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Synthesis of Biodiesel in a High School Lab

by Richard L. Snyder

Chemistry Seminar
Dr. Gary Histand
April 24, 2007
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Abstract

With the growing effects of gasoline prices, the need for an alternative fuel source

is quite obvious. As gas prices continue to be on the rise in upwards of over three dollars

per gallon, alternative fuel sources are becoming increasingly popular in today’s society.

In the year 2000, there were about eight million vehicles around the world that ran on

alternative fuels, indicating the increasing popularity of alternative fuels (Alternative

fuels). Biodiesel requires no modifications to regular diesel engines in order to work

(Filz). In 2001, the first two public filling stations offering biodiesel were opened in San

Francisco, CA, and Sparks, NV (Filz). The importance of learning about alternative fuel

sources is useful knowledge in today’s society. By having the students conduct the

synthesis of biodiesel in a high school lab setting, hopefully the awareness will increase.

Biodiesel uses the process of transesterification of an oil. An alcohol and

a catalyst are added to the oil and converts the esters to those of the corresponding

alcohol. The reaction that takes places looks similar to this:

O
O
R1 C O CH3
H2C O C R1 H2C OH
O O +
cat. base
HC O C R2 R2 C O CH3 + HC OH
O 3 MeOH
H2C O C R3 O + H2C OH
R3 C O CH3
vegetable oil glycerol
triglyceride methyl esters of
fatty acids

The alcohol becomes deprotonated by the base, which in turn makes it a better

nucleophile. The nucleophile then attacks the carbon-oxygen double bond and creates a
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pair of electrons on the oxygen that was originally double bonded to the carbon. The

alcohol becomes attached to the carbon. The electrons come back to the carbon and the

glycol gets kicked off, which in turn forms the ester. The alcohols attack the other two

carbon-oxygen double bonds and the same process occurs, with three ethyl esters being

formed and the glycerol getting kicked off and creating a by-product each time (biodiesel

production).

There are many techniques for creating biodiesel, but most, if not all, of the ones

that have been discussed were meant to produce a large quantity of biodiesel. With

budget concerns, as well as space and storage concerns, most of these methods were not

feasible. The goal in doing this research project was to find a way to teach kids why

finding an alternative fuel source is so important, as well as teaching some other basic

chemistry methodology, such as calculating density and specific heat.

Introduction

The first thing that needed to be done when deciding on a procedure was what oil

should be used. After looking at prices at a supermarket, the choice was narrowed down

to three oils: vegetable oil (soybean oil), canola oil, or corn oil. Research was done on all

of the oils. The information that was found indicated that canola oil comes from the

rapeseed plant, which is part of the mustard family of plants. The rape oil, as it is

sometimes called, was used in mustard gas during WWI. Mustard gas is an extremely

dangerous gas, which causes blistering of the lungs and skin (Graham). It has also been

shown to cause lung cancer, according to the Wall Street Journal. After hearing about the

possibility of having these bad effects happen to students, canola oil was ruled out and all
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the attention became focused on soybean and corn oil. The assumption is that both will

give similar results.

The next problem presented itself in dealing with the catalyst, NaOH. NaOH in

the solid form is very caustic, which means it could eat the fingerprints off of the

students’ hands. Because of this, the decision was made to use extreme caution when

dealing with NaOH and make up a mixture of the NaOH/methanol mixture beforehand.

It should be noted that NaOH is a deliquescent, which means it readily takes moisture

from the air through absorption. Consequently, the concentrated NaOH should be kept in

a tightly sealed container.

Problems kept arising when mixing NaOH and methanol. As soon as it was

mixed with the soybean oil, a soapy emulsion would begin forming. This meant that too

much NaOH was in the solution. The decision came to contact some “biodiesel experts”

by asking them the question of what ratio of NaOH: methanol should be used. This was

done by joining a group on the Internet for fanatics of biodiesel, some of which included

professors with PhD’s (Gian). Their instructions were to figure out how much vegetable

oil was going to be needed. If an estimated 30 kids in a high school classroom were

working in pairs, 15 separate measurements of oil would be needed. The decision was

made to use 20 mL of soybean oil, which came out to 300 mL of soybean oil total. They

said a good number to use was either 4 or 5 g/L of a NaOH:soybean oil ratio. Both trials

were done and the 5 g/L turned out to be a better ratio than the 4 g/L. Next, the

instructions were that normally one should use a ratio of 20% by volume of methanol to

the total volume of vegetable oil. This meant that a solution of 60 mL of methanol with

1.5 g NaOH would be mixed up. This turned out to be the framework for the experiment.
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The final problem that was encountered when designing this experiment was how

long to let the biodiesel and glycerol sit in between washings. In order to be sure that the

washing has run its complete course, it was found that one needed to wait about 2 days.

