuscaloosa, AL, 35487 USA
Dissertation: Perfluoropolyalkylethers (PFPAE): The Synthesis and Characterization of Lubricant Derivatives for New Industrial Applications and Improvements in Thermal Oxidative Environments.

Research Advisor (Alabama): Joseph S. Thrasher, Ph.D.

B.S. Degree in Chemistry, December 1995
B.S.E Degree in Chemistry, December 1995
John Brown University, Siloam Springs, AR, 72761 USA
Magnum Cum Laude

Honours

Vice-Chair/Secretary of Fluorine Chemistry Division of the
American Chemical Society (January 2010-present)
Trinity Western University Research Fellow (2005)
The University of Alabama Graduate Council Research Fellow (1999)

Research Interests

Industrial Fluorine Chemistry

webfigure-1 sm

Figure 1. Flexible Ligands for Fluorous Biphase Systems (FBS).

The focus of my research is on "green chemistry" such as fluorous biphase systems (FBS) utilizing perfluoropolyalkylether technology (see Figure 1). Our current research in fluorous biphase systems is focused on building an array of new ligands for use in organic synthesis such as hydroformylation and to aid in separation methodology (see Figure 2). Other work includes analysis of perfluoropolyalkylether synthetic derivatives via gas chromatography-mass spectrometry, 19NMR, 1H-NMR, and 13C-NMR. Future work is sought in applying this technology to the area of fluoropolymers and creating new polymerization media.

 

Fluorous Biphase Concept sm

 

Figure 2. General concept of fluorous biphase systems (FBS).

PEER REVIEWED JOURNALS

1. Friesen, Chadron M.; Montgomery, Craig D.; Temple, Sebastian A. J. U. “A Fluorous Biphase Hydrogenation Catalyst Utilizing A Perfluoropolyalkylether: [RhCl(PPh2(C6H4 C(O)OCH2CF(CF3)(OCF2CF(CF3))nF))3] with n= 4-9. Green Chemistry 2011 (submitted June 2011.

2. Shtarov, Alexander B.; Howell, Jon L.; Thrasher Joseph S.; Waterfeld, Alfred; Koichi, Murata; Friesen, Chadron M.; Pérez, Erik W.; “Synthesis of New Linear Perfluoroalkyl Polyethers Starting from Diols and Tetrafluoroethylene.” Lubrication Science 2010, 23, 61-80.

3. Howell, Jon L.; Friesen, Chadron M.; Laugesen, Krista L.; van der Ende, Alice E. "Reactions of Poly(hexafluoropropylene oxide) perfluoroisopropyl ketone with Various Amines." Journal of Fluorine Chemistry 2008, 129(3), 178-184.

4. Friesen, Chadron M.; Howell, Jon L.; Jamieson, Ashley; Nyvall Daryl A. "Understanding the Influence of Hydrocarbon Insulators in Fluorinated Amines: Reactivity of Poly(hexafluoropropylene oxide) Amine Containing Methylene Spacers." Journal of Fluorine Chemistry 2008, 129(3), 193-203.

5. Howell, Jon L., Friesen, Chadron M.; Shtarov, Alexander B.; Thrasher, Joseph S.; Waterfeld, Alfred; Pérez, Erik W.; Sullivan, Jonathan F. "Improved Thermal Stability of Perfluoropolyalkylethers (PFPAEs)." Journal of Synthetic Lubrication 2007, 24(4), 227-234.

6. Shtarov, Alexander B.; Howell, Jon L.; Thrasher Joseph S.; Waterfeld, Alfred; Koichi, Murata; Friesen Chadron M.; Pérez, Erik W.; "Synthesis of New Linear Perfluoroalkyl Polyethers Starting from Diols and Tetrafluoroethylene." Journal of Synthetic Lubrication 2007, (submitted).

7. Howell, Jon L.; Lu, Norman; Friesen, Chadron M. "New Derivatives of poly-Hexafluoropropylene Oxide from the Corresponding Alcohol." Journal of Fluorine Chemistry 2005, 126(3), 281-288.

8. Howell, Jon L.; Lu, Norman; Friesen, Chadron M.; Perez, Erik W.; Novak, Irek; Waterfeld, Alfred; Thrasher, Joseph S. "The Preparation of Primary Poly-Hexafluoropropylene Oxide Halides (Poly-HFPO-CF2X where X = I, Br, Cl and F)." Journal of Fluorine Chemistry 2004, 125(10), 1513-1518.

