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Robert H. Grubbs

From Wikipedia, the free encyclopedia
American chemist and Nobel Laureate (1942–2021)

Robert H. Grubbs
Grubbs in 2018
Born
Robert Howard Grubbs

(1942-02-27)February 27, 1942
DiedDecember 19, 2021(2021-12-19) (aged 79)
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 GrubbsForMemRS (February 27, 1942 – December 19, 2021) was an Americanchemist and the Victor and Elizabeth Atkins Professor of Chemistry at theCalifornia Institute of Technology inPasadena, California.[7] He was a co-recipient of the 2005 Nobel Prize in Chemistry for his work onolefin metathesis.[8]

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

He was a co-founder of Materia, auniversity spin-off startup to producecatalysts.[9]

Early life and education

[edit]

Grubbs was born on February 27, 1942, on a farm inMarshall County, Kentucky, midway betweenPossum Trot andCalvert City.[10][11] His parents were Howard and Faye (Atwood) Grubbs.[10][12] Faye was a schoolteacher. After serving inWorld War II, the family moved toPaducah, Kentucky, where Howard trained as a diesel mechanic, and Robert attendedPaducah Tilghman High School.[10][11]

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

Next, Grubbs attendedColumbia University, where he worked withRonald Breslow on organometallic compounds which contain carbon-metal bonds. Grubbs received hisPh.D. in 1968.[2][11]

Career

[edit]

Grubbs worked withJames Collman atStanford University as aNational 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 ofMichigan 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 aSloan Fellowship for 1974–1976.[17] In 1975, he went to theMax Planck Institute for Coal Research inMülheim, Germany, on a fellowship from theAlexander von Humboldt Foundation.[18]

In 1978, Grubbs moved toCalifornia 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[update], Grubbs has anh-index of 160 according toGoogle Scholar[21] and of 137 according toScopus.[22]

Commercial activities

[edit]

Both first and second generation Grubbs catalysts were commercially available from Materia, a startup company that Grubbs co-founded with Mike Giardello inPasadena, 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 throughSigma-Aldrich's chemicals catalogue. Sigma-Aldrich became their exclusive worldwide provider.[24][27] In 2008, Materia partnered withCargill to form Elevance Renewable Sciences to produce specialty chemicals from renewable oils,[28] includingbiofuels.[29] In 2017, Materia sold its catalyst business toUmicore.[30] In 2021, Materia was acquired byExxonMobil.[31]

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

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

Research

[edit]

Grubbs's main research interests were inorganometallic chemistry andsynthetic chemistry, particularly the development of novel catalysts forolefin 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 includingpharmaceuticals,biotechnology, agriculture, and plastics.[14]

Grubbs was instrumental in developing a family ofruthenium catalysts, includingGrubbs catalyst forolefin metathesis.[36] He studied olefin transformations forring-closing metathesis (RCM),[37] cross-metathesis reaction (CMR),[38] andring-opening metathesis polymerization (ROMP) with cyclic olefins such asnorbornene.[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 usingruthenium 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 correspondingtricyclohexylphosphine complex (PCy3)2Cl2Ru=CHCH=CPh2 was also shown to be active.[42] This work culminated in the now commercially available first-generationGrubbs 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 thanmolybdenum, the most promising of the previously discovered catalysts. In addition, Grubbs took agreen chemistry approach to catalysis that reduced the potential to create hazardous waste. TheGrubbs 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

[edit]

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 theCity of Hope Comprehensive Cancer Center inDuarte, California, on December 19, 2021, at age 79.[49][48] At the time of his death, he was being treated forlymphoma.[48]

Awards and honors

[edit]

Grubbs received the 2005Nobel Prize in Chemistry, along withRichard R. Schrock andYves 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

[edit]

