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Robert H. Grubbs

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Robert H. Grubbs
Grubbs in 2018
Born
Robert Howard Grubbs

(1942-02-27)February 27, 1942
Marshall County, Kentucky, U.S.
DiedDecember 19, 2021(2021-12-19) (aged 79)
Duarte, California, U.S.
EducationUniversity of Florida (BS, MS)
Columbia University (PhD)
Known forCatalysts for olefin metathesis in organic synthesis
SpouseHelen O'Kane
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
Other notable studentsPost-docs:
Websitegrubbsgroup.caltech.edu

Robert Howard Grubbs ForMemRS (February 27, 1942 – December 19, 2021) was an American chemist and the Victor and Elizabeth Atkins Professor of Chemistry at the California Institute of Technology in Pasadena, California.[7] He was a co-recipient of the 2005 Nobel Prize in Chemistry for his work on olefin metathesis.[8]

Grubbs was elected a member of the National Academy of Engineering in 2015 for developments in catalysts that have enabled commercial products.

He was a co-founder of Materia, a university spin-off startup to produce catalysts.[9]

Early life and education

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Grubbs was born on February 27, 1942, on a farm in Marshall County, Kentucky, midway between Possum Trot and Calvert City.[10][11] His parents were Howard and Faye (Atwood) Grubbs.[10][12] 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.[10][11]

At the University of Florida, Grubbs initially intended to study agriculture chemistry.[13] However, he was convinced by professor Merle A. Battiste to switch to organic chemistry.[14] Working with Battiste, he became interested in how chemical reactions occur.[11] He received his B.S. in 1963 and M.S. in 1965 from the University of Florida.[14][15]

Next, Grubbs attended Columbia University, where he worked with Ronald Breslow on organometallic compounds which contain carbon-metal bonds. Grubbs received his Ph.D. in 1968.[2][11]

Career

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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 then relatively new area of research.[11]

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.[11] Grubbs was an assistant professor from 1969 to 1973, and an associate professor from 1973 to 1978.[16] He received a Sloan Fellowship for 1974–1976.[17] In 1975, he went to the Max Planck Institute for Coal Research in Mülheim, Germany, on a fellowship from the Alexander von Humboldt Foundation.[18]

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.[19][20]

As of 2021, Grubbs has an h-index of 160 according to Google Scholar[21] and of 137 according to Scopus.[22]

Commercial activities

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Both first and second generation Grubbs catalysts were commercially available from Materia, a startup company that Grubbs co-founded with Mike Giardello in Pasadena, California, in 1998.[23][24][25] Materia has been able to obtain exclusive rights to manufacture many of the known olefin catalysts.[26] Under Giardello, Materia was able to sell their catalysts through Sigma-Aldrich's chemicals catalogue. Sigma-Aldrich became their exclusive worldwide provider.[24][27] In 2008, Materia partnered with Cargill to form Elevance Renewable Sciences to produce specialty chemicals from renewable oils,[28] including biofuels.[29] In 2017, Materia sold its catalyst business to Umicore.[30] In 2021, Materia was acquired by ExxonMobil.[31]

Grubbs was a member of the Reliance Innovation Council formed by Reliance Industries Limited, India.[32]

Grubbs was a member of the USA Science and Engineering Festival's advisory board.[33]

Research

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Grubbs's main research interests were 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.[14][34] The basic technique can be used for creation of polymers, pharmaceuticals and petrochemicals[35] and has broad applications in areas including pharmaceuticals, biotechnology, agriculture, and plastics.[14]

Grubbs was instrumental in developing a family of ruthenium catalysts, including Grubbs catalyst for olefin metathesis.[36] He studied olefin transformations for ring-closing metathesis (RCM),[37] cross-metathesis reaction (CMR),[38] and ring-opening metathesis polymerization (ROMP) with cyclic olefins such as norbornene.[39] He 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.[40]

The Grubbs group successfully polymerized the 7-oxo norbornene derivative using ruthenium trichloride, osmium trichloride as well as tungsten alkylidenes.[41] 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.[39]

Metathesis Grubbs 1992
Metathesis Grubbs 1992

The corresponding tricyclohexylphosphine complex (PCy3)2Cl2Ru=CHCH=CPh2 was also shown to be active.[42] This work culminated in the now commercially available first-generation Grubbs catalyst in 1995.[23][43][44] Second generation catalysts were developed as well.[45][46]

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. The Grubbs catalyst has become a standard for general metathesis applications in ordinary laboratories.[7][36][45]

By controlling the catalyst used, it became possible to synthesize polymers with specialized structures and functional capabilities, including cyclic olefins, alternating copolymers, and multiblock copolymers.[34] Using catalysts allows chemists to speed up chemical transformations and to lower the cost of what were previously complicated multi-step industrial processes.[24]

Personal life

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While at Columbia University, Grubbs also met his future wife, Helen O'Kane, a special-education teacher, with whom he had three children: Barney (born 1972), Brendan H. (born 1974) and Kathleen (Katy) (born 1977).[11][47][48]

Grubbs died from a heart attack at the City of Hope Comprehensive Cancer Center in Duarte, California, on December 19, 2021, at age 79.[49][48] At the time of his death, he was being treated for lymphoma.[48]

Awards and honors

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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.[8][50] He has received a number of other awards and honors, including the following:

AIC Gold Medal recipient, 2010

Publications

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  • Grubbs, Robert (2003). Handbook of Metathesis. Weinheim, Germany; Chichester, England: Wiley-VCH John Wiley distributor. ISBN 978-3-527-30616-9. OCLC 52485738.

