Robert H. Grubbs
AIC Gold Medal recipient, 2010
Robert Howard Grubbs|
February 27, 1942
Marshall County, Kentucky, United States
|Known for||Catalysts for olefin metathesis in organic synthesis|
|Institutions||California Institute of Technology|
|Thesis||I. Cyclobutadiene Derivatives II. Studies of Cyclooctatetraene Iron Tricarbonyl Complexes (1968)|
|Doctoral advisor||Ronald Breslow|
|Doctoral students||SonBinh Nguyen|
Robert Howard Grubbs (born February 27, 1942) is an American chemist and the Victor and Elizabeth Atkins Professor of Chemistry at the California Institute of Technology in Southern California. He was a co-recipient of the 2005 Nobel Prize in Chemistry for his work on olefin metathesis. He is a co-founder of Materia, a University spin-off startup to produce catalysts.
Early life and education
Grubbs was born on February 27, 1942, on a farm in Marshall County, Kentucky, midway between Possum Trot and Calvert City. His parents were Howard and Faye Grubbs. Faye Grubbs was a schoolteacher. After serving in World War II, the family moved to Paducah, Kentucky, where Howard Grubbs trained as a diesel mechanic, and Robert Grubbs attended Paducah Tilghman High School.
At the University of Florida, Robert Grubbs initially intended to study agriculture. However, he was convinced by professor Merle A. Battiste to switch to organic chemistry. Working with Battiste, Grubbs became interested in how chemical reactions occur. He received his B.S. in 1963 and M.S. in 1965 from the University of Florida.
Next, Grubbs attended Columbia University, where he worked with Ronald Breslow 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.
Career and research
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.
In 1969, Grubbs was then 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. He was an assistant professor from 1969 to 1973, and an associate professor from 1973 to 1978. He received a Sloan Fellowship for 1974–1976. In 1975, he went to the Max Planck Institute for Coal Research in Mülheim, Germany on a fellowship from the Alexander von Humboldt Foundation.
Grubbs' 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. The basic technique can be used for creation of polymers, pharmaceuticals and petrochemicals and has broad applications in areas including pharmaceuticals, biotechnology, agriculture, and plastics.
Grubbs has been instrumental in developing a family of ruthenium catalysts including Grubbs' catalyst for olefin metathesis. He has studied olefin transformations for ring-closing metathesis (RCM), cross-metathesis reaction (CMR), and ring-opening metathesis polymerization (ROMP) with cyclic olefins such as norbornene. 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.
The Grubbs group successfully polymerized the 7-oxo norbornene derivative using ruthenium trichloride, osmium trichloride as well as tungsten alkylidenes. 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:
The corresponding tricyclohexylphosphine complex (PCy3)2Cl2Ru=CHCH=CPh2 was also shown to be active. This work culminated in the now commercially available 1st generation Grubbs catalyst in 1995. Second generation catalysts have been developed as well.
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.
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. Using catalysts allows chemists to speed up chemical transformations and to lower the cost of what were previously complicated multi-step industrial processes.
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. Materia has been able to obtain exclusive rights to manufacture many of the known olefin catalysts. Under Giardello, Materia was able to sell their catalysts through Sigma-Aldrich's chemicals catalogue. Sigma-Aldrich became their exclusive worldwide provider. In 2008, Materia partnered with Cargill to form Elevance Renewable Sciences to produce specialty chemicals from renewable oils, including biofuels.
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. He has received a number of other awards and honors as well, including the following:
- 1989: National Academy of Sciences
- 1994: American Academy of Arts and Sciences
- 2000: Benjamin Franklin Medal in Chemistry from the Franklin Institute
- 2000: ACS Herman F. Mark Polymer Chemistry Award
- 2001: ACS Herbert C. Brown Award for Creative Research in Synthetic Methods
- 2002: Tolman Medal
- 2002: Arthur C. Cope Award
- 2003: Tetrahedron Prize for Creativity in Organic Chemistry & BioMedicinal Chemistry (with Dieter Seebach)
- 2005: Nobel Prize in Chemistry (with Richard R. Schrock and Yves Chauvin)
- 2005: Honorary Fellow of the Royal Society of Chemistry
- 2005: Paul Karrer Gold Medal
- 2009: Fellow of the American Chemical Society
- 2010: American Institute of Chemists Gold Medal
- 2015: Inducted into the Florida Inventors Hall of Fame
- 2013: National Academy of Inventors
- 2015: National Academy of Engineering
- 2015: Chinese Academy of Sciences (foreign academician)
- 2017: Elected a Fellow of the Royal Society
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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.
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- 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.
- 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. Retrieved 14 April 2016.
- 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". Journal of the American Chemical Society. 114 (10): 3974–3975. doi:10.1021/ja00036a053. Retrieved 13 April 2016.
- 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. doi:10.1021/ma00171a053. Retrieved 13 April 2016.
- 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.
- 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.
- Notman, Nina (28 January 2015). "Grubbs catalyst". Chemistry World. Retrieved 15 April 2016.
- 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.
- 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.
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- Wilson, GeraldO.; Porter, KeithA.; Weissman, Haim; White, ScottR.; Sottos, NancyR.; Moore, JeffreyS. (14 August 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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