104
SYROEZHKO, BEGAK
. Syroezhko, A.M., Begak, O.Yu., and Proskurya-
2
Me
Me
kov, V.A., Zh. Prikl. Khim., 2003, vol. 76, no. 5,
.
C
O .
OH
k
COOH ,
CHO
pp. 814 820.
8
+
CHO
3. Syroezhko, A.M. and Begak, O.Yu., Zh. Prikl. Khim.,
003, vol. 76, no. 6, pp. 990 995.
2
Me
Me
4
. Korotkova, N.P., Syroezhko, A.M., and Proskurya-
kov, V.A., Zh. Prikl. Khim., 1981, vol. 54, no. 3,
pp. 660 665.
k
9
COOH
COOH
+
O3
+ O2.
CHO
At lower temperatures (15 20 C), the yield of
5. Vikhorev, A.A., Syroezhko, A.M., and Proskurya-
kov, V.A., Zh. Prikl. Khim., 1976, vol. 49, no. 7,
pp. 1592 1597.
lactones reaches 52% [25]. As the temperature is ele-
vated (40 80 C), the reaction selectivity with respect
to acids grows by 12 16% compared to oxidation
with oxygen. Ozonolysis of 4-methylcyclohexanone
yields mainly -methyladipic and -methylglutaric
acids [20 26]. In acidic products of 3-methylcyclo-
6
7
8
9
. Vikhorev, A.A., Syroezhko, A.M., and Proskurya-
kov, V.A., Zh. Prikl. Khim., 1976, vol. 49, no. 3,
pp. 588 592.
. Vikhorev, A.A., Syroezhko, A.M., and Proskurya-
kov, V.A., Izv. Vyssh. Uchebn. Zaved., Khim. Khim.
Tekhnol., 1976, vol. 19, no. 10, pp. 1499 1503.
hexanone ozonolysis, the major components are
-
and -methyladipic and -methylglutaric acids [6].
In ozonolysis of 2-methylcyclohexanone, the major
acidic products are -methyladipic, -ketoenanthic,
and caproic acids. Formation of acids [15, 21] at ele-
vated temperatures presumably occurs via isomeric
keto oxy radicals tending to isomerize with ring
opening:
. Syroezhko, A.M., Korotkova, N.P., Vikhorev, A.A.,
and Proskuryakov, V.A., Zh. Prikl. Khim., 1978,
vol. 51, no. 11, pp. 2562 2567.
. Syroezhko, A.M., Korotkova, N.P., Vikhorev, A.A.,
and Proskuryakov, V.A., Zh. Prikl. Khim., 1978,
vol. 51, no. 12, pp. 2743 2754.
-
Me
Me
1
1
0. Sukharev, B.N., Liquid-Phase Oxidation of Isomeric
Methylcyclohexanols with Atmospheric Oxygen,
Cand. Sci. Dissertation, Leningrad, 1978.
.
OH
.
CHO
.
CHO
COOH
O
C
1. USSR Inventor’s Certificate no. 555084.
O
O
12. Vikhorev, A.A., Syroezhko, A.M., and Proskurya-
kov, V.A., Zh. Prikl. Khim., 1976, vol. 49, no. 5,
pp. 1178 1181.
O3, O2
-
and -methyladipic acids,
1
3. Vikhorev, A.A. and Syroezhko, A.M., in Issledova-
niya v oblasti khimii i tekhnologii produktov perera-
botki goryuchikh iskopaemykh (Studies in the Field of
Chemistry and Technology of Products of Fossil Fuel
Processing), Leningrad: Leningr. Tekhnol. Inst. im.
Lensoveta, 1975, issue 2, pp. 43 45.
Me
O , O
3
2
-
and -methylglutaric acids.
CHO
CH
.
2
Ozonolysis of MCHNs is more selective than their
oxidation with oxygen [14].
1
1
1
1
1
4. Serov, V.V., Syroezhko, A.M., Proskuryakov, V.A.,
and Martynov, Yu.N., Osn. Org. Sint. Neftekhim.
CONCLUSIONS
(
Yaroslavl), 1976, no. 5, pp. 9 18.
5. Vikhorev, A.A., Syroezhko, A.M., and Proskurya-
kov, V.A., Izv. Vyssh. Uchebn. Zaved., Khim. Khim.
Tekhnol., 1976, vol. 19, no. 10, pp. 1499 1503.
(
1) Ozonolysis of isomeric secondary methylcy-
clohexanols to the corresponding isomeric methyl-
cyclohexanones is more selective than oxidation with
atmospheric oxygen.
6. Vikhorev, A.A., Syroezhko, A.M., and Proskurya-
kov, V.A., Izv. Vyssh. Uchebn. Zaved., Khim. Khim.
Tekhnol., 1977, vol. 20, no. 5, pp. 672 676.
(
2) Ozonolysis of isomeric methylcyclohexanones
mainly yields lactones and acids: monocarboxylic,
dicarboxylic, and keto carboxylic.
7. Vikhorev, A.A., Syroezhko, A.M., and Proskurya-
kov, V.A., Zh. Prikl. Khim., 1977, vol. 50, no. 6,
pp. 1310 1314.
REFERENCES
8. Vikhorev, A.A., Syroezhko, A.M., and Yakovlev, A.S.,
in Issledovaniya v oblasti khimii i tekhnologii produk-
tov pererabotki goryuchikh iskopaemykh (Studies in
the Field of Chemistry and Technology of Products of
1
. Syroezhko, A.M., Proskuryakov, V.A., and Be-
gak, O.Yu., Zh. Prikl. Khim., 2002, vol. 75, no. 9,
pp. 1480 1485.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 77 No. 1 2004