ORGANIC SYNTHESIS OF CAFFEINE 3,7-dihydro-1,3,7- trimethyl-1H- purine-2,6-dione Mark Zakariya, Erica Hoey, Daniel Kim, Jeffrey Chyau 4/6/2009
Mar 29, 2015
ORGANIC SYNTHESIS OF CAFFEINE 3,7-dihydro-1,3,7- trimethyl-1H-purine-2,6-dione
Mark Zakariya, Erica Hoey, Daniel Kim, Jeffrey Chyau4/6/2009
Outline (FIX ME FIX ME FIX ME) Background of Friedrich Ferdinand
Runge Discovery of the Synthesis of Caffeine Applications/Uses of Caffeine Impact of caffeine on Society Physical and Chemical Properties of
Caffeine Synthesis Steps required to synthesize caffeine Bibliography (ALA)
4/6/2009Organic Synthesis of Caffeine
2
Background of Friedrich Ferdinand Runge
German analytical chemist Famously discovered various substances,
including: Caffeine The blue dye aniline A variety of coal tar products Paper chromatography
4/6/2009Organic Synthesis of Caffeine
3
Discovery and Synthesis of Caffeine
Friedrich Ferdinand Runge extracted caffeine from a box of Arabian Mocha beans.
His method was paper chromatography (similar to TLC used in this class).
4/6/2009Organic Synthesis of Caffeine
4
+ =
Arabian Mocha Beans Paper Chromatography Caffeine
Applications/Uses of Caffeine Caffeine is a psychoactive (mind-
affecting) drug that serves as a stimulant.
Caffeine is a mild diuretic. Caffeine is used in headache
medications.
4/6/2009Organic Synthesis of Caffeine
5
Impact of Caffeine on Society Caffeine is the most widely used
psychoactive substance in the world. In Western society, at least 80% of
adults consume enough caffeine to have effects on the brain.
4/6/2009Organic Synthesis of Caffeine
6
Impact of Caffeine on Society (cont.’d)
4/6/2009Organic Synthesis of Caffeine
7
Impact of Caffeine on Society (cont.’d)
4/6/2009Organic Synthesis of Caffeine
8
Impact of Caffeine on Society (cont.’d)
4/6/2009Organic Synthesis of Caffeine
9
Physical and Chemical Properties of Caffeine Synthesis
Caffeine appears as a white, odorless powder
Density: 1.23 g·cm−3
Melting point: 227-228°C Boiling point: 178°C
4/6/2009Organic Synthesis of Caffeine
10
4/6/2009
10
Organic Synthesis of Caffeine
USP-Grade Caffeine
Synthesis of Caffeine
Dimethyl-uric acid treated with trichloride + oxychloride of phosphorus (150°C) Chlorotheophylline
In the process, a hydroxyl group is replaced by one chlorine atom
ChlorotheophyllineDimethyl-uric acid
4/6/2009
11
Organic Synthesis of Caffeine
Synthesis of Caffeine (cont.’d)
Hydriotic acid used to reduce chlorotheophylline into theophylline
Then, methyl iodide and theophylline react to produce caffeine
4/6/2009
12
Organic Synthesis of Caffeine
Extraction of Caffeine
Caffeine is relatively difficult to synthesize.
Caffeine is readily available in a variety of plants, such as the kola nut.
Over 90% of caffeine in beverages and medicines are obtained from “decaffeinated” products such as teas and coffees.
Decaffeination processes: Swiss water process, Direct Method, Indirect Method, Supercritical Fluid Extraction, and the Triglyceride Process.
4/6/2009Organic Synthesis of Caffeine
13
4/6/2009
13
Organic Synthesis of Caffeine
Extraction of Caffeine (cont.’d)
4/6/2009Organic Synthesis of Caffeine
14