scheme i. synthesis of (2) pyridine and (3) picoline from … iii: synthesis of collidines using...
TRANSCRIPT
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CH3CH2OH H-Zeolite CH3CH2 OH2 Zeolite -H2O
CH3CH2 Zeolite
NH3
CH3CH2 NH2 H-ZeoliteCH3CH NH -H2
(1)
(2)
CH3
HNHH
O
CH3
HN
H-ZeoliteHH
OHZeolite
CH3
N
OH
H-Zeolite
CH3
N
-H2O
N
NH
-NH3
-H2
Pyridine
(3)NH
CH3
H-ZeoliteNH2
CH3
ZeoliteNH2
CH3
Zeolite
CH3
HN
NH2
CH3HN
H3C
Zeolite
CH3
HN
NH2
CH3HN
H3CZeoliteCH3
NH2H
-2NH3
N
H2C
-H2H-Zeolite
2-Picoline Scheme I. Synthesis of (2) pyridine and (3) picoline from ethanol
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme II: Reaction mechanism for the formation of (2) 3,5-lutidine from n-propanol and (3) 2,6-lutidine from 2-propanol over zeolites.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme III: Synthesis of collidines using 2-propanol over zeolites
Scheme IV: possible reaction mechanism for the formation of 3,5-dipropyl pyridine over zeolite catalysts
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme V: A possible zeolite catalyzed reaction mechanism for the formation of 5-ethyl-2-methyl pyridine.
(i)
(ii)
(iii)
N
CH3
NH3
CH3
H
Zeolite-
+
N
CH3
CH3 H
+ HZeoliteN
CH3
CH3
Zeolite
+
CH3 H
O+ HZeolite
CH3 H
OH
Zeolite-
CH3 H
OH
NH3 +
Zeolite-
CH3 H
OH
NH2
+ HZeolite
CH3 H
OH2
NHH
Zeolite-
HCH3
NH
+
++HZeolite H2O
HCH3
NH+ HZeolite
HCH3
NH2 +
Zeolite- H
NH
HH
H+ CH3 CHNH2
CH2 CH NH + HZeolite
CH3 CH
NH2CH2 CH NH2
H
NH
HH
H+
+
NH2
CH NHCH3
NH2
NH2
CH NHCH3
NH2H
H
NH2
CHCH3
NH2
NH2
H
..NH2
CH NH2CH3
NH2H
+
-+
HCH3
NH2 +
Zeolite-
NH2
CH NH2CH3
NH2H CH
CH3
NH2
+
-
..NCH3
NH2H CH
CH3
NH2
H H
NH2
Zeolite-
+NCH3
NH2H CH
CH3
NH2
H
NH3
Zeolite-
N
CH3
NH2
CH3
NH2
+ HZeolite
-NH3
N
CH3
NH2
CH3
NH3
H
H
Zeolite-
+
NH3..
N
CH3
NH2
CH3
+ HZeolite-NH3
Zeolite-
+
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme VI: Zeolite catalyzed synthesis of 2-ethyl-3,5-dimethyl pyridine
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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H2COH
NH 3
(O)
H2CNH2
H2CH
O
-H2
NH3(1)
H2CNH
CH3
O
NH 3
-H2O
CH3
NH
CH2
NH
CH2
H-Zeolite-H2
Zeolite
NH NH H-Zeolite-H2, -NH3N
(2)
H2CNH
(3) CH2
HN
CH2
NH
-NH3, -H2
N
CH3
2-Phenyl pyridine
3-Picoline Scheme VII: Possible reaction mechanism for the formation of 2-phenyl pyridine and 3-picoline
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme VIII: Reaction mechanism for the synthesis of N-methylpyrrolidine and tetrahydrofuran
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme IX: Zeolite catalysed reaction mechanism for the formation of 3,4 -dihydropyrimidin-2(1H)-ones.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme X: Zeolite catalysed synthesis of 1,4-diazabicyclo (2.2.2) octane and formation of pyrazine
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme XI: Zeolite catalyzed possible reaction mechanism for the synthesis of N,N-dimethylpiperazine.
Scheme XII: Synthesis of N-methylpiperazine over zeolite catalysts.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme XIII: Synthesis of pyrrole, pyrrolidine and THF using 1,4-butane diol over zeolite catalysts.
Scheme XIV: Synthesis of piperazine and pyrazine over zeolite catalysts
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme XV: Possible zeolite catalyzed synthesis of annelated pyridines.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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2
Scheme XVI: Possible reaction mechanism for the synthesis of isoquionline over zeolite catalysts
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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I
NHCOCH3
Pd-Zeolite
Pd-HZeolite
NHCOCH3
I Ph
H
Pd-HZeolite
NHCOCH3
Ph
NHCOCH3
Ph
Pd-HZeoliteNHCOCH3
Ph
NH2COCH3
Ph
Pd-HZeolite-HI
-Pd-HZeolite
NPh
COCH3
Pd-HZeoliteAq. NH4Cl
NH
Ph
2-Phenylindole Scheme XVII: Possible mechanism for the synthesis of 2-phenylindole over Pd-modified zeolites.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme XVIII: Zeolite catalyzed mechanism for the formation of bis(indolyl) methanes.
Scheme XIX: Possible reaction mechanism for synthesis of N-methyl-2-pyrrolidone over zeolites.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme XX: Possible reaction mechanism for the formation of 2-methylquinoxaline over zeolite.
Scheme XXI: Synthesis of 2MEQ and 4MEQ over zeolites.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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NH2
O H-Zeolite OH Zeolite OH H-Zeolite
OH2 Zeolite-H2O
Zeolite
N
N
(1)
4-Methyl quinoline
NH2(2)
H-Zeolite
N
-H2
2-Methyl quinoline
N
-H2
Zeolite
NH2
Zeolite
H
NH2
H
H
H
H-Zeolite
H
Scheme XXII: Synthesis of 4-MEQ, 2-MEQ from crotonaldehyde and aniline.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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Scheme XXIII: Vapor phase alkylation of indole with methanol over zeolites.
Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012
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