Science Buddies: "Ask an Expert"

Hello,
Recently I had come up with a science fair idea to clean up oil spills. After much research I found out that I can make a spray to put on the spills that is natural and better for the environment when cleaning up. When I researched this, I found that I needed Phytol, and a plant fat. I am not concerned about the plant fat as I found out from research that is just things like olive oil. My question is, is there a way to get the Phytol out of the chlorophyll? I also need to make sure that if I was able to separate this, it would not costs too much. Any leads or information is appreciated.

Thank you

Hello Vlance,

Welcome to Science Buddies! What a great project idea! I've found some articles on extracting phytol and they are pretty complicated. If you are working with a lab, they may be able to help you apply some of these methods, but I don't think this can be done easily at home. You also may be able to purchase phytol from a chemical supplier like sigma aldrich, but again you would have to work within a lab to make sure proper safety precautions are followed.

I'm sorry that I can't be more helpful!

Good luck and maybe another expert will be along to help you further.

Hi Aj,
Thank you for the information! I was wondering if you think I could find a lab to help me with this project for free? Last year I did a project with water and the lab tests cost lots of money. I was wondering if you know any labs I could contact in Massachusetts that might be willing to help? Also if any one else has any tips I would love to hear them!

Thanks again!
Vlance

Hi Vlance,

I read your post and thought maybe I can make some suggestions. Working in a research lab is a great way for you to do a project but from the lab manager's point of view it is often too costly for such a short term. It can't hurt to try, however. Do a literature search in your area of interest and see if there are any researchers near you that sound like they might be interested in oil spill remediation.

At the same time, assuming that finding a research lab that will take you on is problematic, it is a good idea to plan experiments for your school lab or home lab. Do you have a school lab to work in? Doing your experiments there could save the expense of buying equipment and reagents.

I wasn't familiar with using phytol-based oil slick thickeners so looked it up:

http://www.conservationmagazine.org/201 ... l-cleanup/

https://www.smithsonianmag.com/innovati ... 180955815/

http://www.audubon.org/news/watch-biode ... -spilt-oil

It sounds like phytol has a lot of potential as a biodegradable oil slick remover to replace the silicone-based chemical 'herder' that is currently being used to clean up an oil spill. The question is where can you get phytol. First off i wanted to know exactly what 'phytol' referred to so here's the wiki info:

https://en.wikipedia.org/wiki/Phytol

This showed what the phytol molecule looks like--a diterpene with an alcohol OH--but did not tell how to make it from some natural source such as chlorophyll. If you look up the structure of chlorophyll (https://en.wikipedia.org/wiki/Chlorophyll) you see the phytol chain sticking out from the chlorin-magnesium complex so really all you need to do is split that part off and you have phytol. This splitting of the phytol from the porphyrin ring is known as hydrolysis and can occur in the presence of dilute acid, but first you need to obtain chlorophyll from some plant material. You can extract chlorophyll from spinach leaves by grinding them in acetone but you have to be careful with this chemical because it is toxic. Do some searching online for the methods of chlorophyll extraction:

https://www.google.com/search?ei=C5_yWc ... Xp0AlcAX74

This is about all I could find so far. I think your project is doable without costing too much. You can create an oil slick in a large tray and then test the phytol extract for its ability to consolidate the oil so it is easier to remove. There are some details to work out but I think we can help you with that.

Good luck!

Sybee

Hi SciB,
Thank you so much! This information is really going to help my project! I just wanted to ask you that when I’m simulating the oil spill if I light it on fire it once I put the spray on? This is what my research had told me to do, but I wanted to ask you if this seemed correct.

Thanks so much,
Vlance

Hi Vlance,

From what I have read about treating oil spills it is preferable to use a pump and a hose to suck the oil into a holding tank and dispose of it safely without further polluting the environment.

If you burn the oil the combustion products will put a lot of smelly, probably toxic black smoke into the air along with carbon dioxide which will further promote human-caused atmospheric warming.

Get a small water pump and test it first to make sure it will work with oily water. If you really wanna do it right you could get an RC model ship and put the pump on that then after you apply the phytol, maneuver the ship near the oil spill and turn on the pump--no more oil!

Good luck!

