Carbon nanomaterials in hydrogenation catalysis

222 Pages·2019·5.099 MB·English

by  Furimsky, Edward

Carbon Nanomaterials in Hydrogenation Catalysis
1
0
0
P
F
8-
5
5
7
1
0
8
8
7
1
8
7
9
9/
3
0
1
0.
1
oi:
d
g |
or
c.
s
s.r
b
u
p
s://
p
htt
n
o
9
1
0
2
h
c
ar
M
2
2
n
o
d
e
h
s
bli
u
P
View Online
Catalysis Series
Editor-in-chief:
Justin S. J. Hargreaves, University of Glasgow, UK
1
0
P0 Series editors:
F
8- Bert Klein Gebbink, Utrecht University, The Netherlands
5
5
7 Jose Rodriguez, Brookhaven National Laboratory, USA
1
0
8
8
7
1 Titles in the series:
8
7
9 1: Carbons and Carbon Supported Catalysts in Hydroprocessing
9/
03 2: Chiral Sulfur Ligands: Asymmetric Catalysis
1
0. 3: Recent Developments in Asymmetric Organocatalysis
1
oi: 4: Catalysis in the Refining of Fischer–Tropsch Syncrude
d
g | 5: Organocatalytic Enantioselective Conjugate Addition Reactions:
or
c. A Powerful Tool for the Stereocontrolled Synthesis of Complex
s
s.r Molecules
b
pu 6: N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient
ps:// Synthetic Tools
htt 7: P-Stereogenic Ligands in Enantioselective Catalysis
n
9 o 8: Chemistry of the Morita–Baylis–Hillman Reaction
1
0 9: Proton-Coupled Electron Transfer: A Carrefour of Chemical Reactivity
2
ch Traditions
ar
M 10: Asymmetric Domino Reactions
2
2 11: C–H and C–X Bond Functionalization: Transition Metal Mediation
n
d o 12: Metal Organic Frameworks as Heterogeneous Catalysts
e
h 13: Environmental Catalysis Over Gold-Based Materials
s
bli 14: Computational Catalysis
u
P
15: Catalysis in Ionic Liquids: From Catalyst Synthesis to Application
16: Economic Synthesis of Heterocycles: Zinc, Iron, Copper, Cobalt,
Manganese and Nickel Catalysts
17: Metal Nanoparticles for Catalysis: Advances and Applications
18: Heterogeneous Gold Catalysts and Catalysis
19: Conjugated Linoleic Acids and Conjugated Vegetable Oils
20: Enantioselective Multicatalysed Tandem Reactions
21: New Trends in Cross-Coupling: Theory and Applications
22: Atomically-Precise Methods for Synthesis of Solid Catalysts
23: Nanostructured Carbon Materials for Catalysis
24: Heterocycles from Double-Functionalized Arenes: Transition Metal
Catalyzed Coupling Reactions
25: Asymmetric Functionalization of C–H Bonds
26: Enantioselective Nickel-catalysed Transformations
27: N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient
Synthetic Tools, 2nd edition
28: Zeolites in Catalysis: Properties and Applications
View Online
29: Biocatalysis: An Industrial Perspective
30: Dienamine Catalysis for Organic Synthesis
31: Metal-free Functionalized Carbons in Catalysis: Synthesis,
Characterization and Applications
32: Modern Biocatalysis: Advances Towards Synthetic Biological Systems
1
0
0 33: NO Trap Catalysts and Technologies: Fundamentals and Industrial
P x
F
8- Applications
5
75 34: Alternative Catalytic Materials: Carbides, Nitrides, Phosphides and
1
80 Amorphous Boron Alloys
8
7 35: Enantioselective Cobalt-catalysed Transformations
1
8
7 36: Noncovalent Interactions in Catalysis
9
39/ 37: Carbon Nanomaterials in Hydrogenation Catalysis
0
1
0.
1
oi:
d
g |
or
c.
s
s.r
b
u
p
s://
p
htt
n
o
9
1
0
2
h
c
ar
M
2
2
n
o
d
e
h
s
bli
u
P
How to obtain future titles on publication:
Astandingorderplanisavailableforthisseries.Astandingorderwillbring
delivery of each new volume immediately on publication.
