Comptes Rendus Chimie

Sonia Ascaso

María Elena Gálvez

Patrick Da Costa

Rafael Moliner

María Jesús Lázaro

On the influence of the alumina precursor in Fe-K/Al2O3 structured catalysts for the simultaneous removal of soot and NOx: From surface properties to reaction mechanism

Mayouf Sellami

Vincent Caignaert

Fatima Z. Kouadri Hanni

Noureddine Bettahar

Naceur Benhadria

Esmahan Sari-Mohammed

Safia Imine

Abdellah Bahmani

Synthesis and characterization of new pyrochlore solid solution Bi1.5Sb1.5–xNbxCuO7

Ummey Rayhan

Hyeokmi Kwon

Takehiko Yamato

S1 
 
Supporting Information 
 
Reduction of aromatic compounds with Al powder 
using noble metal catalysts in water under mild 
reaction condition. 
 
Ummey Rayhan, Hyeokmi Kwon and Takehiko Yamato* 
  
 Department of Applied Chemistry, Faculty of Science and Engineering, Saga 
University, Honjo-machi 1 Saga, 840-8502, Japan 
                   E-mail: yamatot@cc.saga-u.ac.jp 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S2 
 
Table of Contents 
1.  Experimental section………………...………………………………………………………….S3  
2.  Fig S1: GC of Table-1, Entry-1 ..................................................................................................S4  
3.  Fig S2: GC of Table-1, Entry-2....................................................................................................S5 
4.  Fig S3: GC Mass of Table-1, Entry-2....................................................................................S6-S7 
5.  Fig S4: GC of Table-1, Entry-3...................................................................................................S8 
6.  Fig S5: GC Mass of Table-1, Entry-3..........................................................................................S9 
7.  Fig S6: GC of Table-1, Entry-4.................................................................................................S10 
8.  Fig S7: GC Mass of Table-1, Entry-4........................................................................................S11 
9.  Fig S8: GC of Table-1, Entry-5….............................................................................................S12 
10. Fig S9: GC of Table-1, Entry-6.................................................. ...................S13 
11. Fig S10: GC of Table-1, Entry-7..............................................................................S14 
12. Fig S11: GC of Table-1, Entry-8...............................................................................S15 
13. Fig S12: GC Mass of Table-1, Entry-8.....................................................................S16-S17 
14. Fig S13: GC of Table-1, Entry-9......................................................................................S18 
15. Fig S14: GC of Table-3, Entry-2.......................................................................................S19 
16. Fig S15: GC Mass of Table-3, Entry-2.....................................................................S20-S21 
17. Fig S16: GC of Table-3, Entry-3....................................................................................S21 
18. Fig S17: GC of Table-3, Entry-4....................................................................................S22 
19. Fig S18: GC Mass of Table-3, Entry-4…………..................................................S23-S24 
20. Fig S19: GC of Table-3, Entry-4...............................................................................S25 
21. Fig S20: GC Mass of Table-3, Entry-4.............................................................S26-S27 
22. Fig S21: GC of Table-4, Entry-2............................................................................S28 
23. Fig S22: GC Mass of Table-4, Entry-2...........................................................S29-S30 
24. Fig S23: GC of Table-4, Entry-3...........................................................................S31 
25. Fig S24: GC Mass of Table-4, Entry-3..........................................................S32-S33 
26. Fig S25: GC of Table-4, Entry-4...........................................................................S34 
27. Fig S26: GC Mass of Table-4, Entry-4.........................................................S35-S36 
28. Fig S27: GC of Table-4, Entry-5 .........................................................................S36 
29. Fig S28: GC Mass of Table-4, Entry-5 ........................................................S37-S38 
30. Fig S29: GC of Table-4, Entry-6 .......................................................................S38 
S3 
 
31. Fig S30: GC Mass of Table-4, Entry-6 ......................................................................S39 
32 Fig S31: Fluorene reduction.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .S40 
33. Fig S32: GC of Table-5, Entry-2 .......................................................................S40 
34. Fig S33: GC Mass of Table-5, Entry-2 .......................................................S41-S42 
35. Fig S34: GC of Table-5, Entry-3 ........................................................................S43 
36. Fig S35: GC Mass of Table-5, Entry-3.........................................................S44-S46 
37. Fig S36: GC of Table-5, Entry-4..........................................................................S47 
38. Fig S37: GC Mass of Table-5, Entry-4...................................................................S48-S49 
  
