2014 ‫برنامج دعم مشاريع البحوث العلمية في لبنان لعام‬
Grant Research Program 2014

‫تقرير نهائي لمشروع بحث‬
Research project final report
Principal investigator Dr. Leila A. Ghannam
4102 ‫برنامج دعم البحوث العلمية‬
Grant Program for Scientific Research in Lebanon – 2014
1
‫مستند إداري‬
Administrative Document
--------
Administrative information / ‫المعلومات اإلداري‬
:‫المرجع‬
Project Title (in English and Arabic) - )‫عنوان المشروع (عربي وإنكليزي‬
Synthesis Methodologies of Macrocyclic Chelating Systems For the Treatment of
Contaminated Aqueous Effluents
Méthodologies de Synthèse de Systèmes Chélatants Macrocycliques pour le
Traitement d’Effluents Contaminés
‫منهجيات تركيب أنظم ماكرو دائري مخلبي لعالج النفايات السائل في المياه الملوث‬
Principal Investigator - ‫الباحث الرئيسي‬
‫إلحدث‬-‫إلجامعة إللبنانية كلية إلعلوم‬
‫إلعنوإن‬
Address
Lebanese UniversityFaculty of Sciences-Hadath
Leila.ghannam@ul.edu.lb ‫إلعنوإن إاللكتروني‬
leilaghannam@hotmail.com
e-mail
70156567
‫رقم إلهاتف‬
Telephone
‫ليلى إنيس غنام‬
Leila Anis Ghannam
‫إالسم وإلشهرة‬
Lebanese University
‫إلجامعة إللبنانية‬
‫إلمؤسسة‬
Institution
‫إستاذ مساعد‬
Associate professor
‫إلوظيفة‬
Name &
surname
Post
Co-investigators - ‫الباحثون المشاركون‬
‫إلعنوإن إاللكتروني‬
e-mail
stephane.pellet-rostaing@cea.fr
‫إلمؤسسة‬
Institution
Montpellier University
Iyad.Karameh@ul.edu.lb
Lebanese University
4102 ‫برنامج دعم البحوث العلمية‬
Grant Program for Scientific Research in Lebanon – 2014
‫إالسم وإلشهرة‬
Name and surname
Pr.Stéphane pellet Rostaing
Pr. Iyad Karamé
2
.1
Moheddine.WEHBIE@cea.fr
Lebanese University
and Montpellier University
Moheddine Wehbe
PhD student
Duration and starting date of the research / ‫المدة التعاقدي للمشروع وتاريخ بدء البحث‬
2 years
Duration (year) / ‫إلمدة إلتعاقدية للمشروع‬
4/2/4104
Starting date of the research /‫وتاريخ بدء إلبحث‬
Scientific Information / ‫العلمي‬
‫ المعلومات‬.2
ّ
Objectives - ‫الهدف‬
The purpose of this project is the development of new synthetic routes for the preparation
of chelating agents for the extraction and separation of metals. In relation with the
environment protection concepts, the sustainable development and the public health
problems, the essence of this project fits into the broad field of research related to
separation science.
As part of this project, it is:
- To develop synthetic methodologies for the preparation of macrocyclic ligands,
hydrophobic or water-soluble combining chelating properties of sulfonamide
functions and potent ligands generally soluble in aqueous phase (EDTA, DTPA,
PCTA ...) with hydrophobic and pre-organizers properties of macrocyclic
platforms.
- To characterize the prepared ligands and their complexes with heavy metals
(NMR, mass ...) and to determine their stability constants and their toward
competitors cations (Ca2+, Na+, Zn2+, Ni2+ ...) present in aqueous effluents.
Similarly, studies of competitive extractions will be performed in order to propose
the most efficient ligands for the extraction methods considered (liquid-liquid and
membrane).
Achievements - ‫أالنجازات المحقق‬
Synthesis and characterization of chelating agents:
a) We realized the synthesis of 8 resorcinarenes ligands, and in many steps we improved
the synthetic methods already described in the literature. Several syntheses we developed
are less toxic, easier to be performed and more efficient.
b) We developed the synthesis of 7 calixarenes. Now we are working on getting the new
and original calixarenes with carboxylic functions which is not described before in the
literature.
c)All prepared ligands are characterized by nuclear magnetic resonance (NMR) and
sometimes by mass spectrometry (MS).
4102 ‫برنامج دعم البحوث العلمية‬
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Perspectives - ‫آفاق البحث‬
We will consider for further work:

The introduction of other functional groups such as amide, sulfonamides, ureas.

