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Topic: List of Things that annoy us in articles.  (Read 10577 times)

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Offline curiouscat

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List of Things that annoy us in articles.
« on: August 18, 2013, 02:29:53 AM »
Just for fun (motivated by another thread) I decided to list some things that irritate me in Chemistry / Chem. Eng.  papers. Please take this in a fun spirit, perhaps a flippant look at our profession. PS. I'm not immune to committing some of these myself.

Would love list additions to the list, critiques, opinions from others. (Mods: I hope this isn't too off topic?)

1. Reporting both a high selectivity and high conversion in the abstract. ( They forgot to mention that at 15% conversion they got 95% selectivity & they got 95% conversion but then selectivity was only 15% )

2. Almost complete conversion of acetaldehyde were observed. (Only when we used a 10x stoichiometric excess of other reactant)

3. Very high selectivity to desired product were observed. (We were working with 0.5 % aq. solutions)

4. Reporting concentrations as GC Area percents. Ughh.

5. This offers a novel renewable route to motor fuels. (Starting from oil extracted from salmon or some such exotic feedstock 10x the price of diesel )

6. Both high conversion and selectivity were observed. In the same experiment. (But we had to load ~50% of reactor mass with precious Ru catalyst. Yes, stirring was a bit problematic but we swapped in a larger motor.)

7. Very High selectivities make our route a promising route versus current industrial processes that operate at 70% selectivity. (Our dilution factors / low conversions mean that they'll need reactors the size of a Goodyear blimp and recycle lines the size of Hoover Dam water pipes, but that's ok. Oh, and our Catalyst Loadings will mean the plant will rival Fort Knox at precious metals. )

8. We got amazingly high concentrations of desired product in the organic phase. (Material balance? What's that? )

Offline discodermolide

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Re: List of Things that annoy us in articles.
« Reply #1 on: August 18, 2013, 03:37:21 AM »
One I don't like is when someone comes up with a new wonder reagent and says it it general for all substrates. Then you look at their tabulated examples which are usually restricted to the simple aromatics they had in the stock room and a few simple alkanes or the like. But point wonder reagent at something a bit more complicated and it fails miserably.
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Offline DrCMS

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Re: List of Things that annoy us in articles.
« Reply #2 on: August 18, 2013, 04:28:43 AM »
Some of my pet peeves are:

Reports such as "the desired product was obtained in 6% yield and purified by column chromatography";  no your desired product is a byproduct of the reaction you choose and you just used loads of time and solvent to get enough out for the next step and now expect somebody else to figure out how to actually make that key intermediate in your "brilliant" new synthesis.

Anything that quotes 17hr reflux, stirred at room temp for 48hrs, dried for 3 days etc etc.  Yeah but what does it really need to work?

"NMR of the resulting reaction mass indicated the target molecule had been formed"  excellent and what was the yield and could it be isolated?

Any new process that uses ethyl acrylate; yes its a cheap monomer but it stinks so bad a lot of companies (ours included) refuse to handle it.  If you're new product is guaranteed to have sales of >1000T per year by year 2 great it will pay for the investment.  If not it will not get past the cost of scale up facilities.  Anyone who thinks they can guarantee sales >1000T by years 2 for a new product is a deluded fool.

Any new process that uses TDI; yes its a cheap isocyanate but its volatility and toxicity means it has to be handled in a closed system.  Investment as per the above.

Any new process that uses a chlorinated solvent, carbon tet in particular but the rest of them cost a lot to deal with and sooner or later will get banned as well.

Any new process that uses benzene for the obvious reasons

Any new process that uses diethyl ether it's just too flamable.

Any new process that uses THF as I just can not stand the smell of it anymore.

Offline curiouscat

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Re: List of Things that annoy us in articles.
« Reply #3 on: August 18, 2013, 05:18:18 AM »


Any new process that uses a chlorinated solvent, carbon tet in particular but the rest of them cost a lot to deal with and sooner or later will get banned as well.

Any new process that uses benzene for the obvious reasons

Any new process that uses diethyl ether it's just too flamable.


