Using the Abraham Model to Predict
Organic Solubility to Determine a
Recrystallization Solvent
College of Arts and Science...
Open Notebook Science
Releases experiments and results
online in real time
Promotes the sharing and availability of
resear...
Online Notebook
(http://onschallenge.wikispaces.com/EXP321)
Solubility
Amount of a solute (organic solid) that
can dissolve into a solvent (organic
liquid)
Important when choosing a
...
Predicting Solubility with
Abraham Descriptors
Five descriptors for each solute and each solvent
The descriptors for over ...
Solubility Predictions
Using ONS Webservices, can list the predicted
solubility for a compound
Trans-dibenzalacetone
(http...
Solubility Curves
Using a melting point, temperature dependent
solubility curves are generated
Assumes that at the melting...
Temperature Controlled Shake
Flask Method
Add solute to the vials with the solvent and allow to
shake in the 25°C water ba...
Temperature Controlled Shake
Flask Method
Measure the solubility using HNMR
Need to take two consecutive measurements with...
Measuring Solubility with NMR
Compare integration of solute and solvent peaks in
saturated solutions using google app scri...
Benefits of Solubility
Curves
These temperature dependent solubility
curves allow a solvent with the greatest
difference b...
Example
The solvents used to recrystallize compounds in
organic teaching labs can be improved
Trans-dibenzalacetone
Aldol ...
Dibenzalacetone
First recrystallized in ethyl acetate in 1906
Recrystallized in ethyl acetate in Organic Syntheses
(Straus...
Organic Teaching Labs
Many recrystallize in ethyl acetate
Is there a different solvent that could be used?
(http://classes...
SmartPhone App
This app predicts the recrystallization yields of any
compound in different solvents using the solubility
c...
SmartPhone App
Enter compound identification (SMILES, CSID,
name…etc), and desired parameters
(http://onschallenge.wikispa...
SmartPhone App
Lists solvents and their predicted recrystallization
yield
Prediction is generated by the temperature
(http...
Comparison
Ethyl acetate (predicted yield of 69%) vs ethanol
(predicted yield of 91%)
Ethyl acetate
Ethanol
0.09M
1.1M
0.6...
High Boiling Point Solvent
Recrystallize caffeine from 1-octanol (boiling point:
194°C) and wash with pentane (boiling poi...
Recrystallization with 1-octanol
With a 0.25M solution, predicted recrystallization
yield is 92%
(http://onschallenge.wiki...
Further Information
http://onschallenge.wikispaces.com/
http://usefulchem.wikispaces.com/
http://onswebservices.wikispaces...
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Drexel College of Arts and Sciences (COAS) Research Day 2013

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A presentation of my research involving using organic solubility predictions to optimize the process of choosing a recrystallization solvent. This research was conducted using Open Notebook Science to promote the sharing and access of the results and findings. This presentation was given as a 10 minute oral presentation for the 2013 COAS research day at Drexel University on April 9, 2013.

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  • http://onschallenge.wikispaces.com/EXP321
  • What makes a solvent optimal: bp, freezing point, etc. Sol at bp (if too low, impractical).
  • http://onschallenge.wikispaces.com/Benzoic+acid+-+AbrahamMake slide clearer
  • http://lxsrv7.oru.edu/~alang/solubility/soltemp.php?csids=555548&cs=0.092&solvent=ethanol&solmp=-114.1&solbp=78.2&limreact=0.3&limprod=0.03http://onschallenge.wikispaces.com/AbrahamDescriptorsModel003Don’t use an ethanol/water mixture, use another solvent Assumption of model: At melting point, solute is micible with solvent
  • Mention NMR method
  • Link to recrystallization page and webservices
  • http://lxsrv7.oru.edu/~alang/solubility/soltemp.php?csids=555548&cs=.624&solvent=ethyl%20acetate&solmp=-83.6&solbp=73.9&limreact=0.3&limprod=0.03State from bp to rtWrite sol at 25C and sol at bp
  • Drexel College of Arts and Sciences (COAS) Research Day 2013