For further information please contact:
BookSalesDepartment,RoyalSocietyofChemistry,ThomasGrahamHouse,
Science Park, Milton Road, Cambridge, CB4 0WF, UK
Telephone: þ44 (0)1223 420066, Fax: þ44 (0)1223 420247
Email: [email protected]
Visit our website at www.rsc.org/books
View Online
1
0
0
P
F
8-
5
5
7
1
0
8
8
7
1
8
7
9
9/
3
0
1
0.
1
oi:
d
g |
or
c.
s
s.r
b
u
p
s://
p
htt
n
o
9
1
0
2
h
c
ar
M
2
2
n
o
d
e
h
s
bli
u
P
View Online
Carbon Nanomaterials in
Hydrogenation Catalysis
1
0
0
P
F
8-
5
5
7
01 By
8
8
7
1
8
7 Edward Furimsky
9
39/ IMAF Group, Canada
0
0.1 Email: [email protected]
1
oi:
d
g |
or
c.
s
s.r
b
u
p
s://
p
htt
n
o
9
1
0
2
h
c
ar
M
2
2
n
o
d
e
h
s
bli
u
P
View Online
1
0
0
P
F
8-
5
5
7
1
0
8
8
7
1
8 CatalysisSeriesNo.37
7
9
9/
3
0 PrintISBN:978-1-78801-723-7
1
0. PDFISBN:978-1-78801-755-8
1
oi: EPUBISBN:978-1-78801-780-0
d
g | Print:ISSN:1757-6725
or ElectronicISSN:1757-6733
c.
s
bs.r AcataloguerecordforthisbookisavailablefromtheBritishLibrary
u
p
s:// rEdwardFurimsky2019
p
htt
n
o Allrightsreserved
9
1
0
h 2 Apartfromfairdealingforthepurposesofresearchfornon-commercialpurposesorfor
arc privatestudy,criticismorreview,aspermittedundertheCopyright,DesignsandPatents
M Act1988andtheCopyrightandRelatedRightsRegulations2003,thispublicationmaynot
2
2 bereproduced,storedortransmitted,inanyformorbyanymeans,withouttheprior
n
o permissioninwritingofTheRoyalSocietyofChemistryorthecopyrightowner,orinthe
d
e caseofreproductioninaccordancewiththetermsoflicencesissuedbytheCopyright
h
blis LicensingAgencyintheUK,orinaccordancewiththetermsofthelicencesissuedbythe
u appropriateReproductionRightsOrganizationoutsidetheUK.Enquiriesconcerning
P
reproductionoutsidethetermsstatedhereshouldbesenttoTheRoyalSocietyof
Chemistryattheaddressprintedonthispage.
Whilstthismaterialhasbeenproducedwithallduecare,TheRoyalSocietyofChemistry
cannotbeheldresponsibleorliableforitsaccuracyandcompleteness,norforany
consequencesarisingfromanyerrorsortheuseoftheinformationcontainedinthis
publication.Thepublicationofadvertisementsdoesnotconstituteanyendorsementby
TheRoyalSocietyofChemistryorAuthorsofanyproductsadvertised.Theviewsand
opinionsadvancedbycontributorsdonotnecessarilyreflectthoseofTheRoyalSocietyof
Chemistrywhichshallnotbeliableforanyresultinglossordamagearisingasaresultof
relianceuponthismaterial.
TheRoyalSocietyofChemistryisacharity,registeredinEnglandandWales,
Number207890,andacompanyincorporatedinEnglandbyRoyalCharter
(RegisteredNo.RC000524),registeredoffice:BurlingtonHouse,Piccadilly,
LondonW1J0BA,UK,Telephone:þ44(0)2074378656.