Preparation of triazamacrocycles derived from calixarenes, and reduce the
resulting amides into their corresponding amines, and finally introduce acetic acid
groups on the resulting amines.

Screen the best conditions for the Mitsunobu reaction

Evaluation of the ligands towards:
- Lanthanide extraction (strategic metals)
- Heavy metal extraction (pollutants)

Liquid/liquid extraction

Membrane filtration
Publications & Communications - ‫المنشورات والمساهمات في المؤتمرات‬
-
First publication titled: New easy and eco-friendly synthetic way of Tetra-amino
calix[4]resorcinarene. See attached file: paper 1.
This work will be included in the PhD report of Mister Moheddine WEHBIE and which
will be defended around January 2016
Abstract - ‫موجز عن نتائج البحث‬
During these 2 years, we have developed new, easy and ecofriendly approaches to
synthesize 8 cavitands of resorcinarene and 7 cavitands of calixarene. Synthetic
procedures have been modified and improved; it allows us to obtain good yields, to use
less expensive and toxic solvents and to reduce the reaction times. Details are described in
the detailed report.
‫توقيع الباحث‬
4102 ‫برنامج دعم البحوث العلمية‬
Grant Program for Scientific Research in Lebanon – 2014
4
Research project
Final report
Nota bene
1. The final report must be limited to results directly related to the research
project supported by the Council excluding any other activity carried out
by the investigator otherwise the report will be rejected.
2. Appendices may be added or attached to the report.
3. This document could be completed either in English or in French
1. Principal investigator
Name and surname
Leila Anis Ghannam
Institution of
affiliation
Lebanese University, Faculty of Sciences
4102 ‫برنامج دعم البحوث العلمية‬
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2. Title of the project as proposed in the original application
‫منهجيات تركيب أنظم ماكرو دائري مخلبي لعالج النفايات السائل في المياه الملوث‬
Arabic
Synthesis Methodologies of Macrocyclic Chelating Systems For
the Treatment of Contaminated Aqueous Effluents
English or French
Méthodologies de Synthèse de Systèmes Chélatants
Macrocycliques pour le Traitement d’Effluents Contaminés
3. Purpose of the project
The purpose of this project is the development of new synthetic routes for the preparation
of chelating agents for the extraction and separation of metals. In relation with the
environment protection concepts, the sustainable development and the public health
problems, the essence of this project fits into the broad field of research related to
separation science.
As part of this project, it is:
- To develop synthetic methodologies for the preparation of macrocyclic ligands,
hydrophobic or water-soluble combining chelating properties of sulfonamide
functions and potent ligands generally soluble in aqueous phase (EDTA, DTPA,
PCTA ...) with hydrophobic and pre-organizers properties of macrocyclic
platforms.
- To characterize the prepared ligands and their complexes with heavy metals
(NMR, mass ...) and to determine their stability constants and their toward
competitors cations (Ca2+, Na+, Zn2+, Ni2+ ...) present in aqueous effluents.
Similarly, studies of competitive extractions will be performed in order to propose
the most efficient ligands for the extraction methods considered (liquid-liquid and
membrane).
4102 ‫برنامج دعم البحوث العلمية‬
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4. Expected outputs
1) Synthesis of chelating macrocycles
a) Functionalization of calix [4] resorcinarene with specific groups bearing affinity to heavy metals
(Pb, Hg, Cd).
b) Development of synthetic methodology based on the Mitsunobu reaction for the preparation of
calix [4] arenes incorporating one hand chelating functions like EDTA, DTPA and PCTA, and other
lipophilic groups (alkyl) or hydrophilic (SO3H ...) depending on the suitable solubility properties
(soluble macrocycles in organic or in aqueous medium)
c) Characterization of macrocycles
2) Study of complexation properties of ligands
- Preparation of the heavy metals complexes (Pb, Hg, Cd) for detoxification.
- Characterization of complexes (mass spectrometry, UV, X-ray, atomic absorption, LCP ....)
3) Implementation in extraction processes
- Liquid / liquid
- Membrane filtration
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5. Results
A large work of organic synthesis allowed the preparation of several chelating ligands.
These ligands or cavitands belong to two families: resorcinarenes and calixarenes (Figures 1
and 2).
A- Synthesis of Modified Resorcinarenes.
The synthetic scheme for the resorcinarene cavitands presented in Figure 1, shows that
