Petroleum Product Hoopla

Phillips Petroleum chemists invented a new plastic, but transition from lab to market proved difficult. Enter Wham-O.

 

In 1954, the Oklahoma-based oil and natural gas company’s scientists developed high-density polyethylene. Marketing executives named their latest petroleum product Marlex, but searched in vain for buyers of the plastic. Then the Wham-O toy company found the plastic ideal for making hoops and flying platters.

petroleum product hula hoop Arthur Melin and his plastic hula hoops

To make Hula Hoops and Frisbees, Arthur Melin, right, and his Wham-O Company partner Richard Kerr, left, chose Marlex – the world’s first high-density polyethylene plastic.

 

petroleum product hula hoop image of young people hula hooping together

In the 1950s, few companies knew what to do with a revolutionary plastic invented by Phillips Petroleum. Demand for “Marlex” would come from “the great obsession of 1958 – the undisputed granddaddy of American fads.”

Prompted by a post World War II boom in demand for plastics, Phillips Petroleum invested $50 million to bring its own miracle product – Marlex – to market in 1954.

The company gambled that the new plastic would be perfect for all manner of emerging products trying to keep up with consumer demand.

With millions of dollars already committed, investors expected immediate results from the Phillips lab product.

A New Plastic

Marlex, a high-density polyethylene, was developed by Phillips chemists Paul Hogan and Robert Banks – who were researching gasoline additives. In their experiments, Hogan and Banks began to study catalysts.

“In June 1951, they set up an experiment in which they modified their original catalyst (nickel oxide) to include small amounts of chromium oxide,” notes the American Chemical Society. Their work was expected to produce low-molecular-weight hydrocarbons.

“As Paul Hogan recalls it, he was standing outside the laboratory when Banks came out saying, ‘Hey, we’ve got something new coming in our kettle that we’ve never seen before.’

Running inside, they saw that the nickel oxide had produced the expected liquids. But the chromium had produced a white, solid material. Hogan and Banks were looking at a new polymer – crystalline polypropylene.” (more…)

Nylon, a Petroleum Polymer

The world’s first synthetic fiber was the petroleum product “Nylon 6,” discovered in 1935 by a DuPont chemist who produced the polymer from chemicals found in oil.

DuPont Corporation foresaw the future of “strong as steel” artificial fibers. The chemical conglomerate had been founded in 1802 as a Wilmington, Delaware, manufacturer of gunpowder.

petroleum product nylon

“Women show off their nylon pantyhose to a newspaper photographer, circa 1942,” notes historian Jennifer S. Li in “The Story of Nylon – From a Depressed Scientist to Essential Swimwear.” Photo by Dale Rooks.

The chemical company would become a global giant after its scientists created nylon, rayon and lucite.

The world’s first synthetic fiber – nylon – was discovered on February 28, 1935, by a former Harvard professor working at a DuPont Corporation research laboratory.

Later called Nylon 6 by scientists, the revolutionary carbon-based product came from chemicals found in petroleum.

petroleum product nylon

Chemists called the man-made fiber Nylon 6 because chains of adipic acid and hexamethylene diamine each contained six carbon atoms per molecule.

Professor Wallace Carothers had experimented with artificial materials for more than six years. He previously discovered neoprene rubber (commonly used in wetsuits) and made major contributions to understanding polymers – large molecules composed in long chains of repeating chemical structures.

Just 32 years old, Carothers created fibers when he combines the chemicals amine, hexamethylene diamine, and adipic acid. He formed a polymer chain using a process in which individual molecules join together with water as a byproduct.

However, the fibers were weak, explains a PBS series, A Science Odyssey: People and Discoveries. “Carothers’ breakthrough came when he realized the water produced by the reaction was dropping back into the mixture and getting in the way of more polymers forming,” notes the PBS website. “He adjusted his equipment so that the water was distilled and removed from the system. It worked!”



DuPont named the petroleum product nylon – although chemists called it Nylon 6 because the adipic acid and hexamethylene diamine each contain six carbon atoms per molecule.

petroleum product nylon

“Until now, all good toothbrushes were made with animal bristles,” notes a 1938 ad.

Each man-made molecule consists of 100 or more repeating units of carbon, hydrogen, and oxygen atoms, strung in a chain. A single filament of nylon may have a million or more molecules, each taking some of the strain when the filament is stretched.