All true, but for the western hemisphere. Visit a small / medium scale plant in China, India etc. and you'll see benzene, chlorinated solvents etc. quite merrily and rampantly in use.  :)


« Last Edit: August 18, 2013, 05:59:15 AM by curiouscat »

Offline 408

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Re: List of Things that annoy us in articles.
« Reply #4 on: August 18, 2013, 02:56:17 PM »


Anything that quotes 17hr reflux, stirred at room temp for 48hrs, dried for 3 days etc etc.  Yeah but what does it really need to work?



You would hate some of my papers.... ;D  One has "was stirred for nine days at rt" because I was on vacation.   ;D

peeves
Anything with hydrazine or pyridine.
Any synthesis with a yield of <20 mgs
Any synthesis where I need to evaporate a large volume of aqueous solution that is near saturated with inorganic salt.... 6h later...

"The methanol water solution was evaporated"  (oh god the bumping)

"was recrystallized" how hard is it to include the solvent system? Similarly, "purified by column chromatography" without the solvent mixture being included.

synthesis uses a large molar excess of cyanogen azide..."the reaction was evaporated"...IT HAD TO GO SOMEWHERE :o :o

Old Russian papers where the reaction scheme is the entire detail of the synthesis and you need to figure out again all the reaction and workup conditions. 


Offline 408

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Re: List of Things that annoy us in articles.
« Reply #5 on: August 18, 2013, 04:51:07 PM »
And the icing on the cake:
http://www.nrcresearchpress.com/doi/abs/10.1139/v69-606#.UhFBRVKhzD4

"hey lets distill 10g of mixed primary explosives"


Offline Dan

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Re: List of Things that annoy us in articles.
« Reply #6 on: August 19, 2013, 01:37:20 AM »
"was recrystallized" how hard is it to include the solvent system? Similarly, "purified by column chromatography" without the solvent mixture being included.

^This one drives me mad.

"Neutralized with conc HCl/50% NaOH" - Really? You can reliably hit pH 7 using very strong, concentrated acids/bases?

"NaBH4 was quenched with water" - no it wasn't, water is a perfectly good solvent to conduct NaBH4 reductions
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Offline 408

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Re: List of Things that annoy us in articles.
« Reply #7 on: August 19, 2013, 03:26:16 AM »


"Neutralized with conc HCl/50% NaOH" - Really? You can reliably hit pH 7 using very strong, concentrated acids/bases?


with ph paper as your endpoint determination as well as larger scale, sure you can ;)


Forgot one of my worst general peeves: extraction solvent volume of over a litre.  Mass of compound within? 100mgs.  poor scaleup  :(

Offline Corribus

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Re: List of Things that annoy us in articles.
« Reply #8 on: August 19, 2013, 09:53:39 AM »
My pet peeves are more related to presentation and analysis of results than actual usefulness of content. Many times I read articles and find myself asking how this ever got through peer review. Experimental details vague or wholly absent, poor proof-reading and grammatical errors, references that don't actually have anything to do with what they've been referenced for, questionable data analysis procedures (my ultimate favorite: a linear fit through two points, or a polynomial fit through three), complete disregard of statistics (something that is endemic to academic science: e.g., calling something 'significantly larger/smaller' without actually having any statistical basis to do so), poor quality figures, and so forth.

On other pet peeve I have, and I know this is pretty stupid: article titles framed as questions.  I hate this practice with a passion, though I'd be hard pressed to explain why. 

@408

LOL, I had a number of published syntheses where the final yield was ~20 mg or sometimes less.  In my defense, though, as a spectroscopist this was usually about 1000x what I needed to do my experiments.
What men are poets who can speak of Jupiter if he were like a man, but if he is an immense spinning sphere of methane and ammonia must be silent?  - Richard P. Feynman

Offline curiouscat

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Re: List of Things that annoy us in articles.
« Reply #9 on: August 21, 2013, 03:57:09 AM »
complete disregard of statistics (something that is endemic to academic science: e.g., calling something 'significantly larger/smaller' without actually having any statistical basis to do so), poor quality figures, and so forth.