Sybee

Hi SciB,
I am still a little confused about what your saying. So the spray will help break down the oil and then I put a RC model in? Will the boat moving around in the oily water have the oil disappear? Also wouldn’t the water pump just suck up all the water and oil not making the spray the effective part? Your information is helping me a lot, and I just want to make sure that I am understanding everything properly. Thank you so much!

-Vlance

Sorry about the confusing part--I was visualizing a model of how I think the oil could be gelled and collected rather than burned. You are right that a pump would probably not suck up just the oil, but I still like the RC ship idea for the visual interest. Burning the oil would be dramatic but I have a feeling your science fair coordinator would nix that idea as against fire code regulations.

I did a search for using surfactants or what the jargon calls chemical 'herders' to congeal the oil but all the sites I saw burned the oil after it gelled. Your project could really be important if you can figure out a practical, reasonably inexpensive but effective way of pumping or scooping up the congealed oil after phytol treatment so that it doesn't have to be burned and pollute the air.

I really have no idea how thick the resulting gelled oil is--do you know? There are gear-driven pumps that will move very thick oil but I don't know if they would work with yours: https://utahbiodieselsupply.com/goldstreampump.php

Oil skimmers physically collect oil from oils spills on ocean or fresh water. Afterwards the oil can be recovered and does not need to be burned: http://www.oilspillprevention.org/oil-s ... t/skimmers

I don't know if a skimmer could be used to collect congealed oil. Try to find out.

I think you have the makings of a great science project! Think about alternatives to burning the oil spill and see if you can come up with a way to collect the phytol-treated oil. People who clean up oil slicks should be interested in such a method because it eliminates the problems of burning and allows them to recover the oil in a usable form. Sounds like a win-win to me. Don't hesitate to call companies that make oil pumps, skimmers or collectors and ask them for recommendations. They like new ideas because it can mean more money in their pockets so they will talk to you, but you have to be able to explain your method very clearly and use the correct jargon.

Good luck!

Sybee

Hi SciB,
I was thinking about what you said for getting the oil out after it has congealed from the spray. Do you think peat moss would work? I was reasearching and it says that peat moss only collects oil and not water. Do you think this would work because it is a inexpensive material and can collect the oil?

Thanks again,
Vlance

Why don't you try it? Make an oil slick and put some peat moss on it then do it again using phytol first and see how it works. I know peat moss is very absorbent so it might suck up the oil on its own. The phytol might congeal the oil so much that the peat moss won't be able to absorb it. And then, how will you harvest the peat from the water? These are all questions that you need answers to before you can make a hypothesis.

If you think about real-world conditions, how would the oil-slick workers collect the oil-soaked peat? And would they be able to recover oil from it? As an inventor of a new process, you need to think about every detail from start to finish and come up with a plan that would meet every objection. Burning the oil is simple and costs nothing, so that appeals to people who don't care about carbon pollution. On the other hand, collecting the oil in such a way that it can be recovered and sold means extra money and that would be a plus.

Did you figure out a way to obtain phytol that doesn't use hazardous chemicals or cost too much? You need to extract some and try it right away to see if it will make oil gel or else your project is done. It's time to do some prelim experiments and get some real information instead of speculation. Post and let us know what happens.

Sybee

Hi everyone,
For my project I need to extract phytol from spinach leaves. I know that I need to do acid hydrolysis but I don't know how. I have looked all over for a procedure to do acid hydrolysis but I can't find one, and I was hoping someone might know how or have a link that could help me.

Thanks,
Vlance

Moderator note: Hi Vlance, you will notice that I merged this post with your other posts. Please keep these together so the experts who have been helping you will see that you have posted a follow-up question. Thank you and good luck with your project.

Hi everyone,
For my science experiment I need to extract phytol from spinach, and to do that I need to perform acid hydrolysis. I have looked all over the internet to find a procedure on how to perform acid hydrolysis, but have come up empty handed. I was hoping someone could give me a link to a website that would describe the procedure.

Thanks,
Vlance

Hi Vlance,

I'm glad to see you are still working on this project. My last post was in October 2017 and I would not have seen this one if the moderator had not moved it to your old thread. That is why everyone needs to keep all their posts together.

In one of my previous posts, I included all the information that I found on acid hydrolysis of chlorophyll. There was one paper from 1962 that discusses it but it is in the Journal of Organic Chemistry and I do not have access to that one.