There’s disagreement about how the product name originated at DuPont.

“As to the word nylon, it’s actually quite arbitrary. DuPont itself has stated that originally the name was intended to be No-Run (that’s run as in the sense of the compound chain of the substance unravelling), but at the time there was no real justification for the claim, so it needed to be changed,” noted Chris Nickson in a 2017 website post, Where Does the Name Nylon Originate?

Replacing Hog Bristles

The first commercial use of this revolutionary petroleum product was for toothbrushes.

On February 24, 1938, the Weco Products Company of Chicago, Illinois, began selling its new “Dr. West’s Miracle-Tuft” – the earliest toothbrush to use synthetic DuPont nylon bristles.

petroleum product nylon

First used for toothbrush bristles, nylon women’s stockings were promoted in a DuPont 1948 ad.

Americans will soon brush their teeth with nylon – instead of hog bristles, declared an article in the New York Times.

“Until now, all good toothbrushes were made with animal bristles,” noted a 1938 Weco Products advertisement in Life magazine.

“Today, Dr. West’s new Miracle-Tuft is a single exception. It is made with EXTON, a unique bristle-like filament developed by the great DuPont laboratories, and produced exclusively for Dr. West’s.”

Pricing its toothbrush at 50 cents, the Weco Products Company guaranteed “no bristle shedding.” Johnson & Johnson of New Brunswick, New Jersey, will introduce a competing nylon-bristle toothbrush in 1939.

Nylon Stockings

Although DuPont patented nylon in 1935, it was not officially announced to the public until October 27, 1938 in New York City.

A DuPont vice president unveiled the synthetic fiber – not to a scientific society or industry association – but to 3,000 Women’s Club members gathered at the site of the upcoming 1939 New York World’s Fair.



During WWII, Nylon was used as a substitute for silk in parachutes.

During WWII, nylon was used as a substitute for silk in parachutes.

“He spoke in a session entitled ‘We Enter the World of Tomorrow,’ which was keyed to the theme of the forthcoming fair, the World of Tomorrow,” explains DuPont historian David A. Hounshell.

The petroleum product was an instant hit, especially as a replacement for silk in hosiery. DuPont built a full-scale nylon plant in Seaford, Delaware, and began commercial production in late 1939.

The company purposefully did not register “nylon” as a trademark – choosing to allow the word to enter the American vocabulary as a synonym for “stockings.”

Nylon became far and away the biggest money-maker in the history of DuPont, and its success proved so powerful that it soon led the company’s executives to derive a new formula for growth, according to David A. Hounshell in The Nylon Drama.

“By putting more money into fundamental research, Du Pont would discover and develop ‘new nylons,’ that is, new proprietary products sold to industrial customers and having the growth potential of nylon,” he explains.

Carothers did not live to see the widespread application of his work – in consumer goods such as toothbrushes, fishing lines, luggage and lingerie, or in special uses such as surgical thread, parachutes, or pipes – nor the powerful effect it had in launching a whole era of synthetics. “Early in 1937 his favorite sister died suddenly. He never recovered from the loss…and in April of that year he committed suicide. DuPont later named its research station after him.”

The DuPont website notes the Carothers invention changed the way people dressed worldwide –  and rendered the term ‘silk stocking’ obsolete. It had once been an epithet directed at the wealthy elite . Nylon’s success also encouraged DuPont to adopt long-term strategies for new products developed from basic research.

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The American Oil & Gas Historical Society preserves U.S. petroleum history. Become an AOGHS supporting member and help maintain this energy education website and expand historical research. For more information, contact bawells@aoghs.org. © 2020 Bruce A. Wells.

Citation Information – Article Title: “Nylon, a Petroleum Polymer.” Author: Aoghs.org Editors. Website Name: American Oil & Gas Historical Society. URL: https://aoghs.org/products/petroleum-product-nylon-fiber. Last Updated: February 24, 2020. Original Published Date: February 23, 2014.

Carbon Black & Oilfield Crayons

The newest petroleum product of 1903 got its name from the French word for chalk, craie, with an English adjective meaning oily, oleaginous.

 

Crayola crayons began in 1891 with a refining patent by Edwin Binney for manufacturing an intensely black pigment – carbon black. The Pennsylvania-based schoolroom chalk maker, Binney & Smith Company, would soon add oilfield paraffin and colors to create an iconic petroleum product.

