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Half-wracked prejudice leaped forth
“Rip down all hate,” I screamed
Lies that life is black and white
Spoke from my skull. I dreamed
Romantic facts of musketeers
Foundationed deep, somehow
Ah, but I was so much older then
I’m younger than that now
-Bob Dylan, 1964

The epigraph was written by an young man who has grown old while praising youth, and for all that one may lose of youth, and though none of us "Stay Forever Young," I suppose that of what I retain of my youth is discomfort with compromising basic ideals.

Anyone who is familiar with my writing will know that I am no big fan of the car CULTure, and I believe that it - and the dangerous fossil fuels that support it - should be phased out as quickly as is possible.   If that sounds utopian, so be it.

And if this diary itself sounds like compromise with basic utopian ideals, so be that too.  

Then again, I may be that liar for who life is black and white.


This is a diary about biofuels.   In general, I am a critic of so called "renewable energy" - despite the high fashion notion that so called "renewable energy" is a universal good and cannot have any of the assumptions made about it questioned.    

Still, I will write here about a biofuel about which I've thought a lot, and for which I have less of my trademark hostility and about which I manage some ambivalence:   Biodiesel.

The current issue as of this writing of Industrial and Engineering Chemical Research a journal published by the American Chemical Society - a special issue connected with the CAMUR and ISMR meeting in Naantali, Finland - contained several papers connected with biodiesel technology.  I'll focus on one, and perhaps mention some others.

The main paper I will discuss in this diary is entitled "Effects of Sorption Enhancement and Isobutene Formation on Etherification of Glycerol with tert-Butyl Alcohol in a Flow Reactor."   The paper is here:   Ind. Eng. Chem. Res. 2012, 51, 8788–8795   Glycerol, if you don't know, is a major byproduct of the production of biodiesel and of, for that matter, soap.

Many people - most people? - will recall that the first Diesel engine, the one built by, um, well, Rudolf Diesel, ran on peanut oil, which may offer some explanation for Jimmy Carter's somewhat hyperbolic expectations for what biofuels can do, although everyone knows that Jimmy Carter was an ethanol guy in the end.

Rudolf Diesel died - probably a suicide - in 1913.   (He should have died hereafter, there would have been time for such a word.)

Biodiesel thus is not new.   It may now be considered "an alternative fuel" but we should all keep in the back of our mind that petroleum started out as an alternative to peanut oil.

Some eighty years after Diesel's death and the abandonment of "renewable" peanut oil in favor of petroleum the common modern enthusiasm for biodiesel has begun to rise both on an industrial scale and, to a lesser extent, in backyard production facilities.  Germany, for instance, has a "renewable portfolio standard" that requires the addition of biodiesel to petroleum diesel.   This is great if you're into "renewable portfolio standards" and maybe less than great if you're an organgatan or Sumatran tiger or rhino whose habitat has been rototilled to make a monoculture palm oil plantation so Germans can feel all renewally.   (Renewally?)   Organatans and sumatran rhinos and tigers aside, biodiesel can also be made out of waste oil cooking oil as well as waste industrial vegatable oils left over from things like the fractionation of soy bean oil to make lineoleic acid used to make some varnishes and paints.   Indeed, in theory at least, biodiesel can be made from waste sewage grease and oils.

Fats and plant oils, such as canola oil, soybean oil, palm oil, tallow, etc, etc are all esters of fatty acids - long straight chain carbon molecules with a carboxylic acid function on the end - esterified to the three oxygen and three carbon trialcohol that glycerol is, we refer to these oils as triglycerides, or "triesters."

The biodiesel industry  has lead to a huge glut of glycerol in modern times, and generally as a value added chemical, glycerol doesn't cut it, there isn't much demand for it except in specialty uses (in certain pharmaceutical applications for instance).  The demand for glycerol cannot match the production of it: Often glycerol is simply dumped, usually along with all kinds of excuses and rationalizations about how it's "biodegradable."  

Despite Rudolf Diesel's direct use of peanut oil in his early diesel engine, the natural triester oils are less than ideal as a fuel.   In most biodiesel preparations, the triacyl glycerol ester is replaced by monomethyl esters.    Fatty acid methyl esters have much better properties as fuels than native vegetable oils.   If you buy biodiesel or biodiesel blends, it is almost certain that they are methyl esters.

So we have a lot of glycerol on our hands.

