March 2022

100th Anniversary

Industry Pioneers: Polymer science, catalytic cracking, petrochemicals and EPC

Waldo Semon was an American chemist whose detour with assigned laboratory research at B. F. Goodrich led to the development of vinyl—the second best-selling plastic in the world.

WALDO SEMON

Waldo Semon was an American chemist whose detour with assigned laboratory research at B. F. Goodrich led to the development of vinyl—the second best-selling plastic in the world. Dr. Semon’s original research project was to coat metal with synthetic rubber. However, having exhausted his possibilities with rubber, he began experimenting with synthetic polymers, including polyvinyl chloride (PVC). Dr. Semon heated the stiff polymer in a high boiling solvent, obtaining a jelly-like substance that was elastic but not adhesive. PVC was more durable than crude rubber and Semon continued experimenting with it until he finally succeeded, in his first breakthrough, in plasticizing the substance and making it highly resilient. In his second breakthrough, he succeeded in making the material moldable into different shapes, giving the world its second-most employed plastic. Goodrich commercialized this product under the trademark Koroseal,¹ making shock-absorber seals, electric-wire insulation and coated-cloth products.

Semon’s success with vinyl did not deter his original research. By 1934, he had invented over 100 methods of affixing synthetic rubber to metal. He continued to lead teams of researchers to invent other families of plastics, which earned him 116 U.S. patents² and the Charles Goodyear medal in 1944.³ Throughout his career, he was known for his devotion and support of science education in schools.

FREDERIC STANLEY KIPPING

Frederic Stanley Kipping was a British chemist whose pioneering work in the chemistry of silicones formed the basis of 40 yr of continued research at the interface of organic and inorganic chemistry and the commercial development and application of silicones. He was the chief demonstrator in chemistry at the City and Guilds of London Institute and later became a professor of chemistry at University College, Nottingham. Kipping’s research on optically active compounds resulted in his interest and study of organic silicon compounds at Nottingham during the early 1900s. His work was published in a series of 51 journal papers and formed the basis for pioneering research that led to the development of synthetic rubber and silicone-based industries.⁴ With exceptional water resistance, high-temperature stability silicones found a variety of early applications as synthetic rubber, hydrophobic coatings, greases and lubricants.⁵

JAMES FRANKLIN HYDE

Dr. James Franklin Hyde, an American chemist and inventor, is credited with the commercialization of the silicone industry. His research combines organic and inorganic chemistry and the advantages of plastics and glass to create silicones, as an advanced commercial product. Glass is silicon-based, temperature and moisture-resistant, chemically inert and dielectric, while plastics are carbon-based, strong, durable and moldable. Dr. Hyde’s silicone resins exhibit a combination of resistance to water, ultraviolet light, microbial growth and thermal conductivity, while being strong and stable. The substance instantly became applicable in a variety of applications like greases, lubricants, insulators, sealants, waxes and rubbers, among others.

Dr. Hyde’s research built upon Dr. Eugene Sullivan’s radical idea of producing a hybrid material by combining the advantages of glass with those of organic plastics to create an array of organosilicon compounds. Dr. Hyde recognized the commercial importance of some of Kipping’s observations and applied them to forge his hybrid technology. His work led to the formation of Dow Corning, an alliance between the Dow Chemical Co. and Corning Glass Works that was specifically created to produce silicone products in 1943.⁶ At Dow Corning, Dr. Hyde led numerous innovations throughout the mid-20th century, with applications in industries such as automobiles, construction, aerospace, cookware and pharmaceuticals.

Besides silicone compounds, his other notable contributions include a flame hydrolysis method of making fused silica, a high-quality glass employed initially in telescopes and later used in aeronautics, advanced telecommunications, and computer chips. Dr. Hyde was honored with the Perkin Medal, finished his career credited with around 120 patents and was inducted into the National Inventors Hall of Fame.⁷

VLADIMIR IPATIEFF

Vladimir Nikolayevich Ipatieff was a Russian and American chemist who made significant contributions to the field of petroleum chemistry and catalysis. Ipatieff made the important discovery that chemical reactions were influenced by the walls of the container in which they were taking place. One of his noted reaction discoveries was when he found that alcohol flowing through a heated iron reaction coil caused primary, secondary and tertiary alcohols to be dehydrogenated producing aldehydes, ketones and alkenes, respectively. This reaction was absent when the same alcohol was flowing through a quartz tube. He called this phenomenon ‘contact reactions,’ which we now know as heterogeneous catalysis.

