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THEODORE L. CAIRNS
July 20, 1914-September 26, 1994
BY BLAINE C. MCKUSICK
THEODORE L. CAIRNS, commonly known as Ted, was a
DuPont Company research scientist who macle impor-
tant contributions to the science of chemistry, applications
of chemistry, en c! U. S. scientific policy. He spent thirty-
eight years in DuPont's Central Research Department, the
last eight as its director.
Cairns was born in Canada in the city of Edmonton,
Alberta. He attenclec! Edmonton public schools en c! then
enterer! the University of Alberta in 1932 as a chemistry
major. He gracluatec! with a B.S. in 1936. He shower! an
aptitude for research even as an unclergracluate, co-publish-
ing a paper on aminobiphenyls baser! on research clone
uncler the direction of Professor Reuben B. Sanclin.
About a year before graduation, he met Margaret Jean
McDonald, a fellow University of Alberta student majoring
in home economics. The scene of their initial meeting a
smelly chemistry laboratory-was not especially romantic.
His ownership of a rumble-seatec! car, which he hac! pur-
chasec! for twenty-five clolIars, perhaps impressed Margaret.
They often ciatec! cluring their senior year at the university.
Cairns hac! cleciclec! that opportunities for chemists were
greater in the Uniter! States than in Canada en c! sought
Sanclin's help in gaining admittance to an American graclu
65
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BIOGRAPHICAL MEMOIRS
ate school. Sanclin recognizec! Cairns's potential as a chem-
ist en c! recommenclec! him to the renownec! Professor Roger
Aciams of the University of Illinois Chemistry Department.
Cairns was acimittec! to that department in the fall of 1936,
en c! he promptly starter! to work with Professor Aciams on
the stereochemistry of substitutes! biphenyls. The research
went well, en c! Cairns receiver! his doctorate in 1939 after
only three years, insteac! of the normal four.
Academia beckoned, en c! in the fall of 1939, after work-
ing that summer in the laboratories of the Eastman Kociak
Co., Cairns joiner! the faculty of the Chemistry Department
at the University of Rochester as an instructor.
Cairns en c! Margaret McDonaTc! hac! not been able to see
much of each other after their graduation from the Univer-
sity of Alberta (she was working in a Baltimore hospital).
However, they corresponded regularly, and they married in
Toronto in 1940. Their first chilc! John was born in 1941, by
that time Cairns hac! become a U. S. citizen, en c! Margaret
follower! suit a year later.
Life as a professor seemec! less attractive close up than
from a distance, en c! Tecl's former professor, Roger Aciams,
Tong a values! consultant to the DuPont Company, painter!
a bright picture of research opportunities there. IncleecI,
opportunities were very goocI, for Wallace Carothers en c!
DuPont colleagues had recently discovered the first practi-
cal synthetic fiber (nylon) en c! the first practical synthetic
rubber (neoprene). Cairns visitor! the laboratories of the
DuPont Experimental Station in Wilmington, Delaware, was
favorably impressed by the chemists he met en c! the facili-
ties he saw, en c! left the University of Rochester to join
DuPont in 1941, a few months before the Uniter! States
entered World War II.
At the time Cairns came to DuPont, the importance of
nylon was well recognized there. It seemed that its chemi
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THEODORE L. CAIRNS
67
Cal mollification might open up new uses for it, en c! Cairns
stucliec! its mollification by formalclehycle en c! other reac-
tants. Some of the work was instigates! by wartime neecis for
nylon with special properties. Interesting, patentable results
were obtained.
With the coming of peace, expansion of research became
possible, en c! the DuPont Experimental Station grew rap-
icIly. With the expansion came a new! for strong, capable
research leaclers, en c! Cairns soon fount! himself the leacler
of a group of eight or so Ph.D. chemists seeking useful
applications of chemistry. His group looked for a new chem-
istry of cheap, reactive raw materials such as acetylene, eth-
yTene, carbon monoxide, hydrogen sulficle, en c! hydrogen
cyanide. Thus they turner! up N-methylo! polyamicles by
the reaction of formalclehycle with polyamicles.
iCO (CH2) 4CONH (CH2) 6NHin
CH2O
_ > iCO (CH2) 4CO NH (CH2) 6NHin
CH2OH
In examining the effect of very high pressure on chemi-
cals, they fount! that a pressure of 8000 atmospheres con-
vertec! nitrites to s-triazines.