9. Howell, J. L.; Hofmann, M. A.; Waterfeld, A.; Sipyagin, A. M.; Friesen, C. M.; Thrasher, J. S. "Reactions of Perfluoropolyether (PFPE) Acids and Their Corresponding Salts.", Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1998, 39(2), 822.

10. Howell, J. L.; Hofmann, M. A.; Waterfeld, A.; Sipyagin, A. M.; Friesen, C. M.; Thrasher, J. S. "Reactions of Poly-Hexafluoropropylene Oxide Acids and Their Corresponding Salts." Journal of Fluorine Chemistry 1998, 89, 131-135.

 

TECHNICAL REPORTS:

1. Friesen, Chadron M.; Van Dyke, J. D. (Jack).  “PART II-B: Study of the Chlorination of Nylon (PA12), Butyl Rubber(CIIR) & Nylon/Butyl Rubber Blends with and without Isocyanuric Acid (ICA) in Aqueous Sodium Hypochlorite.” Defence R&D Canada – Technical Report DRDC-SUFFIELD-TR-2011, 2011. 

2.  Friesen, Chadron M.; Van Dyke, J. D. (Jack). “Part II-A:  Study of the Chlorination of NYLON & NyLON/Butyl Rubber (CIIR) Blends with and without Isocyanuric Acid (ICA) In Hexanes.” Defence R&D Canada – Technical Report DRDC-SUFFIELD-TR-2011, 2011.

3.  Friesen, C. M.; Howell, J. L.; Thawley. V. A., DuPont Technical Report DSCE-JL-2007-3, 2007.

4. Friesen, C. M.; Howell, J. L.; Nyvall, Daryl A., DuPont Technical Report DSCE-JL-2007-2, 2007.

5. Friesen, C. M.; Howell, J. L. and Nyvall, Daryl A., DuPont Technical Report DSCE-JL-2006-24, 2006.

6. Friesen, C. M.; Howell, J. L. and Nyvall, Daryl A., DuPont Technical Report DSCE-JL-2006-23, 2006.

7. Friesen, C. M.; Howell, J. L.; Jamieson A. L.; and Nyvall, Daryl A., DuPont Technical Report DSCE-JL-2006-18, 2006.

8. Lu, N.; Howell, J. L.; and Friesen, C. M., DuPont Technical Report; DC-JL-2003-8, 2003

9. Friesen, C.M. "A Chemical Perspective of Wood Composites in A Steam Injection Continuous Press." Trus Joist, A Weyerhaeuser Business Technical Report, 2002.

10. Friesen, C. M. "Tricaine Methane Sulfonate (TMS): Improvements in manufacturing quality and quantitative control while minimizing solvent disposal." Western Chemical Inc. Technical Report; WCI-2001-1, 2001.

11. Friesen, C. M. and Howell, J. L., DuPont Technical Report; DCSE-JL-2001-8, 2001.

12. Friesen, C. M. and Howell, J. L, DuPont Technical Report; DCSE-JL-2001-13, 2001.

13. Friesen, C. M. and Howell, J. L., DuPont Technical Report DCSE-JL-99-09, 1999.

PATENTS:

1. Howell, Jon L.; Pérez, Erik W.; Waterfeld, Alfred; Friesen, Chadron Mark; Thrasher, Joseph Stuart; Nowak, Ireneusz. "Perfluoropolyether primary bromides and iodides." U.S. Pat. 7,148,385 B2, December 12, 2006

2. Chadron Mark Friesen; Kevin Anthony Hay, Daryl Nyvall, Jon L. Howell "Insulated perfluoropolyalkylether (PFPAE) alcohols." U.S. Pat. Appl. CH-3063 USN. 2005

3. Chadron M. Friesen Jon L. Howell, Erik W. Pérez, Joseph S. Thrasher, Alfred Waterfeld. "Thermally Stable Perfluoropolyethers And Processes Therefore and Therewith." U.S. Pat. 6,753,301 B2, June 22, 2004.

a. Howell, Jon L.; Pérez, Erik William; Waterfeld, Alfred; Friesen, Chadron Mark; Thrasher, Joseph Stuart. "Perfluoro-C 3-alkyl-terminated perfluoropolyoxyalkylenes and perfluoroolefin-perfluoropolyoxyalkylenes as thermal stabilizers for lubricants." U.S. Pat. Appl. Publ. (2003), 12 pp.