Forfurtherinformationseeourwebsiteatwww.rsc.org
PrintedintheUnitedKingdombyCPIGroup(UK)Ltd,Croydon,CR04YY,UK
7
0
0
P
F
8- Preface
5
5
7
1
0
8
8
7
1
8
7
9
9/
3
0
1
10. Carbons have been attracting increasing attention as supports in various
doi: catalytic applications. It began with the traditional amorphous carbon
g | materialssuchasactivated carbons(ACs)andcarbon blacks (CBs). Because
or
c. of their neutral nature, carbon supports may be suitable for the production
s
s.r of fuels and lubricants via hydroprocessing (HPR). Thus, in the case of
b
u
p carbon-supported HPR catalysts, the adverse effects of nitrogen bases
ps:// present in difficult feeds could be significantly diminished. Consequently,
n htt the catalyst life can be extended. Carbon supports maintain stability in the
o
9 presenceofwaterthatiseitherproducedduringhydrodeoxygenation(HDO)
1
20 orispresentinreactionstreams,asisusuallythecasewithbiomass-derived
h
c feeds. This was one of the major conclusions of the review on Carbons and
ar
M Carbon Supported Catalysts in Hydroprocessing by the present author,
2
n 2 published as part of the Catalysis Series a decade ago.
o
d Gradually,novelcarbonmaterialshavebeendiscoveredandhaveentered
e
sh the world of catalysis science. Among them, the properties of carbon
ubli nanotubes (CNTs), carbon nanofibers (CNFs), carbon nanohorns (CNHs),
P
graphene, graphene oxide (GO), reduced graphene oxide (rGO) and fuller-
eneshavebeendescribedindetail.Theproductionmethodshaveadvanced
to the stage that today, carbon nanomaterials are manufactured com-
mercially. Numerous practical applications of these materials have been
noted in the scientific literature, particularly those in various fields of
catalysis.
As an important field of heterogeneous catalysis, hydrogenation (HYD)
has been playing a key role during the conversion of various feeds to fine
chemicals required for the production of pharmaceuticals, perfumery
products, food additives, etc. Apparently, the severity, in terms of tempera-
ture and H pressure employed during these applications, is much lower
2
than that encountered in HPR for the production of fuels and lubricants.
CatalysisSeriesNo.37
CarbonNanomaterialsinHydrogenationCatalysis
ByEdwardFurimsky
rEdwardFurimsky2019
PublishedbytheRoyalSocietyofChemistry,www.rsc.org
vii
View Online
viii Preface
Because of the severity difference, in this review the former process will be
distinguished from HYD.
The database available in the scientific literature indicates remarkable
activity and selectivity of some catalysts supported on CNT, CNF, CNH, GO
andrGOsupports,comparedwiththosesupportedonACsandCBsandalso
7
0
0 on traditional oxidic supports such as Al O , SiO , TiO , SiO –Al O and
P 2 3 2 2 2 2 3
F
8- zeolites. Amongactivemetals, noble metals suchasPt,Pd,Ru andRhhave
5
5 beenusedmostextensively.Toalesserextent,transitionmetalssuchasNi,
7
1
0 Co, Fe, Cu, Mo and W have also been attracting attention. In an effort to
8
8
7 improve catalyst performance, bimetallic catalysts consisting either of two
1
8
7 noble metals or of one noble metal combined with a transition metal have
9
39/ been developed.
0
0.1 The advances in preparation methodology with the aim of obtaining
1
oi: tailor-made catalysts have been noted. Of particular significance are the
d
g | methods formodification ofthe surface structure of carbon nanomaterials.
or First,thelowreactivityandhydrophobicityofpristinecarbonnanomaterials
c.
s.rs canbechangedbydoping,whichinvolvesthereplacementofcarbonatoms
b
u in a hexagonal aromatic ring with heteroatoms such as nitrogen, sulfur,
p
s:// phosphorus and boron. This results in the modification of the electronic
p
htt properties of the surface. In addition, functionalization can change the
on acidity and basicity of neutral pristine solids. For example, ranges of acidic
9
1 and basic strength can be attained by introducing hydroxyl, carboxyl and
0
2
h sulfonic groups and amino groups, respectively. With such supports avail-
c
ar able, bifunctional catalysts based on functionalized carbon nanomaterials
M
2 can be prepared. Otherwise, such catalysts could be prepared using acidic
2
on supports (e.g. silica–alumina, zeolites).
