Hydrogenolysis of Glycerol to Produce 1,3-Propanediol By ...
1,3-Dihydroxypropan-2-one (DHA) synthesis from Glycerol for pharmaceutical applications
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Transcript of 1,3-Dihydroxypropan-2-one (DHA) synthesis from Glycerol for pharmaceutical applications
Ph.D. Chemical EngineeringA.A. 2014 - III year
TorinoDecember 16th, 2014
Simone Ripandelli
Tutor: Prof. Guido Saracco
Politecnico di Torino - DISAT - Dipartimento di Scienza Applicata e Tecnologia 1
In Bracco is employed in the Iopamidol synthesis:
HO OHNH2
ICl
COClOCOCH3
Acetoluro
CONHCH(CH2OH)2
CONHCH(CH2OH)2COHN
II
IOHIopamidolo
COCl
COClCOHN
II
IOCOCH3Lactoftaluro
IodoftalAminoftal
COOH
COOHH2N
COOH
COOHO2N
COOH
COOHH2NI
I I
Iodoftaluro
COCl
COClH2NI
I I
Iopamidol synthesis
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2[2] X-Ray computeed Tomography Contrast Agents; Hrvoje Lusic and Mark W. Grinstaff; Chemical Reviews; 2011
Serinol is used as building block in the
synthesis of:• non-ionic iodinated X-ray contrast agents
• anti-inflammatory and analgesic drugs• cosmetics
HO OHNH2
Serinol
[1] Serinol: small molecule – big impact ; Bjorn Andreeben, Alexander Steinbuchel; AMB express, a Springer Open Journal; 2011
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Serinol: Bracco Imaging process
Serinol process became not cost-effective because of the high cost of the DHA as starting material!
DHA as starting material
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HO OHNH2
HO OHO 1) NH3
2) H2 / Cat
Usually the DHA is produced at an industrial scale by microbial fermentation of glycerol over Gluconobacter Oxydans with high selectivity.
Low productivity and high production cost are remarkable drawbacks.
[3] Production of Gluconobacter oxydans Cells from Low‐cost Culture Medium for Conversion of Glycerol to Dihydroxyacetone; Shenghua Wei, Qingxun Song and Dongzhi Wei; Preparative Biochemistry and Biotechnology; 2007
[4] Production of 1,3-dihydroxyacetone from glycerol by Gluconobacter oxydans; Hu Z.C., Liu Z.Q., Zheng Y.G., Shen Y.C.; 2010
Glycerol Simone Ripandelli
5Politecnico di Torino - DISAT - Dipartimento di Scienza Applicata e Tecnologia
Glycerol is a by-product of biodiesel fuel production (transesterification of seed oils with MeOH). The rapid expansion of the global production of biodiesel has created a major surplus of glycerol. Consumption of this extra glycerol is a necessary requisite for the commercial viability of biodiesel production.
Glycerol has become a low-cost starting material!
Simone Ripandelli
[5] S. Demirel-Gulen, M. Lucas and P. Claus, Catal. Today, 2005, 102–103, 166–172[6] Oxidation of glycerol to biobased chemicals using supported mono- and bi-metallic noble metal catalysts; Ph.D. Thesis; University of Groningen
6Politecnico di Torino - DISAT - Dipartimento di Scienza Applicata e Tecnologia
General reaction pathways from glycerol
• Glycerol: low-cost starting material with high availability
• Oxygen: terminal oxydant with only water as by-product
• Catalyst: showing selectivity for the secondary carbon
Project aim: DHA from glycerol
OOH OH
OHOH OH 1/2 O2 H2O
cat.
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Catalysts Mono-metallic catalysts Au-NPs based on carbon supports
Bi-metallic catalysts Pt-Bi coupled NPs based on carbon supports
Tri-metallic catalyst Au0,6Pt0,4Bi1,0/C (metal nanoparticles)
Organometallic Palladium based catalyst (homogeneous catalyst)