CH3
N N
3CH3CN-------> a: j~
CHs ~n
3
Such pressures on mixtures of ketones en c! hydrogen sul-
ficle proviclec! gem-clithols, previously unknown.
R2C=0 + OH'S-------> R2C(SH)2 + H2O
Impressed by the properties of poly~tetrafluoroethyTene),
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BIOGRAPHICAL MEMOIRS
or Teflon, cliscoverec! elsewhere in DuPont, Cairns proposer!
the synthesis en c! polymerization of the as yet unknown
tetracyanoethylene. Its initial synthesis was not easy, but once
that hurcIle was passed, it prover! a very reactive, versatile
chemical. Although it failer! as a source of polymers, it former!
six-memberec! ring aciclucts with I,3-clienes, four-memberec!
ring aciclucts with viny! ethers, brilliantly colorer! tricyanoviny!
dyes with aromatic amines, en c! many other classes of procI-
ucts.
(NC) 2 C=C (CN) 2 + CH2=CHCH=CH2 ---->
(NC) 2 C=C (CN) 2 + ROCH=CH2 ---->
(NC) 2 C=C (CN) 2 + R2NC6H5 ---->
(CN) 2
(CN) 2
~ ~ (CN)2
RO I '~CN)2
R2N ~C (CN) =C (CN) 2
Tetracyanoethylene readily forms an anion radical, for ex-
ample, by reaction with potassium:
(NC) 2C=C (CN) 2 + K -----> K+ (NC) 2 C - C (CN) 2
This anion raclical hac! unanticipated! stability, permitting
isolation of various of its salts with interesting electronic,
optical, en c! magnetic properties. These salts have been the
subject of wiclespreac! studies for the past thirty years. The
clecamethy~ferrocenium salt was the first molecule-basec! fer-
romagnetic material ever characterized. Its critical tempera-
ture was only 4.~°K, but a salt prepared from dibenzene-
vanadium is ferromagnetic above room temperature. An
extraordinary variety of magnetic properties is available from
the radical anions of TCNE and other cyanocarbons. This
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THEODORE L. CAIRNS
69
subject was reviewoc! in Chemical and Engineering News fairly
recently. ~
Cairns was graclually given greater responsibility in DuPont,
becoming the laboratory director of the Central Research
Department in 1952, its research director in 1966, en c! cli-
rector of the entire department in 1971. When the Central
Research Department merger! with DuPont's Development
Department in 1977, Cairns became director of the result-
ant Research en c! Development Department, an organiza-
tion of huncirecis of chemists en c! engineers clevotec! to clis-
covering new chemistry and developing practical applications
for it.
Cairns retiree! in 1979, with a multitucle of his co-workers
of the preceding thirty-eight years jamming the DuPont
Country Club ballroom to demonstrate their friendship en c!
admiration for him. He hac! been an inspiring leacler who,
as his long-time colleague Robert M. Joyce has pointer! out,
"was an inspiring leader with a sharp eye for spotting chemical
talent en c! a great sense of putting the right person in the
right job."
Cairns participates! in many professional activities, espe-
cially in the field! of chemical publication. He was on the
Eclitorial Boarc! of Organic Syntheses (1949-56) en c! then servec!
on its Boarc! of Directors for several years. He subsequently
worker! similarly for its sister publication Organic Reactions,
serving on its Eclitorial Boarc! from 1960 to 1969. He playoc!
a truly vital role for Organic Reactions from 1967 to 1969. Its
eclitor-in-chief Arthur Cope suciclenly cliec! in 1967. With
great uncertainty as to the publishing plans en c! commit-
ments that Cope hac! macle, none of the other editors was
willing to take Cope's place. Cairns, unwilling to see this
useful publication clie, became its unofficial eclitor-in-chief
until William Dauben of the University of California, Ber-
keley, with urging from Roger Aciams en c! Cairns, acceptec!