Experimental section 
General Remarks: All melting points are uncorrected. 1H NMR spectra were recorded at 300 MHz 
on a Nippon Denshi JEOL FT-300 NMR spectrometer in CDCl3 with Me4Si as an internal reference. 
IR spectra were measured as KBr pellets on a Nippon Denshi JIR-AQ2OM spectrometer. Mass 
spectra were obtained on Shimadzu GCMS-QP5050A Ultrahigh Performance Mass Spectrometer 
AOC-20I, 100V using a direct-inlet system. G.L.C. analyses were performed by Shimadzu gas 
chromatograph, GC-2010. 
 
Reagent list:  
Al powder (53-150  µ m, 99.5%) (Wako); Pt/C, Pd/C, Ru/C, Rh/C (5 %); Distilled water (Wako)  
 
Typical procedure 
The mixture of substrate (20 mg, 0.13 mmol ) (Wako), Al powder (500 wt%)  (53–150 µm, 
99.5%) (Wako) and Pt/C, Pd/C, Ru/C and Rh/C (20mg) (4.5 mole % metal) were added to water (0.5 
mL) (Wako distilled water). After heating the mixture at 60–80 oC for 12–24 h, it was cooled to 
room temperature. Then the solution was diluted with 1 mL water and stirrer for overnight at room 
temperature in the sealed tube. After 24 h, the solution was extracted with diethyl ether (2 mL× 3). 
The organic layer was combined, dried with MgSO4, filtered through cotton layer and concentrated 
in vacuum to give the corresponding hydrogenated product. The yields were determined by GLC 
analysis by using the standard compound (1,2,3,4-tetrahydronaphthalene) and products were 
identified by GC-MS. 
S4 
 
GC of Table 1: Entry 1 
 
 
Fig S1: Reduction of biphenyl by using only Al powder and H2O at 60oC for 12h. 
 
 
GC Condition: 
 
 
      Rate (oC/min) Temperature (oC) Hold (min) 
1 - 100 - 
2 2 200 5 
 
 
 
 
 
 
 
 
 
S5 
 
GC of Table 1: Entry 2 
 
Fig S2: Reduction of biphenyl by using Al powder, Pt/C and H2O at 60oC for 12h. 
   
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S6 
 
GC Mass of Table 1: Entry 2 
 
 
 
 
 
 
S7 
 
 
 
 
 
Fig S3: Reduction of biphenyl by using Al powder, Pt/C and H2O at 60oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S8 
 
GC of Table 1: Entry 3 
 
 
Fig S4: Reduction of biphenyl by using Al powder, Pt/C and H2O at 80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S9 
 
GC Mass of Table 1: Entry 3 
 
 
 
 
Fig S5: Reduction of biphenyl by using Al powder, Pt/C and H2O at 80oC for 12h. 
 
 
 
 
 
 
 
 
S10 
 
GC of Table 1: Entry 4 
 
 
Fig S6: Reduction of biphenyl by using Al powder, Pd/C and H2O at 60oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S11 
 
GC Mass of Table 1: Entry 4 
 
 
 
Fig S7: Reduction of biphenyl by using Al powder, Pd/C and H2O at 60oC for 12h. 
 
S12 
 
GC of Table 1: Entry 5 
 
Fig S8: Reduction of biphenyl by using Al powder, Pd/C and H2O at 80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S13 
 
GC of Table 1: Entry 6 
 
 
 
Fig S9: Reduction of biphenyl by using Al powder, Ru/C and H2O at 80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S14 
 
GC of Table 1: Entry 7 
 
Fig S10: Reduction of biphenyl by using Al powder, Rh/C and H2O at 80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S15 
 
GC of Table 1: Entry 8 
 
 
 
Fig S11: Reduction of biphenyl by using Al powder, Pd/C and H2O at 60oC for 24h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S16 
 
GC Mass of Table 1: Entry 8 
 
 
 
 
 
 
 
 
 
 
 
 
 
S17 
 
 
 
 
 
 
 
Fig S12: Reduction of biphenyl by using Al powder, Pd/C and H2O at 60oC for 24h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S18 
 
GC of Table 1: Entry 9 
 
 
 
 
Fig S13: Reduction of biphenyl by using Al powder, Rh/C and H2O at 60oC for 24h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S19 
 
GC of Table 3: Entry 2 
 
 
 
 
Fig S14: Reduction of diphenylmethane by using Al powder, Pd/C and H2O at 60oC 
for 24h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
C
H2
C
H2
C
H2
S20 
 
GC Mass of Table 3: Entry 2 
 
 
 
  
 
C
H2
C
H2
C
H2
C
H2
C
H2
S21 
 
 
Fig S15: Reduction of diphenylmethane by using Al powder, Pd/C and H2O at 60oC 
for 24h. 
 
