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MY WORK
HOW SIMPLE ORGANIC CHEMISTRY
SUPPORTED BY CHEMICAL ANALYSIS
RESULTED IN GREAT IDEAS
2002 – 2010
Flor Cabrera, MS.
1
SHORT RESUME – FLOR CABRERA
 STUDIES
 MS Chemistry, U of Houston, 08/2010.
 Professional Chemist, UNMSM, 2005.
 ISO 9001:2000, PUCP, 2003.
 BS in Chemistry, UNMSM, 2000
 WORK EXPERIENCE
 Research/Teaching Assistant, UH,
TX,2007-2010.
 Researcher, ICMBU, France, 2009.
 R&D Chemist, INNOVA ANDINA,
Peru, 2004-2007.
 Laboratory Assistant, REQUISA,
Peru, 2005.
 Student Internship, U Leipzig,
Germany, 2002.
 Student Fellow, Food Processing Pilot
Plant, UNMSM, Peru, 2000.
 LEADERSHIP
 Self-starter in industry, lead meetings
under ISO, team-working,
independent, coaching others.
 SKILLS
 Organic and Organometallic synthesis
 Reactions:
Reductive cyclization of nitro-
compounds, carboxymethylation,
emulsion polymerization, condensation
of arylamines, McDonald condensation,
and coupling reactions.
 Schlenck techniques
 Scale-up
 GC/MS, MALDI-TOF MS, ESI/MS,
LC/MS/MS.
 GC, CE, HPLC, CC, TLC.
 NMR, 1H-NMR, 13C-NMR, 2D-NMR
(COSY, HMQC), UV-Vis, FTIR,
Spectroelectrochemistry.
 Electrochemistry, pH, viscosimetry.
 LANGUAGES
 English/Spanish fluent.
 German/French basic speaking. 2
PORTFOLIO
1. “A molecule from Peruvian corns”
Internship, U Leipzig, Germany, 2002.
2. “Modifying a natural polymer to preserve fruits”
Professional Chemist, Thesis, Peru, 2005.
3. “Formulating products for paper and other industries”
Laboratory Assistant, Requisa SAC, Peru, 2005.
4. “A powerful tool to solve synthetic problems”
R&D Chemist, Innova Andina SA, Peru, 2007.
5. “Synthesis of a porphyrin”
Internship, U Bourgogne, France, 2009.
6. “Organic molecules can modify metal reactivity.”
MS Chemistry, Thesis, UH, Texas, USA, 2010.
3
1. “A MOLECULE FROM PERUVIAN
CORNS”
 Peru is the source of more than 100 species of
corns in the world.
 Why these corns are very resistant to low
temperatures? Benzoxacines, an active specie,
are under study including genetics studies to
improve european crops.
 I worked in the synthesis of a benzoxacine
precursor, a N-heterocyclic compound, by
reductive cyclization of aromatic nitro compounds
in a multistep synthesis.
Internship, U Leipzig, Germany, 2002.
4
Benzoxacine
precursor
5
www.uni-leipzig.de
2.“MODIFYING A NATURAL POLYMER TO
PRESERVE FRUITS IN STORAGE”
 Chitin appears in all exoskeleton of insects and
other marine animals.
 Chitosan is acid soluble derived from Chitin.
 This natural polymer, Chitosan, was chemically
modified to achieve water solubility. Its
preservative properties were tested in strawberries
and other fruits.
 Modifying physicochemical parameters of starting
material to get the desirable compound.
 Analytical techniques: FTIR, UV-VIS, viscosimetry,
pH titrations, 1H-NMR.
Professional Chemist, Thesis, Peru, 2005.
6
n
O
NH2
OH
O
OH
n
O
NH
OH
O
O CH2
O
O
-
CH2
O
O
-
ClCH2CO2Na
Na
+
OH
-
QUITOSANO NOCQ
ClH
36 hrs,
25 °C,
85 %HR
+0%
+1.5%
+1%
Chitin,
insoluble
Chitosan,
soluble in acids
Modified Chitosan,
water soluble.