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BIOGRAPHICAL MEMOIRS
the job in 1969. His acceptance was just in time to see that
volume 17 was issues! en c! that this important chemical pub-
lication got back on its feet. Cairns remainec! on the Acivi-
sory Boarc! of Organic Reactions for several years, cluring
which time he co-authorec! an important chapter on "Cy-
clopropanes from Unsaturates! Compounds, Methylene Io-
clicle, en c! Zinc-Copper Couple."2
Cairns was on the Boarc! of Editors of the Journal of Or-
ganic Chemistry from ~ 965 to ~ 970. He was active in the
American Chemical Society both locally en c! nationally. He
was on the Executive Committee of its Organic Division in
1955-56, its chairman in 1964-65, en c! represented! it on the
American Chemical Society Council cluring most of the pe-
rioc! 1955-65.
He was electec! to the National Academy of Sciences in
1966 after having server! on one of its most important com-
mittees, the Committee for the Survey of Chemistry, in 1964-
65. This committee proclucec! a definitive en c! influential
assessment of basic research in chemistry in the Uniter!
States.
His broad experience and knowledge in science and tech-
nology was put to use through membership on several im
portant government committees:
The Delaware Governor's Council on Science and Technology, 1969-72
President Nixon's Science Policy Task Force, 1969
The President's Science Advisory Committee, 1970-73
The President's Committee on the National Medal of Science, 1974-75
The Polytechnic Institute of New York Advisory Council for Chemistry,
1976-78
For several years Cairns chairec! the Division of Chemis-
try and Chemical Technology of the National Research Coun-
cil. His accomplishments were recognizes! by several awarcis:
The City of Wilmington's Outstanding Citizen Award, 1963
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THEODORE L. CAIRNS
71
The American Chemical Society Award for Creative Work in Synthetic Or-
ganic Chemistry, 1968
SOCMA (Society of Chemical Manufacturers Association) Medal for Cre-
ative Research in Synthetic Organic Chemistry, 1968
Honorary Doctor of Laws degree, University of Alberta, 1970
Perkin Medal, American section of the Society of Chemical Industry, 1973
Cresson Medal, The Franklin Institute, 1974
Cairns wouIc! use the occasion of an aware! to express
views on the progress of technology en c! the future of re-
search, thereby influencing both. For example, on receiv-
ing the Perkin Mecial of the Society of Chemical Industry
in New York in 1973, the topic of his aciciress was "The
Environment for Inclustrial Research." He notes! the impor-
tance of investigation to improve product lines en c! pro-
cesses en c! to fins! alternative raw materials to improve quality
or Tower mill costs. However, he stresses! the value of searching
for new products en c! new ventures to be at the heart of
business ten to fifteen years in the future. He concluclec! by
saying that "the woric! offers no enc! of clifficult problems to
be solver! en c! will be glac! to try whatever solutions we can
provicle at a reasonable price."
Tec! en c! Margaret Cairns hac! four chiTciren: John A., a
Minneapolis lawyer, Margaret Etter, a professor of organic
chemistry, crystallography, en c! solic! state interactions at
the University of Minnesota, who cliec! in 1992, Elizabeth
Reveal, a Washington, D.C., financial aciviser to local gov-
ernments, en c! lames R., a manager of trust accounts for a
Philaclelphia bank. The family was always close knit. As the
chilciren were growing up, the family clic! many things to-
gether, such as tennis, skating, gardening, en c! travel.
After retirement Cairns continued to follow the course
of chemistry en c! other sciences with interest, but he sel-
clom playoc! an active role. He occasionally attenclec! scien-
tific meetings, such as clinner meetings of the editors of
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BIOGRAPHICAL MEMOIRS
Organic Syntheses or Organic Reactions, when the meetings
happenec! to be nearby. He at last hac! time to pursue his
hobby of gardening, especially the raising of unusual variet-
ies of dahlias. However, age gradually caught up with him,
and on September 26, 1994, he died in Wilmington at age
eighty. Besicles his wife en c! three chilciren, Cairns was sur-
vivec! by a sister, Eleanor Cairns Everington of Stony Plain,
Alberta, eight grancichilciren, en c! three great-grancichilciren.
Robert M. Joyce was a close frienc! en c! colleague of Cairns
for four decades, beginning in graduate school days at the
University of Illinois en c! extending through extensive col-
laboration in the DuPont Company. He well described Cairns
as "an inspiring leacler with a sharp eye for spotting chemi-
cal talent en c! a great sense for putting the right person in
the right job."3
NOTES
1. T. S. Miller and A. T. Epstein, "Designer Magnets," Chem. Eng.
News 73 (No. 40) (Oct. 2, 1995~: 30-41.
