Live data from Hacker News

A chemist explains the chemistry behind decaf coffee

theconversation.com

51–60 of 180 posts

Re: A chemist explains the chemistry behind decaf coffee

#51

I'd love if all psychoactive compounds could be removed from coffee beans. The stress response and inability to sleep I get from decaf beans is pretty much comparable to that from normal beans (and distinctly different from pure caffeine or green tea)

Have you looked into L-Theanine? It’s an extract from green tea. I add it to my coffee sometimes and it smooths out the experience

Re: A chemist explains the chemistry behind decaf coffee

#52

I'd love if all psychoactive compounds could be removed from coffee beans. The stress response and inability to sleep I get from decaf beans is pretty much comparable to that from normal beans (and distinctly different from pure caffeine or green tea)

Do you put sugar in your (decaf) coffee? A lot of energy comes from sugar.

Re: A chemist explains the chemistry behind decaf coffee

#53

I'd like to talk a bit more about the cheapest and most common process here. They state that ethyl acetate is below the FDA limits and therefore safe. For a start ethyl acetate is still pretty bad but it's not the cheapest. Another common solvent not mentioned here is Dichloromethane. It's a pretty clear cancer causing agent https://www.reddit.com/r/todayilearned/comments/pr8k9v/til_s... You know what else is a solve…

This reminds me of a reddit post from about 10 years ago where people started to notice that when they get decaf coffee at work it sometimes bleeds through the styrofoam cup while the regular coffee never does. There have been several other reports of this since. The most credible theory was that sometimes there is solvent left over after the decaf process: https://www.reddit.com/r/mildlyinteresting/comments/2m2fiy/o…

It's been a hot minute since I've seen a styrofoam cup in the wild.

Re: A chemist explains the chemistry behind decaf coffee

#54
post #27

It is somewhat magical to me that these processes can be as selective as they are. Coffee beans must have hundreds if not thousands of organic compounds in them, and somehow something as simple as co2 (or the other solvents) picks up mainly caffeine. Somehow that is very counterintuitive to me.

I was interested and looked at the actual patent: https://patents.justia.com/patent/4348422 (there seem to be multiple patent documents, but this one adds some explanation), and he writes "I have now surprisingly discovered".

https://tastydecafs.com/blogs/learn-about-decaf/co2-decaf further explains "The story of C02 decaffeination goes back to 1967. It was then when a chemist at Max Planck Institute named Kurt Zosel stumbled upon an interesting discovery. Zosel, like many other chemists, was using high-pressure C02 to remove individual substances from other mixtures."

It must have something to do with caffeine being an alkaloid, while coffee overall is acidic. So I suspect that this pressurized CO2 is able to dominantly remove such alkaloids... I leave the details to a chemist :)

Re: A chemist explains the chemistry behind decaf coffee

#55
So, in the Swiss Water process, caffeine-free coffee is made by soaking the beans in... caffeine-free coffee?

(My initial though was, "then how do you get the cafeeine-free coffee in the first place", but I see the answer is that you can decaffeinate liquids by running them through charcoal filters... something you can't do with solid beans.)

Re: A chemist explains the chemistry behind decaf coffee

#56
post #7
post #4

The decaf process seems expensive so you might expect the end result to cost more, but it never does. Which means either the producers are making less profit on decaf, or they are using lower quality beans. If the latter is true, which seems more likely, that might explain why decaf sometimes tastes less good, separately from the effect of the process itself on taste.

Maybe the extracted caffeine has some market value that can make up for some of the cost of extracting it.

[deleted]

Re: A chemist explains the chemistry behind decaf coffee

#57

Earlier quoted context omitted.

This reminds me of a reddit post from about 10 years ago where people started to notice that when they get decaf coffee at work it sometimes bleeds through the styrofoam cup while the regular coffee never does. There have been several other reports of this since. The most credible theory was that sometimes there is solvent left over after the decaf process: https://www.reddit.com/r/mildlyinteresting/comments/2m2fiy/o…

It's been a hot minute since I've seen a styrofoam cup in the wild.

Ya, the styrofoam is almost as shocking as what this solvent might be doing to the bodies of those who drink it.

Re: A chemist explains the chemistry behind decaf coffee

#58
post #46
post #4

The decaf process seems expensive so you might expect the end result to cost more, but it never does. Which means either the producers are making less profit on decaf, or they are using lower quality beans. If the latter is true, which seems more likely, that might explain why decaf sometimes tastes less good, separately from the effect of the process itself on taste.

CO2 can be reused so it's not that expensive, and the caffeine that gets extracted is sold separately, so it's possible decaffeinated coffee could have more profit that caffeinated. After all, we don't really make synthetic caffeine, we extract it from tea and coffee and add it to a lot of things.

Synthetic caffeine has been commercially used in beverages and medicine for over 100 years. I believe that most caffeine consumed today is actually synthetic, but it's hard to find a good citation for its prevalence. Most of the web pages mentioning synthetic and natural caffeine are spam for "market research" reports or natural health woo.

You can see section "2.1. Production and use" for some relevant information about synthetic and natural caffeine production, as well as dated 20th century statistics about synthetic production:

"Coffee, Tea, Mate, Methylxanthines and Methylglyoxal"

https://www.ncbi.nlm.nih.gov/books/NBK507027/

Re: A chemist explains the chemistry behind decaf coffee

#60

I'd love if all psychoactive compounds could be removed from coffee beans. The stress response and inability to sleep I get from decaf beans is pretty much comparable to that from normal beans (and distinctly different from pure caffeine or green tea)

I had a similar problem. Coffee, decaf, even dark chocolate would be very stimulating and would mess with my sleep, even a single cup in the morning. I tried quite a few things to solve this and ended up discovering that supplementing with molybdenum solved it. Molybdenum is an essential element important in the metabolization of some compounds, including caffeine. It's cheap and may be worth trying.

Also, I found that L-Theanine helped but only for maybe a week or so before it became less and less effective. For me, it was obviously a band-aid solution that wasn't correcting the underlying problem.

Post reply on HN