We often refer, in the course of our reportage concerning Coal conversion technology, to our sentimental favorite "West Virginia Process", a technique for the direct liquefaction of Coal developed by WVU, which employs the Hydrogen-donor solvent most commonly identified by it's shorthand name: "Tetralin".
One of our more recent reports concerning WVU's work with Tetralin is accessible via
WVU Hydrogenates Coal Tar | Research & Development; which includes details of the thesis:
"Hydrogenation of Naphthalene; Abhijit Bhagavatula; College of Engineering and Mineral Resources at West Virginia University; 2009; Abstract: The hydrogenation of naphthalene ... (to form) the hydrogenated product, tetralin (for use in) the conversion of coal to refinable crude hydrocarbons, from which liquid fuels such as gasoline, diesel, kerosene, etc., can be produced."
And, almost of course, the efficacy of using an hydrogenated Coal tar to convert Coal into "gasoline, diesel, kerosene, etc" hasn't gone undetected by Big Oil, as we reported, for just one example, in:
Exxon 1982 CoalTL Uses WVU CoalTL Hydrogen Donor Solvent | Research & Development; concerning: "United States Patent 4,345,989 - Catalytic Hydrogen-donor Liquefaction Process; 1982; Assignee: Exxon Research and Engineering Company; Abstract: Coal or a similar solid carbonaceous feed material is converted into lower molecular weight liquid hydrocarbons by (reaction) with a hydrogen-donor solvent (and) Tetralin ... is ...an extremely good hydrogen-donor solvent."
We have documented the use of Tetralin in Coal liquefaction processes developed by other petroleum companies, as well; as we will document even further in another report to follow in coming days. But, for more information, concerning what "Tetralin" and "Decalin" actually are, where they come from, see:
Naphthalene - Wikipedia, the free encyclopedia; which tells us that: "naphthalene is derived from coal tar", (and, it) "can be hydrogenated ... to give ... tetralin (and, further) hydrogenation yields ... decalin".
Herein, we wanted to illustrate that "Tetralin", and it's close hydrogenated-Naphthalene relative, "Decalin", which can also be utilized in Coal liquefaction processes, aren't new, recent-decade discoveries.
And, to that end, a number of links, with excerpts, follow excerpts from the initial link in this dispatch to:
"United States Patent 1,582,310 - Hydrogenation of Naphthalene
Date: April, 1926
Inventor: Georg Schroeter, Berlin, Germany
(Abstract:) The present invention relates to the hydrogenation of commercial naphthalene in a technical manner, whereby products can be produced on a technical scale which are suitable for various purposes, such as substitutes for mineral oil distillates, including gasoline ... .
The present invention ... is easily and economically carried out and can be used on a large scale and has the advantage that the catalyzer employed can be used for a long time, or used for the hydrogenation of large quantities of naphthalene.
The naphthalene, after it's purification (according to the described and specified cleaning and filtration processes) can then be subjected to hydrogenation (in a described process using Nickel as a catalyst under a pressurized Hydrogen atmosphere).
This produces substantially pure tetrahydronaphthalene (i.e., "Tetralin", and) the operation can be continued further (so that) the end product will be decahydronaphthalene.
(Note: To clarify, such "decahydronaphthalene" is better known as "Decalin". It has figured in some of our previous reports as another Coal hydrogenation and liquefaction solvent, and will, in reports to come, be seen to have some rather interesting potentials, especially in combination with Tetralin.)
In the production of the tetrahydronaphthalene it has been found in operation of the present process that substantially the entire amount of naphthalene was converted into tetrahydronaphthalene before any material amount of the naphthalene will be converted into more highly hydrogenated products.
(Such products) can be used as a substitute for kerosene for lamps, as a motor fuel, as a fine lubricating oil, as a material for the production of explosives and as a starting material for various chemical processes.
(Tetralin, in other words, can, itself, even without further processing, be used as a "motor fuel".)
One can, therefore, obtain lower hydrogenated products by this process.
Claims: The hydrogenation of naphthalene."
---------------
The concept of hydrogenating what are, in essence, the by-product tars of Coke ovens, in order to produce what was, even back in 1926, such a needful thing as liquid "motor fuel", must have been widely and broadly contemplated, since, only a few years later, another process was developed to accomplish such Coal oil hydrogenation, as seen in:
"United States Patent 1,733,908 - Procedure for the preparation of hydrogenated naphthalene
Date: October 29, 1929
Inventor: Walter Schrauth, Germany
Assignee: Newport Manufacturing Company, Wisconsin
(Abstract: In earlier, specified patents) there are described methods for the purification and hydrogenation of naphthalene.
I have discovered by further research (a process for the hydrogenation of naphthalene which) possesses a distinctly better efficiency.
Claims: In a process for preparation of hydrogenated naphthalene, the step of subjecting pre-purified naphthalene to the action of hydrogen under pressure at a temperature of at least 100 degrees C and in the presence of a mixture of hydrogenation catalysts containing a nickel salt."
-----------------
The date of Schrauth's patent, October 29, 1929, as above, better known in the history books as "Black Tuesday", might be significant. Perhaps Big Oil, even back then, and already, the predominant powerhouse of finance and industry, heard about the patent's issuance on the wires from DC, swooned, and dragged the financial markets down with him as he collapsed in a faint.