tetrabrominated cavitand III constitute the intermediate from which we synthesized another
cavitands by nucleophilic substitution.
Figure 1
A-1. Synthesis of cavitands I, II and III
The compound I was prepared as described by Cram et al (prix Nobel 1989),
methylresorcinol and acetaldehyde are mixed in stoichiometric proportions in a mixture of
water and ethanol and in the presence of HCl, the cavitand I is obtained with a high 90%
yield similar to that mentioned in the literature.
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We transform cavitand I to cavitand II with conic structure by introducing a methylene
bridge using CH2Cl2. In the literature bromochloroethane (CH2BrCl) was used as described
by Cram et al [Cram, D. J.; Karbach, S.; Kim, H-E.; Knobler, C. B.; Maverick, E. F.; Ericson,
J. L.; Helgeson, R. C. J. Am. Soc. 1988, 110, 2229-2237].
In fact, the dichlormethane CH2Cl2 used as a solvent in many chemical reactions, it has
two advantages:
-
Replaces Bromochloromethane which destroys the ozone layer; and whose production
has been banned since 1st January 2002, at the Eleventh Meeting of the Parties of Montreal
Protocol on the substances that deplete the ozone layer.
-
The dichloromethane is less expensive and available in large quantities.
The cavitand II was obtained by our method with very good yield (84 %) much better than
that obtained by Cram’s group.
Afterthat, a bromination reaction was performed using N- bromosuccinimide (NBS) in
tetrachloromethane as already described [Sorrell, T. N.; Pigge F. C. J. Org. Chem. 1993, 58,
784-785]. The yield of the reaction was improved by using distilled CCl 4, and thus we
reached up to 79%, better than that obtained by the literature (60%).
A-2. Synthesis of cavitand IV (tetra-azide) and cavitand V (tatramine)
To achieve the synthesis of cavitand IV using sodium azide NaN3, we have adopted a
method developed in our laboratory using acetone as solvent in place of DMF or DMSO.
This reaction is done properly, no side products or impurities were obtained, and a simple
filtration followed by evaporation of the solvent affords the desired product with a very good
yield (85%).
At the same time, in order to prepare a cavitand substituted with triazole group for the
oxidation catalysis with iron, Hooley’s group have published very recently (2012), the
synthesis of a compound similar to cavitand IV, their method consist of using THF as a
solvent mixed with a solution of NaN3 in DMSO [K. E. Djernes; O. Moshe; Mr. Mettry; D. D.
Richards; Hooley R. J. Org. Lett. 2012, 14, 788-791] This method allows to obtain the
corresponding compound with good yield but it is more complicated than our method.
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Furthermore, acetone is much less toxic and less odorous than THF and DMSO and it is
elimination by evaporation is easier.
The cavitand V was prapared in our Lab by reduction under hydrogen of the the tatraazide
cavitand IV, The hydrogenation reaction is catalyzed by platinum on charcoal (Pt/C, 5%). An
amino resorcinarene, similar to cavitand V is used recently by Sheela et al (2011) as a
stabilizer for the dispersion of nanodiamands in organic solvents for the purpose of growing
diamond films. [V. P. Sheela; W. Xiao; S. Han; X. Zhou; S. Albin; R. Balasubramanian, J.
Mater. Chem., 2011, 21, 6395-6400]. This group uses synthetic procedures already described
in the literature to prepare the cavitand tetra amines in two steps from tetra brominated
cavitand. This method enables the transformation of the tetra brominated cavitand into
tetrakis (phthalimidomethyl), and then the phthalimido group is hydrolyzed by hydrazine
hydrate under reflux in ethanol / THF. Our method seems to be cleaner and much simpler and
affords the product V with a very high yield (95%).
A-3. Synthesis of cavitands VII and VIII
We have prepared the cavitand VII by two different methods: the first method described in
the literature by our collaborator [Pellet-Roasting, S.; Nicod, L.; Chitry, F.; Lemaire, M.
Tetrahedron lett. 1999, 40, 8793-8796] consists on the conversion of III (tetra bromide) to
cavitand VII using KCN in DMSO at 70°C during 24h. The cavitand VII was obtained with
a yield of 55%.
The second method we developed consists on the using of a mixture of acetone and
acetonitrile as solvents instead of DMSO. This method which allowed us to obtain the desired
product VII in a much better yield of 75%, and was carried out using solvent less toxic, more
friendly and easily removed by evaporation.
The cyano groups of VII are then hydrolyzed under reflux in basis medium in a mixture
