Robert H. Grubbs, 79, dies; chemistry breakthrough led to a Nobel

Robert H. Grubbs, an American chemist who helped find a way to streamline the manufacturing of compounds that are used to make everything from plastics to pharmaceuticals so that they produce less hazardous waste, a “green chemistry” breakthrough that brought him a share of the Nobel Prize in 2005, died on Sunday in Duarte, Calif. He was 79.

His son Barney said the cause was a heart attack, which Dr. Grubbs suffered while being treated for lymphoma at the City of Hope Comprehensive Cancer Center.

The process that Dr. Grubbs helped perfect is called metathesis (pronounced meh-TATH-eh-sis), which means “changing places.” It allows molecules to break and then form again as strong “double bonds” of carbon atoms, creating new compounds.

Metathesis was first discovered and used in the 1950s, but how it worked remained a mystery until it was explained in 1971 by the French chemist Yves Chauvin and a student of his, Jean-Louis Hérrison.

They showed how a metal-carbon catalyst can pair with the fragment of a molecule to create a temporary bond, like two dancers clasping their four hands. The newly created bond then finds another, similar pair of molecules — the two dancers are joined by two others — forming a ring. The ring then breaks apart, and the catalyst goes off with a molecular piece from the second pair, which rearranges its carbon bonds.

Metathesis is extremely effective, but some of the early catalysts were difficult to work with and could be unstable. In 1990, Richard H. Schrock, a professor at the Massachusetts Institute of Technology, made a breakthrough by developing catalysts based on the metals tungsten and molybdenum. The new catalysts were more efficient, but they still had shortcomings, notably that they fell apart when exposed to air.

Working separately, Dr. Grubbs, who had begun his research on metathesis in the 1970s, in 1992 came up with catalysts that used the metal ruthenium. His catalysts were not always as efficient as Dr. Schrock’s, but they were stable in air and more selective in how they bonded with molecular chains.

Dr. Schrock said of Dr. Grubbs’s work, “He was the one who really took what I did and turned it into something practical.”

The remarkable thing about metathesis was that it worked at all, Dr. Grubbs said. “Carbon-carbon double bonds are usually one of the strongest points in the molecule,” he explained. “To be able to rip them apart and put them back together very cleanly was a complete surprise to organic chemists.”

The work of Dr. Grubbs and Dr. Schrock paved the way for metathesis to become a cornerstone of chemical manufacturing. The catalysts they developed, which are named for them, are in wide use today in making chemicals for a variety of manufacturing processes.

In addition to their other advantages, the new catalysts produced far less waste, particularly hazardous waste. In announcing that Dr. Grubbs, Dr. Chauvin and Dr. Schrock would share the 2005 Nobel Prize in Chemistry, the Royal Swedish Academy of Sciences, which manages the prizes, said, “This represents a great step forward for ‘green chemistry,’ reducing potentially hazardous waste through smarter production.”

Robert Howard Grubbs was born on Feb. 27, 1942, on a farm in western Kentucky between Calvert City and Possum Trot. He was the second of three children of Howard and Faye Grubbs.

Robert’s maternal grandmother was well read and educated, and his mother became a schoolteacher, working for more than 35 years in small rural schools. She had received a teaching certificate when she was younger, but it took her 28 years to earn her bachelor’s degree by taking night and weekend classes, sometimes with Robert in tow.

Dr. Grubbs’s father was a mechanic who built the farmhouse where his children were born. He worked for the Tennessee Valley Authority, operating and maintaining heavy equipment for dams in western Kentucky and Tennessee.

In an autobiographical sketch for the Nobel committee, Dr. Grubbs wrote, “The academic model of my mother and grandmother and the very practical mechanical training from my father turned out to be perfect training for organic chemical research.”

Enrolling at the University of Florida, he majored in agricultural chemistry, combining his interest in science, developed in junior high school, and his boyhood passion for farming.

One summer, while working in an animal nutrition laboratory analyzing steer feces, he was invited by a friend to work in an organic chemistry laboratory being run by a new university faculty member, Merle Battiste. Around that time, Dr. Grubbs became absorbed in a book called “Mechanisms and Structure in Organic Chemistry,” by E.S. Gould, which explained how chemical reactions work. His lab experience and the book persuaded him to devote himself to chemistry, he said.

It was a lecture at the university by Rowland Pettit, an Australian chemist, that inspired Dr. Grubbs to begin looking into the use of metals in organic chemistry, exploratory work that would lead to the Nobel.

After earning his undergraduate and master’s degrees at the University of Florida, he moved to Columbia University in New York for his doctoral degree, working under Ronald Breslow. Dr. Battiste had been Dr. Breslow’s first Ph.D. student. While at Columbia, Dr. Grubbs met and married Helen O’Kane, who is a speech-language pathologist from Brooklyn.

He obtained his Ph.D. in 1968 and then worked for a year at Stanford University as a National Institutes of Health fellow. In 1969, he joined the faculty of Michigan State University and worked there until 1978. During that time he started his research on catalysts in metathesis.

Dr. Grubbs was hired by the California Institute of Technology in 1978 and worked there until his death, advising and mentoring more than 100 Ph.D. candidates and almost 200 postdoctoral associates over they years.

In 1998, he and a chemistry postdoctoral fellow, Mike Giardello, founded Materia, a Pasadena-based technology company that has the exclusive rights to manufacture Dr. Grubbs’s catalysts. The business was sold in 2017 to Umicore and then to ExxonMobil this year.

Dr. Grubbs received the Benjamin Franklin Medal from the Franklin Institute in 2000 and was a member of the National Academy of Sciences, a fellow of the American Academy of Arts and Sciences and a member of the Royal Society of Chemistry.

In addition to his wife and his son Barney, he is survived by another son, Brendan; a daughter, Kathleen; two sisters, Marie Maines and Bonnie Berry; and four grandchildren.

As Dr. Grubbs wrote in his autobiographical sketch, his path toward the Nobel had been set as a boy.

“As a child I was always interested in building things,” he recalled. “Instead of buying candy, I would purchase nails, which I used to construct things out of scrap wood.”

Sometimes he would help his father rebuild car engines, install plumbing and build houses on the farms owned by his aunts and uncles, who mostly lived close by in Kentucky.

But in the end, he wrote, he discovered that “building new molecules was even more fun than building houses.”