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Acetylene 61

to ultraviolet and nuclear radiation and general weather- Walter Reppe of the I. G. Farben, who is one of the leg-
ing. It can be cross-linked via electron-beam radiation to endary figures of acetylene chemistry and its application
give further improved properties. to the production of valuable chemicals for Germany dur-
It is used extensively in the interior coating of pipes ing World War II. Reppe’s research spanned the 1930s
and as a base for long-lasting decorative finishes on alu- and reached commercial importance during the war years
minum, galvanized steel, and other architectural metals. in the 1940s. Ethynylation technology to produce the key
Other applications include wire insulation and connectors starting materials 2-butyne-1,4-diol and propargyl alcohol
for computer boards, telecommunications uses, and resis- (1-propyn-3-ol) is summarized in Section IX.B.
tant coatings for harsh environments.
CuC 2 H
The U.S. suppliers of PVDF are Pennwalt, Solvay, and C 2 H 2 + HCHO −−−→
Dynamit Nobel. Du Pont produces PVDF for its own in-
HOCH 2 C CCH 2 OH + HOCH 2 C CH
ternal use, primarily to produce Viton plastic. The total 2-Butyne-1,4-diol Propargyl alcohol
U.S. production of this polymer is significantly greater
Productsderivedfrombutynediolare2-butene-1,4-diol,
than that of PVF.
1,4-butanediol, γ -butyrolactone, N-methyl-2-pyrroli-
done, 2-pyrrolidone, N-vinyl-2-pyrrolidone, polyvinyl-
VI. REPPE PRODUCTS pyrrolidone (PVP), and polypyrrolidone. The reaction
flow diagram in Fig. 1 shows the interrelationship of
Reppe products, a line of large-volume, acetylene-based these products. Other Reppe chemicals such as vinyl
specialty chemicals, bear the name of their discoverer, ethers, polyvinyl ethers, vinyl ether–maleic anhydride

FIGURE 1 Reaction flow diagram: Reppe chemicals. (1) 2-Butyne-1,4-diol; (1a) propargyl alcohol; (2) 2-butene-1,
4-diol; (3) butane-1,4-diol; (4) tetrahydrofuran; (5) γ -butyrolactone; (6) 2-pyrrolidone; (7) N-vinylpyrrolidone;
(8) polyvinylpyrrolidone; (9) N-methylpyrrolidone.