Science Fair Project: Cleaning Up Oil Spills

[Vlance]

Hi Sybee,
I now realize I was not very clear about what I was asking. My teacher was wondering if could put the liquid chlorophyll in the steamer and get the phytol out that way. Sorry about the confusion. I was also wondering if this would work as a steamer because it is my only glass bowl and this is the pot it fit in best [photo removed by student].

-Vlance

[SciB]

Oh, I should have realized that's what you meant. You already had the chlorophyll extract so just go ahead and steam that until it turns brown (hopefully it will!).

Your steamer set-up looks fine. I'm debating whether or not to put a lid over the bowl. What do you think? How much chlorophyll extract plus vinegar do you have? I just don't want to have all the water evaporate; but, on the other hand, maybe evaporating some of the water would be a good idea to make the extract more concentrated.

Did you use spinach leaves to make the chlorophyll extract? How much leaves did you use? How much phytol are you supposed to use to clean up an oil spill of a certain area? Will you have enough to do the experiment at least three times? I'm trying to think of any potential problems now before you get too far along. Please, if you think of something or have any questions--now is the time to bring them up.

For a control you could add vinegar to water in the same proportions as for your phytol preparation but without adding any chlorophyll. Then you would neutralize the vinegar with baking soda and use that solution as the control.

What is your deadline for finishing this project? You still have a lot to do.

I think that's all. Please answer my questions so I have that information. Good luck getting the chlorophyll to release its phytol.

Sybee

[Vlance]

Hi Sybee,
I think that I will leave the lid to the steamer off so that the phytol will be more concentrated. I bought the liquid chlorophyll at the vitamin shop already extracted for when I was trying the vinegar without heat. I realized that I would most likely not get very much phytol when I tried to separate it from the chlorophyll so I will be doing micro chemistry. I am going to combine the phytol with olive oil to try and align the phytol molecules better so it can break the surface tension and congeal the oil better. I have lots of liquid chlorophyll so I can do many tests with it. I need to have my data in by March 4th. If we can't figure out how to get the phytol out by the middle of February my parents said that we can buy some already extracted phytol but I would like to extract it myself.
-Vlance

[SciB]

Hmm...
And here I thought you were cooking spinach leaves!

It is just my opinion without evidence, but I think fresh chlorophyll would be the best choice for an experiment. What do you think? The procedure for isolating chlorophyll from spinach leaves is pretty easy. Can you find out how the liquid chlorophyll you bought was prepared? It may have some chemical stabilizers added to it that make it more difficult to break the bond to release the phytol. Let me know what you find out about the liquid chlorophyll and whether you want to try making the chlorophyll extract yourself.

Now, that we've spent all this time figuring out how to make phytol, I did a search for where to buy it and found a company that sells it--2 ml for $13

https://trueterpenes.com/products/terpenes/phytol/

I still think preparing it yourself from fresh spinach leaves is the most satisfying way to do it, and it may turn out to be the most active phytol. You can try the liquid chlorophyll, but if you heat it with vinegar on the steamer and it never turns brown then it may have been modified in some way to prevent the phytol from being broken off by acid.

I hope whatever you decide to do works!

Sybee

[Vlance]

I think that the easiest thing for me to do is try with the liquid chlorophyll first and if that doesn’t work I will try to get the Phytol out of the spinach. I will try using the steamer method on the liquid chlorophyll tomorrow and let you know what happens. Do you know what the maximum amount of time I should simmer the liquid chlorophyll trying to get the Phytol out for before I try the spinach?

-Vlance

[SciB]

I really have no idea. When I cook green beans or kale I only steam them for 3-4 minutes in the microwave on high, so I would estimate that it takes maybe 20 minutes on fairly high heat to make them turn brownish green, but that is without acid present.

How much vinegar are you adding to how much chlorophyll? Vinegar is a weak acid and is not going to break the phytol bond as well as a strong acid like hydrochloric, which is what you would use in the lab.

Remember to take before and after pictures of the chlorophyll. Hope it works!

Sybee

[Vlance]

Hi Sybee,
Today my mom had a question about my experiment and I didn't know the answer. She once put a glass bowl in a pot of boiling water and it exploded, will that happen when I put the bowl in the simmering water? Also she was wondering if the judges would question my project and think it was more about getting the phytol out than creating a oil spill removal spray? I thought no because this is me getting the phytol out to start the project but I wanted to ask your opinion.

-Vlance

[SciB]

Hi VL,

I am so glad that you are asking questions! That's the mark of a scientist.

A glass bowl could break if it was cold and immediately immersed in boiling water. Likewise, a hot bowl put into cold water could shatter. Pyres glass like the Fire King or Anchor Hocking brands is more resistant to thermal stress.

What I would do is is put a couple inches of water in the bottom of the pot, put the glass bowl on it and heat the water. That way the bowl will be heating at the same rate and won't crack. You can also put the chlorophyll solution in the bowl so that it can start heating.

Your project asks the question, Does using phytol improve the removal of oil from an oil spill on water? The phytol is the key part of your project, but it is not the object of it. When you write up the results you don't need to spend a lot of time describing the phytol preparation. Just show a diagram of the hydrolysis reaction of the chlorophyll molecule with acid and heat to produce phytol plus the remnant of the chlorophyll (phaeophorbide)--http://www.ch.ic.ac.uk/local/projects/steer/chloro.htm

Take note that we are making an assumption here that the mixture of phytol and phaeophorbide that you prepare will promote oil recovery exactly the same as phytol alone. I don't know whether that is true, but I am betting that it is. You could go ahead and order the phytol from the source I sent you so that you could test it along with your phytol prep. Testing two different compounds will strengthen your results and make your project A++.