Now some excerpts from the paper, beginning with a less sarcastic statement of what I have already said:

Fast depletion of oil reserves and the continuing increase of the prices of petroleum products initiated major research for the development of nonpetroleum transportation fuel alternates.1,2Measures taken in Europe necessitated that the biocomponent content of the transportation fuels should be increased up to5.75% in 2010.3,4 Biodiesel, which consists of alkyl esters derived through trans-esterification of oils with alcohols, is considered as one of the most promising nonpetroleum transportation fuel alternates. It is considered as a nontoxic, renewable compression engine fuel with a cetane number as high as petroleum derived diesel fuel. Glycerol (G) is the main byproduct of biodiesel production. One mole of glycerol is produced per three moles of methyl esters, in the trans-esterification of oils with methanol. This is equivalent to about 10% (wt) of the product stream in biodiesel production. Recent increasing trends in the use of biodiesel as a transportation fuel alternate has the potential to create significant surplus of glycerol. Overall economics of the biodiesel production through the trans esterification process strongly depends upon the effective utilization of the side product glycerol.
Let's be clear on something though.   If we rototilled all of Java, all of Sumatra, all of Borneo and put in palm oil plantations, there would still not be enough biodiesel on this planet to support the European version of the car CULTure.

This would even be true if there were no major tsunamis in Indonesia like the one that killed a quarter of a million people in Indonesia and the surrounding area in 2004, not that anyone remembers that tsunami, since that tsunami didn't offer the very enjoyable opportunity for millions of anti-nukes to have thousands, if not millions of tons of coal burned to power their computers so they can all wonder, interminably, about the question of whether one, two, or even maybe ten people might conceivably someday die from exposure to radiation at Fukushima.

That's one of the few joys of being an Orangatan, I would suppose, you don't have to think about these kinds of things.

Now for some interesting stuff from the paper:


Alternative conversion processes of glycerol to value-added products was reviewed by Pagliaro et al.5 Selective oxidation of glycerol to glyceric acid, dihydroxyacetone, mesoxalic acid, etc.;hydrogenolysis to propylene glycol; dehydration to acrolein,etc.;6 and reforming to synthesis gas and acetylation to esters7are some of the possible alternative routes to convert glycerol to valuable products. One other highly attractive process for the conversion of glycerol to value added products is its etherification with iso-butene (IB) or alcohols to produce fuel oxygenates.4,5,8
So you see a lot of other work has been done to find something useful to do with glycerol.   The rest of this paper is about the latter products, the "etherification" products with isobutene.

Isobutene is a very important commodity chemical around the world, with somewhere in the neighborhood of a million tons, plus or minus a few hundred thousand tons, being manufactured each year.    The main use is to make so called "butyl rubber" which is a copolymer of isobutene and isoprene, and which is the main material in nearly all of the tires on earth.    As it happens, butyl rubber, which is synthetic, is very close to the biological product obtained from rubber trees.  Isobutylene occurs in trees - when Ronald Reagan made his insipid remarks about how air pollution is caused by trees - he was mangling this information about the release of isobutylene from trees, where it serves as a precursor to various kinds of terpenes associated with the odors that trees generate.  However almost all of the isobutylene in commerce is derived from dangerous fossil fuels, primarly petroleum.   (Methanol is also generally made from the dangerous fossil fuel natural gas, although it is relatively straight forward to obtain it via the hydrogenation of carbon dioxide or carbon monoxide.)

The United States industrialized the production of synthetic butyl rubber because during World War II, Japan controlled most of Indonesia and Malaysia, where the rubber trees grew (and still grow).  The United States at that time had lots of oil, and was, in fact, the world's main exporter of oil and had, in 1941, cut off oil supplies to Japan.   So Japan, wanting Indonesian oil, attacked the US fleet which threatened its flanks, giving Japan, albeit temporarily, all the oil and rubber it could use.  

And the United States, then without rubber trees but with lots of oil,  abandoned "renewable" rubber in favor of petroleum rubber.

Cute, I think.

Watch out you damn Orangatans, "natural" "renewable" rubber could come back.

But not to worry, we have lots of glycerol on our hands now that we're making lots of "renewable" biodiesel and according to the paper, we could use this to make even more fuel:

As a result of etherification of glycerol with iso-butene or with tert-butyl alcohol (TBA) over solid acid catalysts, a mixture of monotert-ethers of glycerol (3-tert-butoxy-1,2-propanediol (MTBG1)and 2-tert-butoxy-1,3-propanediol (MTBG2)), ditert-ethers of glycerol (2,3-ditert-butoxy-1-propanol (DTBG1) and 1,3-ditertbutoxy-2-propanol (DTBG2)), and tritert ether of glycerol(1,2,3-tritert-butoxy-propane (TTBG)) are expected to be produced.9,10,12,13 These ethers were reported to have very high-octane numbers9 and can be considered as alternative gasoline blending oxygenates to MTBE and ETBE. They were also reported to have good burning properties with reduced pollutant and particulate matter emissions, when blended to diesel fuel.8,10,14Due to their higher solubility in diesel fuel, diethers of glycerol were preferred over monoethers, as fuel additives.
MTBE, famously, was widely used in gasoline formulations and was spectacularly successful at reducing air pollution, which kills, on average, 3.3 million people per year.   Unfortunately, it also led to some intractable issues with ground water, leading to a high level of excitement that caused it to be banned.   The ethers being proposed here are similar to MTBE, but also are different, probably with respect to their water solubility and biodegradability.   It may - and I'm not sure that it would be fair to say will instead of may be far less noxious than MTBE, although, as someone who's worked with MTBE a fair amount, it does seem possible to me that MTBE is probably not as bad as advertised, certainly not as bad as air pollution itself.

