Page 343 - Carrahers_Polymer_Chemistry,_Eighth_Edition

306 Carraher’s Polymer Chemistry

Another project undertaken by the testing laboratory was an attempt to improve the synthesis
of ethylene glycol, the major ingredient in antifreeze, from the hydrolysis of ethylene chlorohydrin.
They used sodium sulfide in the process. Instead of getting the desired antifreeze, he got a gunk.

Instead of throwing away the gunk, which was often done during this time, he studied it. The mate-
rial was foul smelling, much like rotting eggs, and it was stable in most solvents it was placed in. He
called this material “Thiokol” after the Greek for “sulfur” and “gum” (Kommi). He got funds from
Standard Oil Company of Indiana to do further work with Thiokol to try to eliminate its odor.
Sulfur naturally comes in packages of eight forming an octagon. Through varying the reaction
conditions a variety of thiokols can be formed with the Thiokol chains having varying averages of
sulfurs. Thiokols are formed from the reaction of ethylene with chlorine forming ethylene dichlo-
ride that is reacted with sodium polysulfi de.

H C=CH + Cl → H C(Cl)–C(Cl)H (9.39)
2 2 2 2 2

H C(Cl)–C(Cl)H + NaS → –(–CH –CH –S–S–)– + NaCl (9.40)
2 2 x 2 2
Butyl rubber was discovered by R. M. Thomas and W. J. Sparks in 1937 and was developed by
the Standard Oil Company (NJ) and was part of an exchange of information between the German
chemical giant I. G. Farbenindustrie AG and Standard Oil.
Butyl rubber is a copolymer of 1-butene, (CH ) C=CH , and small amounts (about 2%–3%) of
3 2 2
isoprene or other unsaturated compounds. The unsaturation allows subsequent cross-linking of the
material.
As World War II loomed with America pushed into the war by the Pearl Harbor attack, the
need for an independent rubber supply was critical. The government instituted several nation-wide
efforts, including the Manhattan and Synthetic Rubber Projects. Carl “Speed” Marvel was one of
the chemists involved in the Synthetic Rubber Project.
When I first met “Speed” Marvel, there was little “speedy” about his gate but he was speedy

with his mind and pleasant personality. As with many of the polymer pioneers, he was friendly and
commented on the importance of my work before I could talk about my admiration of him and his
efforts. Now that is a way to turn the tables on a young (now older) researcher. I had read about
“Speed” and his part in “saving the war” and was anxious to simply meet him.
Carl Shipp “Speed” Marvel was born in 1894 on a farm in Waynesville, IL, and spent much of
his 93 years furthering synthetic polymer chemistry. He acquired his name because when he regis-
tered for his first semester as a graduate student, in 1915, at the University of Illinois, it was believed

he lacked some of the basic chemistry background so was given extra courses to take. He worked
late into the night in the laboratory and studying but wanted to get to the breakfast table before the
dining room door closed at 7:30 AM. His fellow students commented that was the only time he ever
hurried and gave him the name “Speed” because of it.
During this time, chemistry was prospering in Europe but not in America so there was an effort
by American chemists to establish routes to important chemicals, such as dyes, in academia and
industry. There was a flow of chemists from academia to industry and from one academic institution

to another. Roger Adams, one of the foremost organic chemists of the time, moved from Harvard
to the University of Illinois at this time. This was a time of rapid growth in the chemical industry
because before World War I much of the chemical industry centered in Germany and because of the
war, this was changing. The American Society membership grew from 7,400 in 1915 to more than
10,600 in 1917. (Today, the ACS has a membership of about 160,000 and is the largest single disci-
pline organization.) The shortage of chemicals was so severe that Adams had graduate students such
as Speed Marvel actually work on the production of special chemicals related to the new chemical
warfare that was introduced by the Germans. It was quite a task to make these dangerous chemicals
because of the poor ventilating hoods used by the students.

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