WWII German Synthetic Base Oil Production...

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I stumbled upon this old article dating from 1945 which looks very much like an Allied post-war assessment of the synthetic base oil technology the Germans used during WWII... http://www.fischer-tropsch.org/primary_d..._lubricants.htm If like me, you're a chemical engineer who's dabbled in lubricant formulation, this is fascinating stuff. Lacking sufficient supplies of crude oil, the Germans took something they had lots of, namely ethane, and steam reformed it into ethylene. After a complex purification process, the ethylene was polymerised in the presence of Aluminium Chloride catalyst to what looks to me like a crude form of heavy Poly Alpha Olefin (PAO) base oil. The plant could be operated to make a very heavy base oil (SS.906) with a minimum KV100 of 43 centistokes or a lighter base oil (SS.903) with a maximum KV100 of about 21 cst (so roughly in SAE 50 territory). One of the things that made me smile was that even way back then, the Germans were using the 250C Noack volatility test as a quality control test! It looks like this synthetic base oil was blended with other stuff derived from crude oil. Very little seems to have been added to the base oil by way of additive (no ZDDP for example) before it being shipped out for use. The article also shows how the Germans were making Di-ester base oils with excellent low temperature qualities from Adipic Acid. The tech is very clever in that the di-ester base oil is put together from various derivatives of cyclohexane. Finally, the Germans seem to have used a complex tin-based additive to minimise ring stick on their aero-engines. I have never come across anything quite like this before. If there are any chemists out there, what is this stuff and more importantly, is it something we should be rediscovering today?
 

MolaKule

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Originally Posted By: SonofJoe
...Finally, the Germans seem to have used a complex tin-based additive to minimise ring stick on their aero-engines. I have never come across anything quite like this before. If there are any chemists out there, what is this stuff and more importantly, is it something we should be rediscovering today?
I believe that was tin decanoate and I see no advantages over present day compounds.
 
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Originally Posted By: MolaKule
Originally Posted By: SonofJoe
...Finally, the Germans seem to have used a complex tin-based additive to minimise ring stick on their aero-engines. I have never come across anything quite like this before. If there are any chemists out there, what is this stuff and more importantly, is it something we should be rediscovering today?
I believe that was tin decanoate and I see no advantages over present day compounds.
Couldn't some company with whip-smart marketing use it just as a product differentiator and take out ads stating, "JUST LIKE THE NAZIS USED!!!"....???
 
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For those interested in further reading on the chemistry developed in Germany and elsewhere at this time, there is an detailed book by Gunderson & Hart titled "Synthetic Lubricants" published in 1962. This was my bible when I entered ester sales in 1979. Gunderson & Hart Based mostly on research into the German records, a diester (Di 2-Ethylhexyl Sebacate) was selected for the first synthetic jet engine oils in the USA in 1952. The oil was formulated by Esso and called EEL Oil 1, (Esso Engineering Laboratories). The diester was supplied by Hatco and the anti-oxidant was Phenothiazine, very potent but a bit dirty at high temperatures. This type of oil was adopted by the US Air Force as specification MIL-L-7808, and was very light, only 3 cSt at 100°C. In the early 60s the Navy and Army adopted MIL-L-23699, a 5 cSt oil based on polyol esters, again most supplied by Hatco. In the late 70s the Air Force switched to a polyol ester based oil under MIL-L-7808 but retained the 3 cSt version because they operated bases in colder climates than other military branches and needed better low temperature starting capability. Today all commercial airlines and most militaries worldwide continue to fly on a 100% polyol ester based 5 cSt oil, but the US Air Force and some foreign militaries still use the 3 cSt version. Most of the polyol esters are supplied by Hatco, ExxonMobil, and Calumet with some smaller quantities made in Russia, Belgium, and China. Tom NJ/VA
 
