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Cou
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[*] posted on 8-6-2020 at 16:10
Cou's esters megathread


current collection with scent description:


  1. Acetate esters

    1. methyl acetate (ethereal sweet fruity)
    2. ethyl acetate (ethereal fruity sweet)
    3. propyl acetate (pear)
    4. isopropyl acetate (pear)
    5. butyl acetate (apple)
    6. isobutyl acetate (cherry)
    7. (RS)-sec-butyl acetate (grape)
    8. pentyl acetate (banana)
    9. isopentyl acetate (banana candy)
    10. hexyl acetate (green floral pear)
    11. heptyl acetate (rum woody)
    12. octyl acetate (orange mushroomy)
    13. nonyl acetate (green herbal mushroomy)


  2. Propionate esters

    1. ethyl propionate (pineapple)
    2. isopentyl propionate (real banana fruit)


  3. Salicylate esters

    1. methyl salicylate (rootbeer minty fresh wintergreen)
    2. isopropyl salicylate (green leather floral)



I'm now branching out into more novel esters. today i will try making: isopentyl propionate, to find out if it will share that same delicious banana candy smell with isopentyl acetate.

i am planning a multistep synthesis of pentan-3-yl acetate (the ester of pentan-3-ol and acetic acid)



[Edited on 9-6-2020 by Cou]




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[*] posted on 8-6-2020 at 18:02


did you make or buy all of those esters ?



CAUTION : Hobby Chemist, not Professional or even Amateur
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Cou
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[*] posted on 8-6-2020 at 18:05


Made them all



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[*] posted on 8-6-2020 at 20:32




Liquid in beaker on right is distilled isopentyl propionate.
Boiling point matches CRC literature value of 160 C

It smells similar to isopentyl acetate, but smells like actual banana fruit instead of banana-flavored candy. it has the slight tart that cavendish bananas have.




[Edited on 9-6-2020 by Cou]




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[*] posted on 8-6-2020 at 21:45


I need to get a better space and a selection of alcohols like yours, I just have methanol, isopropanol, n-butanol and n-pentanol and for organic acids salicylic acid and sorbic acid.
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[*] posted on 8-6-2020 at 21:55


www.consolidated-chemical.com is a good source for many alcohols and a few carboxylic acids, they ship to individuals. Many can be found on amazon, if not on their webpage.

[Edited on 9-6-2020 by Cou]




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[*] posted on 9-6-2020 at 00:49


you should also try with benzoic acid c:




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[*] posted on 9-6-2020 at 05:36


Are you going to try it with chiral ester?
I mean, using chiral alcohols.
That would be really interesting!

In another thread I gave you the recommendation to make chiral alcohols by the yeast reduction of ketones.
I can tell you, I made chiral alcohols by the reduction with yeast and celery, from phenyl-2-propanone, resulting in both enantiomers, and they smell really different... and even more surprising, the sum of both, the racemic alcohol made with NaBH4, also smells different to each of the chiral ones.
I haven't tried mixing both together though, too valuable :D

A good compound to try this out with would be acetophenone I would say, or propiophenone, which are easily made or cheaply and then can be esterified as usual.
Maybe that would be a cool addition to your experiments?
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[*] posted on 9-6-2020 at 07:28


Quote: Originally posted by Cou  
www.consolidated-chemical.com is a good source for many alcohols and a few carboxylic acids, they ship to individuals. Many can be found on amazon, if not on their webpage.

[Edited on 9-6-2020 by Cou]


Awesome, I am checking the page out now.
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[*] posted on 9-6-2020 at 09:49


Quote: Originally posted by karlos³  
Are you going to try it with chiral ester?
I mean, using chiral alcohols.
That would be really interesting!

In another thread I gave you the recommendation to make chiral alcohols by the yeast reduction of ketones.
I can tell you, I made chiral alcohols by the reduction with yeast and celery, from phenyl-2-propanone, resulting in both enantiomers, and they smell really different... and even more surprising, the sum of both, the racemic alcohol made with NaBH4, also smells different to each of the chiral ones.
I haven't tried mixing both together though, too valuable :D

A good compound to try this out with would be acetophenone I would say, or propiophenone, which are easily made or cheaply and then can be esterified as usual.
Maybe that would be a cool addition to your experiments?