2. Cyclopropanes from unsaturated compounds, methylene io-
dide, and zinc-copper couple. Org. React. 20~1973~:1-131.
3. R. M. Joyce. "Theodore L. Cairns," Org. React. 47~1995~:vii
. . .
vail.
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THEODORE L. CAIRNS
SELECTED BIBLIOGRAPHY
1936
With R. B. Sandin. Formation of cyclic azo compounds from 2,2'
diaminobiphenyls. 7. Am. Chem. Soc. 58:2019.
1939
With R. Adams. 2-substituted biphenyls. 7. Am. Chem. Soc. 61:2179.
1946
N-methylol polyamides. U. S. Patent 2,393,972.
1947
73
Polyamide/formaldehyde reactions and products thereof. U. S. Patent
2,430,860.
N-alkoxymethyl polyamides. U. S. Patent 2,430,908.
1948
Polyamides. U. S. Patent 2,441,057.
With R. E. Benson. Chemical reactions of caprolactam. 7. Am. Chem.
Soc. 70:2115.
1949
With H. D. Foster, A. W. Larchar, A. K. Schneider, and R. S. Schreiber.
Preparation and properties of N-methylol, N-alkoxymethyl, and
N-alkylthiomethyl polyamides. 7. Am. Chem. Soc. 71:665.
1950
With A. W. Larchar and B. C. McKusick. High-pressure synthesis of
s-triazines. U. S. Patent 2,503,999.
With R. E. Benson. Some new reactions of cyclooctatetracne. 7. Am.
Chem. Soc. 72:5355.
1951
N-vinylalkyleneureas and polymers thereof. U. S. Patent 2,541,152.
1952
With V. A. Engelhardt, H. L. Jackson, G. H. Kalb, and J. C. Saner.
The reaction of acetylene with acrylic compounds. 7. Am. Chem.
Soc. 74:5636.
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74
BIOGRAPHICAL MEMOIRS
With G. L. Evans, A. W. Larchar, and B. C. McKusick. Gem-dithiols.
J. Am. Chem. Soc. 74:3982.
With A. W. Larchar and B. C. McKusick. The trimerization of n
triles at high pressures. J. Am. Chem. Soc. 74:3633.
1954
With D. D. Coffman, R. Cramer, A. W. Larchar, and B. C. McKusick.
Olefin-carbon monoxide-alcohol copolymers. J. Am. Chem. Soc.
76:3024.
1957
With others. Cyanocarbon chemistry: Synthesis and chemistry of
tetracyanoethylene. J. Am. Chem. Soc. 79:2340.
1958
With others. Preparation and reactions of tetracyanoethylene.J. Am.
Chem. Soc. 80:2775.
With B. C. McKusick, R. E. Heckert, D. D. Coffman, and H. F.
Mower. Cyanocarbon chemistry. VI. Tricyanovinylamines. J. Am.
Chem. Soc. 80:2806.
1960
With C. G. Krespan and B. C. McKusick. Dithietene and bicyclooctatriene
ring systems from bis-~fluoroalkyl~acetylenes. J. Am. Chem. Soc.
82:1515.
1961
With C. G. Krespan and B. C. McKusick. Bis-(polyfluoroalkyl~acetylenes.
II. Bicyclooctatrienes through 1,4-addition of bis-
(polyfluoro~acetylenes to aromatic rings.J. Am. Chem. Soc. 83:3428.
With B. C. McKusick. Cyanocarbon chemistry. Angew. Chem. 73:520.
1962
With D. R. Eaton, A. D. Josey, R. E. Benson, and W. D. Phillips.
Unpaired electron distribution in pi-systems. J. Am. Chem. Soc.
84:4100.
1963
With B. Graham and H. G. Tanner. Radiation grafting onto pre-
swollen polymers. U. S. Patent 3,101,275.
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THEODORE L. CAIRNS
1964
75
With E. G. McGeer. Colored 1:1 pi complexes of tetracyanoethylene
and aromatic compounds. U. S. Patent 3,140,308.
1965
With E. Graef. Tetracyanoethylene. U. S. Patent 3,166,584.
Representative terms from entire chapter:
organic reactions
