lignin breakdown products as fuel? was (I want to GCMS Ponderosa Pine bark smell)

[Nathan McCorkle]

Would vanillin make a good fuel? It would smell awesome if it spilled
out a bit at the fuel pump.

On Thu, May 23, 2013 at 4:15 PM, Patrik D'haeseleer <pat...@gmail.com> wrote:
> Yeah, it's mainly vanillin. Vanillin is actually a common degradation
> product of the phenolic compounds in lignin. If anything, I'm surprised
> there aren't more woody plants that smell like it.
>
> Next time you happen to visit a winery that has freshly toasted oak barrels,
> have a sniff: vanilla! That's where those vanilla overtones in some aged
> wines (or brandy, or tequila) come from.
>
> Actually, there are a number of other aroma compounds that are offshoots of
> the lignin biosynthesis or modification pathways. Wikipedia has a
> surprisingly good page on aroma compounds that could be pursued for
> DIYbiosynthesis:
>
> http://en.wikipedia.org/wiki/Aroma_compounds#Aromatic
>
> Patrik
>
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--
-Nathan

[Patrik D'haeseleer]

Plant biomass is about 1/3 lignin, so if we hope to make millions of gallons of biofuels out of plants, being able to use the lignin would be a *huge* advantage. Actually, instead of just burning it, you'd probably want to use it as precursor for phenolic plastics or other bioproducts - much more valuable that way.

Unfortunately, lignin utilization has proven to be a very challenging problem. Nobody so far has managed to do anything truly valuable with lignin, and not for a lack of trying!

As the saying goes in the industry, "you can make anything with lignin, except for money"...

Patrik

[Nathan McCorkle]

Do you think vanillin itself would burn, or be directly useful in
existing engines?

> https://groups.google.com/d/msgid/diybio/b18ad33b-95a8-4119-b427-3bd5b67ac9e3%40googlegroups.com?hl=en.

[Patrik D'haeseleer]

On Saturday, May 25, 2013 11:55:58 PM UTC-7, Nathan McCorkle wrote:

Do you think vanillin itself would burn, or be directly useful in
existing engines?

Well, it's listed as flammable, with a flash point of 147 °C. Compatibility with existing engines depends on a range of factors though.

By the way, the paper industry has had to deal with lignin for decades. An important byproduct of the process of extracting cellulose fibers from pulpwood is something called black liquor - really nasty stuff with the consistency of heavy bunker fuel. The best use they've come up with so far is simply to burn it to run the paper mill. Which seems like a real waste of a lot of really interesting phenolic compounds...

Patrik

[Nathan McCorkle]

seems this sulphite liquor is essentially the same as black liquor:
http://diyhpl.us/~nmz787/pdf/Vanillin_Synthetic_Flavoring_from_Spent_Sulfite_Liquor.pdf

yield with this chemical method is only around 5%

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[Dakota Hamill]

Yeah I was reading about this company Borregaard yesterday that makes Vanillin and a few other fine chemicals from lignin from trees.  I don't remember where I first found the link to start reading about them but...

http://link.springer.com/chapter/10.1007%2F978-3-642-28418-2_12#page-1

http://www.youtube.com/watch?v=z84xFSJi2oM

(the video is pretty bad and boring)

and a google of "Borregaard+vanillin from lignin" will yield some interesting results I assume.

Biomass Conversion: The Interface of Biotechnology, Chemistry and Materials Science

was on google books and has some more detailed info on the process

http://books.google.com/books?id=GSiWctog1WoC&pg=PA393&lpg=PA393&dq=lignin+as+Source+of+Fine+Chemicals:+Vanillin+and+Syringaldehyde&source=bl&ots=IJvRBGMGBs&sig=1nv96T_s-9R49zL3VU-2zlzzU4Y&hl=en&sa=X&ei=kieiUdI7q9vgA9T6geAF&ved=0CD0Q6AEwBA#v=onepage&q=lignin%20as%20Source%20of%20Fine%20Chemicals%3A%20Vanillin%20and%20Syringaldehyde&f=false

Long link....I don't know if that goes to the page w/search on the book or not

[poli]

Lignin can be burned for fuel and is actually very energy dense but isn't allowed in the US. I started this wiki page to collect info on the conversion of lignin to industrial aromatic compounds. Take a look and if anyone is interested enough add some info.

[Dakota Hamill]

I like the link to the UC235 p-toluenesulfonic acid synthesis down bottom, he's one of my favorite chemists on youtube, does some serious stuff.  Makes nurdrage look like a kid!