 
 
 
GC of Table 3: Entry 3 
 
 
Fig S16: Reduction of diphenylethane by using Al powder, Pd/C and H2O at 60oC 
for 24h. 
 
C
H2
CH2 CH2
CH2 CH2
S22 
 
GC of Table 3: Entry 4 
 
 
Fig S17: Reduction of fluorene by using Al powder, Pd/C and H2O at 60oC for 24h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S23 
 
GC Mass of Table 3: Entry 4 
 
 
 
 
 
 
 
 
 
 
 
 
S24 
 
 
 
 
 
 
 
 
 
 
 
Fig S18: Reduction of fluorene by using Al powder, Pd/C and H2O at 60oC for 24h. 
 
S25 
 
GC of Table 3: Entry 4 
 
 
Fig S19: Reduction of 9,10-dihydroanthracene by using Al powder, Pd/C and H2O 
at 60oC for 24h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
S26 
 
GC Mass of Table 3: Entry 4 
 
 
 
S27 
 
 
 
 
 
Fig S20: Reduction of 9,10-dihydroanthracene by using Al powder, Pd/C and H2O 
at 60oC for 24h. 
S28 
 
GC of Table 4: Entry 2 
 
 
 
Fig S21: Reduction of diphenylmethane by using Al powder, Pt/C and H2O at 80oC 
for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
C
H2
C
H2
C
H2
S29 
 
GC Mass of Table 4: Entry 2 
 
 
 
 
 
 
C
H2
C
H2
C
H2 CH2
S30 
 
 
 
 
 
 
Fig S22: Reduction of diphenylmethane by using Al powder, Pt/C and H2O at 80oC 
for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
                
C
H2
C
H2
S31 
 
GC of Table 4: Entry 3 
 
 
 
Fig S23: Reduction of fluorene by using Al powder, Pt/C and H2O at 80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
S32 
 
GC Mass of Table 4: Entry 3 
 
 
 
 
 
 
 
S33 
 
 
 
 
 
 
Fig S24: Reduction of fluorene by using Al powder, Pt/C and H2O at 80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S34 
 
GC of Table 4: Entry 4 
 
  
 
Fig S25: Reduction of 9,10- dihydroanthracene by using Al powder, Pt/C and H2O 
at 80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
S35 
 
GC Mass of Table 4: Entry 4 
 
 
 
S36 
 
 
Fig S26: Reduction of 9,10- dihydroanthracene by using Al powder, Pt/C and H2O 
at 80oC for 12h. 
 
 
GC of Table 4: Entry 5 
 
 
Fig S27: Reduction of diphenylether by using Al powder, Pt/C and H2O at 80oC for 
12h. 
O
O
OH
S37 
 
GC Mass of Table 4: Entry 5 
 
 
 
 
O
O
O
O
O
S38 
 
 
Fig S28: Reduction of diphenylether by using Al powder, Pt/C and H2O at 80oC for 
12h. 
 
GC of Table 4: Entry 6 
 
 
   
Fig S29: Reduction of diphenylamine by using Al powder, Pt/C and H2O at 80oC 
for 12h. 
H
N
H
N
NH2
OH
O
S39 
 
GC Mass of Table 4: Entry 6 
            
 
 
Fig S30: Reduction of diphenylamine by using Al powder, Pt/C and H2O at 80oC 
for 12h. 
H
N
H
N
H
N
H
N
S40 
 
 
Fig S31: Reduction of fluorene by using Al powder, Pt/C, Pd/C, Ru/C, Rh/C and 
H2O at 80oC for 12h. 
 