References

[edit]
  1. ^abAnon (2017)."Professor Robert Grubbs ForMemRS".royalsociety.org. London:Royal Society.
  2. ^abGrubbs, 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. RetrievedDecember 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. RetrievedDecember 20, 2021.Research Advisor(s): Grubbs, Robert H.
  5. ^"People – The Sanford Group".WordPress Websites – Offered by LSA Technology Services. October 29, 2021. RetrievedDecember 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. RetrievedDecember 20, 2021.Research Advisor(s): Grubbs, Robert H.
  7. ^abc"American Institute of Chemists Gold Medal".Science History Institute. March 22, 2018.
  8. ^abc"Press Release, 5 October 2005".The Nobel Prize in Chemistry 2005. NobelPrize.org. RetrievedApril 12, 2016.
  9. ^"Lanxess rubber employs Materia catalysts".Chemical & Engineering News.84 (34): 23. August 21, 2006. RetrievedJanuary 9, 2018.
  10. ^abc"Jackson Purchase Nobel Laureate".Jackson Purchase Historical Society. RetrievedApril 12, 2016.
  11. ^abcdefg"Robert H. Grubbs – Biographical".The Nobel Prize in Chemistry 2005. NobelPrize.org. RetrievedApril 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. RetrievedDecember 22, 2021 – via Google Books.
  13. ^"Nobel laureate Robert Grubbs dies at 79".cen.acs.org. RetrievedDecember 22, 2021.
  14. ^abcdJanine Young, Sikes (October 6, 2005)."A Gator wins Nobel in chemistry".The Gainesville Sun. Archived fromthe original on April 21, 2016. RetrievedApril 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. RetrievedDecember 22, 2021.
  16. ^"Robert H. Grubbs PhD " Leadership Board".Department of Chemistry, University of Florida. RetrievedApril 14, 2016.
  17. ^"Nobel Laureates".Alfred P. Sloan Foundation. RetrievedApril 15, 2016.
  18. ^"Chemistry Nobel Prize for two Humboldtians".The Alexander von Humboldt Foundation. October 5, 2005. Archived fromthe original on November 14, 2018.
  19. ^"Robert H. Grubbs American chemist".Encyclopædia Britannica. April 26, 2024.
  20. ^ab"2002 Robert H. Grubbs, Caltech".Southern California Section of the American Chemical Society. July 20, 2012. RetrievedApril 12, 2016.
  21. ^Robert H. Grubbs publications indexed byGoogle ScholarEdit this at Wikidata
  22. ^Robert H. Grubbs publications indexed by theScopus bibliographic database.(subscription required)
  23. ^abNotman, Nina (January 28, 2015)."Grubbs catalyst".Chemistry World. RetrievedApril 15, 2016.
  24. ^abc"Industry's Secret Ingredient".Caltech News. Archived fromthe original on September 10, 2015. RetrievedApril 17, 2014.
  25. ^"Leading Innovation in Catalysis".Materia. RetrievedApril 15, 2016.
  26. ^"The History of Materia".Materia. RetrievedApril 15, 2016.
  27. ^"Materia and Sigma-Aldrich Announce Exclusive Distribution Deal for Grubbs' Metathesis Catalysts".Business Wire. August 18, 2003. RetrievedApril 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. RetrievedApril 15, 2016.
  30. ^"Materia, Inc. Sells Catalyst Business to Umicore".Materia. December 20, 2017. RetrievedJune 10, 2021.
  31. ^"ExxonMobil acquires Materia, Inc., a high-performance structural polymers company".ExxonMobil. RetrievedDecember 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 fromthe original on December 16, 2021. RetrievedDecember 20, 2021.
  33. ^"Nobel Laureates".USA Science & Engineering Festival. Archived fromthe original on April 21, 2010. RetrievedApril 12, 2016.
  34. ^abMiree-Luke, Lisa (October 8, 2015)."Axalta's Distinguished Lecture Series at the University of Pennsylvania Features Presentation on Methathesis Polymerization".Business Wire. RetrievedApril 14, 2016.