Since it is designed for a Chemistry classroom that meets every day, the suggestion is that

students wait two days between each washing. One day was tried, but the solutions

weren’t transparent, which indicates completion (Leray). The biodiesel needs to be clear

enough to see through and not be a cloudy mixture, which is why two days is sufficient.

After sifting through all these problems, a procedure was developed that makes a

quality amount and gives the desired product. The following experiment should be able

to be used in a high school lab and if followed with precision, a successful synthesis of

biodiesel should be the end result.

Procedure

1. To prepare for the experiment, the teacher needs to mix up the mixture of

methanol and NaOH before class. The amount that was found to work best is

to use 5 g of NaOH per mL of total vegetable oil used in the experiment. The

recommended amount is 20 mL of vegetable oil per group. For the methanol,

use about 20% volume of methanol of the total volume of vegetable oil. For

example, if you have 15 groups, you will have a total of 300 mL of vegetable

oil and will use 60 mL of methanol. To achieve 5 g/mL of NaOH, you would

use 1.5 g of NaOH.

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2. When students arrive in the classroom, make sure all safety procedures are

followed. Safety goggles must be worn at all times.

3. When the students arrive, they need to pour out 4 mL of the methanol/NaOH

solution that has already been prepared.

4. Next, 20 mL of vegetable oil (either soybean or corn oil, preferably) needs to

be measured out in a graduated cylinder.

5. After the NaOH/methanol solution and vegetable oil has been measured out

and recorded, the NaOH/methanol solution needs to be added to the vegetable

oil in a test tube.

6. To make sure the reaction is taking place, put a rubber stopper in the end of

the test tube and shake vigorously for about a minute.

7. The next step is to let the mixture sit for 2 days.

8. After 2 days, the students should notice two distinct layers. The bottom layer

is glycerol and other by-products. The top layer (much more of the solution)

is the biodiesel and needs to be pipeted off. To get the biodiesel off the top,

pipet it into a clean test tube, being careful not to pull any of the glycerol with

it.

9. With the biodiesel in the clean test tube, you want to wash it now. Add about

5.0 mL of water to the biodiesel and SLOWLY invert the test tube to mix the

water and biodiesel. (Note to teacher: Make sure students are inverting the

test tube extremely slow, otherwise if shaken too vigorously, a soapy emulsion

will form, contaminating the biodiesel.

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10. Allow the washing to sit for two days and pipet the biodiesel (top layer) from

the bottom layer (water). Transfer the biodiesel into a clean test tube and

proceed with step 9. Do the washing process 4-5 times, allowing two days to

sit between each washing.

11. After the biodiesel has been washed, the next step is to find the density.

Weigh a graduated cylinder and then zero the scale. Pour the biodiesel into

the graduated cylinder and record the volume. Then place the graduated

cylinder on the scale and find the mass. Divide the mass by the volume, and

that will be the density, in g/mL.

12. The first part of the experiment is now complete. The biodiesel needs to be

stored in a test tube and covered with a rubber stopper until needed.

13. The second part of the experiment involves seeing how well the fuel actually

works. First, get a pop can (any flavor will work, choose a favorite) and cut

off the top of the can and discard it.

14. Next, cut out two holes on opposites sides of each other at the top of the can

so that a glass rod can be inserted to hold up the can on a ring stand.

15. The next part of the experiment involves creating a fuel burner. The

suggested way to do this is to use a dropper bottle. Take the top of the

dropper bottle off and put insulation or glass wool into the dropper, leaving

some sticking out of the top to act as a wick.

16. Pipet the biodiesel that you have just finished creating into the dropper tubing

and let the insulation soak it up inside the tube. Pour the remaining biodiesel
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in the bottom of the dropper bottle. Weigh the mass of the burner initially and

record it on your data sheet.

17. Now, it’s time to take the initial mass of the can without anything in it and

record this data onto your data sheet.