GC of Table 5: Entry 2 
 
Fig S32: Reduction of 4-methylbiphenyl by using Al powder, Pt/C and H2O at 80oC 
for 12h. 
S41 
 
GC Mass of Table 5: Entry 2 
 
 
 
 
 
 
 
 
 
 
 
S42 
 
 
 
 
 
 
 
Fig S33: Reduction of 4-methylbiphenyl by using Al powder, Pt/C and H2O at 80oC 
for 12h. 
 
 
 
 
S43 
 
GC of Table 5: Entry 3 
 
 
 
Fig S34: Reduction of 4-methoxybiphenyl by using Al powder, Pt/C and H2O at 
80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
OCH3
OCH3
OCH3
S44 
 
GC Mass of Table 5: Entry 3 
 
 
 
OCH3
OCH3
OCH3
S45 
 
 
 
 
 
 
OCH3
OCH3
S46 
 
 
 
 
 
 
 
 
Fig S35: Reduction of 4-methoxybiphenyl by using Al powder, Pt/C and H2O at 
80oC for 12h. 
 
 
 
 
OCH3
OCH3
OCH3
S47 
 
GC of Table 5: Entry 4 
 
 
 
Fig S36: Reduction of 4-tert-butylbiphenyl by using Al powder, Pt/C and H2O at 
80oC for 12h. 
 
 
 
 
 
 
 
 
 
 
 
 
 
S48 
 
GC Mass of Table 5: Entry 4 
 
 
 
 
S49 
 
 
 
 
Fig S37: Reduction of 4-tert-butylbiphenyl by using Al powder, Pt/C and H2O at 
80oC for 12h. 
 


Reduction of aromatic compounds with Al powder using noble metal catalysts in water under mild reaction conditions

CV3-Editorial Board - English

Hemant V. Chavan

Dattatraya K. Narale

Synthesis of 2,4,5-triaryl and 1,2,4,5-tetraaryl imidazoles using silica chloride as an efficient and recyclable catalyst under solvent-free conditions

Dileep Ramakrishna

Badekai Ramachandra Bhat

Suresha Kumara T. Hanumanthappa

Cobalt complex in a room temperature ionic liquid: A convenient recyclable reagent for catalytic epoxidation of cyclic alkenes

Hela Njema

Khaled Boughzala

Anis Chaabène

Khaled Bouzouita

Study of the ionic conductivity of Ca6La4(PO4)2(SiO4)4F2 and Ca4La6(SiO4)6F2

Mohammad Reza Mohammad Shafiee

Syed Sheik Mansoor

Majid Ghashang

Abbas Fazlinia

Preparation of 3,4,5-substituted furan-2(5H)-ones using aluminum hydrogen sulfate as an efficient catalyst