Nevertheless, the MTBE case represents a case where an "environmental" solution to an "environmental" problem is itself an "environmental" problem.

Lucky for you you're not an orangatan.

The rest of this paper is fairly technical, and concerns the issue of substituting t-butyl alcohol - the four carbon alcohol where three of the carbons are bonded to 3 hydrogen atoms each, and one is bonded to the other three carbons and a single oxygen that is bonded to a single hydrogen - for isobutylene.

This kind of chemistry is relatively rare:   Most butyl ethers, and for that matter, many butyl esters are made using isobutylene which is acid catalyzed to give the fairly stable corresponding cation, resulting in a classic SN1 type of chemical reaction.

Looking back on the tenor of this diary, I might seem a little bit overly negative.    I do believe that this type of biofuel has a niche, and, if careful attention is paid to its sources and best efforts are used to use waste oil from commercial operations, biodiesel would make an excellent transition tool for the conversion from a very dirty fuel, petroleum diesel (or Fischer-Tropsch diesel) to a much cleaner fuel, DME, or dimethyl ether, which can, although to my knowledge the issue is not industrial - be made by the direct hydrogenation of carbon dioxide, using, in the best case, nuclear hydrogen.

I have written about this before in this space.  

DME is an outstanding fuel and runs diesel engines, and spark ignition engines, quite well, as well as filling all the niches now using dangerous LPG and dangerous natural gas.   However, there are some issues in the diesel case with lubricity, and formulations of DME with biodiesel, dimethyl carbonate (also obtainable from hydrogen and carbon dioxide) or more exotic species like these glycerol butyl mono, di, and tri ethers, might help reduce the time and effort in making a transition to a pure DME culture.

But a pure DME culture will not occur most likely, because what is wise is seldom what is obtained.

Other papers relating to biodiesel and glycerol in this same issue are these:

Biphasic Model Describing Soybean Oil Epoxidation with H2O2 in Continuous Reactors

Glycerol Chlorination in Gas–Liquid Semibatch Reactor: An Alternative Route for Chlorohydrins Production  This paper shows how to make the very important chemical epichlorohydrin from a biological source.

Biodiesel Process Intensification by Using Static Mixers Tubular Reactors


Influence of Hydrogen in Catalytic Deoxygenation of Fatty Acids and Their Derivatives over Pd/C

This may be dry stuff - I'm sure it is - but I thought it interesting, and decided to babble a bit about it.

I certainly hope I didn't annoy anyone.

Have a wonderful day tomorrow.

Originally posted to NNadir on Fri Jul 06, 2012 at 10:08 PM PDT.

Also republished by SciTech.


Does biodiesel make you feel 'renewally.'

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Comment Preferences

  •  Reading technical stuff about biofuels in an... (6+ / 0-)

    ...effort to overcome a bout of insomnia, managing to put everyone but one's self to sleep, tert-butyl anything, abandoning swell renewable rubber tree plantations for oil based butyl rubber, burning tires, bombing Hawaii to secure the rubber plantations and Indonesian oil fields, the failure to phase out Indonesia after the 2004 tsunami proved that Indonesia is not safe, the hidden effects of t-butyl ether fuel additives on ground water, other hide rates, and pure sustainably fueled non-toxic renewable troll rates all go here.

    •  one of your best diaries yet (1+ / 0-)
      Recommended by:

      until the shill for those perfectly safe and intact Fukushima plants.

      and the cheap shot against those who prefer not to have MTBE in their drinking water.

      other than those, a thoroughly engrossing technical read.

      •  Well, I can't say that we've met, but I will say (4+ / 0-)


        I'm not "shilling" for anything, but I have no use whatsoever for arbitrary assignments with respect to risk analysis.

        Nothing on this planet is "safe" since everyone on the planet is mortal.

        I certainly would not characterize anything in a 9.0 earthquake that generates a 15 meter tsunami as "safe" and it would a grotesque technical error to interpret my remarks as being directed at a claim of "safety."

        I would add, however, that it would be a grotesque mistatement - albeit a common grotesque mistatement - to assume that the 20,000 people who died in the Sendai quake from things not in anyway connected to the reactors were "safe" whereas the people who worked in the reactor - the number who have died from radiation is zero - were comparitively "unsafe."

