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

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 ChromatographyCaffeine

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. 80% of adults 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: °C Boiling point: 178°C 4/6/2009Organic Synthesis of Caffeine 10 4/6/ 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 Chlorotheophylline Dimethyl-uric acid 4/6/ 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/ 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/ Organic Synthesis of Caffeine

Extraction of Caffeine (cont.d) 4/6/2009Organic Synthesis of Caffeine 14

PRESENTATION TIPS TAKE A DEEP BREATH BEFORE SAYING ANYTHING. DONT BE NERVOUS. MAKE EYE CONTACT WITH THE CLASS, NOT CHEN. DONT FIDGET WITH YOUR HAIR/HANDS/FACE. Read your script, feel free to paraphrase. DONT STARE AT THE PAPER OR POWERPOINT!!! Read slowly, be calm. No one wants to kill you. I But if we lose points because you screwed up, I will want to kill you. 4/6/2009Organic Synthesis of Caffeine 15