References

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  1. ^ a b Anon (2017). "Professor Robert Grubbs ForMemRS". royalsociety.org. London: Royal Society.
  2. ^ a b Grubbs, Robert Howard (1968). I. Cyclebutadiene Derivatives II. Studies of Cyclooctatetraene Iron Tricarbonyl Complexes (PhD thesis). Columbia University. ProQuest 302317287. (subscription required)
  3. ^ Nguyen, SonBinh TheBao (1995). The designs, syntheses, and applications of well-defined, single component group VIII olefin metathesis catalysts (phd). California Institute of Technology. doi:10.7907/1BVB-S189. Retrieved December 20, 2021. Research Advisor(s): Grubbs, Robert H.
  4. ^ Sanford, Melanie Sarah (2001). Synthetic and mechanistic investigations of ruthenium olefin metathesis catalysts (phd). California Institute of Technology. doi:10.7907/Q96P-VK05. Retrieved December 20, 2021. Research Advisor(s): Grubbs, Robert H.
  5. ^ "People – The Sanford Group". WordPress Websites – Offered by LSA Technology Services. October 29, 2021. Retrieved December 20, 2021.
  6. ^ Swager, Timothy Manning (1988). Precursor Routes to Conducting Polymers from the Ring-Opening Metathesis Polymerization of Cyclic Olefins (phd). California Institute of Technology. doi:10.7907/KF6P-FC76. Retrieved December 20, 2021. Research Advisor(s): Grubbs, Robert H.
  7. ^ a b c "American Institute of Chemists Gold Medal". Science History Institute. March 22, 2018.
  8. ^ a b c "Press Release, 5 October 2005". The Nobel Prize in Chemistry 2005. NobelPrize.org. Retrieved April 12, 2016.
  9. ^ "Lanxess rubber employs Materia catalysts". Chemical & Engineering News. 84 (34): 23. August 21, 2006. Retrieved January 9, 2018.
  10. ^ a b c "Jackson Purchase Nobel Laureate". Jackson Purchase Historical Society. Retrieved April 12, 2016.
  11. ^ a b c d e f g "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.
  12. ^ History and Families, McCracken County, Kentucky, 1824–1989. Turner Publishing Company. December 22, 1989. ISBN 9780938021360. Retrieved December 22, 2021 – via Google Books.
  13. ^ "Nobel laureate Robert Grubbs dies at 79". cen.acs.org. Retrieved December 22, 2021.
  14. ^ a b c d Janine Young, Sikes (October 6, 2005). "A Gator wins Nobel in chemistry". The Gainesville Sun. Archived from the original on April 21, 2016. Retrieved April 14, 2016.
  15. ^ Doerfler, Andrew (December 20, 2021). "UF Mourns the Passing of Robert H. Grubbs, Nobel-Winning Alumnus". News – College of Liberal Arts & Sciences. Retrieved December 22, 2021.
  16. ^ "Robert H. Grubbs PhD " Leadership Board". Department of Chemistry, University of Florida. Retrieved April 14, 2016.
  17. ^ "Nobel Laureates". Alfred P. Sloan Foundation. Retrieved April 15, 2016.
  18. ^ "Chemistry Nobel Prize for two Humboldtians". The Alexander von Humboldt Foundation. October 5, 2005. Archived from the original on November 14, 2018.
  19. ^ "Robert H. Grubbs American chemist". Encyclopædia Britannica. April 26, 2024.
  20. ^ a b "2002 Robert H. Grubbs, Caltech". Southern California Section of the American Chemical Society. July 20, 2012. Retrieved April 12, 2016.
  21. ^ Robert H. Grubbs publications indexed by Google Scholar Edit this at Wikidata
  22. ^ Robert H. Grubbs publications indexed by the Scopus bibliographic database. (subscription required)
  23. ^ a b Notman, Nina (January 28, 2015). "Grubbs catalyst". Chemistry World. Retrieved April 15, 2016.
  24. ^ a b c "Industry's Secret Ingredient". Caltech News. Archived from the original on September 10, 2015. Retrieved April 17, 2014.
  25. ^ "Leading Innovation in Catalysis". Materia. Retrieved April 15, 2016.
  26. ^ "The History of Materia". Materia. Retrieved April 15, 2016.
  27. ^ "Materia and Sigma-Aldrich Announce Exclusive Distribution Deal for Grubbs' Metathesis Catalysts". Business Wire. August 18, 2003. Retrieved April 15, 2016.
  28. ^ 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.
  29. ^ Kotrba, Ron (March 23, 2010). "Newton plant to become biorefinery showcase". Biodiesel Magazine. Retrieved April 15, 2016.
  30. ^ "Materia, Inc. Sells Catalyst Business to Umicore". Materia. December 20, 2017. Retrieved June 10, 2021.