Ipatieff discovered that catalyst efficiency could be enhanced by dispersing catalyst particles on inert support and including small amounts of zinc or copper on the support. Most industrial reactions employ catalysts dispersed on support, along with additives or promoters. He also demonstrated that g-alumina can function as an effective dehydration catalyst, especially in ethanol to ethylene reactions. This discovery led to the development of methods for converting ethanol to alkenes, such as butadiene, which is used in the manufacture of rubber. In the 1940s, these processes were used in the commercial production of butadiene and are still being used today.

Ipateiff made another seminal innovation in chemistry by developing high-pressure autoclaves, often referred to as ‘Ipatieff bombs.’⁸ Ipatieff used these high-pressure autoclaves to synthesize commodity chemicals in processes that were significantly less expensive than traditional methods. He published more than 300 research papers and received more than 200 patents.⁹ Ipateiff’s work at UOP—in collaboration with Herman Pines, especially their breakthrough in fuel chemistry—is his most significant contribution to petroleum chemistry and refining.

HERMAN PINES

Herman Pines was a Polish-American chemist whose work in understanding the chemistry of hydrocarbons and catalysis laid the groundwork for producing high-octane fuels. Paraffins were considered inert substances, with little or no reaction affinity. His research led to the development of processes for paraffin isomerization, aromatic alkylation and base-catalyzed organic reactions. Pines developed a method for catalytic conversion of paraffins, such as n-butane to isobutane. He also demonstrated low temperatures catalysis by successfully reacting isobutane with olefins in the presence of sulfuric acid as a catalyst at low temperatures. The combination of isomerization and alkylation proved to be the breakthrough in developing high-octane fuel initially for aviation and later commercialization in 1941.¹⁰

Pines joined UOP in 1930, which began his long collaboration with Dr. Vladimir Ipatieff.¹¹ They worked on understanding complex reactions affected by temperature, acid concentration and ratio of acid relative to other compounds. Pines used pure hydrocarbons in his research instead of petroleum fractions to understand mechanisms for dehydration of alcohols on alumina, aromatization of alkanes, hydrogen transfer reactions in aromatic hydrocarbons and several other acid and base catalyzed hydrogenation, aromatization and dehydrogenation reactions. Pines’ research team studied a variety of transformations, including polymerization, alkylation, cyclization, additions, eliminations and hydride transfer reactions. Upon leaving UOP in 1953, he continued working on understanding and describing hydrocarbon reaction mechanisms and heterogenous catalysis at Northwestern University as the Ipatieff Professor. He published nearly 265 scientific papers and received 145 patents.¹⁰

VLADIMIR HAENSEL

Vladimir Haensel was an American chemical engineer most known for his invention of the Platforming process—a platinum catalyzed process for reforming hydrocarbons into gasoline. In 1947, he demonstrated that 0.01 platinum on alumina can be used as a stable, active and effective catalyst with long life and high in situ regeneration efficiency.¹² Platinum on alumina functioned as a dual-functional catalyst, where platinum provides excellent hydrogenation and dehydrogenation activity and the unsaturated hydrocarbons formed could be isomerized to rings on the acidic alumina. Associated major process advantages were a high yield of hydrogen, a valuable and environmentally friendly product aiding sulfur removal and high yield of aromatics, valuable for downstream plastics and petrochemicals industries.

Haensel’s method for producing high-octane fuel eliminated tetraethyl lead as an anti-knock additive; made transportation fuel efficient, cheaper and environment friendly; and replaced toxic coal tar processing by generating an aromatics pool for the plastics industry. Haensel is also known for the program he established as Director of Research at UOP,¹³ which led to the development of catalytic converters for automobiles.

J. R. WHINFIELD AND J. T. DICKSON

John Rex Whinfield (left) and James Tennant Dickson (right) investigated thermoplastic polyesters while working in the laboratories of the Calico Printers’ Association Ltd. from 1939–1941.¹⁴ They produced and patented the first polyester fiber in 1941, named Terylene, which equaled or even surpassed the toughness and resilience of nylon.