        Very clearly, as is also demonstrated from the 2004 Indonesian tsunami, coastal cities are not "safe."

        How come you aren't accusing me of "shilling" for coastal cities?

        This culture is out of its mind.   As noted, 3.3 million people per year die from air pollution.  

        One would need to have a very, very, very, very, very disingenuous - possibly deliberately self-delusional - understanding of the entire matter to recognize that the vast majority of the people who will die because the reactors were destroyed will not die from radiation, but rather from the air pollution from the dangerous fossil fuel plants that replaced them.

        My comments on Fukushima are absolutely essential to the technical, and more importantly, moral point associated with this diary and in fact, all of my diaries.

        Did 20,000 people die from radiation or not?

        The international focus in this case - the reactors to the exclusion of everything else - has been absymally stupid and it is a large part of the reason that humanity doesn't have a chance in hell of avoiding a real disaster, like the one that is unfolding right before our eyes with respect to the climate.   The entire midwestern corn crop is wilting in 38oC (100oF)+ temperatures and we want to talk about a few guys who got a 200 mSv radiation dose?

        As for MTBE, I'm not "taking a shot."   I note however that MTBE will never be as dangerous as gasoline, which among other things, is a pretty damn powerful carcinogen.

        I have long advocated the phase out of gasoline.   I oppose all fossil fuels and I oppose, in fact, the entire car CULTure.  

        So don't put me in the position of apologizing for MTBE.  

        That said, I am very fond of methanol infrastructure - which historically was associated with MTBE - because I am an advocate of dimethyl ether.

        This may or may not be quixotic, but it is what it is.

        The technical point that I am always making is about risk analysis and the general ignorance that surrounds what should be an obvious point about the obviously discernable relative risks, which should be easily determined, in Fukushima and everywhere else, by the simple expedient of counting the dead.

        Thanks, but no thanks, for the praise.

  •  palm oil (7+ / 0-)

    is the work of the devil, aided and abetted by rich men who don't live anywhere near those plantations.

    as is growing sugar cane on australia's gold coast, which destroys habitat as well.  


    i wish my city's light rail line was 1 mile longer to the east.  i might never drive again.  

    •  Rails and other forms of mass transit are... (9+ / 0-)

      ...really key technologies, although my gut feeling is that anything we do at this point is almost certain to fall into the "far too late, far too little" category.

      It's amazing, where I live, the subsidies for rail systems are falling rather than rising.

      It now costs me $33.00 bucks for a round trip ticket to New York, no matter what time of day or night I go.

      That's what you get with a Republican governor, mine being the tallow filled Chris Christie, asshole.

      •  i lived in germany for a year (7+ / 0-)

        with a toddler.  no car.  okay rented a car two separate times for specific trips.  walked to everything, took a train to church.  

        lived in sweden for almost a year, only used the car occasionally depending on how much we were drinking in stockholm.  

        at least your state can be blue.  i'm in utah.

        the light rail will go out to the airport early this fall, maybe sooner.  so it goes north/south down the middle of the valley, east to the university, and there's a western line in one of the southern suburbs.

        really, one or two miles down foothill boulevard and they could pick up so much traffic and reduce the cars.  

        the foresight displayed in earlier times seems awfully lacking now.  

        •  I spent a lot of time in Utah. (5+ / 0-)

          When my wife and I were younger, we used to take all of these very romantic camping trips to Bryce Canyon and Zion national parks.

          Those were very beautiful trips...sigh...she was beautiful...the parks were beautiful; everything was beautiful.


          I once had to go to this meeting that was being held at Snowbird, and I got in some pretty fabulous skiing there.

          But no, I wouldn't want to live there.

          I'm something of a New Jersey fascist, and wouldn't want to live anywhere else, even though I grew up - as a New Yorker - thinking of New Jersey as a kind of bucket of oily rags.

          Boy was I wrong.

          But since I've lived here there have been two very, very, very, very unpleasant things, one being Governor Whitman and the other being - how did he manage to be even worse than her - Chris Christie.

          It's doubly painful to have these two in a state that should otherwise be perfect.

          I do get to have Rush Holt as my congressman.   I certainly don't agree with everything he says and does, but he is my ideal of what a congress person should be.

          Actually, we're very bad in New Jersey at picking Governors.    In the time we've lived here, we've only had two that were very good, one being Jim Florio - who was defeated for re-election by Christy Whitman, moron, and the other being Richard Codey, who fell into the chair when McGreevy resigned.

          Other than that, it's been slim pickings, or, more recently a fat chance.

          Good luck out there.   I hope you're away from those fires.

        •  The problem is the middlemen. (1+ / 0-)
          Recommended by:

          They need to suck profit out of everything. Then, to cover their uncertainty, they squirrel money away and we are left with not enough to do what ought to be done.
          What palliative for the middlemen?  How to persuade them that accumulation is not good for them?