18. Add roughly 100 mL of water to the pop can and record the new mass.

Subtract the initial mass from the final mass to figure out the mass of the

water.

19. Set up the pop can on a ring stand, having the glass rod hold up the pop can.

Place the fuel burner directly underneath the pop can. Record the initial

temperature of the water onto your datasheet. Keep a thermometer in the pop

can to measure the temperature throughout the duration of the experiment.

20. Light the wick on your fuel burner using a Bunsen burner. Keep the flame a

few inches from bottom of the pop can. Keep a careful eye on the

temperature. Let the temperature increase about 20oC and then blow out the

flame. Record the highest temperature that the water reached.

21. The next step needs to be done fairly quickly. As soon as the flame has been

extinguished, the mass of the fuel burner needs to be recorded. To find the

mass of the fuel burned, (in grams) subtract the initial mass of the burner from

the final mass of the burner.

22. Clean up the rest of the lab and return all equipment to its proper place.

23. To find the total heat absorbed by the water in calories, a simple calculation

will occur. Take your mass of water (grams) and multiply it by the change in

temperature of the water (oC). This number is then multiplied by the specific
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heat of water, which is 1.00 cal/g* oC. This will leave you an answer in

calories.

24. To find the heat per gram of fuel, take the calories that you just found in the

previous step and divide it by the mass of your fuel burned. This will give

you an answer in calories/gram.

Data Section

Trial Number Mass of NaOH Volume of Methanol Volume of Soybean

Oil
1 .0133 g 1.0 mL 8.0 mL
2 .0106 g 1.0 mL 8.0 mL
3 .0155 g 1.0 mL 8.0 mL

In these trials, there wasn’t much separation, leaving hardly any layers of

biodiesel. This meant that the solutions probably weren’t mixed vigorously enough.

Using a 3:1 mol ratio of methanol to soybean oil obviously didn’t work out.

Trial Number Mass of NaOH Volume of Methanol Volume of Soybean

Oil
4 .1280 g 5.1 mL 40.1 mL
5 .0988 g 5.0 mL 38.8 mL
6 .0874 g 5.2 mL 39.0 mL

Increasing the volumes of the methanol and soybean oil and using a soda pop

bottle to store the solutions was another thought. However, after thinking it through, it

would be difficult to pipet the biodiesel out to wash it. In these trials, there was enough

biodiesel to extract to proceed on. After the first washing, though, an emulsion was
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created instantly, thus proving that the ratios were not correct in the beginning. The

emulsion most likely indicated too much NaOH was used.

The next idea that occurred was to mix up the NaOH and methanol in a big batch

and go from there. Some research was done and found that the best ratio to use was 5 g/L

of NaOH:total volume of vegetable oil. The amount of methanol that should be added to

the NaOH is 20% of the total volume of vegetable oil. 300 mL of vegetable oil ( 20 mL

multiplied by 15 groups of kids) was used. Theoretically then, 60 mL of methanol and

1.5 g of NaOH would be used.

Mass of NaOH Volume of Methanol

1.4962 g 59.7 mL

For all of the following trials, this is the methanol/NaOH mixture that was used.

Trial Number Volume of Soybean Oil Volume of NaOH/Methanol

Mixture
7 20.7 mL 4.1 mL
8 20.1 mL 4.1 mL
9 21.0 mL 4.0 mL

Each solution was allowed to sit for two days. After two days, they were washed

with 5.0 mL of water. Then, they would sit for another two days between each washing.

Five washings were done. When pouring off the water biodiesel into a clean test tube,

not as much biodiesel was extracted as could have been. This provided not quite as good

of results, as only the first trial were the only results. The mass, volume, and density

were found of Trial 7.

Trial Number Mass of Biodiesel Volume of Biodiesel Density of Biodiesel

7 1.7458 g 1.9 mL .919 g/mL
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While doing research on biodiesel, the density was found to be .903 g/mL

(Sarma). The density of soybean oil was also figured out to be .8054 g/mL, so obviously

some form of reaction took place. Some more trials were needed to verify the results that

were found in this experiment.

Trial Number Volume of Soybean Oil Volume of Methanol/NaOH

10 20.1 mL 3.9 mL
11 20.0 mL 4.0 mL
12 20.0 mL 4.0 mL

Again, two days and then the first washing took place. Two days took place

between each washing. After the second washing, trial #11 was not as clear as the others

so the results might not be as accurate on this particular trial. After the final washing, the

densities of the solutions proved my hypothesis correct. Trial #11’s density was a lot

lower than the other’s densities.

