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Two Extraction Methods, one bad one better
by DPB (May 1996)
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Bad: 1st try (adapted from the popular faq's)

  1. 1 cup of seeds were ground in a spice mill.
  2. They were magnetically stirred for several days in 1 liter of 3% acetic acid.
  3. I tried to filter the resultant mud. After failing, I tried again. Then a third time.
  4. The mud still sits (cloudy as ever) in a wine carafe. It hasn't cleared yet and it's been sitting absolutely still for a week.

Conclusion: I don't have the equipment to filter this stuff properly. More mess than it's worth.

Better: 2nd try (and much more interesting)

  1. 1/2 cup of seeds were ground in the spice mill.
  2. They were stirred for 8 hours in 500 ml hexane.
  3. This mixture filtered RAPIDLY and completely through Whatman filter paper.
  4. The powder was allowed to dry completely (4 hrs.)
  5. The powder was then stirred for 8 hours in 500 ml methanol.
  6. The resultant mixture was slowly but easily filtered and the liquor set aside.
  7. The powder was put into 250 ml of clean methanol and stirred for 2 hrs, filtered, and the powder discarded.
  8. The transparent and deeply orange-red liquors were combined in a pyrex pie plate and allowed to evaporate to nearly complete dryness (1 day.) Complete dryness was tough because a nasty, sticky brown resin formed.
  9. The pie plate was rinsed out with approx. 500 ml of 3% acetic acid. With some careful scraping, I was able to get almost everything out of the plate and into the erlenmyer flask.
  10. The 500 ml of aqueous mess was then stirred for 1 hour. The reason for this was that a lot of resin remained as undissolved clumps in the water, and I wanted to make sure it yielded up any goodies it may have trapped. The resinous clumps were then easily filtered out.
  11. The lot was then brought gently to the boil to drive off any remaining methanol (OK maybe I was being anal here.)
  12. I added what I visually estimated (groan) to be 50g NaCl, and put the flask in the fridge overnight.
  13. This morning, I gave it one more hour in the freezer, and wound up with a rust colored liquid with some tan precipitate.
  14. Rather that filter it through paper, and risk heat dissolving my success, I carefully siphoned the rusty liquid off the top leaving a wet tan-colored sludge on the bottom of the flask.
  15. I was pressed for time, so I washed out the flask with a little methanol, put the new fluid back in the pie plate, and whipped out the hair dryer.
  16. After about an hour continuous blowing I was left with a surprising amount of almost completely dry rust colored gunge.
  17. I scraped out the gunge to find that it had stratified during drying. The bottom was yellow to white, while the top was rusty brown. Being late for work, I made a mental note to find out more about this later on, and set about grinding the stuff into a homogenous tan powder. I was left with perhaps two to three tablespoons of a yellow-tan powder. When I was done, I rinsed the mortar and pestle with a little water and drank it just to see what the small bit that clung there would do. It made me light headed and numbed my lips and tongue.

I'm not sure how lossy this procedure is, but with esphand at $7 a POUND in NYC, who cares?

I am sure that another vinegar/salt/crystallization pass would purify things even more, but this stuff is pretty potent on it's own. Would more really be necessary?

Conclusion: While it seems labyrinthine, this cobbled together hybrid method worked without any truly exotic equipment, and without producing unfilterable mud. I picked up my magnetic stirrer/hot plate from a local electronics surplus store for cheap, and it's the only piece of real lab equipment I own. Everything else was just flasks and funnels and filter paper.