 

The worldwide oil and natural gas industry supplies countless varieties of petroleum products, some often “hiding in plain sight.”

oilfield paraffin patent drawing for carbon black device

Binney & Smith Company received an 1891 patent for an “Apparatus for the Manufacture of Carbon Black,” which produced a fine, soot-like black pigment – far better than any other in use at the time.

 

oil field paraffin

Teachers loved dustless chalk, shown here circa 1904.

For Binney and C. Harold Smith, early Pennsylvania oilfields proved to be the key for success, which began with invention of an “Apparatus for the Manufacture of Carbon Black.”

Binney & Smith Company already had found success manufacturing dustless chalk and a red iron oxide for the red paint farmers used on barns. The company’s carbon black refining process produced a fine, soot-like substance of incredible blackness – a better pigment than any other in use at the time.

Binney & Smith then took common oilfield paraffin and changed the company’s destiny by adding color to children’s imaginations.

Mrs. Binney’s Classroom Chalk (more…)

Ethyl Anti-Knock Gas

General Motors scientists discovered amazing anti-knock properties of tetraethyl lead gasoline in 1921.

 

By early 1923, many American motorists would be driving into service stations nationwide and say, “Fill ‘er up with Ethyl.” 

 

tetraethyl lead gasoline

General Motors chemists Thomas Midgely Jr. and Charles F. Kettering.

In early internal combustion engines, “knocking” resulted from the out-of-sequence detonation of the gasoline-air mixture in a cylinder. The constant shock added to exhaust valve wear and frequently damaged engines.

After five years of lab work to find an additive to eliminate pre-ignition “knock” problems of gasoline, General Motors researchers Thomas Midgely Jr. and Charles Kettering discovered the anti-knock properties of tetraethyl lead. Their early experiments had examined the properties of knock suppressors such as bromine, iodine and tin – and compare these to new additives such as arsenic, sulfur, silicon and lead.

tetraethyl lead gasoline

Halth concerns resulted in the phase-out of tetraethyl lead beginning in 1976.

On December 9, 1921, when the two chemists synthesized tetraethyl lead and tried it in their one-cylinder laboratory engine, the knocking abruptly disappeared and fuel economy improved. “Ethyl” vastly improved gasoline performance.

Although being diluted to a ratio of one part per thousand, the lead additive yielded gasoline without the loud, power-robbing knock. With GM scientists watching, the first car tank filled with leaded gas took place on February 2, 1923, at the Refiners Oil Company service station in Dayton, Ohio.

In the beginning, GM provided Refiners Oil Company and other service stations special equipment, simple bolt on adapters called “Ethylizers” to meter the proper proportion of the new additive.

“By the middle of this summer you will be able to purchase at approximately 30,000 filling stations in various parts of the country, a fluid that will double the efficiency of your automobile, eliminate the troublesome motor knock, and give you 100 percent greater mileage,” Popular Science Monthly reported in 1924.

ethyl gas


“Ethyl” gasoline goes for the first time at this Dayton, Ohio, gas station. In foreground pump, GM’s bolt-on “Ethylizer” is visible, running vertically alongside the visible reservoir. Photo courtesy Kettering/GMI Alumni Foundation.

Anti-knock gasoline containing a tetraethyl lead compound also proved vital for aviation engines during World War II, even as danger from the lead content increasingly became apparent.

Powering Allied Victory in World War II 

Aviation fuel technology was still in its infancy in the 1930s. The properties of tetraethyl lead proved vital to the Allies during World War II.

tetraethyl lead gasoline

Phillips Petroleum produced tetraethyl leaded aviation fuels from high-quality oil found in Osage County, Oklahoma, oilfields.

Advances in aviation fuel increased power and efficiency, resulting in the production of 100-octane aviation gasoline shortly before the war.

Phillips Petroleum – today’s ConocoPhillips – was involved early in aviation fuel research and had already provided high gravity gasoline for some of the first mail-carrying airplanes after World War I.

Phillips Petroleum produced aviation fuels before it produced automotive fuels. The company’s gasoline came from the high-quality oil produced during the Osage County oil boom, which began in 1917.

Although today still an ingredient of 100 octane “avgas” for piston-engine aircraft, tetraethyl’s danger to public health was underestimated for decades.

