Robert H. Grubbs

Robert Howard Grubbs ForMemRS (born February 27, 1942) is an American chemist and the Victor and Elizabeth Atkins Professor of Chemistry at the California Institute of Technology in Pasadena, California.[3] He was a co-recipient of the 2005 Nobel Prize in Chemistry for his work on olefin metathesis.[4] He is a co-founder of Materia, a university spin-off startup to produce catalysts.[5]

Robert Grubbs
Robert Grubbs at the Royal Society admissions day in London, July 2018
Born
Robert Howard Grubbs

(1942-02-27) February 27, 1942
Marshall County, Kentucky
Alma materUniversity of Florida (BS)
University of Florida (MS)
Columbia University (PhD)
Known forCatalysts for olefin metathesis in organic synthesis
Spouse(s)Helen O'Kane-Grubbs
Awards
Scientific career
FieldsOrganic chemistry
InstitutionsStanford University
Michigan State University
California Institute of Technology
ThesisI. Cyclobutadiene Derivatives II. Studies of Cyclooctatetraene Iron Tricarbonyl Complexes (1968)
Doctoral advisorRonald Breslow[2]
Doctoral students
SonBinh Nguyen
Websitechche.divisions.caltech.edu/people/robert-h-grubbs

Early life and education
AIC Gold Medal recipient, 2010

Grubbs was born on February 27, 1942, on a farm in Marshall County, Kentucky, midway between Possum Trot and Calvert City.[6][7] His parents were Howard and Faye Grubbs.[6] Faye was a schoolteacher. After serving in World War II, the family moved to Paducah, Kentucky, where Howard trained as a diesel mechanic, and Robert attended Paducah Tilghman High School.[6][7]

At the University of Florida, Grubbs initially intended to study agriculture. However, he was convinced by professor Merle A. Battiste to switch to organic chemistry.[8] Working with Battiste, he became interested in how chemical reactions occur.[7] He received his B.S. in 1963 and M.S. in 1965 from the University of Florida.[8]

Next, Grubbs attended Columbia University, where he worked with Ronald Breslow[2] on the antiaromaticity of cyclobutadiene. This work aroused his interest in metals and organometallic compounds which contain carbon-metal bonds. Grubbs received his PhD in 1968.[2][7]

Career

Grubbs worked with James Collman at Stanford University as a National Institutes of Health fellow during 1968–1969. With Collman, he began to systematically investigate catalytic processes in organometallic chemistry, a relatively new area of research.[7]

In 1969, Grubbs was appointed to the faculty of Michigan State University, where he began his work on olefin metathesis. Harold Hart, Gerasimos J. Karabatsos, Gene LeGoff, Don Farnum, Bill Reusch and Pete Wagner served as his early mentors at MSU.[7] Grubbs was an assistant professor from 1969 to 1973, and an associate professor from 1973 to 1978.[9] He received a Sloan Fellowship for 1974–1976.[10] In 1975, he went to the Max Planck Institute for Coal Research in Mülheim, Germany on a fellowship from the Alexander von Humboldt Foundation.[11]

In 1978 Grubbs moved to California Institute of Technology as a professor of chemistry. As of 1990 he became the Victor and Elizabeth Atkins Professor of Chemistry.[12][13]

Grubbs's main research interests are in organometallic chemistry and synthetic chemistry, particularly the development of novel catalysts for olefin metathesis. In olefin metathesis, a catalyst is used to break the bonds of carbon molecules, which can then re-form to create chemical bonds in new ways, producing new compounds with unique properties.[8][14] The basic technique can be used for creation of polymers, pharmaceuticals and petrochemicals[15] and has broad applications in areas including pharmaceuticals, biotechnology, agriculture, and plastics.[8]

Grubbs has been instrumental in developing a family of ruthenium catalysts including Grubbs catalyst for olefin metathesis.[16] He has studied olefin transformations for ring-closing metathesis (RCM),[17] cross-metathesis reaction (CMR),[18] and ring-opening metathesis polymerization (ROMP) with cyclic olefins such as norbornene.[19] He has also contributed to the development of "living polymerization", in which the termination ability of a polymerization reaction is removed. The polymer will continue to replicate until a quenching agent is presented.[20]

The Grubbs group successfully polymerized the 7-oxo norbornene derivative using ruthenium trichloride, osmium trichloride as well as tungsten alkylidenes.[21] They identified a Ru(II) carbene as an effective metal center and in 1992 published the first well-defined, ruthenium-based olefin metathesis catalyst, (PPh3)2Cl2Ru=CHCH=CPh2.[19]

