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Smith, Robert (ed.) / The Wisconsin engineer
Vol. 70, No. 6 (March 1966)

Bottom of the barrel,   pp. 48 ff.

Invitation from
We need the new
ways of techni-
cal thinking,
fresh from a
good campus.
CLASS OF '66       CLASS OF '65         CLASS OF '64        CLASS OF '63
      CLASS OF '62
If it has been
necessary to
pick up some in-
structive experi-
ence before se-
lecting a long-
haul employer,
that's fine.
The box below permits a chemical engineer, just for kicks, to test himself
possible interest in our kind of problems. Bright M.E.s, E.E.s, and other
neers will pick up enough of the general idea to transpose the test to their
fields of competence. The next step would be to drop us a line about yourself
and your ambitions. If mutuality of interest develops and if the mundane
of compensation should come up, we feel that now and far into the foreseeable
future we can afford the best.
EASTMAN KODAK COMPANY, Business and Technical Personnel Dept.
                            Rochester, N.Y. 14650
An equal-opportunity employer offering a choice of three communities: Rochester,
N. Y., Kingsport, Tenn., and Longview, Tex.
We can react diketene and tert-butyl alcohol to tert.-butyl
acetoacetate [CH3COCH2COOC(CH,).] by methods
that bring the price down to $3.50 a pound-about one-
sixth the prevailing research-quantity price-with the usual
prospect for a substantial further plunge as volume de-
velops. A plunge to reach the price level of methyl aceto-
acetate and ethyl acetoacetate, two currently large-vol-
ume acetoacetic esters of ours, is unlikely. The tert.-butyl
ester, however, has an advantage over the other two. When
alkylated to CH3COCHRCOOC(CH3)3, mere heating
with a trace of acid catalyst drives off first (CH3)2C -:CH,
and then CO2, leaving CH3COCHR. With the cheaper
acetoacetate esters for making ketones, there is no such
neat cleavage. There the ethyl or methyl group has to be
hydrolyzed off, and if R happens to be hydrolysis-sensitive
itself, poof goes the yield. This same readiness of a-alkyl-
ated tert.-butyl acetoacetic esters to split out isobutylene
and then decarboxylate opens up promising routes also to
carboxylic acids, pyrroles, pyrazalones, uracils, and cou-
Now assume we have large supplies of diketene and tert.-butyl alcohol, as
indeed we do.
The problem: multiply their combined economic value to many times the sum
of their separate values.

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