          Willard's forte = "catch 'n' cage"

          People to Wall Street, "let our money go."

          by hannah on Sat Jul 07, 2012 at 02:23:32 AM PDT

          [ Parent ]

      •  Full of biofuel, Christy is (5+ / 0-)

        Also, fertilizer.

        Mitt Romney is a T-1000 sent back from the Future as a harbinger of the upcoming Robot Apocolypse.

        by mbayrob on Fri Jul 06, 2012 at 11:23:17 PM PDT

        [ Parent ]

      •  When you say (0+ / 0-)

        "tallow filled Chris Christie," you begin to touch on what could be one of the most abundant sources of lipids for biodiesel production there is - the gross excess of fat that Americans weigh themselves down with these days. And it's those obese (and headed that way) people who do much of the 'work' producing the fat, eliminating the need for dedicated cropland and associated pollution loads/fuel use from the growing.

        Think "Ajax Biofuels, Inc." with nice strip mall walk-in storefronts all across the country that trade liposuction for the fat they remove. Instead of being 'medical waste', the fat goes to scattered rendering stations where it is liquified, then piped to refineries for final mixing/processing into biodiesel. Ajax gets the resource for free, Americans like Christie get slim for awhile so they can get to work converting more food into adipose tissue! Win-win all around...

        •  Oh geeze... (1+ / 0-)
          Recommended by:

          I hate it when you comment in my diaries, which is probably the reason I do.

          Today a few million corn plants will die in the United States from temperatures approaching 40oC.

          In my last science diary you came to offer this bit of unhelpful climate denial rhetoric about precisely this sort of thing:

          Could just be weather, (0+ / 0-)
          you know. Which is quite a different subject than actual climate change. I did look at the calendar today, and sure enough, it's July 1st. Honest to goodness summer here in the northern hemisphere, where it gets up into the 90s and even triple digits for days at a time through the height of the season. Pretty much always has, just like it gets bone-chilling cold for days at a time through the height of winter. Always has...

          Hence while it's sure darned hot, it's not exactly unheard-of. Oddly enough, droughts aren't that rare either. Why, back in my parents' day there was a whole Dust Bowl thing happening in the southern midwest, it didn't rain for years and years. crops dried up, houses and town got buried in blowing dust, Okies migrated en masse to California looking for viable cropland.

          Honestly, if we're to panic and scream that every heat wave, cold snap, tornado outbreak, thunderstorm, hurricane and/or blizzard is Global Climate Change Writ Large, we just might end up shooting ourselves in the proverbial foot. People who actually live their lives in the world with enough functional memory to recall the last decade or two or three's worth of weather will simply tune it out as hyperbole (Chicken Little stuff). Is that going to be helpful?

          by Joieau on Sun Jul 01, 2012 at 04:08:05 PM EDT

          [ Parent | Reply to this ]

          This diary is about something you clearly despise:  Science.

          There are people, they're called "scientists" who are trying to do something, anything about a crucial issue that you neither know about or care about.

          Couldn't you find some conspiracy theory to write about in some other diary?

          Maybe you can write of those wonderfully unenlightened diaries you write for the intellectual pit of a cheering section you have about how you absolutely hate - out of fear, ignorance, and superstition - the world's largest, by far, source of climate change gas free energy?

          Go away.


          Thanks in advance for your consideration.

          •  Heh. (0+ / 0-)
            I hate it when you comment in my diaries, which is probably the reason I do.
            Probably the reason you do what? You can't blame your perpetual grumpiness on me, Rococo. Diaries may be commented upon here, last I checked.
            Today a few million corn plants will die in the United States from temperatures approaching 40oC.
            A few million corn plants die every day all summer from all sorts of things, always have. Heat will interfere with photosynthesis, but they can survive that if it doesn't last too long. Drought, insect predation, blight, severe storms… my entire crop got savaged by hail day before yesterday, just as it was beginning to ripen. Gorgeous 12' tall plants I was SO proud of, first time in 20 seasons here that corn hasn't been entirely pitiful - planted heirlooms instead of hybrids this time. Shit happens.
            In my last science diary you came to offer this bit of unhelpful climate denial rhetoric about precisely this sort of thing:
            Your reading comprehension isn't getting better than it ever was. My post was in response to yet another outcry from another commenter - NOT you - that because it's hot in July, global warming is somehow proven. That's silly, as it's almost always hot in July. Because it's summer, and it gets hot in the summer in these latitudes. One heat wave no more 'proves' global warming than one cold snap in the middle of winter 'proves' global warming false. That's the truth, though I know you're not keen on truths.

