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Selectivity control in one-pot myrtenol amination over Au/ZrO2 by molecular hydrogen addition. / Demidova, Yu S.; Suslov, E. V.; Simakova, I. L. и др.
в: Journal of Molecular Catalysis A: Chemical, Том 426, 01.01.2017, стр. 60-67.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Selectivity control in one-pot myrtenol amination over Au/ZrO2 by molecular hydrogen addition
AU - Demidova, Yu S.
AU - Suslov, E. V.
AU - Simakova, I. L.
AU - Mozhajcev, E. S.
AU - Korchagina, D. V.
AU - Volcho, K. P.
AU - Salakhutdinov, N. F.
AU - Simakov, A.
AU - Murzin, D. Yu
N1 - Publisher Copyright: © 2016 Elsevier B.V.
PY - 2017/1/1
Y1 - 2017/1/1
N2 - The one-pot myrtenol amination was studied over Au (3 wt.%)/ZrO2 catalyst under mixed N2/H2 atmosphere (9 bar). The effect of hydrogen addition was explored with the aim to increase selectivity to the target amines. Hydrogen addition timing depending on myrtenol conversion and hydrogenation temperature affected selectivity to the reaction products. Hydrogen addition (1 bar) after almost complete myrtenol conversion at 100 °C increased the yield to amine up to 68% preserving C[dbnd]C bond in the initial myrtenol structure. Hydrogen addition at 180 °C irrespective of the myrtenol conversion level provoked reduction of both C[dbnd]C and C[dbnd]N bonds with formation of two diastereomers (yield up to 93%), with trans-isomer formation being preferred when hydrogen was added at almost complete myrtenol conversion. It was shown, that in the presence of a gold catalyst controlled hydrogenation of competitive C[dbnd]C and C[dbnd]N groups can be performed during one-pot alcohol amination by regulation of the reaction conditions.
AB - The one-pot myrtenol amination was studied over Au (3 wt.%)/ZrO2 catalyst under mixed N2/H2 atmosphere (9 bar). The effect of hydrogen addition was explored with the aim to increase selectivity to the target amines. Hydrogen addition timing depending on myrtenol conversion and hydrogenation temperature affected selectivity to the reaction products. Hydrogen addition (1 bar) after almost complete myrtenol conversion at 100 °C increased the yield to amine up to 68% preserving C[dbnd]C bond in the initial myrtenol structure. Hydrogen addition at 180 °C irrespective of the myrtenol conversion level provoked reduction of both C[dbnd]C and C[dbnd]N bonds with formation of two diastereomers (yield up to 93%), with trans-isomer formation being preferred when hydrogen was added at almost complete myrtenol conversion. It was shown, that in the presence of a gold catalyst controlled hydrogenation of competitive C[dbnd]C and C[dbnd]N groups can be performed during one-pot alcohol amination by regulation of the reaction conditions.
KW - Biomass
KW - Competitive hydrogenation
KW - Gold
KW - Hydrogen borrowing
KW - Monoterpenoid
KW - One-pot alcohol amination
KW - Selectivity control
KW - OXIDATION
KW - GOLD
KW - ISOMERIZATION
KW - HETEROGENEOUS CATALYSIS
KW - ANALGESIC ACTIVITY
KW - ALUMINA
KW - ALCOHOLS
KW - STEREOSELECTIVITY
KW - REDUCTION
KW - DERIVATIVES
UR - http://www.scopus.com/inward/record.url?scp=85000733340&partnerID=8YFLogxK
U2 - 10.1016/j.molcata.2016.10.034
DO - 10.1016/j.molcata.2016.10.034
M3 - Article
AN - SCOPUS:85000733340
VL - 426
SP - 60
EP - 67
JO - Journal of Molecular Catalysis A: Chemical
JF - Journal of Molecular Catalysis A: Chemical
SN - 1381-1169
ER -
ID: 8968193