In the late 1930s, there was significant emphasis on finding an alternative to Carother’s aliphatic nylon fiber. Aromatic polyesters had remained largely unexplored during this time. By 1939, there was enough research evidence to support micro crystallinity as essential for the formation of strong synthetic fibers. The need for molecular symmetry in forming microcrystalline polymers formed the basis for Whinfield and Dickson’s research approach in using an aromatic polymer with a sufficiently high melting temperature for the manufacturing of synthetic fiber. Whinfield and Dickson discovered a method to condense terephthalic acid and ethylene glycol to yield a new polymer that could be drawn into fibers. Their patent was published in 1946.¹⁵

Whinfield joined Imperial Chemical Industries (ICI) in 1947 and ICI manufactured Terylene, while rival Dupont produced their own version of the polyester fiber commercialized as Dacron.¹⁵

CHARLES A. STONE AND EDWIN S. WEBSTER

Charles A. Stone and Edwin S. Webster—friends, electrical engineers and MIT classmates of 1888—founded Massachusetts Electrical Engineering Company, one of America’s first engineering consulting firms. The company was renamed Stone & Webster and grew to an engineering services company providing engineering, construction, environmental, and plant operation and maintenance services.

By the early 1950s, the company was involved with several noteworthy oil and gas, petrochemical and power generation projects, including 27 hydroelectric power generation projects and interstate gas pipelines in the U.S.¹⁶ The company also worked on various projects in chemical and plastics processing in the U.S., Canada, Japan and other countries serving the growing demand for plastics. Their efforts to standardize designs in areas of proven success and building project teams were successfully applied to address problems that developed in the energy supply sector in the mid- to late-1960s. These were used in the design of synthetic natural gas plants, an LNG distribution center, and demonstration projects in coal and oil gasification.

Stone & Webster was acquired and integrated into The Shaw Group in 2000. In 2012, the energy and chemical business, and process technologies and associated oil and gas engineering capabilities of The Shaw group were acquired by Technip.¹⁶ Today, the company is known as Technip Energies. HP

ACKNOWLEDGEMENTS

Hydrocarbon Processing would like to thank several institutions/companies for the use of archived images of industry pioneers. These include Northwestern University, MIT Museum, Wikipedia, Corning, Plastics Historical Society, University of Massachusetts and Nottingham Trent University.

LITERATURE CITED

1. Britannica, “Waldo Semon,” online: https://www.britannica.com/biography/Waldo-Semon
2. Lemelson MIT, “Waldo Semon, Plasticized PVC” online: Waldo Semon | Lemelson (mit.edu)
3. Wikipedia, “Waldo Semon,” online: https://en.wikipedia.org/wiki/Waldo_Semon (Image credit)
4. Encyclopedia, “Frederic Stanley Kipping,” online: https://www.encyclopedia.com/science/encyclopedias-almanacs-transcripts-and-maps/frederic-stanley-kipping
5. Nottingham Trent University, “Heritage trail, Frederic Stanley Kipping,” online: https://www.ntu.ac.uk/about-us/curated-and-created/heritage-trail/frederick-kipping (image credit)
6. Corning, “Legendary scientists Hyde,” online: https://www.corning.com/worldwide/en/innovation/culture-of-innovation/legendary-scientists-hyde.html (image credit)
7. Wikipedia, “James Franklin Hyde,” online: https://en.wikipedia.org/wiki/James_Franklin_Hyde
8. Jacoby, M., “Vladimir Ipatieff is the catalysis superhero you’ve never heard of,” C&EN., May 2019, online: https://cen.acs.org/people/profiles/Vladimir-Ipatieff-catalysis-superhero-ve/97/i19
9. Wikipedia, “Vladimir Ipatieff,” online: https://en.wikipedia.org/wiki/Vladimir_Ipatieff
10. Northwestern University, Archival and Manuscript collections, online: https://findingaids.library.northwestern.edu/agents/people/2106
11. New York Times “Herman Pines, Chemist who enhanced fuels,” New York Times, May 2019, online: https://www.nytimes.com/1996/04/21/us/herman-pines-94-chemist-who-enhanced-fuels.html
12. Buchholz, S.R., “Professor Vladimir Haensel,” The campus Chronicle, University of Massachusetts, December 2002, online: https://www.umass.edu/pubaffs/chronicle/archives/02/12-20/Haensel16.html (Image credit)
13. Gembicki, S., “Vladimir Haensel,” Biographical Memoirs, Vol. 88, National Academic Press, online: Vladimir Haensel | Biographical Memoirs: Volume 88 | The National Academies Press (nap.edu)
14. Plastics historical society, “Dickson and Whinfield,” online: http://plastiquarian.com/ (Image credit)
15. Wikipedia, “Joh Rex Whinfield,” online: https://en.wikipedia.org/wiki/John_Rex_Whinfield
16. Wikipedia, “Stone and Webster,” online: https://en.wikipedia.org/wiki/Stone_%26_Webster

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