4. Howell, Jon L.; Pérez, Erik W.; Waterfeld, Alfred; Friesen, Chadron Mark; Thrasher, Joseph Stuart; Nowak, Ireneusz. "Perfluoropolyether primary bromides and iodides." U.S. Pat. 6,653,511 B2, Nov 25, 2003..,

a. Howell, Jon L.; Pérez, Erik William; Waterfeld, Alfred; Friesen, Chadron Mark; Thrasher, Joseph Stuart; Nowark, Ireneusz. Perfluoropolyether primary bromides and iodides prepared from reactions of perfluoroether acid fluorides with metal iodide and bromides." U.S. Pat. Appl. Publ. (2003), 5 pp.

5. Chadron M. Friesen Jon L. Howell, Erik W. Pérez, Joseph S. Thrasher, Alfred Waterfeld. "Thermally Stable Perfluoropolyethers And Processes Therefore and Therewith." World Intellectual Property Organization, WO 0206375/ A2, 2002.

CONFERENCE PRESENTATIONS:

 1. Chadron M. Friesen*, Sebastian A. J. U. Temple, Craig D. Montgomery, and Jon L. Howell “Incorporating Poly(hexafluoropropylene oxide) into Wilkinson’s Catalyst:  A Fluorous Biphase Approach.” 94th Canadian Chemistry Conference and Exhibition, Montréal, Quebec, Canada, June 5-9, 2011.

2.  Chadron M. Friesen*, Sebastian A. J. U. Temple, Craig D. Montgomery, and Jon L. Howell “Fluorinated Ethers:  A Question of Their Benefit to Catalytic Systems.” 20th Winter Fluorine Conference, St. Petersburg, Florida, USA January 9-14, 2011.

3.  Elizabeth Krieter, Sebastian Temple, Rose Rogawski , and Chadron M. Friesen. “Synthesis of Tris(4-Diphenylphosphinyl Polyhexafluoropropylene Oxide Methylene Benzoate) Rhodium Chloride for Use in the Catalytic Hydrogenation of 2-Cyclohexen-1-one.” 19th Regional Murdock Charitable Trust Undergraduate Research Conference,  Linfield College, McMinnville, Oregon, November 12-13, 2010.

4.  Chadron M. Friesen*, Sebastian A. J. U. Temple, Craig D. Montgomery, and Jon L. Howell "Incorporating Poly(hexafluoropropylene oxide) into Wilkinson's Catalyst:  A Fluorous Biphase Approach."  16th European Symposium on Fluorine Chemistry, Ljubljana, Slovenia, July 18-23, 2010. 

5.   Andrew Dawn* and Chadron M. Friesen.  “A Clothing Solution.” Western Canadian Undergraduate Chemistry Conference, Lethbridge, Alberta, May 6-8th, 2010.

6.   A. Rose Rogawski* and Chadron M. Friesen “Methodology for Rrotecting and Deprotecting Triaryl Phosphines.” 18th Regional Murdock Charitable Trust Undergraduate Research Conference, University of Gonzaga University, WA, October 30-31, 2009. 

 7.  Chadron M. Friesen*, J. Christopher Greever, Jon L. Howell, and Justin M. Hoerter “The Use of Perfluorobutyl Methyl Ethers as Methylating Agents for Amines.” 19th International Symposium on Fluorine Chemistry, Jackson Hole, Wyoming, USA, August 23-28, 2009. (Invited Speaker) 

 

8.  Crystal M. Wuthrich* and Chadron M. Friesen “Synthesis of (4-chlorobenzyl) Diphenyl Phosphine oxide, a Precursor to Fluorous Triarylphosphine Ligand.”  17th Regional Murdock Charitable Trust Undergraduate Research Conference, University of Puget Sound, Tacoma, WA, November 7-8, 2008 and Western Canadian Undergraduate Chemistry Conference May 7-9th, 2009.

9.  Chadron M. Friesen* and Jon L. Howell. "Efforts to Prepare Poly(hexafluoropropylene oxide) perfluorovinyl ether." 15th European Symposium on Fluorine Chemistry, Prague, Czech Republic, July 15-2016, 2007.

10. Chadron M. Friesen*, Ashley, Jamieson, Daryl Nyvall, Jon L. Howell "Understanding Fluorinated Amines Reactions of Poly(hexafluoropropylene oxide) [polyHFPO] Methylene Amine" 18th Winter Fluorine Conference, St. Petersburg, Florida, USA January 14-19, 2007.

11. Chadron M. Friesen*, Ashley, Jamieson, Daryl Nyvall, Jon L. Howell "The development of ethyl and propyl alcohols from Radical reactions with poly(hexafluoropropylene oxide) primary iodides" 17th Winter Fluorine Conference, St. Petersburg, Florida, USA January 9-14, 2005.