You think applied science / industry are better with statistics? :)

Offline curiouscat

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Re: List of Things that annoy us in articles.
« Reply #10 on: August 21, 2013, 04:03:34 AM »
One I don't like is when someone comes up with a new wonder reagent and says it it general for all substrates. Then you look at their tabulated examples which are usually restricted to the simple aromatics they had in the stock room and a few simple alkanes or the like. But point wonder reagent at something a bit more complicated and it fails miserably.

@disco:

You having a rich industrial experience, a question:

What were the lowest concentrations of reactants you remember  using in any of your commercial (or almost commercial) processes?

I keep coming across  low conc. synthesis: e.g.

"The following general procedure was used for the aldol condensation. First, 4-nitrobenzaldehyde (76 mg, 0.5 mmol) was dissolved in acetone (10 mL), and the respective catalyst was added (0.05 mmol total amines and/or acids)"

That's effectively <1% conc. of reactant.  I'm wondering if this is not too odd for you pharma guys etc. With my petro / commodities background these are bizarrely low conc. to me. Absolutely unworkable for any viable process.

Offline Archer

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Re: List of Things that annoy us in articles.
« Reply #11 on: August 21, 2013, 05:07:38 AM »

"was recrystallized" how hard is it to include the solvent system? Similarly, "purified by column chromatography" without the solvent mixture being included.


Sometimes the crystallisation solvent system is given as "aqueous methanol" or "a mixture of DCM and hexane". Very helpful, thanks!

Or another favourite of mine, "a seed crystal was added". I don't have any seed crystals because I am trying to make this compound!

I am currently in day 394 of "protracted standing" waiting for crystallisation to occur from a patent method. It is an ongoing joke, I intend to leave it in the lab with a message to call me when it does and hope that crystals form before I shuffle off this mortal coil.

@curiouscat

When I was working in industry I had to aim for 1:5 reagent to solvent ratio. All costings were calculated in litre hours.

This can be a nuissance for compounds with very low solubility if it's a low temperature reaction but as we made large amounts of low value materials this was the only way to do it.
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Offline curiouscat

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Re: List of Things that annoy us in articles.
« Reply #12 on: August 21, 2013, 05:14:07 AM »
@curiouscat

When I was working in industry I had to aim for 1:5 reagent to solvent ratio. All costings were calculated in litre hours.

This can be a nuissance for compounds with very low solubility if it's a low temperature reaction but as we made large amounts of low value materials this was the only way to do it.

Thanks! 1:5 is at the practical limit I can imagine. That or anything beyond seems just too expensive from a solvent handling / distillation / solvent losses etc. Of course, most products I've handled are below $30/kg so perhaps for more expensive products high dilutions are ok?

Offline Archer

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Re: List of Things that annoy us in articles.
« Reply #13 on: August 21, 2013, 05:48:07 AM »
It depends on the cost of your feed material. If higher dilutions are unavoidable then this drives the cost up.

I usually worked at 1:10 in the lab so up to about 50g just because representative external cooling can be difficult to achieve until you get onto pilot scale. I had a 5 Lt reactor which was reasonable for 250g of material and that is when we would start trying to reduce the solvent down.

We had one material what we could only prepare 100g in a 5 lt (1:25) reactor and that was after a lot of R&D to keep it from exceeding 0°C. It was a high value input material but as it was a specialist substance I think the added value was £1500 per kg for the reaction. This was a niche chemical of which we only ever made a few kg's which I suspect meant that it was an unusual case.
“ I love him. He's hops. He's barley. He's protein. He's a meal. ”

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Offline curiouscat

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Re: List of Things that annoy us in articles.
« Reply #14 on: August 21, 2013, 05:52:26 AM »

We had one material what we could only prepare 100g in a 5 lt (1:25) reactor and that was after a lot of R&D to keep it from exceeding 0°C. It was a high value input material but as it was a specialist substance I think the added value was £1500 per kg for the reaction. This was a niche chemical of which we only ever made a few kg's which I suspect meant that it was an unusual case.

I think $2300/kg is the key detail. At that price, I can condone all sorts of exotic conditions including fantastic dilutions I guess. :)

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