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Originally Posted By: SonofJoe
I stumbled upon this old article dating from 1945 which looks very much like an Allied post-war assessment of the synthetic base oil technology the Germans used during WWII... http://www.fischer-tropsch.org/primary_d..._lubricants.htm If like me, you're a chemical engineer who's dabbled in lubricant formulation, this is fascinating stuff. Lacking sufficient supplies of crude oil, the Germans took something they had lots of, namely ethane, and steam reformed it into ethylene. After a complex purification process, the ethylene was polymerised in the presence of Aluminium Chloride catalyst to what looks to me like a crude form of heavy Poly Alpha Olefin (PAO) base oil. The plant could be operated to make a very heavy base oil (SS.906) with a minimum KV100 of 43 centistokes or a lighter base oil (SS.903) with a maximum KV100 of about 21 cst (so roughly in SAE 50 territory). One of the things that made me smile was that even way back then, the Germans were using the 250C Noack volatility test as a quality control test! It looks like this synthetic base oil was blended with other stuff derived from crude oil. Very little seems to have been added to the base oil by way of additive (no ZDDP for example) before it being shipped out for use. The article also shows how the Germans were making Di-ester base oils with excellent low temperature qualities from Adipic Acid. The tech is very clever in that the di-ester base oil is put together from various derivatives of cyclohexane. Finally, the Germans seem to have used a complex tin-based additive to minimise ring stick on their aero-engines. I have never come across anything quite like this before. If there are any chemists out there, what is this stuff and more importantly, is it something we should be rediscovering today?
They added ionised vegetable oil to some finished products, to improve the properties. Search for VOLTOL or ELEKTRION.
 

JHZR2

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Ive worked on F-T R&D a few years ago, lots about compact processing, post processing of the waxes, and manipulation of catalyst-wall heat transfer to get the heat out (which limits the reaction) to get better product distributions than regular fluidized bed reactors. Interesting stuff. There is a recurring class by some BYU professors that occurs outside of SLC for those interested in real engineering of plants. Interesting how much of what we are re-learning was covered long ago in the old literature...
 

SonofJoe

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I was thinking about that funny organo-tin compound and it reminds me a bit of neutral Calcium Phenate. My chemistry was always pretty rubbish but I sort of recall that Calcium Phenate starts off as Nonyl Phenol which is Sulphur bridged, reacted with Calcium Hydroxide to form the salt and then blown with Carbon Dioxide to get overbased (high TBN) Calcium Phenate. This stuff seems to start off as Sulphur bridged Iso-butyl Phenol. This is then part-esterified with Hexanol (or maybe Hexanoic Acid?) probably to increase its oil solubility. Two of these molecules are then bonded together with Tin. There's no overbasing step. If it is a neutral Tin Alkyl Phenate it might explain why the Germans found it to be effective against ring stick. As well as leading the world in terms of synthetic lubricant science it looks like they were also well ahead of The Allies in detergent chemistry. Maybe someone ought to see how this stuff does on LSPI?
 
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The Nazis were way to advanced for their time. Its to bad that Hitler was a bloody thirst D-Bag. Think of what we could have now! Jet powered VW Beatles? Yes please!
 

MolaKule

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Originally Posted By: SonofJoe
... As well as leading the world in terms of synthetic lubricant science it looks like they were also well ahead of The Allies in detergent chemistry. Maybe someone ought to see how this stuff does on LSPI?
The Germans developed most of their chemistry out of necessity rather than being true leaders in R&D.
Originally Posted By: SonofJoe
If it is a neutral Tin Alkyl Phenate it might explain why the Germans found it to be effective against ring stick.
The IF's abound since we may not know the true molecular structure. An ester-based tin compound would not only reduce friction but also act as a mild cleaner.
 
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Bit off-topic but the same site, along with loads of other stuff, has a US Intelligence appraisal of the Japanese pine-root distillation program for aviation fuel. Interesting to me because I've heard they also ran that program here, along with butanol fermentation from sweet potatoes, and much bombing ensued. IIRC the first post-war Honda motorcycles also ran on pine-root distillate.
 
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Originally Posted By: MolaKule
The Germans developed most of their chemistry out of necessity rather than being true leaders in R&D.
As the saying goes, necessity truly is the mother of invention.
 
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