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N
N
H3C
H3C
PdN
N
CH3
CH3
PdO
O
CH
CH
O
O
CH3
CH3
2
2 OTf[7] Elodie Rodrigues, Manuel F.R. Pereira, Juan J. Delgado, Xiaowei Chen, José J.M. Orfao; Cat.
Comm. 2011[8] Selective Oxidation of Glycerol to Dihydroxyacetone over Pt-Bi/C Catalyst: Optimization of
Catalyst and Reaction Conditions Wenbin Hu, Daniel Knight Ind.Eng.Chem.Rev. 2010[9] Aerobic Alcohol oxydation with cationic Palladium Complexes: insights into catalyst design and
decomposition; Nicholas J. Conley, Liezel A. Labios, David M. Pearson, Charles C.L. McCrory and Robert M. Waymouth, May 2007
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Heterogeneous catalyst PtBi (I)Literature : z 70% y 42 % ; 3 wt% Pt – 0,6 wt% Bi
Method : Impregnation and subsequent chemical reduction with NaBH4
Support : Carbon Black, Graphite and Graphite Oxide (Hummers 1958 and its modifications)
Characterization : XRD, XPS, STEM, ICP
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Heterogeneous catalyst PtBi (II)Deposition + Characterization : XPS
PtBiCoupled :157.10 eV &159.00 eV [7-8]
[10] NIST X-Ray Photoelectron Spectroscopy Database
[11] The chemistry of Graphene Oxide; Daniel R.Dreyer, Sungjin Park, Christoper W. Bielawski and Rodney S. Ruoff; The Royal Society of chemistry; 2010
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Heterogeneous catalyst PtBi (III)
[8] Selective Oxidation Of Glycerol to Dihydroxyacetone over Pt-Bi/C catalyst: optimisation of catalyst and reaction conditions; Wenbin Hu, Daniel Knight, Brian Lowry, Arvind Varma; Ind. Eng.Chem.Res. 2010
Glycerol oxydation
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[12] S. Demirel-Gulen, M. Lucas and P. Claus, Catal. Today, 2005, 102–103, 166–172
GC-FID
GC-MS
HPLC-UV
The sample analysis (I) : GC-FID
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- Derivatization with TFAA- Capillary Column: DB 624 – 30m x 0,32
mm x 1,8 m- Constant pressure (11 psig)- Detector FID 240°C
DHA Glycerol
Glyceraldehyde B-hydroxypiruvic Glyceric Acid Tartronic acid
The sample analysis (II) : GC-MS
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Glycerol
DHA
TFAA CF3
GlycerolDHA
Reaction Mixture
References
The sample analysis (III) : HPLC- Derivatization with PFBHA- Column: 250 mm x 4,6 mm Zorbax Eclipse XDB-C8 column- UV detection 263 and 215 nm
DHA Pyruvic Acid Glyceraldehyde
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Oxidations in the laboratory batch reactor
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The oxidation experiments were performed in a 500 ml laboratory batch reactor sited at the Politecnico of
Turin.The O2 is provided by an external
cylinder at 200 bar.
An external digital and an analogic
barometer allow the pressure control
inside the reactor.
The temperature is tuned by an
external jacket and a cooling loop is
used to keep it constant.
A particular caved impeller is used for
the O2 recirculation.
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Heterogeneous catalyst PtBi results (I)
Catalyst Solution Conditions zmax[%]
y DHA[%]
PtBi on GO III
Pt 0,5, Bi 0,65 wt%
T = 60 °CP = 30 bar
pHin-pHfin = 5.5 – 5.0
Reaction Time = 240 min
Water solution 110 ml
Glycerol 0.1 M
Molar Ratio (Gly/cat) = 46.5
33.25 0
Pt on GO V
Pt 7 wt%
T = 60 °CP = 30 bar
pHin-pHfin = 5.0 – 5.0
Reaction Time = 300 min
Water solution 110 ml
Glycerol 0.1 M
Molar Ratio (Gly/cat) = 46.5
21.07 0