    1. 1. Using the Abraham Model to Predict Organic Solubility to Determine a Recrystallization Solvent College of Arts and Sciences Research Day Drexel University Matthew McBride Undergraduate Chemistry Major Bradley Research Group April 9, 2013
    2. 2. Open Notebook Science Releases experiments and results online in real time Promotes the sharing and availability of research Provides all the details associated with an experiment Allows for “failed experiments” to be available
    3. 3. Online Notebook (http://onschallenge.wikispaces.com/EXP321)
    4. 4. Solubility Amount of a solute (organic solid) that can dissolve into a solvent (organic liquid) Important when choosing a recrystallization solvent to obtain maximum yield Accurate solubility predictions for a compound allows for the optimal solvent to be used
    5. 5. Predicting Solubility with Abraham Descriptors Five descriptors for each solute and each solvent The descriptors for over 80 solvents, including some ethanol/water mixtures, are known [William Acree](http://onschallenge.wikispaces.com/Benzoic+acid+-+Abraham) Caffeine Descriptors
    6. 6. Solubility Predictions Using ONS Webservices, can list the predicted solubility for a compound Trans-dibenzalacetone (http://showme.physics.drexel.edu/onsc/models/solventselector.php?csids=555548) Solvent Model003 (M) AD Measured (M) Experimental (M) BP (°C) (www.chemspider.com/55 5548) [Andrew Lang]
    7. 7. Solubility Curves Using a melting point, temperature dependent solubility curves are generated Assumes that at the melting point the compound is miscible with the solvent Solubility in Ethanol (Concentration M vs. Temperature °C) (http://showme.physics.drexel.edu/onsc/models/solventselector.php?csids=555548)[Andrew Lang]
    8. 8. Temperature Controlled Shake Flask Method Add solute to the vials with the solvent and allow to shake in the 25°C water bath (http://onschallenge.wikispaces.com/e xp324)
    9. 9. Temperature Controlled Shake Flask Method Measure the solubility using HNMR Need to take two consecutive measurements without the solubility changing to confirm the solution is saturated (http://onschallenge.wikispaces.com/EXP311)
    10. 10. Measuring Solubility with NMR Compare integration of solute and solvent peaks in saturated solutions using google app scripts 1.5M Saturated solution of dibenzalacetone in THF Dibenzalacetone THF (http://onschallenge.wikispaces.com/EXP308) [Andrew Lang]
    11. 11. Benefits of Solubility Curves These temperature dependent solubility curves allow a solvent with the greatest difference between solubility at room temperature and at the boiling point to be used Reduces reliance on only recrystallizing in solvents listed in literature Optimizes the process of choosing a recrystallization solvent
    12. 12. Example The solvents used to recrystallize compounds in organic teaching labs can be improved Trans-dibenzalacetone Aldol condensation between two molecules of benzaldehyde and one molecule of acetone (http://showme.physics.drexel.edu/onsc/reactionattempts/advancedsearch.php?compound=&solvent=&reactiontype =&researcher=Matthew+McBride) [Andrew Lang]
    13. 13. Dibenzalacetone First recrystallized in ethyl acetate in 1906 Recrystallized in ethyl acetate in Organic Syntheses (Straus and Ecker, Ber. 39, 2988 (1906))
    14. 14. Organic Teaching Labs Many recrystallize in ethyl acetate Is there a different solvent that could be used? (http://classes.kvcc.edu/chm230/MIXED%20ALDOL%20CONDENSATION.pdf) (http://www.xula.edu/chemistry/documents/orgleclab/Aldol_notes.pdf)
    15. 15. SmartPhone App This app predicts the recrystallization yields of any compound in different solvents using the solubility curves: Provides experimental and predicted values for melting point and LogP [Andrew Lang] (http://onschallenge.wikispaces.com/recrystallization)
    16. 16. SmartPhone App Enter compound identification (SMILES, CSID, name…etc), and desired parameters (http://onschallenge.wikispaces.com/rec ation) [Andrew Lang]
    17. 17. SmartPhone App Lists solvents and their predicted recrystallization yield Prediction is generated by the temperature (http://onschallenge.wikispaces.com/recrystalliz ation) [Andrew Lang]
    18. 18. Comparison Ethyl acetate (predicted yield of 69%) vs ethanol (predicted yield of 91%) Ethyl acetate Ethanol 0.09M 1.1M 0.62M 2.06M (http://showme.physics.drexel.edu/onsc/m odels/solventselector.php?csids=555548) [Andrew Lang]
    19. 19. High Boiling Point Solvent Recrystallize caffeine from 1-octanol (boiling point: 194°C) and wash with pentane (boiling point: 36°C) Temperature curve for caffeine in 1-octanol (M vs. °C) (http://showme.physics.drexel.edu/onsc/models/solventselector.php?csids=2424)
    20. 20. Recrystallization with 1-octanol With a 0.25M solution, predicted recrystallization yield is 92% (http://onschallenge.wikispaces.com/EXP343)
    21. 21. Further Information http://onschallenge.wikispaces.com/ http://usefulchem.wikispaces.com/ http://onswebservices.wikispaces.com/

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