12. Chadron M. Friesen* "Poly(hexafluoropropylene oxide): From the Manufacturing Process to Utilization in Fluorous Biphase Systems" Simon Fraser University, Burnaby, British Columbia, Canada. October 12, 2004.

13. Joseph S. Thrasher*, Alfred Waterfeld, Yangliu Zhou, Erik W. Perez, Ireneusz Novak, Michael A. P. Beukama, Kevin A. Hay, Chadron M. Friesen, Jon L. Howell "Syntheses and application of poly-hexafluoropropylene oxide primary and secondary bromides and iodides" Fluoropolymer 2004, Savannah, Georgia, October 7-9, 2004.

14. Jon L. Howell*, Krista. L. Laugesen, Alice. E. Van der Ende, Chadron. M. Friesen "Reactions of Perfluorinated Ketones with Amines" 14th European Symposium on Fluorine Chemistry, Poznań, Poland, July 11-16, 2004.

15. Chadron M. Friesen*, Michael A. P. Beukama, Kevin A. Hay, Jon L. Howell "The development of ethyl and propyl alcohols from Radical reactions with poly(hexafluoropropylene oxide) primary iodides"14th European Symposium on Fluorine Chemistry, Poznań, Poland, July 11-16, 2004.

16. Michael A.P. Beukema* and Chadron M. Friesen "Synthesis of poly-hexafluoropropylene oxide (poly-HFPO) propyl alcohol: A precursor to insulated triarylphosphines" 17th Annual Western Canadian Undergraduate Chemistry Conference, Regina, Saskatchewan, Canada May 1-4, 2003.

17. Chadron M. Friesen*, Krista L. Laugesen, Jon L. Howell, Joseph S. Thrasher, Yangliu Zhou, Alfred Waterfeld "Synthesis of a novel fluorous triarylphospine-containing poly-hexafluoropropylene oxide (poly-HFPO)" 16th Winter Fluorine Conference, St. Petersburg, Florida, USA January 12-17, 2003.

18. Jon L. Howell*, Alexander B. Shtarov, Joseph S. Thrasher, Alfred Waterfeld, Koichi Murata , Erik W. Pérez, Alexey M. Siyagin, Chadron M. Friesen "Synthesis of New Perfluoroalkyl Polyethers Starting from Glycols and Tetrafluoroethylene" 13th European Symposium on Fluorine Chemistry, Bordeaux, France, July 15-20, 2001.

19. Chadron M. Friesen*, Erik W. Pérez*, Jon L. Howell, Joseph S. Thrasher, Alfred Waterfeld, Irik Nowak, Andy N. Wood, Jonathan F. Sullivan, "Fluorous Biphase Chemistry Utilizing Perfluoropolyalkylethers" 219th American Chemical Society National Meeting & Exposition, San Francisco, California, USA March 26-30, 2000. & 16th International Symposium on Fluorine Chemistry, Durham, UK, July 16-21, 2000.

20. Jon L. Howell*, Joseph S. Thrasher, Alfred Waterfeld, Koichi Murata , Erik W. Pérez, Chadron M. Friesen "Degradation of Hexafluoropropylene Oxide (HFPO) Polymers Containing Various End Groups in the Presence of Aluminium Fluoride." 16th International Symposium on Fluorine Chemistry, Durham, UK, July 16-21, 2000.

21. Joseph S. Thrasher*; Alfred Waterfeld, Alexey M. Sipyigin, Chadron M. Friesen, Jon L. Howell, Michael A. Hofmann; "The use of carbon-13 NMR spectroscopy to determine the end groups in perfluoropolyethers (PFPEs)". 216th ACS National Meeting, Boston, August 23-27, 1998.

 

PROFESSIONAL SOCIETIES

Member of The American Chemical Society (ACS), Division of Analytical Chemistry
Member of ACS Division of Fluorine Chemistry (1996-present)

COURSES: 

General Chemistry I (CHEM 103)
General Chemistry II (CHEM 104)
Organic Chemistry I (CHEM 221)
Organic Chemistry II (CHEM 222)
Thermodynamics (CHEM 240)
Analytical Chemistry I (CHEM 357)
Analytical Chemistry II (CHEM 358)
Fluorine Chemistry (CHEM 400)
Senior Research Thesis (Chem 409/410)

Hobbies and Interesting Facts:

  • Enjoy Running, Swimming, Hiking, Skiing (Snow or Water), Camping
  • Currently working on building a sail boat (The Weekender)
  • Eagle Scout
  • Birth Place is Säffle, Sweden