  35. ^abPearson, Rodney (April 3, 2001)."South Pasadena chemist wins national award for designing new catalysts".EurekaAlert. Archived fromthe original on April 15, 2016. RetrievedApril 14, 2016.
  36. ^abSingh, Okram Mukherjee (2006)."Metathesis catalysts: Historical perspective, recent developments and practical applications"(PDF).Journal of Scientific & Industrial Research.65 (December):957–965. RetrievedApril 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.Bibcode:2006ACIE...45.3760G.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.Bibcode:2003JAChS.12511360C.doi:10.1021/ja0214882.PMID 16220959. RetrievedApril 14, 2016.
  39. ^abNguyen, 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.Bibcode:1992JAChS.114.3974N.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.Bibcode:1988JAChS.110..960N.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.Bibcode:1993JAChS.115.9858N.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 (1):100–110.Bibcode:1996JAChS.118..100S.doi:10.1021/ja952676d.
  45. ^abAstruc, 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 fromthe original(PDF) on June 16, 2016. RetrievedApril 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 fromthe original on March 1, 2017. RetrievedJuly 21, 2016.
  48. ^abcMcClain, Dylan Loeb (December 24, 2021)."Robert H. Grubbs, 79, Dies; Chemistry Breakthrough Led to a Nobel".The New York Times. RetrievedDecember 24, 2021.
  49. ^"Caltech Mourns the Loss of Nobel Laureate Robert H. Grubbs". Caltech. December 19, 2021. RetrievedDecember 19, 2021.
  50. ^"Robert H. Grubbs – Facts".The Nobel Prize in Chemistry 2005. NobelPrize.org. RetrievedApril 15, 2016.
  51. ^"National Academy of Sciences Members".Caltech. RetrievedApril 15, 2016.
  52. ^"Robert H. Grubbs".American Academy of Arts & Sciences. November 18, 2021. RetrievedDecember 20, 2021.
  53. ^"Robert H. Grubbs".The Franklin Institute. January 10, 2014. RetrievedApril 14, 2016.
  54. ^"Herman F. Mark Award 2000".Division of Polymer Chemistry, Inc. of the American Chemical Society. Archived fromthe original on March 15, 2016. RetrievedApril 14, 2016.
  55. ^"Pasadena chemist wins national award for cata".EurekAlert!. RetrievedDecember 20, 2021.
  56. ^"Arthur C. Cope Award".ACS Chemistry for Life. American Chemical Society. RetrievedApril 12, 2016.
  57. ^"Tetrahedron Prize for Creativity".Elsevier B.V. RetrievedApril 12, 2016.
  58. ^"Members Grubbs".rsc.org.Royal Society of Chemistry. RetrievedApril 15, 2016.
  59. ^"Robert H. Grubbs 31st Paul Karrer Lecture 2005".University of Zurich. Archived fromthe original on April 23, 2016. RetrievedApril 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 fromthe original on February 24, 2019. RetrievedApril 15, 2016.
  62. ^"2015 Inductees: Robert Howard Grubbs".Florida Inventors Hall of Fame. September 28, 2015. RetrievedApril 14, 2016.
  63. ^"Current NAI Fellows".National Academy of Inventors. RetrievedApril 15, 2016.
  64. ^"Professor Robert Howard Grubbs".National Academy of Engineering. RetrievedApril 12, 2016.
  65. ^"New Academicians and Foreign Members of the Chinese Academy of Sciences".Angewandte Chemie International Edition.55 (8):2633–2634. February 2016.Bibcode:2016ACIE...55.2633..doi:10.1002/anie.201511637.
  66. ^"12 Famous Scientists Elected 2015 CAS Foreign Members".CASAD. RetrievedApril 12, 2016.
  67. ^Wang, Linda (February 13, 2017)."Robert Grubbs wins Remsen Award".Chemical & Engineering News.59 (7). American Chemical Society. RetrievedDecember 20, 2021.

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