EtOH: H2O (1:1) to give the cavitand VIII with four groups of carboxylic acid in good yield
(70%). [Pellet-Roasting, S.; Nicod, L.; Chitry, F.; Lemaire, M. Tetrahedron lett. 1999, 40,
8793-8796].
The trials to prepare cavitands VI and IX are failed, in both cases we obtained a white
solid not soluble in any solvents, that is why we did not arrived to characterized theses solids.
B- Synthesis of Calixa(4)arene moieties:
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The synthetic schemes for the calixarene macrocylcles (R = H or t-butyl) presented in
Figure 2, shows the synthesis method correspond to the cyclization by traditional
nucleophilic substitution.
Figure 2
B-1. Synthesis of Calixa(4)arene moieties (1), (2) and (3)
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The compound (1) was prepared as described in the literature [Francoise A.; Elizabeth M.
C.; Mary D.; George F.; Stephen J. H.; Branko K.; Alan J. L.; M. Anthony M.; Elizabeth M.;
Barbara L. R; Marie J. S; and Eileen M. S. J. Am. Chem. Soc., 1989, 111, 8681-8691], it is
obtained in high yield (78%).
The compound (2) was prepared by alkylation of the left two phenolic groups by MeI in
DMF in the presence of NaH as a base to give the pure compound in 70 % yield after column
chromatography.
The obtained compound (2) was further reduced with LiAlH4 in THF at room temperature
for 12 hrs to give its corresponding diethyl alcohol (3) in 60 % yield.
B-2. Mitsonobu coupling: Synthesis of compound (4)
The Mitsunobu reaction is very famous reaction since it can be used to convert primary or
secondary alcohols into various other functional groups such as ether esters, amines, amides,
lactams, lactones. As described by [Abidi, R.; Oueslati, I.; Amri, H.; Thuery, P.; Nierlich, M.;
Asfari, Z.; Vicens. J. Tetrahedron Lett. 2001, 42, 1685–1689]. One of the objectives of our
research is to screen the best condition for the Mitsunobu reaction by varying the coupling
reagents and the trialkyl/triaryl phosphines, and the temperature of the reaction.
The nucleophilic substitution of the two hydroxyl groups can be done by refluxing
together both the calixarene (3) and triprotected diethylene triamine (Figure 3) under
Mitsunobu condition as described by [J. Hovinen, R. Sillanpää. Tetrahedron Letters, 2005,
46, 4387–4389]. The reaction to prepare the compound (4) was carried out in the presence of
the coupling reagent diethyl azadicarboxylate and triphenyl phosphine in THF, the progress
of the reaction was followed by TLC which showed many spots corresponding to the desired
product, the side products, the coupling reagents, triphenyl phosphine and triphenyl
phosphine oxide. Furthermore all the purification trials, precipitation, crystallization, even
flash chromatography failed to purify the desired product. One efficient way to follow such
reaction is to inject it in HPLC at different instants.
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RR
RR
RR
Ns
NH
HN
sN
N
sN
MeO O MeO O
HO
RR
PPh3, DEAD
THF Reflux
MeO O MeO O
Ns N
HO
N sN
N
sN
(4)
(3)
Figure 3
In Mitsunobu reaction the hydrogen of sulfonamide group must be acidic enough in order
to be deprotonated easily by the coupling reagent, then the amino groups were protected by a
highly electron withdrawing group such as o-nitrobenzene sulfonyl group, therefore the
diethylene triamine (DETA) was protected by reacting it with slight excess amount (little
more than three equivalents) of o-nitrobenzene sulfonylchloride in THF and in the presence
of NaHCO3 as a base (Figure 4). In this reaction we improved the condition for the
triprotection of (DETA) described by [Jean-Michel Siaugue; Fabienne Segat-Dioury; Alain
Favre-Reguillon; Charles Madic; Jacques Foosa and Alain Guyb. Tetrahedron Lett., 2000, 41,
7443–7446] in which we refluxed the reaction mixture at 400C rather than at room
temperature, to obtain the desired product in better yield 85% with shorter reaction time 50
hrs rather than 96 hrs. Also we purified the resulting triprotected (DETA) as crystals by slow
precipitation from a binary mixture of ethanol and dichloromethane.
Figure 4
B-3. Synthesis of Calixa(4)arene moieties (5) and (7)
The compound (5) was synthesized by direct nucleophilic substitution of the ester groups
of compound (1) by the amine groups of the triamine (DETA) as described by [Abidi, R.;
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Oueslati, I.; Amri, H.; Thuery, P.; Nierlich, M.; Asfari, Z.; Vicens. J. Tetrahedron Lett. 2001,
42, 1685–1689]. The macrocyle (5) was obtained in high yield (95%).
The amide groups of the compound (5) are subjected to reduction using LiAlH4 to prepare
