1. EXTRACTING ORGANIC CAFFEINE IN A SMALL ROOM Martin the Morph-Man

2. Overview Caffeine may be isolated from coffee, tea and other aqueous solutions by a simple acid-base extraction procedure

3. Disclaimer It is legal to extract compounds (e.g. caffeine) from a wide range of natural sources It is NOT legal to extract compounds from some other sources, nor to possess those compounds obtained by any means This talk is for your general interest only You are urged NOT to apply the following procedures to any natural products You are encouraged to be aware of the legal implications of any extraction procedures performed without legal sanction

4. Safety ToxicFlammableCorrosiveEnvironment DichloromethaneEthersHydrochloric acid DCM MethanolAcetoneSodium hydroxide Chloroform BenzeneMethanolCarbon tetrachloride EthanolBenzene Toluene

5. Theory : Caffeine and Alkaloid Chemistry Alkaloids are heterocyclic organic compounds - ring containing carbon and nitrogen May contain (non-ring) oxygen N and O confer acid/base properties Acid/base properties influence solubility in various solvents

6. Theory: Acid-Base Extractions Generally: N-atoms are charged positive in acid conditions and are neutral in basic (alkaline) conditions O-atoms are neutral in acid conditions and are charged negative in basic conditions Charged compounds are more soluble in polar solvents such as water & methanol Neutral compounds are more soluble in non-polar solvents such as ether and toluene

7. Target compound NAME :Caffeine CHEMICAL NAME :3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione ALTERNATE CHEMICAL NAMES :1,3,7-trimethylxanthine; 1,3,7-trimethyl-2,6-dioxopurine; coffeine ALTERNATE NAMES :thein; guaranine; methyltheobromine; No-Doz CHEMICAL FORMULA:C 8 H 10 N 4 O 2 MOLECULAR WEIGHT:194.19 APPEARANCE:White hexagonal or needle-like crystals MELTING POINT:238ºC SOLUBILITY:Water, Ethanol, Methanol, Acetone, Chloroform LD50 Dog:140mg/kg oral LD50 Rat:105mg/kg IV LD Low (Lethal Dose):Human deaths reported at less than 4 grams oral.

8. Technique 1) Cook up 2) Clarify 3) Remove fatty impurities 4) Make solution alkaline 5) Extract alkaloids to organic solvent 6) Separate organic from aqueous phase 7) Repeat extraction to solvent (steps 5&6) 8) Dry organic solvent 9) Evaporate organic solvent 10) Purify compound by recrystallisation, often from another organic solvent

9. Equipment Coffee/spice mill Pyrex or stainless steel pans Strainers, filter papers & funnels Separating funnel Drying dish & dryer Measuring cylinders, pipettes etc

10. Reagents Acid: Hydrochloric, citric, acetic Alkali: Sodium hydroxide, ammonium hydroxide Solvents: Dichloromethane, methanol, diethyl ether, petroleum ether (Vietti™ lighter fluid)

11. Precautions Ventilation – toxic volatiles No flame – flammable volatiles Protective clothing – toxic or corrosive liquids Be discreet – solvent smells attract attention - “loose lips sink ships”

12. Step 1: Cook-up

13. Step 2: Filtration

14. Step 3: Defatting

15. Step 4: Raise pH

16. Step 5: Organic solvent extraction

17. Step 6: Separation of phases

18. Step 7: Rinse organic phase

19. Step 8: Dry organic phase

20. Step 9: Evaporation & crystallisation

21. Mission successful!

22. Extraction of anything in a small room Be careful Be discreet Be safe Happy extractions and happy travelling!