Sure did get back up on his feet and come out swinging, though, didn't he?
By our last count, at least seven, and perhaps a dozen, Coal hydrogenation and liquefaction plants in Europe and Asia got knocked out and obliterated, in terms both of actual existence and of humanity's awareness of them, in the decade and a half following Black Tuesday.
See, for example:
NETL: Gasifipedia; wherein our own USDOE National Energy Technology Laboratory tells us, that:
"By the 1920s, Germany had realized its dependence on imported petroleum as a result of the blockades of World War I. The war had also depleted Germany’s economic ability to purchase foreign oil. Amid world wide rumors that petroleum reserves would soon run out, Germany decided to develop a means for producing liquid petroleum fuels from their substantial coal reserves.
During the years 1910 to 1925, German Friedrich Bergius developed a process of high pressure coal hydrogenation or liquefaction; known as the Bergius process, to convert coal into liquid fuels. German scientists Franz Fischer and Hans Tropsch developed a second process for this purpose which now takes their name, the Fischer-Tropsch process, in which syngas produced from coal could be processed into liquid fuels. By the time World War II ended in 1945, 12 coal hydrogenation plants and nine Fischer-Tropsch plants were constructed in Germany."
More can be learned via:
Not Counting Chemistry: How We Misread the History of 20th-Century Science and Technology | Chemical Heritage Foundation; wherein we're told that
"A largely forgotten achievement ... was the great coal hydrogenation works that kept Germany fighting in (the) war.
Without various gasoline-from-coal technologies Germany could not have fought World War II as it did."
The title of the above publication includes the phrase "How We Misread".
Hasn't been anything published of late about the potentials of Coal liquefaction to be mis-read, has there?
In any case, the diligent Germans did keep at it in the years following issuance of the Black, black as Coal, Tuesday "US Patent 1,733,908 - Procedure for the Preparation of Hydrogenated Naphthalene", and were a few years later rewarded with:
"United States Patent 1,876,007 - Process for the hydrogenation of naphthalene
Date: September, 1932
Inventor: Richard Hupe, Konstane, Germany
Assignee: Deutsche Gold & Silber, Frankfort-on-the-Main, a corporation of Germany
(Abstract:) This invention relates to the production of benzol and hydrocarbons of the benzol series by treatment of naphthalene with hydrogen in the presence of a catalyst.
(Note, to be clear, and according to: What is benzol? definition and meaning; "benzol" is just another "term for benzene", one of the components of the "BTX" mix, along with Toluene and Xylene, from which Gasoline is, basically, blended.)
(Prior art) processes of hydrogenating naphthalene are based on the idea that sulphur compounds constitute contact poisons and must be removed as far as possible before hydrogenation. Subsequent working on these known processes has shown that they give rise only to a very small amount of conversion of naphthalene and the yields of products of hydrogenation of high value are relatively small.
This invention, on the other hand, effects the hydrogenation of naphthalene with very high speed and produces large yields of benzol or of hydrocarbons of the benzol series.
(And, immediately following is a "kicker".)
(Care) is taken that such amounts of hydrogen sulfide are present that the action of the catalysts containing the metal is improved.
(In this particular process, Sulfur, in the form of Hydrogen Sulfide, which we might derive in the generation of the Coke oven tars from high-Sulfur Coal, is a good thing. It can help the reactions along.)
The catalysts employed may be compounds of ... iron, nickel and cobalt ... . Further, sulphur compounds that is to say, sulphides of the said metals may be employed ... .
(Certain) catalysts, actually iron, nickel and cobalt (can) be improved considerably in their activity by the presence of definite amounts of hydrogen sulfide,
(So, a little Sulfur can actually be a good thing.)
In addition primary products of hydrogenation of naphthalene such as tetrahydronaphthalne (i.e., "Tetralin") and decahydronaphthalene (i.e., "Decalin) can also be employed as starting materials in certain cases. This may be effected by bringing (them) again into the process in order to convert them together with freshly introduced naphthalene into benzol hydrocarbons.
(In other words, the hydrogenated derivatives of a primary Coal oil can convert that Coal oil into Benzene, which can be a major constituent of Gasoline.)
A special advantage of the process consists in the fact that the direct treatment of crude naphthalene containing sulphur may be effected so that the purification of this starting material which was usual previously can be omitted.
(In other words, no expensive pre-treatment for the removal of Sulfur seems to be necessary.)
Claims: A process for the hydrogenation of naphthalene."
------------------
Note that the products Tetralin and Decalin can themselves, apparently, be used as "motor fuel".
In point of fact, they can, together, actually, according to our own United States Navy, as we will document in a report to follow in coming days, be combined together into a superior, high-performance type of "rocket fuel" for advanced combat aircraft.
Or, of perhaps more interest to the regular Joe's among us, they can be used, either separately or together, we suppose, in such processes as that explained in our above-referenced Exxon invention: "United States Patent 4,345,989", to convert solid Coal "into lower molecular weight liquid hydrocarbons"; which "liquid hydrocarbons", we are also compelled to suppose, must include, as above, as in US Patent 1,582,310, "gasoline".