1) development of green chemistry labs 2) development of new organic chemistry hydrogenation labs 3)...

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1) DEVELOPMENT OF GREEN CHEMISTRY LABS 2) DEVELOPMENT OF NEW ORGANIC CHEMISTRY HYDROGENATION LABS 3) DEVELOPMENT OF ORGANIC CHEMISTRY LABS USING TECHNOLOGY TO MONITOR THE REACTION Focus of Dr. O’Connor’s Research

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Page 1: 1) DEVELOPMENT OF GREEN CHEMISTRY LABS 2) DEVELOPMENT OF NEW ORGANIC CHEMISTRY HYDROGENATION LABS 3) DEVELOPMENT OF ORGANIC CHEMISTRY LABS USING TECHNOLOGY

1) D E V E L O P M E N T O F G R E E N C H E M I S T RY L A B S

2) D E V E L O P M E N T O F N E W O R G A N I C C H E M I S T RY H Y D R O G E N AT I O N L A B S

3) D E V E L O P M E N T O F O R G A N I C C H E M I S T RY L A B S U S I N G T E C H N O L O G Y T O M O N I T O R T H E R E A C T I O N

Focus of Dr. O’Connor’s Research

Page 2: 1) DEVELOPMENT OF GREEN CHEMISTRY LABS 2) DEVELOPMENT OF NEW ORGANIC CHEMISTRY HYDROGENATION LABS 3) DEVELOPMENT OF ORGANIC CHEMISTRY LABS USING TECHNOLOGY

Hydrogenation of Methyl Trans-Cinnamate

Good reaction conditions Less than 1 hour reaction time. 1.0 atm.

Ph

CO2CH3 H25% Pd/C

RT, EtOH 1.0 atm

Ph

CO2CH3

Methyl Trans-Cinnamate Methyl-3-phenylpropionate

Page 3: 1) DEVELOPMENT OF GREEN CHEMISTRY LABS 2) DEVELOPMENT OF NEW ORGANIC CHEMISTRY HYDROGENATION LABS 3) DEVELOPMENT OF ORGANIC CHEMISTRY LABS USING TECHNOLOGY

oCHOOSE TO USE ENVIRONMENTALLY FRIENDLY CHEMICALS.oUSE CATALYSTS WHEN POSSIBLE.oPREVENT WASTE BY USING A SOLVENTLESS PROCESS.oMINIMIZE AMOUNTS OF SOLVENTS AND REAGENTS USED.

Some Principles of Green Chemistry

Page 4: 1) DEVELOPMENT OF GREEN CHEMISTRY LABS 2) DEVELOPMENT OF NEW ORGANIC CHEMISTRY HYDROGENATION LABS 3) DEVELOPMENT OF ORGANIC CHEMISTRY LABS USING TECHNOLOGY

General Reaction for the THP Protection of Alcohols.

O

+ ROH

O OR

Catalyst

This can be done with and without solvent. The goal is to run the reaction solventless.THP is a protecting group in organic chemistry.

Page 5: 1) DEVELOPMENT OF GREEN CHEMISTRY LABS 2) DEVELOPMENT OF NEW ORGANIC CHEMISTRY HYDROGENATION LABS 3) DEVELOPMENT OF ORGANIC CHEMISTRY LABS USING TECHNOLOGY

O

+ PhCH2OH

O O

AlCl3 6H2O

Ph35o C, 45 Min

Avg Yield = 80%

These are Examples of Solventless

Tetrahydropyranylation Reactions

O

+ PhCH2OH

O O

Sulfamic Acid

Ph

90 Min

Avg Yield = 88%

(H2NSO3H)

The identification of other solventless reactions is presently under investigation.

TetrahydropyranBenzyl alcohol