WE CLAIM:
1. A method of producing e-caprolactam through adipamide as an intermediate,
the method comprising a lactamization step of reacting adipamide, formed from a
5 material compound, with hydrogen and ammonia in the presence of a catalyst,
wherein the catalyst comprising:
a metal oxide mainly containing an oxide(s) of one or more metallic elements
selected from the group consisting of metallic elements of group 5 and groups 7 to 14
in the 4th to 6th periods of the periodic table; and
10 a metal and/or a metal compound having a hydrogenation ability.
2. The method according to claim 1, wherein the material compound is a
carboxylic acid represented by the following General Formula (I) or (II):
O O °yO O
R^X^OR2 Y-^-^OR3
(I) (E)
[wherein in Formula (I) and Formula (II), R , R , and R each independently
15 represent a hydrogen atom (H) or an alkyl group having 1 to 6 carbon atoms; in
Formula (I), X represents -CH2-CH2-CH2-CH2-, -CH2-CH2-CH=CH-, -CH2-CH=CH-
CH2-, -CH=CH-CH=CH-, -CH2-CH2-CH2-CH(OH)-, -CH2-CH2-C(OH)H-CH2-, -
CH=CH-C(OH)H-CH2-, -C(OH)H-CH2-CH=CH-, or -CH2-CH=CH-CH(OH)-; and,
in Formula (II), Y represents -CH2-CH2- or -CH=CH-],
20 or a salt or an ester thereof, or a mixture thereof.
3. The method according to claim 1 or 2, wherein the material compound is one
or more compounds selected from the following group of compounds:
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o o o
""^^AlH "^V^^AjCH, C2H5°Y~^^AOC2H5
o o o
(1-1) (1-2) (1-3)
o o o
HS)C2H5
(II- -1) (II —2) (II—3)
ox ox 9X
hi o H> o K o
\X ^OH ^^-^OCH3 ^^^OC2H5
(ii- -4) (II—5) (II —6)
or a salt(s) thereof, or a mixture thereof.
4. The method according to any one of claims 1 to 3, wherein the material
compound is one or more carboxylic acids selected from the group consisting of
5 adipic acid, muconic acid, 3-hydroxyadipic acid, a-hydromuconic acid, 3-
hydroxyadipic acid-3,6-lactone, and muconolactone, or a salt(s) thereof, or a mixture thereof.
5. The method according to any one of claims 1 to 4, wherein the oxide(s) of the
metallic element(s) is/are an oxide(s) of one or more metallic elements selected from
10 the group consisting of vanadium, niobium, tantalum, manganese, iron, cobalt, nickel,
copper, zinc, gallium, indium, thorium, germanium, tin, and lead.
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6. The method according to any one of claims 1 to 5, wherein the metal and/or
the metal compound having a hydrogenation ability contain(s) one or more transition
metal elements selected from the group consisting of palladium, platinum, ruthenium,
rhodium, rhenium, nickel, cobalt, iron, iridium, osmium, copper, and chromium.
5 7. The method according to any one of claims 1 to 6, wherein the lactamization
step is carried out in the absence of oxygen.
8. A method of producing 5-cyanovaleramide through adipamide as an
intermediate, the method comprising converting adipamide, formed from a material
compound, to 5-cyanovaleramide in the presence of a metal oxide mainly containing
10 an oxide(s) of one or more metallic elements selected from the group consisting of
metallic elements of group 5 and groups 7 to 14 in the 4th to 6th periods of the periodic table.
9. The method according to claim 8, wherein the material compound is a
carboxylic acid represented by the following General Formula (I) or (II):
O O °^0 O
R1O^XADR2 Y^-^OR3
is (i). (n)
[wherein in Formula (I) and Formula (II), R , R , and R each independently
represent a hydrogen atom (H) or an alkyl group having 1 to 6 carbon atoms; in
Formula (I), X represents -CH2-CH2-CH2-CH2-, -CH2-CH2-CH=CH-, -CH2-CH=CH-
CH2-, -CH=CH-CH=CH-, -CH2-CH2-CH2-CH(OH)-, -CH2-CH2-C(OH)H-CH2-, -
2 0 CH=CH-C(OH)H-CH2-, -C(OH)H-CH2-CH=CH-, or -CH2-CH=CH-CH(OH)-; and,
in Formula (II), Y represents -CH2-CH2- or -CH=CH-], or a salt or an ester thereof, or a mixture thereof.
10. The method according to claim 8 or 9, wherein the material compound is one
or more compounds selected from the following group of compounds:
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0 0 0
H0^_^A0H H3C0Y^^J.OCH3 C2H50^^^^QC2H5
0 0 0
(1-1) (1-2) (1-3)
0 0 0
H0^^^OH H3CO^^^AOCH3 C2H5O^^^AOC2Hs
0 0 0
(1-4) (1-5) (1-6)
0 0 0
Hcy^^\H H3C0Y^^XOCH3 ^^Y^^^OC^
0 0 0
(1-7) (1-8) (1-9)
OH O OH O OH O
HCY\A-X0H H3C0^^AOCH3 C^0Y^^OC2H5
0 0 O
(1-10) (1-11) (1-12)
o o o
T^po r-Q o y-o o
^-^OH \^ADCH3 ^^"OC2H5
(II-1) (II —2) (II—3)

o, °x °v
h s h 0 h 0
V^AOH vk ^OCH3 vk ^OC2H5
(II-4) (II- -5) (II- -6)
or a salt(s) thereof, or a mixture thereof.
11. The method according to any one of claims 8 to 10, wherein the material
compound is one or more carboxylic acids selected from the group consisting of
5 adipic acid, muconic acid, 3-hydroxyadipic acid, a-hydromuconic acid, 3-
hydroxyadipic acid-3,6-lactone, and muconolactone, or a salt(s) thereof, or a mixture thereof.
12. The method according to any one of claims 8 to 11, wherein the oxide(s) of
the metallic element(s) is/are an oxide(s) of one or more metallic elements selected
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from the group consisting of vanadium, niobium, tantalum, manganese, iron, cobalt, nickel, copper, zinc, gallium, indium, thorium, germanium, tin, and lead.
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