            A survey of climate swings over the past century or so demonstrate that weather in any given season can fluctuate very significantly year to year. That's just weather, like heat waves in summer and cold snaps in winter. Droughts, floods, tree species die-offs, etc., etc., etc. Climate hyperbole during every single weather event isn't all that helpful in demonstrating the validity of climate change.

            ACTUAL climate change - warming, in my case - is 'proven' by the fact that USDA finally changed my growing zone this year to the next warmer one. Because overall, the average temperature has indeed risen, and we no longer (and haven't in well more than the 20 years I've been growing things here) get a last freeze on May 10. Or any date past mid-April, and even those are rare.

            This diary is about something you clearly despise:  Science.
            What a strange thing to say about someone whose father was a scientist, whose 5 offspring boast a record of 4 scientists and a one who went into practical medicine instead of biology or physics. You just don't like the fact that I think your physics/nuclear technology expertise is poor to nonexistent. Tough titty.
            Go away.
            Being as I am much more amenable to the request of a fellow kossack than others in your club have proven to be, I'll honor your request. You can be a dick in your own diary.


  •  EtOH from sane sources makes more sense (1+ / 0-)
    Recommended by:

    fuck everything about palm oil

  •  If there is any scientist (5+ / 0-)

    (especially chemists) surprised that glycerol is an excellent basic fuel, I'm smacking them upside the head with the CRC. Sacrilege or not.

    Glycine (the amine analog to glycerol) is the most basic amine, the building block of life. What food is broken down into in order to be utilized by the body, at least the sugar analog is. (it's very late for my brain) How could a scientist worth their NaCl be surprised that such a basic molecule is an efficient fuel?

    Biology has figured that out by a few million years. Or more.

    (fine. I'll use the Merck Index instead of the CRC. Pthft.)

    I am much too liberal to be a Democrat.

    by WiseFerret on Sat Jul 07, 2012 at 12:38:08 AM PDT

  •  You didn't annoy me. However, it is easy ... (2+ / 0-)
    Recommended by:
    NNadir, palantir

    ... to explain. The terminology in some part of your diary is so foreign to my physics background, I don't have any idea what it means.

    solid acid catalysts, a mixture of monotert-ethers of glycerol (3-tert-butoxy-1,2-propanediol (MTBG1)and 2-tert-butoxy-1,3-propanediol (MTBG2)), ditert-ethers of glycerol (2,3-ditert-butoxy-1-propanol (DTBG1) and 1,3-ditertbutoxy-2-propanol (DTBG2)), and tritert ether of glycerol(1,2,3-tritert-butoxy-propane (TTBG)) are expected to be produced.
    I am going with a hunch here. I think you probably know what they mean. I still felt I learned something new. Not sure what it was yet.

    Thanks for the 'babble about it'. I hope your tomorrow is good, too.

    Universe started with a Big Bang. It's big, getting bigger, and mostly dark.

    by jim in IA on Sat Jul 07, 2012 at 09:25:27 AM PDT

    •  Well, I'll do my best with physics type language. (2+ / 0-)
      Recommended by:
      jim in IA, palantir

      Consider the three oxygens on glycerol - a three carbon chain with one oxygen attached to each of them - as being an object where one (or more) of the oxygens is "hit" according to a Poisson distribution.    (This is actually probably a bad analytical term since each oxygen can only be "hit" once.

      The oxygens are numbered 1, 2, 3.   The number of permutations would normally be 3! except that once either 1 or 3 are hit, the permutations are equivalent.   Thus there are really just two permuations, 1 and 2.

      Then there are 2 possible doubly substituted analogues, 2,3 and 1,3.

      Finally there is one, and only one, trisubstituted analogues.

      This is all that this language refers to, the six possible ways that a "tert-butyl" function can be attached to an alcoholic function's oxygen atom.

      The term "tert-butoxy" just refers in chemist language to the structure of the attachment.

      Here is the structure of di-tert-butoxy ether.   If you replace the two "tert-butoxy" structures with hydrogen, you have water.

      A solid "acid catalyst" is just what it sounds like.   It is an insoluble acid.   There are many types of these, including many definitions of what an "acid" is, a Bronsted-Lowry acid, a Lewis acid...etc...

  •  DME is a gas at STP, yes? (0+ / 0-)

    It just seems that, although it's been done before with natural gas, that using a gas as a fuel is fraught with dangers that are expensive to mitigate against in the distribution channels. Am I missing something there?

    My current favorite alternative fuel would be butyl alcohol. Its a liquid, nearly as energy dense as gasoline and isn't hydrophilic like ethanol.

    •  In contrast to methane, the critical temperature (2+ / 0-)
      Recommended by:
      palantir, squarewheel

      of DME is higher than the boiling point of water, 127oC.

      This means that it is easily transported as a liquid, and in fact, used as a liquid.    