[8] Selective Oxidation of Glycerol to Dihydroxiacetone over Pt-Bi/C catalyst: Optimisation of Catalyst and Reaction Conditions; Wenbin Hu, Daniel Knight, Brian Lowry and Arvind Varma; ; Ind. Eng.Chem.Res. 2010
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Heterogeneous catalyst PtBi results (II)
Catalyst Solution Conditions zmax[%]
y DHA[%]
PtBi on Graphite
Pt 0,75, Bi 11,8 wt%
T = 60 °CP = 30 bar
pHin-pHfin = 5.5 – 4.5
Reaction Time = 300 min
Water solution 110 ml
Glycerol 0.1 M
Molar Ratio (Gly/cat) = 46.5
0 0
Pt on GO VI
Pt 3,8 wt%
T = 60 °CP = 30 bar
pHin-pHfin = 5.5 – 5.0
Reaction Time = 300 min
Water solution 110 ml
Glycerol 0.1 M
Molar Ratio (Gly/cat) = 46.5
1.6 0
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Heterogeneous catalyst AuPtBi resultsTri-metallic catalyst Au0,4Pt0,6Bi1,0/C ; glycerol 1 M
Catalyst Solution Conditions zmax y DHA
[mg] [-] [-] [%] [%]
102MR = 7000 H2O
pH = 7P =30 barT = 60°C
29,4 0
100MR = 7000 H2O
pH = 91 eq NaOH
P =30 barT = 60°C
40,7 0
102MR = 7000 H2O
pH = 11 eq HCl
P =30 barT = 60°C
4,2 0
N° Solvent MR Ox. Time z s y
[-] [-] [Gly/cat.] [-] [h] [%] [%] [%]
1 CH3CN:H2O(10:1)
10 O2 4 95 / 69
5 CH3CN:H2O(10:1)
10 air 18 / / 73
2 DMSO 20 air 24 47 80 /
3 CH3CN 20 benzoquinone 24 97 99 /
4 CH3CN:H2O(7:1)
20 benzoquinone 3 97 99 /
Legend :
z: conversions: selctivity Y: yieldMR : Molar Ratio
[13] Selective Catalytic Oxidation of Glycerol to Dihydroxyacetone; Ron M. Painter, David M. Pearson, and Robert M. Waymouth; 2010
Conditionsroom temperature1 atm air [13]
The results in the literature (I) Homogeneous catalyst
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N
N
H3C
H3C
PdN
N
CH3
CH3
PdO
O
CH
CH
O
O
CH3
CH3
2
2 OTf
The results in the literature (II)
[13] Aerobic Alcohol Oxydation with Cationic Palladium Complexes: Insights into Catalyst Design and Decomposition; Nicholas R. Conley, Liezel A. Labios, David M. Pearson, Charles C.L. McCrory and M. Waymouth; American Chemical Society 2007
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Research aims:N° Solven
tMR Ox. Tim
ez s y
[-] [-] [Gly/cat.] [-] [h] [%] [%] [%]
1 CH3CN:H2O
(10:1)
10 O2 4 95 / 69
5 CH3CN:H2O(10:1)
10 air 18 / / 73
2 DMSO 20 air 24 47 80 /3 CH3CN 20 benzoquinon
e24 97 99 /
4 CH3CN:H2O(7:1)
20 benzoquinone
3 97 99 /
Solvent:Avoid solvents as DMSO and ACN
Molar Ratio:Increase the MR of 1 or 2 order of magnitude
Terminal Oxidant:Avoid not environmental friendly ones
(BQ) Time:Reduce the reaction timeYield and selectivity:Maximize DHA yield
The results in the literature (III)
[13] Aerobic Alcohol Oxydation with Cationic Palladium Complexes: Insights into Catalyst Design and Decomposition; Nicholas R. Conley, Liezel A. Labios, David M. Pearson, Charles C.L. McCrory and M. Waymouth; American Chemical Society 2007
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II
III
IV OTf2
2
N NCH3 CH3
PdN N
C CCH3 CH3
N NCH3 CH3
PdO OO
CH3
OCH3
OTf2
2
N
N
H3C
H3C
PdN
N
CH3
CH3
PdO
O
CH
CH
O
O
CH3
CH3
+ 2 CH3CN
NH2CCH3
OSCF3
OO
N NCH3 CH3
PdO OO
CH3
OCH3
N NCH3 CH3
PdN N
C CCH3 CH3
2
2 OTf2
F CF
FSO
OOH C
CH3
OSCF3
OO
NH2CH3CN
N NCH3 CH3
Pd2+CO
-O CH3 2N N
CH3 CH3Pd
O OO
CH3
OCH3
MW = 208.26 MW = 224.51
MW = 432.76
I PdNc_C
PdNc_A
PdNc_D
A synthetic description for the dimer synthesis
[14 ]
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[14] Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structures; George E. Salnikov, Alexander M. Genaev, Vladimir G. Vasiliev and Vyacheslav G. Shubin 2012