Tetraethyl lead’s Deadly Side

Leaded gasoline was extremely dangerous from the beginning, according Deborah Blum, a Pulitzer-Prize winning science writer. “G.M. and Standard Oil had formed a joint company to manufacture leaded gasoline, the Ethyl Gasoline Corporation,” she noted in a January 2013 article. Research focused solely on improving the formula, not on the danger of the lead additive.

Eythl gas additive

A 1932 magazine ad promoted wildly improved high-compression engine performance.

“The companies disliked and frankly avoided the lead issue,” Blum wrote in “Looney Gas and Lead Poisoning: A Short, Sad History” at Wire.com. “They’d deliberately left the word out of their new company name to avoid its negative image.”

In 1924, dozens were sickened and five employees of the Standard Oil Refinery in Bayway, New Jersey, died after they handled the new gasoline additive. By May 1925, the U.S. Surgeon General called a national tetraethyl lead conference, Blum reported, and an investigative task force was formed. Researchers concluded there was ”no reason to prohibit the sale of leaded gasoline” as long as workers were well protected during the manufacturing process.

So great was the additive’s potential to improve engine performance, the author notes, by 1926 the federal government approved continued production and sale of leaded gasoline. “It was some fifty years later – in 1986 – that the United States formally banned lead as a gasoline additive,” Blum added.

By the early 1950s, American geochemist Clair Patterson discovered the toxicity of tetraethyl lead; phase-out of its use in gasoline began in 1976 and was completed by 1986. In 1996, EPA Administrator Carol Browner declared, “The elimination of lead from gasoline is one of the great environmental achievements of all time.”

Learn more about high-octane fuel in Flight of the Woolaroc and and early engines in Cantankerous Combustion – First U.S. Auto Show.

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The American Oil & Gas Historical Society preserves U.S. petroleum history. Join AOGHS and help maintain this energy education website, expand historical research, and extend public outreach. For annual sponsorship information, contact bawells@aoghs.org. © 2020 Bruce A. Wells.

Citation Information – Article Title: “Ethyl Anti-Knock Gas.” Author: Aoghs.org Editors. Website Name: American Oil & Gas Historical Society. URL: https://aoghs.org/products/tetraethyl-lead-gasoline. Last Updated: January 26, 2020. Original Published Date: December 7, 2014.

 

Oleaginous History of Wax Lips

Petroleum paraffin soon found its way from refinery to candles, crayons, chewing gum…and an unusual candy.

wax lips petroleum product in Christmas story
The 1984 holiday classic “A Christmas Story” featured Ralphie, his 4th-grade classmates – and an unusual petroleum product. Photos courtesy MGM Home Entertainment.

When Ralphie Parker and his 4th-grade classmates dejectedly hand over their Wax Fangs to Mrs. Shields in “A Christmas Story,” a generation may be reminded of what a penny used to buy at the local Woolworth’s store.

But there is far more to these paraffin playthings than a penny’s worth of fun. Paraffin, a byproduct of petroleum distillation, quickly found its way from refinery to marketplace in the form of candles, sealing waxes – and peculiar American candies.

It’s hard to recall a time when there were no Wax Lips, Wax Moustaches, or Wax Fangs for kids to smuggle into classrooms. Many grownups may remember the peculiar disintegrating flavor of Wax Lips from bygone Halloweens and birthday parties, but few know where these enduring icons of American culture actually started. The answer is in America’s oilfields.

The August 1859 birth of the U.S. oil industry brought kerosene to illuminate America, an early and popular petroleum products “This flood of American petroleum poured in upon us by millions of gallons, and giving light at a fifth of the cost of the cheapest candle,” wrote British chandler James Wilson in 1879. Kerosene lanterns soon replaced candles for illumination and the much-reduced candle business turned from tallow to a versatile byproduct of petroleum distillation – paraffin.After collecting samples from Pennsylvania oilfields, Robert Chesebrough invented a method for turning paraffin into a balm he called “petroleum jelly,” later “Vaseline.” Chesebrough himself consumed a spoonful of Vaseline each day and lived to be 96 years old. His product also led to a modern cosmetic giant (learn more in A Crude History of Mabel’s Eyelashes)

Meanwhile, paraffin quickly found its way from refinery to marketplace in candles, sealing waxes – and even chewing gums. Ninety percent of all candles by 1900 used paraffin as the new century brought a host of novel uses. Thomas Edison’s popular new phonographs also needed paraffin for their wax cylinders.