      (The boiling point is around 4oC, meaning that on a cold day, it will remain liquid.)

      It also has a fairly high heat of vaporization.

      It is completely non-toxic and is easily removed from spills even into water by simple aeration.   (In this regard it is superior to methanol, which is of course, a liquid.)

      It's atmospheric half life is on the order of 5 days, as compared to many decades for methane.

      It has no carbon carbon bonds and therefore its combustion produces little or no particulates.

      I have looked at many thousands of compounds that have been considered as fuels of the years and there are none with such outstanding properties.

      It is superior to any alcohol and any alkane or any other liquid fuel.

      DMC, dimethyl carbonate, is also a pretty good fuel, but DME is the winner in my mind on any combinatorially optimized system of criteria.

      Regrettably what is ideal is not always what is adopted.

      However, DME is an up and coming fuel in Asia and is seriously being evaluated in Europe.   Sweden if I recall has the most advanced program.

      Predictably we have little or no interest in the United States.

      Here is the webpage of the International DME Association.

  •  Thanks for the Diary... (0+ / 0-)

    Much of the chemistry is beyond my reach, having forgotten much of what I learned in high-school.

    I don't necessarily agree with everything that you have said (particularly in regard to the impacts of Fukushima, which I do not believe are yet fully known.)

    However, your presentation seems well considered.

    Certainly, we face tough choices in the future, and there is no "free-lunch". ALL options have environmental impacts, some more obvious than others.

    Our use and production of energy sources is a complicated topic, and oversimplified discussions and approaches may be easier to digest, but they are far less realistic.

    Thanks again for your Diary.

    I'm a "No Rate" pariah. So when I give a comment "+110% n/t", please consider that a recommend. (That's my workaround fix to participating in this community!)

    by The Angry Architect on Sat Jul 07, 2012 at 12:11:49 PM PDT

    •  Well one things for sure, the effects of air... (1+ / 0-)
      Recommended by:

      ...pollution are well known, 3.3 million dead per year.

      If you don't know, one year after Fukushima what the effects of Fukushima will be, then they're probably not going to be as dramatic as the effects of the explosion of the Piper Alpha oil platform disaster, which killed 167 people instantly.

      Piper Alpha.

      I am really, really, really, really, really at a complete and total loss about the obsession with Fukushima.

      How many millions of people have to die from air pollution from the normal operations of dangerous fossil fuel plants before we get off our asses and recognize that the world's largest, by far, source of climate change gas free primary energy represents one of the most robust systems of energy known?

      I mean, 8 people died at Fukushima from a dam collapse.   How come no one is waiting around to find out if the Hoover dam is "safe?"

      (I note that in 1976 the serial dam failures at Banqiao killed 250,000 people in a matter of days, and yet everyone has forgotten it to focus on Fukushima.)

      What exactly does nuclear energy need to do to prove its worth?

      •  generally I agree with the fact that the risk and (0+ / 0-)

        death associated with fossil fuels is understated to an amazing extent.


        radioactivity via pollution through radioisotopes has the very distinct possibility of making many, many square km of the planet uninhabitable for a long time.  chernobyl and surrounding area is quite nasty.  the area around fukushima is also going to be uninhabitable, and for centuries.

        the disposal of radioactive waste is still an unsolved problem, granted it seem to be mostly a political problem, but it's still unsolved at this time.  it is an accident waiting to happen, which could end up making many, many square km of the planet uninhabitable for a long time.

        having said that, as the Romans were made into babbling idiots due to water contact with lead, so are we on are way to being babbling idiots to the dissipation of Hg in our environment.

        the elephant in the room is truly the number of people on the planet, and if you think getting people to do the right thing when it comes to energy production is tough, just try to even start a conversation about the fact that there too many people on this planet.  world population growth is what will lead to collapse, regardless of what kind of fuel you use to power civilization.

        big badda boom : GRB 080913

        by squarewheel on Sat Jul 07, 2012 at 10:30:10 PM PDT

        [ Parent ]

        •  Hg, of course, due to burning coal (0+ / 0-)

          and I believe large amounts of thorium too.

          good thing we're going to mine even more and send it to China.

          Most days I have to admit that nukes look a whole lot better than coal.

          of course, there's solar, but I don't want to get you started on that.

          big badda boom : GRB 080913

          by squarewheel on Sat Jul 07, 2012 at 10:35:20 PM PDT

          [ Parent ]

        •  I am distinctly uninterested in theoretical deaths (0+ / 0-)

          The fact is, that both at Fukushima and more dramatically at Chernobyl huge amounts of radiation were released, and combined neither event did not equal the destruction and death associated with the next three months of normal operations of dangerous fossil fuel facilities.

          As it happens, nuclear by products have the happy property of decaying while they are formed.