Could I use yeast to make the R and S enantiomers of 2-butanol from 2-butanone?




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[*] posted on 9-6-2020 at 10:38


Well no, you can only get the (S) enantiomer with yeast.
For the (R) enantiomer you have to use something else.
But options are plenty, cheap and easy to get, just not so nice to work with since you use like 100g of (plant) material for 1g of substrate.
As said, I used celery root for example.
Here is the thread in which I posted some papers describing that route: http://www.sciencemadness.org/talk/viewthread.php?tid=154179
One of them has a table in which several of those biocatalysts are listed, together with the respective part of the plant and the resulting enantiomer.
Onions are, if I remember correctly, another biocatalyst resulting in (R)-alcohols for example.
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[*] posted on 9-6-2020 at 15:12


Quote: Originally posted by karlos³  
Well no, you can only get the (S) enantiomer with yeast.
For the (R) enantiomer you have to use something else.
But options are plenty, cheap and easy to get, just not so nice to work with since you use like 100g of (plant) material for 1g of substrate.
As said, I used celery root for example.
Here is the thread in which I posted some papers describing that route: http://www.sciencemadness.org/talk/viewthread.php?tid=154179
One of them has a table in which several of those biocatalysts are listed, together with the respective part of the plant and the resulting enantiomer.
Onions are, if I remember correctly, another biocatalyst resulting in (R)-alcohols for example.


One of the papers shows that they use 2-Methyl-CBS-oxazaborolidine to reduce butan-2-one to (R)-butan-2-ol. It doesn't name any plants for the R enantiomer. I might consider buying that from chemsavers if I'm serious about making stereospecific alcohols and their esters. It's very expensive but it's catalytic so I think a tiny amount can go a long way.

[Edited on 9-6-2020 by Cou]




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[*] posted on 9-6-2020 at 17:38


I might have forgotten the one or other general overview giving paper?
This here names a few though, like red beet or coriander: https://www.researchgate.net/publication/239197278_Edible_ca...

Well, there was none in the papers that was used to reduce phenylacetone either.
The papers just said, carrot cells reduce ketones to (S)-alcohols, just like yeast does too, and that celery reduces ketones to (R)-alcohols.
And then I tried, and it worked for both.

2-butanone is cheap and a trip to the grocery store won't be costly either for these materials, maybe you should simply try if it works for you too?
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[*] posted on 9-6-2020 at 23:43


Motivation here

https://jameskennedymonash.files.wordpress.com/2013/12/table...


table-of-esters-and-their-smells.jpg - 1006kB

[Edited on 10-6-2020 by j_sum1]




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[*] posted on 10-6-2020 at 00:20


I have that poster on the wall

The image is way too big. Resize it to 25% on mspaint and post new imgur link




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[*] posted on 10-6-2020 at 04:43


Quote: Originally posted by Cou  
I have that poster on the wall

The image is way too big. Resize it to 25% on mspaint and post new imgur link

Due to the size of the image, this is truly a megathread :cool:
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[*] posted on 11-6-2020 at 12:49


as someone who likes mailing stuff also as a hobby, I would like to mail tiny samples of esters (1 mL) to anyone who wants to see for themselves what they smell like. Can mail domestically in USA or internationally
all I would request is enough money thru Venmo to cover the cost of chemicals used, postage, and the vial it comes in. Probably about $5 starting price and then addition $0.50 per ester.
Send me U2U if you are interested, which ester you would like to receive, or i can even make a custom ester if you request one not already on the list. I can send a free sample to a trustworthy SM member first

[Edited on 11-6-2020 by Cou]




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[*] posted on 11-6-2020 at 14:17


I gotta say, Cou. I am really impressed with this project. It was a cool idea to begin with and you seem to have executed it well.

Just a couple of questions: how thoroughly are you working up your products? I presume carbonate wash, water wash then sep funnel. But are you also drying over sieves and redistilling? Is your goal a highly pure anhydrous product or do you simply want to make the ester at sufficient purity to smell it?