Several papers talk about acid hydrolysis and show reactions in which it splits the phytol from the chlorophyll, but I have not seen any specific methods which gives the type of acid used, the concentration, temperature and length of treatment. A couple of websites talked about the color change that chlorophyll undergoes when exposed to acid and heat http://homeguides.sfgate.com/plant-pigm ... 00250.html

The bright green of the chlorophyll turns to a dull brownish green when the chlorophyll is hydrolyzed, so you could use the color change as an indicator of hydrolysis. You could try using vinegar or lemon juice at a temperature of 45C to hydrolyze the chlorophyll using the color change as the endpoint.

Did you plan to try and separate the phytol from the rest of the chlorophyll molecule? It would be easier to just use the acid hydrolyzate after neutralizing it with sodium bicarbonate.

Let me know what you want to do and if you have more questions.

Sybee

Hi,

I found a link to a similar science buddies topic that might be helpful: viewtopic.php?t=18324

It seems that treating something (in your case the spinach) with a dilute acid will allow acid hydrolysis to occur. Any other expert input would be great.

I hope this helps! Sorry that I couldn't find a more specific procedure for your experiment.

Elena

Hi everyone,
For my project I need to do acid hydrolysis to get phytol out of spinach leaves, but I find myself not knowing how to do this. I have looked online but can't find a straight forward procedure on to do the acid hydrolysis. Can anyone send me a link or describe how to do the acid hydrolysis?

Thanks,
Vlance

PLEASE keep ALL your questions about your project in one thread!

If you fail to do that then others may not see the questions and answers that have already been discussed.

I have tried to help you with the formation of phytol from chlorophyll by acid hydrolysis. In my most recent post to your other thread (Jan.12) I suggested that you try adding acetic acid (vinegar) or citric acid to a chlorophyll preparation and looking for a color change. Did you do that?

If you cannot find a specific recipe for a method then you have to experiment and improvise. You know that acid will split phytol from chlorophyll and when this happens the color changes from bright green to olive brown. I suggest that you not try to separate phytol but rather use the plant extract after neutralizing the acid with sodium bicarbonate. If you have pH paper you can use it to see when the solution is neutral, otherwise just add bicarb until it stops bubbling off carbon dioxide.

Sybee

Ok, next time I will make sure to post to the correct thread, sorry about that. Thank you for the information.
-Vlance

Ok, but the important thing is what are you planning to do? What do you think of my suggestion about using acid-treated chlorophyll without separating phytol? I think you have a really interesting idea for oil-spill remediation and I would like to see you test it. Scientists always have to do preliminary experiments to test their conditions. Just try your chlorophyll prep with and without acid treatment and see what happens. At least then you would have some data.

Sybee

I think you idea provides me with a good solution. So far this is my top choice for separating the Phytol. I do not have to have my data in until March, but the experiment must be performed before that. I will research the bicarbonate sodium to understand more about it and how to get it. Once I figure out how I will get the Phytol out I can start the rest of the project.

Thanks,
Vlance

Ok. But I am still advising that you DO NOT try to separate phytol from chlorophyll. Just try it first.

Sodium bicarbonate is a common chemical that you can buy in the grocery store. When you add It to the chlorophyll acid mixture after acid hydrolysis It simply neutralizes the acid. Buy some bicarbonate, add it to some vinegar and you will see what I mean.

Don't wait to start experimenting. Your project has a lot of details that still need to be worked out.

Sybee

Hi Sybee,
I just wanted to update you that on Tuesday I will actually be testing, your suggested method, to get the Phytol out. Thank you for all of your help! I will update you with my results after the experiment. Also I just wanted to ask you how to use the bicarbonate sodium (I will use baking soda), do I put it on after I use the vinegar or mix it in with the vinegar?

-Vlance

Hi VL,

Glad that you are going ahead. I'm always impatient to see some results!

The purpose of adding the bicarb is to neutralize the acid. So, how do you know how much bicarb to add? The best way is to use pH paper. Are you familiar with that from chemistry? Have you had chemistry? You can get pH paper test strips at Petsmart or Petco or an aquarium supply store and they come with instructions. I think even some Walmart stores have them.

The bicarb (baking soda) is added AFTER the hydrolysis. I don't exactly know how to judge when the hydrolysis reaction is finished, but I would let it go at least one hour at a temperature of 75 F (24 C) or warmer.