Metathesis Grubbs 1992

The corresponding tricyclohexylphosphine complex (PCy3)2Cl2Ru=CHCH=CPh2 was also shown to be active.[22] This work culminated in the now commercially available 1st generation Grubbs catalyst in 1995.[23][24][25] Second generation catalysts have been developed as well.[26][27]

Ruthenium is stable in air and has higher selectivity and lower reactivity than molybdenum, the most promising of the previously discovered catalysts. In addition, Grubbs took a green chemistry approach to catalysis that reduced the potential to create hazardous waste. Grubbs catalyst has become a standard for general metathesis applications in ordinary laboratories.[3][16][26]

By controlling the catalyst used, it becomes possible to synthesize polymers with specialized structures and functional capabilities, including cyclic olefins, alternating copolymers, and multiblock copolymers.[14] Using catalysts allows chemists to speed up chemical transformations and to lower the cost of what were previously complicated multi-step industrial processes.[28]

Commercial activities

Both first and second generation Grubbs catalysts are commercially available from Materia, a startup company that Grubbs co-founded with Mike Giardello in Pasadena, California in 1998.[23][28][29] Materia has been able to obtain exclusive rights to manufacture many of the known olefin catalysts.[30] Under Giardello, Materia was able to sell their catalysts through Sigma-Aldrich's chemicals catalogue. Sigma-Aldrich became their exclusive worldwide provider.[28][31] In 2008, Materia partnered with Cargill to form Elevance Renewable Sciences to produce specialty chemicals from renewable oils,[32] including biofuels.[33]

Grubbs is a member of the Reliance Innovation Council formed by Reliance Industries Limited, India.[34]

Grubbs is a member of the USA Science and Engineering Festival's Advisory Board.[35]

Awards and honors

Grubbs received the 2005 Nobel Prize in Chemistry, along with Richard R. Schrock and Yves Chauvin, for his work in the field of olefin metathesis.[4][36] He has received a number of other awards and honors, including the following:

Personal life

While at Columbia University, Grubbs also met his future wife, Helen O'Kane, a speech language pathologist, with whom he has three children: Barney (born 1972), Brendan H. (born 1974) and Kathleen (Katy) (born 1977).[7][53]

gollark: It's pointless to say "I don't like this! Let's do it better" without any idea of what that would mean.
gollark: And ones which require some retroactive change like "let's all have become better at hygiene and gotten masks for everyone" or something obviously can't actually work.
gollark: If you have a better idea I'm sure someone will listen.
gollark: I mean, the UK initially went for an "ignore it and hope it goes away" sort of approach based on flawed modelling for flu, but then changed their strategy to the lockdown/social distancing one when updated models suggested this was a bad idea.
gollark: Like what? I'm pretty sure there has been thought about this.