The synthesis of PdNc_C (II)
N NCH3 CH3
Pd2+CO
-O CH3 2N N
CH3 CH3Pd
O OO
CH3
OCH3
MW = 208.26 MW = 224.51
MW = 432.76
Molar ratio Neoc./Pd(OAc)2 = 1
Reaction solventsToluene-Dicloromethane
Product isolationPetroleum EtherFiltrationDry under vacuum
YIELD = 87.54 %Politecnico di Torino - DISAT - Dipartimento di Scienza Applicata e Tecnologia
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The synthesis of PdNc_C (III)
Sample Weight Pd amount
Average s
[-] [mg] [%w/w] [-] [-]
A 8.95 20.932 21.7
± 0.6B 8.62 22.082
C 9.44 21.960
Sample Weight Water Amount
Average
[-] [mg] [wt%] [wt%]A 109.2 8.70
7.86B 103.1 7.69C 101.9 7.20
ICP assay = 95.52 %
ICP analysis:Karl-Fischer analysis
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The synthesis of PdNc_A (I)
I F CF
FSO
OOH C
CH3
OSCF3
OO
NH2CH3CNN N
CH3 CH3Pd
O OO
CH3
OCH3
N NCH3 CH3
PdN N
2
2 OTf
CH3C
CCH3
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Molar ratio TfOH/PdNc_C1 = 2,5
Reaction solventsCH3CN anhydrous
Product isolationDiethyl Ether + FiltrationDry under vacuumYIELD = 84.15 %
The synthesis of PdNc_A (II)
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Karl-Fischer analysisSample Weight Water
AmountAverage
[-] [mg] [wt%] [wt%]A 100.6 2.32
2.39B 96.5 2.04C 102.0 2.63
Sample Weight Pd amount
Average s
[-] [mg] [%w/w] [-] [-]
A 17.73 14.334 14.2
± 0.2B 17.60 14.173
C 11.39 13.969
ICP analysis:
1
54 3
2 ICP assay = 96.9 %
The synthesis of PdNc_D (I)
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OTf2
2
N NCH3 CH3
PdN N
C CCH3 CH3
N NCH3 CH3
PdO OO
CH3
OCH3
OTf2
2
N
N
H3C
H3C
PdN
N
CH3
CH3
PdO
O
CH
CH
O
O
CH3
CH3
+ 2 CH3CN
Karl-Fischer analysis Sample Weight Pd amount
Average s
[-] [mg] [%w/w] [-] [-]
A 5.29 17.013 17.3
± 0.8B 4.02 16.729
C 5.48 18.248
ICP analysis: Sample Weight Water
AmountAverage
[-] [mg] [wt%] [wt%]A 44.4 1.87
1.825B 44.1 1.78
NMR
Reagents molar ratio PdNc-A : PdNc-C: 1:1
Reaction Solvent: CH3CN anhydrous
Product Isolation: Diethyl Ether + filtration
The synthesis of PdNc_D (II)
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Yield = 77.5 %
ICP assay = 89.1 %
Matrix-Assisted Laser Desorption/Ionization (MALDI):-High Molecular Weight (> 400-500 g/mol)-Mild Ionization
[15] Chemoselective Pd-Catalyzed Oxidation of Polyols: Synthetic Scope and Mechanistic Studies Kevin Chung, Steven M. Banik, Antonio G. De Crisci, David M. Pearson, Timothy R. Blake, Johan V. Olsson, Andrew J. Ingram, Richard N. Zare, and Robert M. Waymouth
Experimental Strategy
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Catalysts under screening:
To be Investigated:
Nature of the solvent : pure Water, CH3CN:Water (10:1; 1:1)
Molar Ratio between substrate and catalyst (MR= 16,160,1600)
Oxygen pressures: 3, 10 and 30 bar Reaction temperatures: 23°C, 40°C and 60°C
2
2OTfN
N
CH3
CH3
PdO
OPd
N
H3C
N
H3C
O
O
CH
CH
CH3
CH3
N NCH3 CH3
PdN O O
CH3C
30
Monomer active catalyst
Oxygen solubility
A briefly consideration on the glycerol and DHA solubility (90 mg/mL = 1 M) at room temperature
Solution (H2O:CH3CN
)
DHA Glycerol
100:0 Yes Yes75:25 Yes Yes50:50 Yes Yes25:75 Yes (slow) Incomplete1:10 Yes (slow) Incomplete
• Glycerol uncomplete solubility in CH3CN• Sampling in CH3CN:Water (10:1) is not
representative for glycerol during the reaction
No specific study about mass-transfer was made.Anyway the different solubility of O2 into the two solvents (CH3CN and H2O) was evaluated.