Preservation properties - aqueous solns. of modified Chitosan:
40
60
80
100
120
0 2 4 6
Tiempo (hrs)
a 25°C
Contenidode
AcidoCítrico
(mg/10gfresa)
N O C Q 1%
Q uito s a no 1.5%
C o ntro l
595
557
462
419
232
211
R2
=0.96
50%
60%
70%
80%
90%
100%
Peso Molecular (MW)
GradodeDeacetilación
(%DD)
0 2 4 6 8 10 12 14
Tiempo de Reacción (hrs)
Insolubilidad Solubilidad Quitosano de Langostinos ChL Quitosano Estándar ChF
PesoMolecular
(MW)
0
20
40
60
80
100
0.0 0.4 0.8 1.2 1.6 2.0 2.4
g de CH2ClCOOH/ g Quitosano ChL
Rendimiento (%)
Solubilidad(%)
NaOH
7UNMSM
unmsm.edu.pe
3. “FORMULATING PRODUCTS FOR PAPER
AND OTHER INDUSTRIES”
 Emulsion polymerization of methyl acrylic, vinyl
acetate, styrene monomers. PVOH, surfactants
aids and others.
 Modification of existing recipe (formulation) to
reduce costs and improve quality.
 Evaluation by physicochemical methods.
 Achievements: four (4) formulated products
introduced into the market. Leading edition of
ISO manual and passed audit.
Laboratory Assistant, Requisa SAC, Peru, 2005.
8
Water
Emulsifier
Initiator
catalyst
Monomer Chemistry: RATF radical chain polymerization mechanism
Emulsion polymerization:
Other products:
-Plastisols, and
-Surfactant based emulsion
product (softener) for
fabrics.
-Tar-based product for nets
of fishing industry.
Products with different applications:
9www.requisa.com.pe
4. “A POWERFUL TOOL IN SYNTHETIC
PROBLEMS”
 Planning and monitoring synthesis using patents
at laboratory scale. Scale-up procedures (amines
and inorganic sulfates). Technical support:
Statistics and reporting. Supervision of a
technician.
 Achievements: Discordant analytical reports
solved by GC implemented method. Increased
yield to 75% of synthetic hydroxyquinoline.
 Implementation of analytical methods. Example:
residual monomer in acrylamide, surfactants, oils
in natural products.
R&D Chemist, Innova Andina SA, Peru, 2007.
10
EXAMPLE OF WORK DONE:
-Check purity of raw
materials b.p., FTIR, density.
-Evaluation of by-products
theoretically and by GC/MS.
-Discordant results in UV-VIS
and titration methods were
solved. GC method was
implemented.
-3 different patents were
tested.
-Continuous reaction-
distillation method, and batch
method were evaluated.
-Yield was increased in 75%.
GC Rxn Mixture analysis
11
Laboratory scale
Pilot scale
www. innova.com.pe
5. “SYNTHESIS OF A METAL
PORPHYRIN”
 Porphyrins occurs widely in nature.
 Synthetic porphyrins have wide applications in
food, pharmaceuticals, etc. Porphyrins can stick
in cancer cells make them interesting for
targeting therapies.
 I synthesized a zinc-porphyrin dihalide in
multisptep synhtesis.
 Additionally, I implemented new microwave
methods to prepare dipyrromethane and for the
cyanation of carbazole, which are good
alternatives methods for routine synthesis used
in this lab.
Researcher, Institute of Molecular Chemistry, ICMBU, France, 2009.
12
3
5
4
MALDI/TOF MS, 5
UV-VisSynthesis:
1H-NMR, 5
Spectroelectrochem, 4
13
6. “A MOLECULE CAN MODIFY METAL
REACTIVITY: CANCER DRUGS?”
 Metal complexes are used as drugs, catalysts, additives
and other applications.
 Ru is currently studied as good alternative to Pt cancer
drugs, and Ru 3+ are promising source of anti-cancer
activity.
 I prepared new pyrazine-pyridine ligands in two steps
organic synthesis, improved conditions 100% more
efficient than reported similar ones in the literature.
Their diruthenium complexes resulted in 6+ oxidation
state, and many analytical techniques where used for
chemical characterization.
MS Chemistry, Thesis, UH, Texas, USA, 2010.
14
Ru2
6+
*Allardyce, C.; Dyson, P. J. Platinum Metals Rev., 2001, 45 (2), 62.
[Ru2(apb)(OAc)3]2+
HH-COSY NMR of appb
New amine ligands synthesis:
GC/MS, EI spectrum of apb
New complexes with two Ru(III) units:
Question: Could these
complexes have good
anticancer reactivity* as
many other recently
synthesized anti-cancer Ru3+
drugs?:
MALDI-TOF MS FTIRElectrochemistry
Complexation
The pyrazine
ligands
induced
formation of
Ru(III) units
in the
complex.