Hurry up and make the phytol! I want to know how well this hydrolysis method works.

Best wishes,

Sybee

[Vlance]

Hi Sybee,
I wanted to update you on my project. I currently have the chlorophyll mixed with vinegar in the "steamer" at medium heat and the chlorophyll is moving around. I'm not sure what is happening. This a video of what I was seeing. I hope you can tell me whats happening [removed by student].

-Vlance

[Vlance]

Hi Sybee,
I think that I need to purchase the phytol. I tried heating up the chlorophyll will the vinegar mixed with it but nothing happened. I gave it a couple of hours but my stove started making abnormal noises when the "steamer" was on it. Thank you so much for you advice I will make sure to tell the judges all of the things I tried. For my science fair board I could use your name and talk about how all the ways you helped me?

Thanks for all the help,
Vlance

[SciB]

Hi VL,

Thanks for updating me on your progress. That's the world of real science, unfortunately, where things often don't work the way you expect. I'm pretty sure the problem is that you are not able to use an acid at the strength needed to break the phytol bond. You would probably need to use hydrochloric acid at a concentration of 15-20%.

If you heated a bunch of spinach leaves with some salad oil in a pan to stir-fry temperatures (325 F or so) I think you could achieve breakage of phytol from the chlorophyll. That is what i do when I cook greens like chard and Napa cabbage and they always turn a little brown if i heat them too long.

Well, go ahead and order the phytol. I don't know how much you will need but 1-2 ounces of pure phytol should do it. The next challenge will be measuring the exact amount of oil recovered from the clean-up of the 'spill' and the sooner you get started on that the better.

Thank you for wishing to acknowledge me personally. It is my pleasure to try and help you do your project and to understand how the scientific method works. The U.S. needs more good, young scientists and you might be the one to discover a great new process or invention. Scientific research and engineering are great careers--challenging, satisfying and exciting. You can say that you received help and mentoring from the experts at Scibuddies and that you highly recommend us. I am already looking forward to working with you on your next science project!

Good luck,

Sybee

[Vlance]

Hi Sybee,
I know that I said that I was just gonna buy the phytol but my teacher just emailed me and told me she had sulfuric acid. I will give that a try some time next week to try and get the phytol out but if I can't then I will buy the already extracted phytol. I will update you if this will allow me to get the phytol out. I will also be heating the chlorophyll at the same time just not in a "steamer".

-Vlance

[SciB]

Hi V,

Hmm...
Sulfuric acid would not be my first choice. Doesn't she have or can get hydrochloric acid (HCl)? Sulfuric acid is a very strong oxidizer and I would be concerned that it might destroy part of the phytol molecule.

Ask your teacher if she has HCl. If not it can usually be purchased from a place that sells pool supplies or from a home or hardware store. Just tell her to ask for muriatic acid, the common name for hydrochloric acid. The concentration is usually about 32% HCl. Be careful with this! Your teacher should know how to handle acids safely. You must wear goggles or face shield, nitrile gloves and a lab coat as personal protection. The acid should be used in a fume hood because its vapors are very irritating.

I will try to find out what concentration of HCl you should use for hydrolysis of chlorophyll. I still think you should make a fresh preparation of chlorophyll from spinach leaves. I'm concerned that the chlorophyll preparation that you are using may have a chemical stabilizer added to it that prevents breakage of the phytol bond. Just do a search on Google or Youtube for how to prepare spinach chlorophyll. This is a common lab exercise and fairly simple to do.

Sybee

[SciB]

Hi VL,

I was wondering what you had decided to do for producing the phytol you need. I did another search for acid hydrolysis of chlorophyll and did find out that sulfuric acid can be used for hydrolysis:

https://pubs.acs.org/doi/pdf/10.1021/ic00134a056

I tried to get this 1982 article through my university library but could not find the citation. I don't think their databases go back that far for this journal.

If there is a method for acid hydrolysis of chlorophyll on the web, I don't know where it is hiding. I could not find it!

What I would do is make a range of dilutions of acid in your chlorophyll solution and record what happens. Just be careful working with strong acids. ALWAYS where eye protection, gloves and a lab coat or full apron to protect your clothing. Work with your teacher or someone familiar with chemistry in your school lab.

Let me know what you decide to do.

Sybee

[Vlance]

Hi Sybee,
I am very sorry for not updating you sooner about my project. I had to give up on trying to get the phytol out myself, so I just bought about 8 ml for my project. So far it looks like I will be actually performing the experiment this Wednesday. Last night I was doing somemore research about my project and I saw that the phytol was going to reat with a cation (salt in the salt water) and I did not need the olive oil. I reaized this caused a problem beause I do not have enough pure phytol to perform this experiment and I have confirmed this as a engineering project. I was thinking that I could just use fresh water to fill in what I was going to use the olive oil for each prototype. I found out that phytol was actually hazardous so I will be using a fume hood but I thought that the water might actually help dilute the phytol so it will be less hazardous but still work. Do you think this will work, and if not what could I use with the phytol instead?

-Vlance