Trial Number Mass of Biodiesel Volume of Biodiesel Density of Biodiesel

10 1.2846 g 1.4 mL .918 g/mL
11 2.5944 g 3.0 mL .865 g/mL
12 0.4618 g 0.5 mL .923 g/mL

Since all of these densities were pretty close to each other,the total heat absorbed

in calories and also the heat of gram per fuel was found.

Trial Number 7 10 12
Mass of Can + Water 107.7448 g 107.2648 g 107.6582 g
Mass of Empty Can 9.5215 g 9.4664 g 9.1274 g
Mass of Water 98.2233 g 97.7984 g 98.5308 g
Final Temp of Water 37.0 oC 41.5 oC 32.7 oC
Initial Temp of Water 23.3 oC 23.3 oC 22.9 oC
Temp Change 13.7 oC 18.2 oC 9.8 oC
Initial Mass of Burner 77.2777 g 77.1881 g 76.1178 g
Final Mass of Burner 76.9368 g 76.7850 g 75.8773 g
Mass of Fuel Burned .3409 g .4031 g .2405 g
Total Heat Absorbed 1345.7 cal 1779.9 cal 965.6 cal
Heat per gram of Fuel 3947.5 cal/g 4415.6 cal/g 4015.0 cal/g
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In order to prove that the results were not just pure luck, three more trials using

soybean oil were done. To see if other oils had the same effect as vegetable oil, corn oil

was also used in a few trials.

Trial Number Volume of Soybean Oil Volume of Methanol:NaOH

13 20.0 mL 4.1 mL
14 20.0 mL 4.0 mL
15 21.0 mL 4.0 mL

The standard two day waiting period was used after mixture and between

washings for the vegetable oil.

Trial Number Volume of Corn Oil Volume of Methanol:NaOH

16 20.0 mL 3.9 mL
17 20.0 mL 3.9 mL
18 20.0 mL 4.0 mL

Even with corn oil, the same waiting period between each mixing and washing

was used.

After all the washings were completed, these were the densities that were

calculated for the soybean oil and corn oil.

Trial Number Mass of Biodiesel Volume of Biodiesel Density of Biodiesel

13 7.8572 g 8.6 mL .914 g/mL
14 7.6273 g 8.3 mL .919 g/mL
15 7.8369 g 8.5 mL .922 g/mL

Trial Number Mass of Biodiesel Volume of Biodiesel Density of Biodisel

16 7.9046 g 8.6 mL .919 g/mL
17 7.4683 g 8.1 mL .922 g/mL
18 7.9698 g 8.7 mL .916 g/mL
Reminder: Trials # 13-15 were with soybean oil and trials # 16-18 were with

corn oil.
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The next step was to test all of the trials by finding the total heat absorbed and

heat of fuel per gram.

Trial Number 13 14 15
Mass of Can + Water 108.4621 g 105.6833 g 107.3800 g
Mass of Empty Can 9.2368 g 9.4147 g 9.3956 g
Mass of Water 99.2253 g 96.2686 g 97.9844 g
Final Temp of Water 41.2 oC 40.6 oC 38.1 oC
Initial Temp of Water 23.0 oC 23.1 oC 23.4 oC
Temp Change 18.2 oC 17.5 oC 14.7 oC
Initial Mass of Burner 81.1073 g 80.9636 g 81.1589 g
Final Mass of Burner 80.6847 g 80.5739 g 80.7915 g
Mass of Fuel Burned .4226 g .3897 g .3674 g
Total Heat Absorbed 1805.9 cal 1684.7 cal 1442.5 cal
Heat per gram of Fuel 4273.3 cal/g 4323.1 cal/g 3926.2 cal/g

Trial Number 16 17 18
Mass of Can + Water 107.3476 g 106.9744 g 107.5918 g
Mass of Empty Can 9.3264 g 9.2784 g 9.4738 g
Mass of Water 98.0212 g 97.6960 g 98.1180 g
Final Temp of Water 39.7 oC 41.3 oC 40.6 oC
Initial Temp of Water 23.1 oC 23.3 oC 23.2 oC
Temp Change 16.6 oC 18.0 oC 17.4 oC
Initial Mass of Burner 81.2824 g 80.8695 g 81.0037 g
Final Mass of Burner 80.9157 g 80.4601 g 80.6141 g
Mass of Fuel Burned .3667 g .4094 g .3896 g
Total Heat Absorbed 1627.2 cal 1758.5 cal 1707.3 cal
Heat per gram of Fuel 4437.4 cal/g 4295.3 cal/g 4382.2 cal/g