their resulting amines (7), the reaction is done in diethylether according to the procedure
described by [K. No; H. J. Lee; K. M. Park; S. S. Lee; K. H. Noh; S. K. Kim; J. Y. Lee; and J.
S. Kim; J. Heterocyclic Chem., 2004, 41, 211].
Figure 5
B-4. Synthesis of Calixa(4)arene (8)
Regarding to the effectiveness of the compound (5) in the field of extraction of metallic
cations from contaminated water as described in [Abidi, R.; Oueslati, I.; Amri, H.; Thuery, P.;
Nierlich, M.; Asfari, Z.; Vicens. J. Tetrahedron Lett. 2001, 42, 1685–1689], we decided to go
on further to prepare a compound similar to (5) but with two macrocycles on the lower rim
similar in structure to PCTA.
To do this, we first inserted four ethylacetate groups on the four phenol groups of the
starting calixarene, by refluxing together the calixarene with ethyl bromoacetate at 700C, to
direct our substitution toward tetra-alkylation and to prevent obtaining a mixture of di, tri,
and tetra alkylated products, Na2CO3 was used instead of K2CO3, in acetone instead of
MeCN, leading us to improve the procedure of this reaction over the procedures described by
[Francoise A.; Elizabeth M. C.; Mary D.; George F.; Stephen J. H.; Branko K.; Alan J. L.; M.
Anthony M.; Elizabeth M.; Barbara L. R; Marie J. S; and Eileen M. S. J. Am. Chem. Soc.,
1989, 111, 8681-8691], as we added 5 equivalent of ethylbromoacetate instead of 40
equivalent described in the literature and we obtained the good product (8) with higher yield
and shorter reaction time.
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B-5. Synthesis of Calixa(4)arene moiety (9)
Compound (8) is reacted with two equivalents of (DETA) at 800C in a binary mixture of
toluene/methanol to produce its corresponding bicyclic tetra-amide derivative (9) in good
yield (75%), Figure 6.
Figure 6
C. Conclusion
During these 2 years, we have synthesized 8 cavitands of resorcinarene and 7 cavitands of
calixarene. Synthetic procedures have been modified and improved; it allows us to obtain
good yields, to use less expensive and toxic solvents and to reduce the reaction times.
–
Tetrakis (aminomethyl) calix-4-resorcinarene V is obtained according to a synthetic
route consists of five steps. Our alternative method to those described in the literature
consists of preparing the tetrakis (azidomethyl) calix-4-resorcinarene IV and then reducing
under hydrogen atmosphere.
–
Bromochloromethane is banned worldwide because it destroys the ozone layer, and
we replaced it by dichloromethane during the preparation of the intermediate II. This
procedure also allows obtaining a good yield, and usage of less dangerous solvents for the
environment.
–
The synthesis of cavitand IV in acetone using NaN3 has two major advantages over
the recently described method by Sheela et al (2012) [27]. The Sheela group used NaN 3 in a
solution of THF/DMSO. Acetone which has an acceptable dielectric constant can dissolve
sodium azide, easier to evaporate, less toxic and facilitates purification of the final product.
–
Also concerning the calix(4)arene we improved the procedures for the preparation of
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compounds 5, 7, and 9.
1. During the preparation of compound 5 we used exactly 1:1 equivalents of both
calixarene diethylester and DETA in a diluted solution 10-1 mol/L, and by giving the
reaction the necessary time (12 hrs) it proceed with complete conversion. Therefore
there is no need to purify the compound by flash column as described by the
literature, evaporating the solvent under reduced pressure was enough to give the pure
product with excellent yield up to 100%.
2. In the literature [J. Heterocyclic Chem., 2004 41, 211] they prepared the compound 7
by using large excess amount of LiAlH4 and after quenching the reaction by H2O it
gives heavy white precipitate which avoid the separation of the two layers
(H2O/CH2Cl2) during extraction, instead of this we made filtration first to get rid of
the precipitate, and then extraction by CH2Cl2. Moreover the compound did not elute
from the column chromatogaraphy as they describe and it is normal since it contains
three amine groups, instead of this a simple recrystallization from a mixture of ethyl
acetate and cyclohexane was more evident.
3. While the procedure to prepare the compound 9 was improved by using only slight
excess amount of ethyl bromoacetate (1.1 equivalent) instead of 100% molar excess
described in [J. Am. Chem. Soc., 1989, 111, 8681-8691], and we got a pure product
with the same yield within shorter reaction time.
We will consider for further work:

The introduction of other functional groups such as amide, sulfonamides, ureas.

Preparation of triazamacrocycles derived from calixarenes, and reduce the resulting
amides into their corresponding amines, and finally introduce acetic acid groups on
the resulting amines.

Screen the best conditions for the Mitsunobu reaction

Evaluation of the ligands towards:
- Lanthanide extraction (strategic metals)
- Heavy metal extraction (pollutants)

Liquid/liquid extraction

Membrane filtration
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6. Summary table of expected and obtained results
Expected outputs / Résultats attendus
1. Synthesis of chelating macrocycles:
Obtained results / Résultats obtenus
1. Synthesis of chelating agents:
a) Functionalization of calix [4]
resorcinarene with specific groups bearing
affinity to heavy metals (Pb, Hg, Cd...).
a) We realized the synthesis of 8
resorcinarenes ligands, and in many
steps we improved the synthetic methods
already described in the literature.
Several syntheses we developed are less
toxic, easier to be performed and more
efficient. We did not arrive yet to prepare
the cavitands containing sulfonamide
arms.
b) Development of synthetic methodology
based on the Mitsunobu reaction for the
preparation of calix [4] arenes
incorporating one hand chelating functions
like EDTA, DTPA and PCTA, and other
lipophilic groups (alkyl) or hydrophilic
(SO3H ...) depending on the suitable
solubility properties (soluble macrocycles
in organic or in aqueous medium).
b) We developed the synthesis of 7
calixarenes. Now we are working on
getting the new and original calixarenes
with carboxylic functions which is not
described before in the literature.
c) Characterization of macrocycles
c) All prepared ligands are characterized
by nuclear magnetic resonance (NMR)
and sometimes by mass spectrometry
(MS).
2. Study of complexation properties of
ligands
- Preparation of the heavy metals
complexes (Pb, Hg, Cd) for detoxification.
- Characterization of complex (mass
spectrometry, UV, X-ray, atomic
absorption, LCP ....)
3. Implementation in extraction
processes
- Liquid / liquid
- Membrane filtration
2. The study of the complexation will
start very soon, the PhD student
working on this project will do
this in CEA of Marcoule- France
3. This part is not done yet, we hope
realize that in one year, after
finishing the previous 2 steps.
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7. Possible encountered difficulties
None
8. Scientific publications )articles in peer reviewed journals, books,
communications, etc …)
-
