Health & Safety Evaluation Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Benzaldehyde B1334 5.1 mL Allyl bromide 337528 5.2 mL *F * Zinc powder 243469 3.9 g *R * Ammonium chloride solution, saturated 213330 50 mL Tetrahydrofuran 401757 25 mL Diethyl ether 346136 50 mL *F Sodium sulfate, anhydrous 239313 50 g
Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Magnesium 254118 2.5 g *R Bromobenzene B57702 16.5 g Diethyl ether 346136 135 mL *F Dry ice (carbon dioxide) 50 g Hydrochloric acid, 3M 320331 100 mL Sodium hydroxide, 3M 221465 60 mL Water n/a 60 mL Comparative Analysis of Traditional vs. Suggested Experiments Greener methods reduce the use of diethyl ether Greener methods do not require anhydrous conditions and therefore decreases the amount of unnecessary waste resulting from experiments contaminated with moisture
the designated section of the laboratory away from the flammable solvents, check the ease of lighting each lamp, quality of flame, and time required for the flame to extinguish itself. Fill one Pasteur pipette with vegetable oil and another with biodiesel, and allow them to drain without the bulb simultaneously. Record the time it takes each pipette to empty. Health and Safety Health & Safety Evaluation Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Vegetable Oil n/a 1000 mL 1-propanol 402893 400 mL Sulfuric acid, conc. 258105 7.5 mL Sodium chloride, 1M sol 746398 2250 mL Magnesium sulfate, anhydrous 793612 100g
Glacial acetic acid 695092 150 mL Sodium bicarbonate (5%) S6014 300 mL Sulfuric acid, conc 258105 5 mL Sodium sulfate, anhyd. 258105 25 g Comparative Analysis of Traditional vs. Suggested Experiments Greener method introduces the concepts of bio-based resources and renewable raw materials Greener method produces the product, which can be used in diesel engines, along with aqueous waste Traditional esterification reaction uses various alcohols all have moderate EH&S profiles The comparative costs for all reagents per 100 students for this experiment is $41 for the Greener method and $21 for the Traditional method. Actual cost will vary. Reduction (per 100 students) “Greener” Benefits Greener method 1400 mL biodiesel product 2.3 mL aq. waste 100 g solid waste Traditional method 525 mL aq. 25 g waste Additional Resources & Further Reading The following are additional greener alternative laboratory experiment options:
Reference Dehydration of cyclohexanol to cyclohexene with phosphoric acid, Macroscale and Microscale Organic Experiments, 6e; Brooks/Cole, 2011; p. 335-357. Health & Safety Evaluation Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Cyclohexanol 105899 100 mL Phosphoric acid, conc. W290017 25 mL Toluene 179418 150 mL Sodium chloride 793566 42 g Calcium chloride C1016 25 g Ethanol E7023 250 mL Acetone 34850 250 mL
Reference The Oxidation of a Ketone to a Carboxylic Acid: Cyclohexanone from Cyclohexanol, Macroscale and Microscale Organic Experiments, Williamson, K.L., Masters, K.M., 6th Edition, Brooks/Cole Cengage Learning, 2011, pp. 358-359. Health & Safety Evaluation Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Sodium dichromate dihydrate 398063 375 g * Acetic acid, 1M 965092 1000 mL Cyclohexanol 105899 375 g Water n/a 2500 mL Sodium chloride 746398 400 g Anhydrous diethyl ether 346136 750 mL * Sodium hydroxide, 3M 221465 500 mL Sodium chloride, sat. solution 750 mL
One of the following aldehydes are used (the amounts listed are the total amounts for each aldehyde needed if only that aldehyde was selected): p-anisaldehyde A88107 34 g p-tolualdehyde T35602 30 g 4-chlorobenzaldehyde 112216 35 g 3-chlorobenzaldehyde C23403 35 g Benzaldehyde 26.5 g One of the following acetophenones are used (the amounts listed are the total amounts for each acetophenone needed if only that acetophenone was selected): Acetophenone A10701 29 mL 4’-methylacetophenone M26615 37.5 g 4’-bromoacetophenone B56404 50 g 4’-methoxyacetophenone 117374 33.5 g Continued from Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Sodium hydroxide 221465 10 g *C Water n/a
Ethanol, 95% 459836 500 mL Toluene 244511 250 mL Traditional Aldol Condensation Reaction The Aldol Condensation is an important carbon-carbon bond forming reaction. In this classic reaction, an ,-unsaturated carbonyl compound is formed by a crossed-aldol condensation. Reference Preparation of trans-p-Anisalacetophenone, Experimental Organic chemistry, 2011, 5th Edition, Gilbert and Martin, p. 620. Health & Safety Evaluation Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S p-anisaldehyde A88107 10 mL Acetophenone A10701 10 mL Sodium hydroxide 221465 25 g *C Water n/a 25 mL
Reference Friedel-Crafts Acylation of m-Xylene with Phthalic Anhydride, Experimental Organic Chemistry, Gilbert and Martin, 5th Edition, 2011, p. 505-506. Health & Safety Evaluation Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Phthalic anhydride 320064 50 g Aluminum chloride, anhydrous 237051 100 g m-xylene 185566 300 mL Hydrochloric acid, conc. 320331 100 mL * Water n/a 500 mL Diethyl ether 346136 1400 mL * Hydrochloric acid, 6M 320331 250 mL Sodium sulfate 239313 500 g
Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Benzyltriphenylphosphonium chloride B32807 10 g 4-bromobenzaldehyde B57400 4.75 g Ethyl acetate 270989 100 mL Ethanol 459836 100 mL Heptane 246654 400 mL * Potassium phosphate, tribasic P5629 21.3 g Water n/a 750 mL Traditional Wittig Reaction The Wittig reaction is a classic reaction for converting a carbonyl compound to an olefin through a intermediate. This reaction traditionally proceeds using a hazardous solvent, such as dichloromethane or dimethyl formamide. Reference Synthesis of trans-9-(2-phenylethenyl) anthracene (microscale), Macroscale and Microscale Organic Experiments, 6e; Brooks/Cole, 2011; pp. 509-510.
Health & Safety Evaluation Chemical Name Aldrich Catalog # Amount per 100 students (g or mL) EH&S Benzyltriphenylphosphonium chloride B32807 10 g 9-anthraldehyde 8.2011 5.75 g Dichloromethane 676853 155mL Sodium hydroxide, 50% 221465 13 mL Water n/a 75 mL Calcium chloride 793639 50 g 2-propanol 278475 150 mL Comparative Analysis of Traditional vs. Suggested Experiments Greener method avoids the use of chlorinated solvent – dichloromethane.