6+/5+
C=O
15www.uh.edu
 Thanks.
Flor Cabrera, MS.
florcabreraa@yahoo.com
Phone: 713-518-3318.
16

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Organic Chemistry Ideas from Simple Synthesis

  • 1. MY WORK HOW SIMPLE ORGANIC CHEMISTRY SUPPORTED BY CHEMICAL ANALYSIS RESULTED IN GREAT IDEAS 2002 – 2010 Flor Cabrera, MS. 1
  • 2. SHORT RESUME – FLOR CABRERA  STUDIES  MS Chemistry, U of Houston, 08/2010.  Professional Chemist, UNMSM, 2005.  ISO 9001:2000, PUCP, 2003.  BS in Chemistry, UNMSM, 2000  WORK EXPERIENCE  Research/Teaching Assistant, UH, TX,2007-2010.  Researcher, ICMBU, France, 2009.  R&D Chemist, INNOVA ANDINA, Peru, 2004-2007.  Laboratory Assistant, REQUISA, Peru, 2005.  Student Internship, U Leipzig, Germany, 2002.  Student Fellow, Food Processing Pilot Plant, UNMSM, Peru, 2000.  LEADERSHIP  Self-starter in industry, lead meetings under ISO, team-working, independent, coaching others.  SKILLS  Organic and Organometallic synthesis  Reactions: Reductive cyclization of nitro- compounds, carboxymethylation, emulsion polymerization, condensation of arylamines, McDonald condensation, and coupling reactions.  Schlenck techniques  Scale-up  GC/MS, MALDI-TOF MS, ESI/MS, LC/MS/MS.  GC, CE, HPLC, CC, TLC.  NMR, 1H-NMR, 13C-NMR, 2D-NMR (COSY, HMQC), UV-Vis, FTIR, Spectroelectrochemistry.  Electrochemistry, pH, viscosimetry.  LANGUAGES  English/Spanish fluent.  German/French basic speaking. 2
  • 3. PORTFOLIO 1. “A molecule from Peruvian corns” Internship, U Leipzig, Germany, 2002. 2. “Modifying a natural polymer to preserve fruits” Professional Chemist, Thesis, Peru, 2005. 3. “Formulating products for paper and other industries” Laboratory Assistant, Requisa SAC, Peru, 2005. 4. “A powerful tool to solve synthetic problems” R&D Chemist, Innova Andina SA, Peru, 2007. 5. “Synthesis of a porphyrin” Internship, U Bourgogne, France, 2009. 6. “Organic molecules can modify metal reactivity.” MS Chemistry, Thesis, UH, Texas, USA, 2010. 3
  • 4. 1. “A MOLECULE FROM PERUVIAN CORNS”  Peru is the source of more than 100 species of corns in the world.  Why these corns are very resistant to low temperatures? Benzoxacines, an active specie, are under study including genetics studies to improve european crops.  I worked in the synthesis of a benzoxacine precursor, a N-heterocyclic compound, by reductive cyclization of aromatic nitro compounds in a multistep synthesis. Internship, U Leipzig, Germany, 2002. 4
  • 6. 2.“MODIFYING A NATURAL POLYMER TO PRESERVE FRUITS IN STORAGE”  Chitin appears in all exoskeleton of insects and other marine animals.  Chitosan is acid soluble derived from Chitin.  This natural polymer, Chitosan, was chemically modified to achieve water solubility. Its preservative properties were tested in strawberries and other fruits.  Modifying physicochemical parameters of starting material to get the desirable compound.  Analytical techniques: FTIR, UV-VIS, viscosimetry, pH titrations, 1H-NMR. Professional Chemist, Thesis, Peru, 2005. 6
  • 7. n O NH2 OH O OH n O NH OH O O CH2 O O - CH2 O O - ClCH2CO2Na Na + OH - QUITOSANO NOCQ ClH 36 hrs, 25 °C, 85 %HR +0% +1.5% +1% Chitin, insoluble Chitosan, soluble in acids Modified Chitosan, water soluble. Preservation properties - aqueous solns. of modified Chitosan: 40 60 80 100 120 0 2 4 6 Tiempo (hrs) a 25°C Contenidode AcidoCítrico (mg/10gfresa) N O C Q 1% Q uito s a no 1.5% C o ntro l 595 557 462 419 232 211 R2 =0.96 50% 60% 70% 80% 90% 100% Peso Molecular (MW) GradodeDeacetilación (%DD) 0 2 4 6 8 10 12 14 Tiempo de Reacción (hrs) Insolubilidad Solubilidad Quitosano de Langostinos ChL Quitosano Estándar ChF PesoMolecular (MW) 0 20 40 60 80 100 0.0 0.4 0.8 1.2 1.6 2.0 2.4 g de CH2ClCOOH/ g Quitosano ChL Rendimiento (%) Solubilidad(%) NaOH 7UNMSM unmsm.edu.pe