First publication titled: New easy and eco-friendly synthetic way of Tetra-amino
calix[4]resorcinarene. See attached file: paper 1.
-
Second publication under preparation on the Uranium complexe with the Tetrakis
(amidomethyl) calix-4-resorcinarene (realized in collaboration with the ICSMCEA (Marcoule-France)
-
At least one publication will be realized soon on the calixarenes ligands
This work will be included in the PhD report of Mister Moheddine WEHBIE and which
will be defended around January 2016
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9. Oral presentations or posters in national, regional and international
conferences
(Attach a copy of each presentation as it was presented or published in refereed
conference proceedings)
4102 ‫برنامج دعم البحوث العلمية‬
Grant Program for Scientific Research in Lebanon – 2014
19
How to submit the final report ?
Comment soumettre le rapport final ?
-------The final report must be submitted to CNRS in two versions:
 A hard copy which can be mailed or delivered directly to the Council
administrative seat;
 An electronic version, Word document, on CD-ROM or USB drive or email sent to the Council at the following address : grp@cnrs.edu.lb
4102 ‫برنامج دعم البحوث العلمية‬
Grant Program for Scientific Research in Lebanon – 2014
20
‫برنامج دعم البحوث العلمي في لبنان لعام ‪2015‬‬
‫‪‬‬
‫كيفي تقديم التقرير النهائي لمشروع البحث‬
‫‪‬‬
‫‪ .0‬خالل فترة أقصاها شهرين من تاريخ إنتهاء إلمشروع (سنة أو سنتين)‪ ،‬على إلباحث تقديم تقرير‬
‫نهائي (نسخة ورقية ونسخة إلكترونية بصيغة ‪ WORD‬على قرص مدمج أو ‪ USB‬أو ترسل إلى‬
‫إلمجلس بوإسطة إلبريد إإللكتروني على إلعنوإن إلتالي‪ ،grp@cnrs.edu.lb :‬وذلك وفقاً للنموذج‬
‫إلمعتمد في إلمجلس وإلموجود على موقع إلمجلس ‪ http://www.cnrs.edu.lb‬مرفقاً بالتصفية‬
‫إلمالية لمشروع إلبحث إلبحث ونسخاً عن الفواتير العائدة لجميع النفقات ممهورة بختم الموسس‬
‫التي ينتمي اليها الباحث‪ .‬ال يقبل التقرير النهائي إالّ إذا عرض الباحث بشكل واضح جدوالً مفصالً‬
‫يبين فيه ما تم إنجازه مقارن مع تصوره لمخرجات المشروع عند قبوله‪ ،‬على أن ال يتضمن سوى‬
‫ّ‬
‫ما له عالقة مباشرة بمشروع إلبحث إلمدعوم من إلمجلس دون إغرإقه بأية تفاصيل أو نشاطات أخرى‬
‫وإلتركيز حص إًر على إلنتائج إلتي توصل إليها إلباحث‪.‬‬
‫‪ .4‬يعتمد إلمجلس في تقييم إلتقرير إلنهائي على إألهمية إلعلمية للمنجزإت وإلمقاالت إلصادرة عن‬
‫إلباحث وذإت عالقة مباشرة بمشروع إلبحث إلمدعوم من إلمجلس‪ ،‬على أن يتم إلنشر في دورية‬
‫علمية عالمية محكمة بما فيها إلمجلة إلعلمية إللبنانية (‪ )Lebanese Science Journal‬أو‬
‫إلمتخصصة شرط أن يوإفق عليها إلمجلس ويعتبرها بمثابة نشر‬
‫كمساهمة علمية في أحد إلكتب‬
‫ّ‬
‫محكم‬
‫علمي ّ‬
‫‪21‬‬
‫برنامج دعم البحوث العلمية ‪4102‬‬
‫‪Grant Program for Scientific Research in Lebanon – 2014‬‬