When you think the chlorophyll extract has been hydrolyzed, read the pH using the paper strips and add a tsp of bicarb. You should see fizzy bubbles of carbon dioxide (CO2) being given off. That's from the bicarb. Check the pH again. It should be a little higher (neutral is 7.0). Keep adding bicarb and checking the pH until it gets to 7--you're done!

Let me know what happened, ok?

Have a good weekend.

Sybee

Hi Sybee,
Sorry I was having some technical issues and all my updates are now posted in the post below.

-Vlance

Hi Sybee,
Today I did the experiment of trying to separate the phytol. I had 2 viles one with vinegar and chlorophyll and the other with citric acid and chlorophyll. I did not see any obvious results of separation but when I got home I examined the solutions again. I found that the vinegar solution had formed a yellowish green outer layer after about an hour. This is a photo of what I saw, [photo removed by student]. On the top left is the vinegar solution, the top right is the citric acid solution, and the bottom left is the control chlorophyll. After I while I have noticed in the vinegar solution that it started separating. This is a picture of what the separation looks like in the vile, [photo removed by student], and this is what it looks like compared to regular chlorophyll [photo removed by student] (the darker liquid is the chlorophyll, and the lighter liquid is the separated part of the vinegar solution). I was wondering if you could tell me if I had extracted phytol.

-Vlance

Moderator note: I have merged all your posts under your first topic: Oil Spills. As Sybee has told you, please keep all of posts on this project in this topic, otherwise she won't know that you have posted a reply to her very excellent guidance. Thank you!

Hi Vlance,

Hmm! If its green, it's still chlorophyll. That means the acid treatment was not strong enough to break the bond between the phytol and the other part of the chlorophyll.

Ask your science teacher if the school has a lab where you could use a strong acid under supervision.

If strong acid is out, there's still one more Plan B--vinegar plus heat. Have you ever boiled green beans too long and had them turn a disgusting khaki color? That's phytol! To heat your chlorophyll I would use a steamer.

You can make a steam generator by putting a pan of water on the stove and bringing it to a boil. Turn down the heat so that it is just simmering and put a glass bowl on top of the pan. The bowl has to be small enough so that the bottom is in the steam but large enough to rest on the lip of the pan. Place some chlorophyll in the bowl and add twice its volume of white vinegar. Take a Before picture. Let it steam for 15 minutes or so and observe the color. Take a picture. If it looks brownish, that's good. If not...well, just try heating it longer.

I just had an idea. You might be able to get phytol by cooking spinach leaves in a pan with vinegar until they turn brownish. All green vegies that I have cooked too long or on too high a heat turned brown, So, instead of making a chlorophyll extract first, cook the leaves first and then make an extract from them. Hey, it's worth a try! Do you like spinach?

Good luck!

Sybee

Hi Sybee,
I am very happy that you came up with another plan to get the phytol out. Do I have to use white vinegar or will any vinegar do? Do I neutralize the phytol and vinegar mixture with baking soda after I take the spinach leaves out? Could I do this part of the experiment by myself or do I need adult supervision? Thank you so much for your help without you this science fair project would have never happened!

-Vlance

You are welcome, Vlance! Happy to keep your project on track.

Use only distilled white vinegar because the others (wine, apple cider, balsamic) have fruit esters and other ingredients that might interfere.

So, once you cook your spinach with vinegar, let it cool and check the pH with pH paper. You don't want to add too much baking soda. Add a little and when it stops bubbling, check the pH. Try to get close to pH 7.

Take pictures again and put them on flickr. I want to see nice yukky brown-green phytol!

Sybee

Hi Scybee,
I told my science teacher about making and using a steamer to get the phytol out, but she wanted me to use the already extracted chlorophyll. Would this work the same as the spinach and be as successful? I will either do the steamer experiment today or some time in the next couple of days, and I wanted to make sure that I am choosing the most successful route.

-Vlance

Brown, brown--think brown = phytol

No, you can't do the experiment with chlorophyll. Your original procedure calls for phytol and that's what you should use. Just cook some spinach until it turns brown, then do the chlorophyll extraction on that.

The steaming method allows you to control the temperature better--steam by definition is about 212 F. If the leaves stubbornly refuse to turn brown, then just stick them in a pot and keep cooking them until they do. But do take pictures and record what you do carefully in your lab notebook.

Sybee

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.

-Vlance