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Synthesis of Biodiesel Fuel
Synthesis of Biodiesel Fuelfrom Vegetable Oil
References: Pavia - p. 207 – 216
- p. 194 – 202 (Essay – Petroleum and Fossil Fuels
Schornick
http://classweb.gmu.edu/jschorni/chem318
04/18/23 1
Synthesis of Biodiesel Fuel Background
Fossil fuels
Slow decay of marine animal and plant organisms over periods of millions of years
Significant source of pollution
Significant contributor to green house gases, principally CO2
High potential for environmental disasters such as oil spills, drilling rig failures, chemical plant explosions & fire, etc.
Finite – We are depleting this non recoverable supply
04/18/23 2
Synthesis of Biodiesel Fuel Background
Biofuels: Fuels produced from biological materials Ethanol (Gasohol)
Starch (polymer of Glucose) Corn (Enzymes catalyze corn starch into
glucose Expensive to produce Energy inefficient Produces more green house gases
Sucrose (Fermentation of Sugar Cane & Beets) Cellulose
Switchgrass Agricultural waste, including corn stalks Waste wood from milling
04/18/23 3
Synthesis of Biodiesel Fuel Background
Biofuels
Ethanol
Syngas (CO & Hydrogen converted to Alcohol)
Utilizes wide array of Carbon-containing matter
Municipal Waste
Old Tires
Agricultural Waste
More Energy Efficient Than Ethanol
Produces less greenhouse gases
04/18/23 4
Synthesis of Biodiesel Fuel Background
Biofuels Biodiesel (from fats & oils, including
vegetable oil) Farm products
Large investment in farmland not dedicated to food production
Net energy produced is greater than from Ethanol but less than for cellulose
Produces more greenhouse gases than fossil fuels
Destruction of forested areas to establish farmland (loss of forest’s capacity to absorb CO2)
New higher efficiency method emerging utilizing a Sulfated Zirconia catalyst
04/18/23 5
Synthesis of Biodiesel Fuel Background
Biofuels
Biodiesel (from fats & oils, including vegetable oil)
Algae
Can produce oils for making biodiesel
Grown in ponds or sewage waste water
Several approaches, catalysts, self-contained manufacturing facilities, etc. are being investigated in search of economically viable processes
04/18/23 6
Synthesis of Biodiesel Fuel The Experiment
In the Banana Oil experiment, an organic acid is combined with an alcohol in a catalyzed Fischer Esterification (condensation) reaction to produce a mono ester
In this experiment the reverse of the process (hydrolysis by H2O, Acid or OH- to the alcohol and acid) is modified in a transesterification reaction, in which an original trimester is converted to three (3) mono esters by reaction with an alkoxide base
04/18/23 7
Synthesis of Biodiesel Fuel Analysis of Biodiesel product
The trimester is cleaved sequentially by the alkoxide base (a mixture of Potassium Hydroxide and Methyl Alcohol), liberating the mono-esters and glycerol
The Mono esters are produced sequentially because the Alcohol/Alkoxide base has only one Hydroxyl group
The mono esters are Fatty Acid Methyl Esters (FAME)
The Vegetable oil and biodiesel product molecules have variable composition
Three Methyl esters of fatty acids are formed each with a different “R” group consisting of 12-18 carbons arranged in straight chains
04/18/23 8
Synthesis of Biodiesel Fuel Analysis of Biodiesel product
Thus, the computation of moles directly from the peanut oil mass is not practical
Show the stoichiometric and mechanism reactions
The Methyl Alcohol is in excess, but the theoretical yield cannot be determined; omit summary table
Calculate a “percent yield” from the initial mass of the Vegetable oil and the mass of the diesel fuel product
Compare the original IR of the vegetable oil (seep. 102 in Slayden Manual) to the biodiesel IR
04/18/23 9
Synthesis of Biodiesel Fuel Reaction
04/18/23 10
Alkoxide
An Alkoxide is the Conjugate Base of an Alcohol
It consists of an organic group bonded to a negatively charged Oxygen atom
Alkoxides are strong Bases and, when R is not bulky, good nucleophiles and good ligands
Fatty Acid Methyl Esters (FAME)
Synthesis of Biodiesel Fuel Reaction – Mechanism
04/18/23 11
The same mechanism is repeated two more times on the 2 other ester groups of the trimester until the final product is3 Fatty Acid Methyl esters (FAME) and one glycerol.The three reactions occur sequentially.
The negative charge of the Alkoxide (Methoxide) ion attacks the positive charge of the carbonyl carbon atom (from the resonance dipole form of the carbonyl group)
Fatty Acid Methyl Ester (FAME)
Tetrahedral (sp3)Intermediate
Alkoxide ion
Trimester of Glycerol (1,2,3-propanetriol)and a long chain fatty acid
1st Stage
Repeat for stages 2 & 3
Synthesis of Biodiesel Fuel Procedure
Reagents 10 mL Vegetable Oil (Crisco) – A Trimester 2.0 mL Potassium Hydroxide/Methyl Alcohol
solution
(forms Methoxide ion, an Alkoxide ion) Prepare a water bath in a 150 mL beaker on a hot
plate Heat the water bath to a temperature of 55oC Tare weight an empty 100 mL beaker or small cork
ring sitting on the balance to the nearest 0.001 g Place an empty 25 mL round-bottom flask onto the
beaker top or on the cork ring Determine the mass of the empty flask by difference
04/18/23 12
Synthesis of Biodiesel Fuel Procedure (con’t)
Place 10 mL of vegetable oil into the pre-weighed distillation flask
Determine the mass of the flask and vegetable oil Determine the mass of the vegetable oil by
difference Add ~2.0 mL of the fresh KOH/CH3OH solution to
the distillation flask Swirl the mixture to ensure a uniform solution Insert a small magnetic stir bar into the flask Attach and secure (with a blue plastic clamp) the
flask to a water-jacket condenser clamped vertically to a ring standNote: No need to run water through the condenser
Lower the distillation flask into the water bath
04/18/23 13
Synthesis of Biodiesel Fuel
04/18/23 14
Mixture of vegetable oil,Methyl Alcohol, andPotassium Hydroxide
CondenserNo Water Flow
Blue PlasticClamp
Water Bath55oC
Synthesis of Biodiesel Fuel Procedure (con’t)
Turn on the magnetic stirrer (Left knob on hot plate)to the highest level possible that allows the bar to spin smoothly
Stir for 30 minutes Transfer all of the liquid in the flask to a 15-mL
centrifuge tube with a cap Let the mixture sit for about 20 minutes Two layers should form
The top layer is the biodiesel product The lower layer is mainly glycerol
Using a plastic pipet, carefully remove the top layer and transfer product to a pre-weighed 50-mL beaker(leave a little product behind with the bottom layer to avoid contamination)
04/18/23 15
Synthesis of Biodiesel Fuel Procedure (con’t)
Place the beaker on the hot plate and insert a thermometer into the biodiesel, holding the thermometer in place with a clamp
Heat the biodiesel to about 70oC for 15-20 minutes to remove all the Methyl Alcohol
Remove the beaker from the hot plate and allow it to cool to room temperature
Weigh the beaker and obtain the mass of biodiesel produced
Record the appearance of the biodiesel
Obtain an IR spectrum
CAS No. for diesel fuel – 68476-34-604/18/23 16