Are you doing screw-top vials or something with a more permanent seal? And how would they go with posting?
If you had something that was resealable, I might be interested in a full set. I have shown that graphic above to students before but it is another thing entirely to get them to smell these things. And having a range would be really good. Let me also join Ubya in suggesting the next step might be benzoic acid esters. (I have one myself in the next room waiting workup.)

Anyway, let me know what sort of price you would need for a range of esters in vials packaged well and posted to Australia. Send a U2U.

J.
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[*] posted on 11-6-2020 at 16:58


Cou,

bravo. You've found a niche and i actually look forward to seeing your posts now.

U2U sent......




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[*] posted on 11-6-2020 at 17:49


After finishing Fisher esterification reflux, I first wash with a large volume of water, then wash ester with saturated sodium bicarbonate solution until it stops fizzing. Then dry with calcium chloride pellets, then do simple distillation. If the alcohol is bigger than 6 carbons, andr the boiling point is significantly lower than expected, theres probably some alcohol that the water washes couldnt remove, so I then wash with a deep eutectic solvent, 1:2 molar mixture of choline chloride and glycerol, which removes fatty alcohols. Then dry and distill once more



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[*] posted on 13-6-2020 at 01:08





Octyl butyrate boils at 239 C
Not a very interesting one. it has a very faint slightly sweet waxy smell. might be contaminated with trace amounts of butyric acid, really hard to remove since it taints all distillation equipment. it makes me think of the color hot pink.

I am about to send my first package of esters to an SM user. I am happy to send 1 mL samples of esters to anyone who wants to smell them. $4 starting price and an additional $0.50 for each additional ester.

[Edited on 13-6-2020 by Cou]

[Edited on 13-6-2020 by Cou]

[Edited on 13-6-2020 by Cou]




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[*] posted on 13-6-2020 at 16:20


Cou, it is really joyful to see you having found a niche, it is obvious you really found something which in turn gives you a lot back :)

I have found my own nichein hobby chemistry only a few years ago, and boy, that was a ride so far, and it never ends!
For me, it is the class of aminoketones, making them and making something in turn out of them, and over time it only gets larger and larger, and this is so cool :)
The fascination with them always sticked to me, and over time I realised the gigantic potential of being well accustomed with substances from this class, as so many belong to it, and I discovered additional ones of interest like, weekly.
While I make two of them, ten or twenty others pop up I never knew before, yada yada, and the whole thing exponentially grows :D
And I got really good at it, and while at it, my general chemistry skills also got much better, oh how it makes me happy to remember the day of my first aminoketone - a gamechanger and the begin of a joyful trip :)

Let me tell you one thing: at the point when you have accessed all the obvious and common target compoiunds, you might experience a little slowdown regarding finding new and interesting products, and that comes along with whatever you find being also harder to make.... I had that too when I made, maybe around 20 different and easily accessed products...
But don't let that affect you negatively!
This is the point where the real fun begins!
With increasing difficulty, they also increase the amount of fun and experience you gain, exponentially, and in turn a hugely growing confidence :)
From then on, it will get much better and really good :)

In maybe just three years people probably know whom to ask preferably for ester related stuff ;)
I hope you will enjoy the ride and stick on that topic as long as it really gives you as much satisfaction as it obviously seems to do :D
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[*] posted on 13-6-2020 at 22:57


Hi Cou, very nice! I'm planning to synthesize heptyl butyrate, which should be wasp attractant, I want to create a trap for wasps.



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[*] posted on 15-6-2020 at 06:18


Very nice! I'm also a big fan of Esters! I can really recommend making Methyl and Ethyl Cinnamate! I made them using the acid chloride via SOCl2 :)



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[*] posted on 15-6-2020 at 07:28


Quote: Originally posted by Tellurium  
Very nice! I'm also a big fan of Esters! I can really recommend making Methyl and Ethyl Cinnamate! I made them using the acid chloride via SOCl2 :)


I second the methyl, which is easily purified by crystallization. Not a big fan of the ethyl, which is much harder to crystallize.




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