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Elrik
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[*] posted on 5-10-2018 at 11:05
Chemistry Gardening


Its the time when I can start planning what will be in next years garden and I'm largely drawing a blank on ideas for new plants that could produce materials of general use in the organic chemistry lab, so I was wondering if others knew of plants with such general usefulness.

Some examples are the easy and surprisingly high yielding production of furfural from corn cobs, ethanol from sugar beets, I've seen spearmint oil used in decarboxylations as the main constituent carvone is a good catalyst for those reactions, and while more of a wild-harvest plant scotch broom can yield sparteine used as a chiral ligand.
I wouldnt mind an otherwise unreactive tertiary amine to use in place of triethylamine. Tobacco is easy to grow but pure nicotine is just too poisonous for a general use like that. Nicotiana glauca produces a good yield of the less poisonous alkaloid anabasine [3-(2-piperidyl)pyridine] as nearly the sole alkaloid but as a secondary amine it would be less generally useful.

Are there plants you've considered growing for reasonable yield of useful catalysts or reagents?
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j_sum1
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[*] posted on 5-10-2018 at 14:43


I know nearly nothing. But my first choice would be some thyme for thymol.
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Sulaiman
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[*] posted on 5-10-2018 at 16:14


Rhubarb stems for cooking and leaves for oxalic acid ?

I gave it one try my first year of chemistry hobby and abandoned the extraction due to frustration :(
The following year I relocated the rhubarb and it died.
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macckone
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[*] posted on 6-10-2018 at 08:44


Let us not forget red cabbage for indicator.

Most of the plant produced chemicals I can think of are drugs.
Some controlled drugs (morning glories, poppies) and some not (foxglove).

Benzoic acid is produced by some plants but not much.
Rubbers and gums of various kinds.
Tannins from appropriate plants.
Dyes from another subset of plants.
Pepper compounds some of which lead to drugs.
Safrole from sassafrass again drugs.
Ephedrine species - drugs.
Gallic acid - specific infection in plants.

Obviously wood for methanol and cellulose.
Sugar cane for sugar and then ethanol and acetic acid.
acetic acid can be converted to acetone via decarboxylation of calcium acetate.
ethanol can be converted to ethylene, ethyl ether and ethane.
acetone can be converted to isopropyl alcohol and then propylene and propane.
Sugar can also be converted to carbon and then acetylene.
Decomposing plant matter can produce methane.
Sugar can also produce oxalic acid.

Basically from sugar and wood you can produce almost any organic chemical given the correct reagents to do the reaction and as long as yields aren't a major concern. And lots of plants can and are used as starting materials for drugs.
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Swinfi2
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[*] posted on 6-10-2018 at 10:52


I just got some wintergreen seeds (Gaultheria Procumbens) should be an easy jumping off point for getting methyl salicylate, hydrolysis gives salicilic acid, transesterification with AcOH should yield aspirin, decarboxylation leads to phenol etc.

Seems like a good plant to have in an apocalypse. (Since its not native here)

And who doesn't like mint berries?

[Edited on 6-10-2018 by Swinfi2]
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Elrik
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[*] posted on 6-10-2018 at 14:36


Rhubarb is a good one. The root is also used as digestive medicine. Sugar beet greens could similarly yield soluble oxalate to process.
Fun fact that many gardeners can tell you, if you collect your own urine and it routinely gets a day or more old in the jug, sheets of calcium oxalate crystals will accumulate in the bottom.
Red cabbage is, indeed, a classic universal pH indicator. Black beans are useful as well, green above pH 7, pink below, grey or purpleish at pH 7.
Tannin was an interesting suggestion. I have a feral mess of Sanguisorba plants I could extract and tannin could indicate for some metals or precipitate some alkaloids.
Woad or indigo would be fun for making dye, but I'm not sure if they could be processed to make any generally useful lab chemicals. I need to dust off 80 year old books.

I thought I remembered in middle school reading in some 1920's chemistry text that sucrose could be heated with something very common, like epsom's salts, to obtain a useful acid or aldehyde in reasonable purity but searching google scholar now doesnt reveal anything that makes something other than a mess of lots of different things, lol
A sugar reaction I do remember is heating with an amino acid for the oxidative decomposition to an aldehyde 1 carbon shorter. Sugar is dirt cheap in stores though.

[Edited on 2018-10-6 by Elrik]
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unionised
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[*] posted on 7-10-2018 at 01:28


Quote: Originally posted by Elrik  

Fun fact that many gardeners can tell you, if you collect your own urine and it routinely gets a day or more old in the jug, sheets of calcium oxalate crystals will accumulate in the bottom.

[Edited on 2018-10-6 by Elrik]

In at least some people's cases the precipitate will be uric acid.

Fairly easy to distinguish- uric acid's a lot more soluble in alkali.
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beerwiz
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[*] posted on 7-10-2018 at 16:30


Add Persian poppies (Papaver bracteatum, 50% thebaine content) to your list, Bentley compounds will make your rich!
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Elrik
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[*] posted on 7-10-2018 at 20:34


I do not regard illicit opioids as useful compounds.
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symboom
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[*] posted on 7-10-2018 at 21:10


There is hundreds sepcies of plants that can work just as good as illicit drugs anyway
Kratom and akuamma very little is known about these plants and the compounds which they contain but what is known is it is ingestable pain releving plant.

thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects. Sounds like what cocaine is suppose to be.

Probally why its ilegal status.
High risk for addiction and dependence. Can cause respiratory distress and death when taken in high doses or when combined with other substances, especially alcohol.


Back on topic
produce materials of general use in the organic chemistry lab
Lemonene from lemons as a solvent
Anisole, or methoxybenzene, It is an ether from anise seeds
benzaldehyde from bitter almond oil

Off topic a little
Pine trees we once used for gasoline replacrment in ww2 due to there high turpine contentand not much carborator adjustment.

And if you have any left over plastic it can be distilled to produce oil and benzene.



[Edited on 8-10-2018 by symboom]




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[*] posted on 8-10-2018 at 18:02


eucalyptus olida. if you can find some seed



Beginning construction of periodic table display
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[*] posted on 9-10-2018 at 03:22


Maybe Dysphania Ambrosio ides (wormseed) could be fun, it's essential oil contains ascaridole (up to 70%), limonene, p-cymene, and smaller amounts of numerous other monoterpenes and monoterpene derivatives (α-pinene, myrcene, terpinene, thymol, camphor and trans-isocarveol), but the fun part is the ascaridole, an organic peroxide, nice for explosions. Exploding plant oil :D




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Sulaiman
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[*] posted on 9-10-2018 at 03:54


Wherever we live we always grow a little Aloe Vera,
we use it on minor burns, and it soothes minor cuts and abrasions,
anything that does not require hospital treatment.

An apple tree adds height and interest to a garden
and supplies apples for fermentation.
I have some apples fermenting as I write
- for vinegar, others prefer cider, or you could distil for ethanol)
Similarly pear and plum trees (and probably others that I've not tried) provide bumper crops of fruit for eating, cooking or fermenting.

I have encouraged blackberry bushes to spread along the outside of my rear fence,
it prevents kids from considering burglary of my lab/shed
(I'm more worried that kids will cause or suffer harm than I am of losing stuff)
and provides a crop of berries, for eating, cooking or fermenting.
Gooseberries make excellent wine.
(tale to tell if asked)

On a purely gardening note,
having a variety of trees, shrubs, flowers, including fruit and vegetable flowers,
and especially a small pond,
increases life and interest massively.

If you feel depressed, sit in a garden - or make one.
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