Crayons were introduced by the Binney & Smith Company in 1903 and were instantly successful. Alice Binney came up with the name by combining the French word for chalk, craie, with an English adjective meaning oily, oleaginous: Crayola (see Carbon Black and Oilfield Crayons).

wax lips petroleum product red candy lips
Concord Confections, part of Tootsie-Roll Industries, continues to produce Wax Lips and other paraffin candies for new generations of schoolchildren.

Paraffin Candyman

An inspired Buffalo, New York, confectioner soon used fully refined, food-grade paraffin and a sense of humor to find a niche in America’s imagination.

When John W. Glenn introduced children to paraffin “penny chewing gum novelties,” his business boomed. By 1923, his J.W. Glenn Company employed 100 people, including 18 traveling sales representatives.

Later, Glenn Confections became the wax candy division of Franklin Gurley’s nearby W.&F. Manufacturing Company. There, the ancestors of Wax Lips chattered profitably down the production line. Among the most popular of these novelties at the time were Wax Horse Teeth (said to taste like wintergreen). By 1939, Gurley was producing a popular series of holiday candles for the Socony-Vacuum Oil Company using paraffin from a nearby refinery at Olean, New York – once home to the world’s largest crude oil storage site. A field of metal tanks, some holding 20,000 gallons of paraffin, stood next to Gurley’s W.&F. Manufacturing Company in Buffalo.

Decorative and scented paraffin candles soon became the company’s principal products, accounting for 98 percent of W.&F. Manufacturing sales. Gurley’s “Tavern Candle” Santas, reindeer, elves and other colorful Christmas favorites today are prized by collectors on eBay, as are his elaborately molded Halloween candles. As W.&F.’s wax candy division, Glenn Confections, has continued to manufacture Fun Gum Sugar Lips, Wax Fangs, and Nik-L-Nips.

wax lips petroleum product Glenn Confections candy
Glenn Confections, the candy division of W. & F. Manufacturing Company, produced Fun Gum Sugar Lips, Wax Fangs, and Nik-L-Nips.

In Emlenton, Pennsylvania, a few miles south of Oil City, the Emlenton Refining Company (and later the Quaker State Oil Refining Company) provided the fully refined, food-grade paraffin for these bizarre but beloved treats.

Retired Quaker State employee Barney Lewis remembers selling Emlenton paraffin to W.&F. Manufacturing. During a 2005 interview he noted, “It was always fun going to the plant…they were very secret about how they did stuff, but you always got a sample to bring home,” adding, “Wax Lips, Nik-L-Nips…the little Coke bottle-shaped wax, filled with colored syrup.”

Today, Concord Confections, a small part of Tootsie-Roll Industries, continues to produce Wax Lips and other paraffin candies for new generations of schoolchildren. The petroleum industry produces an astonishing range of products for modern consumers, but few are as unique, peculiar, or revered as Wax Lips.

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The American Oil & Gas Historical Society preserves U.S. petroleum history. Support this AOGHS.ORG energy education website with a contribution. For membership information, please contact bawells@aoghs.org. © 2019 Bruce A. Wells.

Citation Information – Article Title: “Oleaginous History of Wax Lips.” Author: AOGHS.ORG Editors. Website Name: American Oil & Gas Historical Society. URL: https://aoghs.org/products/an-oleaginous-history-of-wax-lips. Last Updated: December 22,2019. Original Published Date: December 1, 2006.

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Asphalt Paves the Way

American mobility would soon depend on a petroleum product from the bottom of the distillation process.

asphalt

Pennsylvania Avenue was first paved bitumen imported from Trinidad bitumen in 1876. Thirty-one years later, a better asphalt derived from petroleum distillation was used to repave the famed pathway to the Capitol, above.

President Ulysses S. Grant directed that Pennsylvania Avenue be paved with Trinidad asphalt. By 1876, the president’s paving project covered about 54,000 square yards, according to A Century of Progress: The History of Hot Mix Asphalt, published in 1992 by National Asphalt Pavement Association.

“Brooms, lutes, squeegees and tampers were used in what was a highly labor intensive process. Only after the asphalt was dumped, spread, and smoothed by hand did the relatively sophisticated horse-drawn roller, and later the steam roller, move in to complete the job.” (more…)