CV3 - Editorial Board - English

Farid Chemat

Maryline Abert-Vian

Anne-Sylvie Fabiano-Tixier

Gr
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C. R. Chimie 17 (2014) 179–180
163
httpeen extraction of natural products (GENP2013)
eword
Green extraction is based on the discovery and design of
raction processes that will reduce energy consumption,
w the use of alternative solvents and of renewable
ural products, and ensure a safe and high-quality
ract and ingredients for pharmaceutical, food, cosmetic,
 chemistry, and bio-fuels. Three major solutions have
n identified to design and demonstrate green extrac-
 at the laboratory and industrial scales to approach an
imal consumption of raw materials, solvents and
rgy: (1) improving and optimization of existing
cesses, (2) using non-dedicated equipment, and (3)
ovation in processes and procedures but also in
overing alternative solvents. The listing of the ‘‘six
ciples of Green Extraction of Natural Products’’ should
viewed for industry and scientists as a direction to
blish an innovative and green label, charter and
dard, and as a reflection to innovate, not only in
cess, but in all aspects of solid–liquid extraction:
rinciple 1: innovation by selection of varieties and use
f renewable plant resources;
rinciple 2: use of alternative solvents and principally
ater or agro-solvents;
rinciple 3: reduction of energy consumption by energy
covery;
rinciple 4: production of co-products instead of waste
 include bio-refinery;
rinciple 5: reduction of unit operations and favoring
fe, robust and controlled processes;
rinciple 6: prioritizing a non-denatured and biodegrad-
ble extract without contaminants.
In this International Conference on Green Extraction of
ural Products (GENP2013), the whole value chain has
n considered, from cultivation, extraction, processing
 recycling steps to the applications: agro, food,
fume, cosmetic, chemical, fuel, and energy sectors.
Avant-propos
L’éco-extraction est basée sur la découverte et la
conception de procédés d’extraction permettant, d’une
part, la réduction de la consommation énergétique, mais
aussi, d’autre part, le recours à des solvants alternatifs et à
des ressources végétales renouvelables, tout en permet-
tant de garantir des extraits sûrs et de qualité, utilisables
comme ingrédient pour la pharmacie, la cosmétique,
l’agroalimentaire, la chimie fine et les bio-fuels. Trois
voies majeures ont été identifiées pour parvenir à
imaginer, concevoir et faire la démonstration à l’échelle
industrielle de ces principes : l’amélioration des procédés
existants, en proposant des ruptures technologiques et de
mise en œuvre ; le détournement d’appareils non dédiés
afin d’atteindre des conditions optimales de consomma-
tion de matière première et d’énergie et, pour finir,
l’innovation méthodologique et technologique. Plusieurs
ateliers de réflexion ont permis de lister les attentes, mais
aussi d’envisager les visions futures, dans un contexte de
développement durable, aussi bien au niveau des produc-
teurs de matières premières végétales que des industriels
transformateurs ou bien formulateurs de produits finis que
des chercheurs académiques et institutionnels. Une des
conclusions qui en ressortent est la nécessité de la notion
d’« éco-extrait » à travers des principes directeurs qui
montrent des bonnes pratiques à suivre et des exemples de
réussite :
 principe 1 : favoriser l’innovation et l’utilisation de
ressources végétales renouvelables ;
 principe 2 : privilégier les solvants alternatifs ;
 principe 3 : réduire la consommation énergétique ;
 principe 4 : favoriser la création de coproduits pour
intégrer la bio-raffinerie ;
 principe 5 : réduire les opérations unitaires grâce à
l’innovation technologique ;
 principe 6 : privilégier un produit porteur de valeurs
(« éco-extrait »).
Contents lists available at ScienceDirect
Comptes Rendus Chimie
ww w.s c ien c edi r ec t . c om1-0748/$ – see front matter  2014 Académie des sciences. Published by Elsevier Masson SAS. All rights reserved.
://dx.doi.org/10.1016/j.crci.2014.01.001
Green extraction of natural products (GENP2013) / C. R. Chimie 17 (2014) 179–180180More than 250 scientists and experts from industry (50%)
and academia (50%) from 25 countries have participated in
this conference held in Avignon, France, a venue that
created an environment for information exchange, gen-
eration of new ideas, and acceleration of applications that
benefit science and society. GENP2013 had served as a
catalyst for the advancement of research in the field of
‘‘green extraction: products and processes’’ by connecting
scientists and experts within and across disciplines from
around the world in the vibrant City of the Popes, Avignon,
France.
Farid Chemat*1
Maryline Abert-Vian1
Anne-Sylvie Fabiano-Tixier1
Université d’Avignon et des pays de Vaucluse, Inra, UMR408,
GREEN extraction team, 33, rue Louis-Pasteur, 84000
Avignon, France
*Corresponding author
E-mail address: farid.chemat@univ-avignon.fr
1Guest editors/Rédacteurs invités.
Available online 29 January 2014
Le congrès « Éco-extraction des produits naturels »
(GENP2013) a permis au domaine de l’extraction d’entrer
dans sa révolution « verte », en opérant une mutation vers
l’« éco-extraction », pour développer et proposer une
chimie plus « durable » utilisant moins de solvants, moins
d’énergie et diminuant les rejets, tout en assurant la qualité
des produits finis. Plus de 250 chercheurs et experts,
représentant plus de 25 pays, venant des milieux industriel
(50 %) et académique (50 %) ont participé à ce premier
congrès sur l’éco-extraction des produits naturels
(GENP2013) dans la Cité des papes, Avignon, France.


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On the influence of the alumina precursor in Fe-K/Al<sub>2</sub>O<sub>3</sub> structured catalysts for the simultaneous removal of soot and NO<sub><i>x</i></sub>: From surface properties to reaction mechanism

Synthesis and characterization of new pyrochlore solid solution Bi<sub>1.5</sub>Sb<sub>1.5–<i>x</i></sub>Nb<sub><i>x</i></sub>CuO<sub>7</sub>