Results

Trial Number Density Heat of Fuel per gram

7 .919 g/mL 3947.5 cal/g
10 .918 g/mL 4415.6 cal/g
12 .923 g/mL 4015.0 cal/g
13 .914 g/mL 4273.3 cal/g
14 .919 g/mL 4323.1 cal/g
15 .922 g/mL 3926.2 cal/g
16 .919 g/mL 4437.4 cal/g
17 .922 g/mL 4295.3 cal/g
18 .916 g/mL 4382.2 cal/g
Average .919 g/mL 4224.0 cal/g
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This is the average of all the trials added together and divided by 9. The next

table will look at individual variances and percent error within each trial.

Trial Number Variance Density Percent Error Variance Heat Percent Error
Density per gram of fuel Heat per gram
of fuel
7 0 g/mL 0% -276.5 cal/g -6.55 %
10 -.001 g/mL -.109 % 191.6 cal/g 4.54 %
12 .005 g/mL .544 % -209.0 cal/g -4.95 %
13 -.005 g/mL -.544 % 49.3 cal/g 1.17 %
14 0 g/mL 0% 99.1 cal/g 2.35 %
15 .003 g/mL .326 % -297.8 cal/g -7.05 %
16 0 g/mL 0% 213.4 cal/g 5.05 %
17 .003 g/mL .326 % 71.3 cal/g 1.69 %
18 -.003 g/mL -.326 % 158.2 cal/g 3.75 %

Discussion of Results

After looking at the results, the densities for all trials were very precise. The

range was .009 g/mL. They were all right around the same area. They were also

accurate, as the density of biodiesel ranges from .900 g/mL to .930 g/mL. All of the trials

were within this range. When calculating the results of percent error of the heat per gram

of fuel, the percent errors were a little higher, but still fairly precise. The greatest percent

error was -7.05 %, while the lowest was 1.17 %. There was also a direct correlation

between the mass of fuel burned and the temperature change. The more the temperature

changed meant more fuel (in terms of mass) was being burned.
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Conclusions

After spending many hours researching in the library, conversing with “self-called

biodiesel experts,” and conducting trial after trial, there are many conclusions. The first

one is that there are many problems that have been identified in the process of creating

biodiesel in a high school setting and solutions were created to help make the synthesis

go as smoothly as possible. There were soapy emulsions, but the reasons they happened

were found. A good ratio of methanol/NaOH and oil mixture that would end up creating

a good batch of biodiesel was found. Test tubes were much easier to extract the biodiesel

from than a pop bottle. A good amount of time to let the reaction take place and finish to

completion was figured out. The last obstacle that was overcome was whether or not the

oil made a difference. All of the problems arose during the experimentation, but a good

procedure was still developed to use in a high school lab setting. The results were very

precise and accurate, also indicating that the procedure was a success. It was a joy

working on this project, because it not only teaches valuable chemistry aspects, but it has

an effect on the lives of young people. This shows the students how important it is to

develop an alternative fuel source, one that is cheaper and still as efficient. This

experiment that was designed will allow them to learn both of these concepts.
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Works Cited

Alternative fuels. Wikipedia. March 2007.

http://en.wikipedia.org/wiki/Alternative_fuels.

Biodiesel production. Wikipedia. February 2007.

http://en.wikipedia.org/wiki/Biodiesel_production.

Filz, George M. Environmental Science and Technology. August 1, 2001. “First

two public filling stations containing biodiesel open.”

Gian, Michael. March 14, 2007. biodiesel@yahoogroups.com

Graham, Doug. Optimal Breathing. 2003. www.breathing.com/articles/canola-

oil.htm

Leray, Claude. Cyberlipid Center. 2006. www.cyberlipid.org/glycer/biodiesel.htm

Sarma, Anil Kumar. ACS Archives. “A comprehensive analysis of fuel properties

of biodiesel.” September 29, 2004.

pubs.acs.org/cgi-bin/article.cgi/enfuem/2005/19/i02/pdf/ef04975f.pdf