References
  1. Anon (2017). "Professor Robert Grubbs ForMemRS". royalsociety.org. London: Royal Society.
  2. Grubbs, Robert Howard (1968). I. Cyclebutadiene Derivatives II. Studies of Cyclooctatetraene Iron Tricarbonyl Complexes (PhD thesis). Columbia University. ProQuest 302317287. (subscription required)
  3. "American Institute of Chemists Gold Medal". Science History Institute. March 22, 2018.
  4. "Press Release, 5 October 2005". The Nobel Prize in Chemistry 2005. NobelPrize.org. Retrieved April 12, 2016.
  5. "Lanxess rubber employs Materia catalysts". Chemical & Engineering News. 84 (34): 23. August 21, 2006. Retrieved January 9, 2018.
  6. "Jackson Purchase Nobel Laureate". Jackson Purchase Historical Society. Retrieved April 12, 2016.
  7. "Robert H. Grubbs – Biographical". The Nobel Prize in Chemistry 2005. NobelPrize.org. Retrieved April 12, 2016. In some places, my birthplace is listed as Calvert City and in others Possum Trot. I was actually born between the two, so either one really is correct.
  8. Janine Young, Sikes (October 6, 2005). "A Gator wins Nobel in chemistry". The Gainesville Sun. Retrieved April 14, 2016.
  9. "Robert H. Grubbs PhD " Leadership Board". Department of Chemistry, University of Florida. Retrieved April 14, 2016.
  10. "Nobel Laureates". Alfred P. Sloan Foundation. Retrieved April 15, 2016.
  11. "Chemistry Nobel Prize for two Humboldtians". The Alexander von Humboldt Foundation. October 5, 2005.
  12. "Robert H. Grubbs American chemist". Encyclopædia Britannica.
  13. "2002 Robert H. Grubbs, Caltech". Southern California Section of the American Chemical Society. July 20, 2012. Retrieved April 12, 2016.
  14. Miree-Luke, Lisa (October 8, 2015). "Axalta's Distinguished Lecture Series at the University of Pennsylvania Features Presentation on Methathesis Polymerization". Business Wire. Retrieved April 14, 2016.
  15. Pearson, Rodney (April 3, 2001). "South Pasadena chemist wins national award for designing new catalysts". EurekaAlert. Retrieved April 14, 2016.
  16. Singh, Okram Mukherjee (2006). "Metathesis catalysts: Historical perspective, recent developments and practical applications" (PDF). Journal of Scientific & Industrial Research. 65 (December): 957–965. Retrieved April 12, 2016.
  17. Grubbs, Robert H. (2006). "Olefin-Metathesis Catalysts for the Preparation of Molecules and Materials (Nobel Lecture)". Angewandte Chemie International Edition. 45 (23): 3760–3765. doi:10.1002/anie.200600680. PMID 16724297.
  18. Chatterjee, Arnab K.; Choi, Tae-Lim; Sanders, Daniel P.; Grubbs, Robert H. (September 2003). "A General Model for Selectivity in Olefin Cross Metathesis" (PDF). Journal of the American Chemical Society. 125 (37): 11360–11370. doi:10.1021/ja0214882. PMID 16220959. Retrieved April 14, 2016.
  19. Nguyen, SonBinh T.; Johnson, Lynda K.; Grubbs, Robert H.; Ziller, Joseph W. (May 1992). "Ring-opening metathesis polymerization (ROMP) of norbornene by a Group VIII carbene complex in protic media" (PDF). Journal of the American Chemical Society. 114 (10): 3974–3975. doi:10.1021/ja00036a053.
  20. Schrock, R. R.; Feldman, J.; Cannizzo, L. F.; Grubbs, R. H. (September 1987). "Ring-opening polymerization of norbornene by a living tungsten alkylidene complex". Macromolecules. 20 (5): 1169–1172. Bibcode:1987MaMol..20.1169S. doi:10.1021/ma00171a053.
  21. Novak, Bruce M.; Grubbs, Robert H. (1988). "The ring opening metathesis polymerization of 7-oxabicyclo[2.2.1]hept-5-ene derivatives: a new acyclic polymeric ionophore". Journal of the American Chemical Society. 110 (3): 960–961. doi:10.1021/ja00211a043.
  22. Nguyen, Sonbinh T.; Grubbs, Robert H.; Ziller, Joseph W. (1993). "Syntheses and activities of new single-component, ruthenium-based olefin metathesis catalysts". Journal of the American Chemical Society. 115 (21): 9858–9859. doi:10.1021/ja00074a086.
  23. Notman, Nina (January 28, 2015). "Grubbs catalyst". Chemistry World. Retrieved April 15, 2016.
  24. Schwab, Peter; France, Marcia B.; Ziller, Joseph W.; Grubbs, Robert H. (1995). "A Series of Well-Defined Metathesis Catalysts–Synthesis of [RuCl2(CHR')(PR3)2] and Its Reactions". Angew. Chem. Int. Ed. Engl. 34 (18): 2039–2041. doi:10.1002/anie.199520391.
  25. Schwab, Peter; Grubbs, Robert H.; Ziller, Joseph W. (1996). "Synthesis and Applications of RuCl2(=CHR')(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity". Journal of the American Chemical Society. 118: 100–110. doi:10.1021/ja952676d.
  26. Astruc, Didier (2005). "The metathesis reactions: from a historical perspective to recent developments" (PDF). New Journal of Chemistry. 29 (1): 42. doi:10.1039/b412198h. Retrieved April 12, 2016.
  27. Wilson, Gerald O.; Porter, Keith A.; Weissman, Haim; White, Scott R.; Sottos, Nancy R.; Moore, Jeffrey S. (August 14, 2009). "Stability of Second Generation Grubbs' Alkylidenes to Primary Amines: Formation of Novel Ruthenium-Amine Complexes". Advanced Synthesis & Catalysis. 351 (11–12): 1817–1825. doi:10.1002/adsc.200900134.
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  32. Tullo, Alexander H. (March 31, 2008). "Cargill, Materia Launch New Firm Elevance will make specialty chemicals from vegetable oils". Chemical & Engineering News. 86 (13): 6. doi:10.1021/cen-v086n013.p006.
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  42. "Tetrahedron Prize for Creativity". Elsevier B.V. Retrieved April 12, 2016.
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