  31. ^ "ExxonMobil acquires Materia, Inc., a high-performance structural polymers company". ExxonMobil. Retrieved December 18, 2021.
  32. ^ "Reliance Innovation Council (2007–2017) – Raghunath Mashelkar – Mukesh Ambani – Jean-Marie Lehn – Robert Grubbs – George Whitesides – Gary Hamel – William Haseltine". Reliance Industries Limited. Archived from the original on December 16, 2021. Retrieved December 20, 2021.
  33. ^ "Nobel Laureates". USA Science & Engineering Festival. Archived from the original on April 21, 2010. Retrieved April 12, 2016.
  34. ^ a b 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.
  35. ^ a b Pearson, Rodney (April 3, 2001). "South Pasadena chemist wins national award for designing new catalysts". EurekaAlert. Archived from the original on April 15, 2016. Retrieved April 14, 2016.
  36. ^ a b 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.
  37. ^ 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.
  38. ^ 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.
  39. ^ a b 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.
  40. ^ 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.
  41. ^ 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.
  42. ^ 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.
  43. ^ 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.
  44. ^ 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.
  45. ^ a b 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. Archived from the original (PDF) on June 16, 2016. Retrieved April 12, 2016.
  46. ^ 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.
  47. ^ "Columbia News ::: Alumnus Robert Grubbs Wins Nobel Prize in Chemistry". www.columbia.edu. Archived from the original on March 1, 2017. Retrieved July 21, 2016.
  48. ^ a b c McClain, Dylan Loeb (December 24, 2021). "Robert H. Grubbs, 79, Dies; Chemistry Breakthrough Led to a Nobel". The New York Times. Retrieved December 24, 2021.
  49. ^ "Caltech Mourns the Loss of Nobel Laureate Robert H. Grubbs". Caltech. December 19, 2021. Retrieved December 19, 2021.
  50. ^ "Robert H. Grubbs – Facts". The Nobel Prize in Chemistry 2005. NobelPrize.org. Retrieved April 15, 2016.
  51. ^ "National Academy of Sciences Members". Caltech. Retrieved April 15, 2016.
  52. ^ "Robert H. Grubbs". American Academy of Arts & Sciences. November 18, 2021. Retrieved December 20, 2021.
  53. ^ "Robert H. Grubbs". The Franklin Institute. January 10, 2014. Retrieved April 14, 2016.
  54. ^ "Herman F. Mark Award 2000". Division of Polymer Chemistry, Inc. of the American Chemical Society. Archived from the original on March 15, 2016. Retrieved April 14, 2016.
  55. ^ "Pasadena chemist wins national award for cata". EurekAlert!. Retrieved December 20, 2021.
  56. ^ "Arthur C. Cope Award". ACS Chemistry for Life. American Chemical Society. Retrieved April 12, 2016.
  57. ^ "Tetrahedron Prize for Creativity". Elsevier B.V. Retrieved April 12, 2016.
  58. ^ "Members Grubbs". rsc.org. Royal Society of Chemistry. Retrieved April 15, 2016.
  59. ^ "Robert H. Grubbs 31st Paul Karrer Lecture 2005". University of Zurich. Archived from the original on April 23, 2016. Retrieved April 12, 2016.
  60. ^ "Golden Plate Awardees of the American Academy of Achievement". www.achievement.org. American Academy of Achievement.
  61. ^ "2009 ACS Fellows". American Chemical Society. Archived from the original on February 24, 2019. Retrieved April 15, 2016.
  62. ^ "2015 Inductees: Robert Howard Grubbs". Florida Inventors Hall of Fame. September 28, 2015. Retrieved April 14, 2016.
  63. ^ "Current NAI Fellows". National Academy of Inventors. Retrieved April 15, 2016.
  64. ^ "Professor Robert Howard Grubbs". National Academy of Engineering. Retrieved April 12, 2016.
  65. ^ "New Academicians and Foreign Members of the Chinese Academy of Sciences". Angewandte Chemie International Edition. 55 (8): 2633–2634. February 2016. doi:10.1002/anie.201511637.
  66. ^ "12 Famous Scientists Elected 2015 CAS Foreign Members". CASAD. Retrieved April 12, 2016.
  67. ^ Wang, Linda (February 13, 2017). "Robert Grubbs wins Remsen Award". Chemical & Engineering News. 59 (7). American Chemical Society. Retrieved December 20, 2021.
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