d
e Thebiofeedsderivedfromdifferenttypesofbiomasshaveemergedasan
h
s
bli important source of various value-added products. In this regard, catalysts
u
P supportedoncarbonnanomaterialsseemtooutperformthosesupportedon
traditional supports. This was evident in the depolymerization of the com-
ponents of lignocellulosic biomass such as cellulose, hemicellulose and
lignin. Thus, under mild conditions, the yields of monomeric products ob-
tained over catalysts supported on carbon nanosupports exceeded those
obtainedoverothercatalysts.Similarly,fortheformercatalysts,highactivity
and selectivity for the products of interest were also obtained during the
conversion of vegetable oils and algae biomass components. Under more
severe conditions, such as those encountered in HPR, the biomass-derived
feeds are converted to hydrocarbons for transportation fuels. It should be
noted that in all of these applications, the presence of water did not affect
the performance of catalysts supported on carbon nanosupports.
Reactants containing a,b-conjugated CQC and CQO double bonds, such
as cinnamaldehyde and citral, have been extensively investigated for the
production of fine chemicals. In these applications, the high selectivity re-
quirementforhydrogenationoftheCQObondwhileleavingtheCQCbond
intact could be achieved over noble metal catalysts supported on carbon
nanosupports.
View Online
Preface ix
Hydrocarbons have been studied over catalysts supported on carbon
nanomaterials either as individual reactants or as part of the feeds derived
from conventional petroleum and also from nonconventional sources. The
streams of alkenes (e.g. ethylene and styrene) from pyrolysis require a final
polishtoremove alkynes (e.g.acetyleneandphenylacetylene) before further
7
0
0 utilization. To ensure stability, the final traces of alkenes must be removed
P
F
8- from gasoline and diesel fractions. Regulatory limits on the aromatics
5
5 content of fuels can also be met by final polishing. In these applications,
7
1
0 catalysts consisting of noble metals supported on CNTs and/or CNFs
8
8
7 exhibited good performance at ambient temperature and with near atmos-
1
8
7 pheric pressure H .
9 2
39/ Resultsontheconversionofrealfeedsderivedfrompetroleumandthose
0
0.1 obtained from nonconventional sources confirmed that with respect to
1
oi: activity and selectivity, catalysts supported on carbon nanomaterials
d
g | exhibited better performance than those supported on conventional oxidic
or supports. Also, the performance of the former catalysts was better than
c.
s.rs that of the corresponding catalysts supported on amorphous carbons such
b
u as ACs and CBs. Therefore, great potential of carbon nanomaterials as
p
s:// supports for HYD and HPR catalysts is anticipated.
p
htt
on Edward Furimsky
9
1
0
2
h
c
ar
M
2
2
n
o
d
e
h
s
bli
u
P
0
1
0
P
F
8- List of Acronyms
5
5
7
1
0
8
8
7
1
8
7
9
9/
3
0
1
10. AC Activated carbon
oi: AGO Atmospheric gas oil
d
g | AR Atmospheric residue
or
c. ASA Amorphous silica–alumina
s
s.r CALC Cinnamyl alcohol
b
u
p CALD Cinnamaldehyde
ps:// CB Carbon black
n htt CNF Carbon nanofiber
o
9 CNH Carbon nanohorn
1
20 CNT Carbon nanotube
h
c CSTR Continuous stirred tank reactor
ar
M CVD Chemical vapor deposition
2
2 DBT Dibenzothiophene
n
d o DMF Dimethylfuran
e
h EOR End of run
s
ubli FB Fullerene black
P
FCC Fluid catalytic cracking
FF Furfural
FFA Furfuryl alcohol
FLG Few-layers graphene
FT Fischer–Tropsch
GNP Graphene nanoplatelet
GNR Graphene nanoribbon
GO Graphene oxide
GVL g-Valerolactone
HCALC Hydrocinnamyl alcohol
HCALD Hydrocinnamaldehyde
HCR Hydrocracking
CatalysisSeriesNo.37
CarbonNanomaterialsinHydrogenationCatalysis
ByEdwardFurimsky
rEdwardFurimsky2019
PublishedbytheRoyalSocietyofChemistry,www.rsc.org
x