  • 8. 3. “FORMULATING PRODUCTS FOR PAPER AND OTHER INDUSTRIES”  Emulsion polymerization of methyl acrylic, vinyl acetate, styrene monomers. PVOH, surfactants aids and others.  Modification of existing recipe (formulation) to reduce costs and improve quality.  Evaluation by physicochemical methods.  Achievements: four (4) formulated products introduced into the market. Leading edition of ISO manual and passed audit. Laboratory Assistant, Requisa SAC, Peru, 2005. 8
  • 9. Water Emulsifier Initiator catalyst Monomer Chemistry: RATF radical chain polymerization mechanism Emulsion polymerization: Other products: -Plastisols, and -Surfactant based emulsion product (softener) for fabrics. -Tar-based product for nets of fishing industry. Products with different applications: 9www.requisa.com.pe
  • 10. 4. “A POWERFUL TOOL IN SYNTHETIC PROBLEMS”  Planning and monitoring synthesis using patents at laboratory scale. Scale-up procedures (amines and inorganic sulfates). Technical support: Statistics and reporting. Supervision of a technician.  Achievements: Discordant analytical reports solved by GC implemented method. Increased yield to 75% of synthetic hydroxyquinoline.  Implementation of analytical methods. Example: residual monomer in acrylamide, surfactants, oils in natural products. R&D Chemist, Innova Andina SA, Peru, 2007. 10
  • 11. EXAMPLE OF WORK DONE: -Check purity of raw materials b.p., FTIR, density. -Evaluation of by-products theoretically and by GC/MS. -Discordant results in UV-VIS and titration methods were solved. GC method was implemented. -3 different patents were tested. -Continuous reaction- distillation method, and batch method were evaluated. -Yield was increased in 75%. GC Rxn Mixture analysis 11 Laboratory scale Pilot scale www. innova.com.pe
  • 12. 5. “SYNTHESIS OF A METAL PORPHYRIN”  Porphyrins occurs widely in nature.  Synthetic porphyrins have wide applications in food, pharmaceuticals, etc. Porphyrins can stick in cancer cells make them interesting for targeting therapies.  I synthesized a zinc-porphyrin dihalide in multisptep synhtesis.  Additionally, I implemented new microwave methods to prepare dipyrromethane and for the cyanation of carbazole, which are good alternatives methods for routine synthesis used in this lab. Researcher, Institute of Molecular Chemistry, ICMBU, France, 2009. 12
  • 14. 6. “A MOLECULE CAN MODIFY METAL REACTIVITY: CANCER DRUGS?”  Metal complexes are used as drugs, catalysts, additives and other applications.  Ru is currently studied as good alternative to Pt cancer drugs, and Ru 3+ are promising source of anti-cancer activity.  I prepared new pyrazine-pyridine ligands in two steps organic synthesis, improved conditions 100% more efficient than reported similar ones in the literature. Their diruthenium complexes resulted in 6+ oxidation state, and many analytical techniques where used for chemical characterization. MS Chemistry, Thesis, UH, Texas, USA, 2010. 14
  • 15. Ru2 6+ *Allardyce, C.; Dyson, P. J. Platinum Metals Rev., 2001, 45 (2), 62. [Ru2(apb)(OAc)3]2+ HH-COSY NMR of appb New amine ligands synthesis: GC/MS, EI spectrum of apb New complexes with two Ru(III) units: Question: Could these complexes have good anticancer reactivity* as many other recently synthesized anti-cancer Ru3+ drugs?: MALDI-TOF MS FTIRElectrochemistry Complexation The pyrazine ligands induced formation of Ru(III) units in the complex. 6+/5+ C=O 15www.uh.edu
  • 16.  Thanks. Flor Cabrera, MS. florcabreraa@yahoo.com Phone: 713-518-3318. 16