The O2 results from 8 to 9 times more soluble in CH3CN than in Water
The gas volume above the liquid works as a O2 provision storage
Considerations
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Activity results: effect of the MR
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Legend :z: conversionMR : Molar Ratio
The conversion level was valuable only at the end of the reactionThe conversion is comparable between MR = 16 and Mr = 1600An higher amount of catalyst guarantees an higher DHA yield (up to 35-40%)
Activity results: effect of the water
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Legend :z: conversionMR : Molar Ratio
The trend of the conversion level was valuable using only water as solventAn higher amount of catalyst guarantees an higher conversionAn higher amount of catalyst guarantees an higher DHA yieldThe maximum yield is no higher than 18 % (MR 16)
Activity results: effect of the solvent
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Legend :RED line : WaterBLUE line : CH3CN:Water
A comparison between the glycerol conversion into different mixturesPure Water and CH3CN:water (10:1)Conversion is comparableThe maximum yield is higher with CH3CN:Water (10:1)
Considerations (I)Summarizing 60 °C - 30 bar
Using CH3CN:Water (10:1 v/v) as solvent
z is independent from the MRy depends on the MR; higher is MR lower is the DHA yield
Using Water as solvent
z and y depend on the MR
Dy between CH3CN:Water and Water ≈ 20%
Similar results were obtained from the experimental campaign at 40°C and 10 bar
Low conversions and yields were obtained at mild conditions (23-65°C; 3 bar)Politecnico di Torino - DISAT - Dipartimento di Scienza Applicata e Tecnologia
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Experimental Results from batch reactor (IV)
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Regeneration Factor:
Ratio between the moles of glycerol
(at zmax) converted and the moles of
catalyst at t = 0
The mechanism proposed
[13] Aerobic Alcohol Oxydation with Cationic Palladium Complexes: Insights into Catalyst Design and Decomposition; Nicholas R. Conley, Liezel A. Labios, David M. Pearson, Charles C.L. McCrory and M. Waymouth; American Chemical Society 2007
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Dimer results (I)
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2
2OTfN
N
CH3
CH3
PdO
OPd
N
H3C
N
H3C
O
O
CH
CH
CH3
CH3
Monomer Dimer
Conditions Catalystzmax [%]
Monomer Dimer60°C 30 bar; MR=
16CH3CN:Water (10:1)
85,0 91,9
60°C 30 bar; MR= 16
Water
85,2Plateu =170 min
95,91Plateu = 90 min
60°C 30 bar; MR= 160
CH3CN:Water (10:1)
65,9 70,5
Compare Dimer and Monomer
Different behavior Dimer vs. MonomerDependence from the solvent: with CH3CN the yield is higherThe yield with Dimer (MR = 16) is comparable with data from literature.
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Considerations (II)
The results obtained with Dimer z Results obtained were quite similar comparing monomer with dimer in
water as in acetonitrile water mixture 10:1. Y Higher DHA yields were obtained using dimer as catalyst. With the dimer the DHA max. yield reached was around 70% in a mixture acetonitrile water 10:1 which is in accordance with literature results.
Dy between CH3CN:Water and Water ≈ 5 -10% (with monomer was ≈ 20%)
Reaction time was reduced to 2 h at 60°C and 30 bar.Politecnico di Torino - DISAT - Dipartimento di Scienza Applicata e Tecnologia
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2
2OTfN
N
CH3
CH3
PdO
OPd
N
H3C
N
H3C
O
O
CH
CH
CH3
CH3
Summarizing
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Heterogeneous catalysts
Au/C no selectivity to DHA, low conversion
Pt-Bi/GO no selectivity to DHA, conversion comparable with literature
Au-Pt-Bi/C no selectivity to DHA, conversion higher with basic pH
Homogeneous catalysts• Reliable way of synthesis for the monomeric and the dimeric form of the
catalyst with a complete characterization
• The screening on the catalyst activity showed a fundamental role played by
Solvent mixture and Molar ratio to the maximum DHA yield.
Ongoing and future activities
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Homogeneous catalysts
• To develop a kinetic model(s) considering the de-composition of the catalyst
• To support the best catalyst.
• To study the catalyst aging.
• Pt-Bi on GO as Heterogeneous catalysts have found another interesting
catalytic application: the selective oxydation of glucose to D-Saccharic Acid,
used as starting material for the adipic acid synthesis.
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Thank yout for your kind attention …
…and I would like to thank
Dott. Armando Mortillaro (Bracco Imaging)Ph.D. Diego Rozzi (C4T) &My colleagues from DISAT and Chemistry Department of Bracco Imaging