          The "disposal of radioactive waste" is a fantasy problem, and not an urgent problem, since the by products of nuclear operations have been successfully stored for many decades - often on the site where they were generated - without a single loss of life.

          This is decidedly not the case for dangerous fossil fuels.

          So called "nuclear waste" a perceptual problem that is mainly generated by selective attention.   I have observed that the people who make the biggest stick about this "unsolved problem" are precisely the people who know the least about the subject.

          You may think that the "problem" of so called "nuclear waste" is unsolved; but I feel quite differently about the topic.   I contend that the solution is well known and well understood, but that, as is often the case, fear, ignorance and superstition have prevented the solution from being an industrial practice.

          In so stating, I am not minimizing the infinitely more real problem of the carrying capacity of the planet for human beings.

          However, I note that people who discuss that problem to the exclusion of other problems seldom are willing to commit suicide to address it.

          I have never claimed that nuclear energy is a panacea, and in fact, I have stated the opposite:   Should Nuclear Energy Be a Panacea?

          I have merely stated that nuclear energy is the best available technology.   This is different from saying it is "perfect" technology, which is what the class of people I refer to as "nuclear exceptionalists" demand, again, out of fear, ignorance and superstition.    Related is the claim that issues that apply to all forms of energy are only relevant in the nuclear case, and that in nuclear case, what can be imagined somehow trumps what is observed.

          This is not only intellectual garbage, it's moral garbage as well.   This sort of thinking kills people.   It's nothing short of murder.

          The storage of used nuclear fuel has been practiced for more than half a century.   It hasn't killed anyone, and if it did, it is technically impossible that it would kill as many people as have died from the failure to store dangerous fossil fuel waste has killed in the last year.   In fact, it is easy to show that in the period since the commercialization of nuclear energy, dangerous fossil fuels have killed somewhere between 50 to 100 million people, and that's not including the climate change effects.

  •  Celllulosic based fermented butanol will be a (2+ / 0-)
    Recommended by:
    defluxion10, squarewheel

    major contributor to US energy use this decade. It is a direct replacement for gasoline and can be pipelined and doesn't have a water miscibility problem like ethanol. Major breakthoghs? no. MAny incremental breakthroughs like all major scientific advancement.

    I'd tip you but they cut off my tip box. "There is more stupidity than hydrogen in the universe, and it has a longer shelf life.” - Frank Zappa

    by OHdog on Sat Jul 07, 2012 at 02:24:58 PM PDT

    •  interesting but first you'll have to point me to (0+ / 0-)

      someone doing celullosic ANYTHING on a commercial/industrial scale.

      so far it appears to be a unicorn, much like the much ballyhooed thorium reactor.

      many things which could save the planet will not work on the scale they need to work.

      big badda boom : GRB 080913

      by squarewheel on Sat Jul 07, 2012 at 10:31:42 PM PDT

      [ Parent ]

      •  The Shippingport Reactor, America's first... (1+ / 0-)
        Recommended by:

        ...commericial reactor, operated on the thorium fuel cycle from 1977 until 1980.

        Jimmy Carter switched it on.

        In more modern times, India has a huge and active program to move to the thorium fuel cycle, via a fast (plutonium fueled) liquid metal intermediate.   The first step in this program, the PFBR, is due to be completed in 2013, and will generate plutonium that will be used in India's Advanced Heavy Water Reactors designed to generate, and operate on thorium.

        I would guess that this is far more advanced than any unicorn breeding farms about which you may know.

        The first reactor to run on thorium was the Experimental MSR which operated successfully for about 2 years at a power load of approximately 7 MW(th) in the late 1960's.

        I don't know how your unicorn pulled coaches operate, but I would expect that they were not as successful as this experiment, which took place more than 40 years ago.

        The highly trained ORNL team - many of whom were on a first name basis with Nobel Laureates - that operated the reactor were disappointed with the political ignorance that caused the failure to commercialize this technology via the operation of a larger pilot reactor.

        You are confusing, I think, political stupidity with technical issues.

        China has announced its intention to build MSR type reactors, and many Americans are also working on similar projects but have thus far obtained very little support from the peanut gallery.

        The forty year old technology is probably - despite what one hears in the curious google inspired world - not the best technology available, but it workable and is well understood.

        •  we'll talk again in 2013 (0+ / 0-)

          but you've mostly proven my point.

          reactors that operated in the 60s, "intentions" to build reactors.

          when there's an actual thorium reactor supplying electricity to a city, then I'll believe.

          meanwhile, thorium reactors are going to save the world real soon now, much like cellulosic anything.

          I knew that India was allegedly working on a thorium reactor but did not know there was actually a completion date associated with the effort.

          So we'll see what 2013 brings.

          big badda boom : GRB 080913

          by squarewheel on Sun Jul 08, 2012 at 07:37:41 PM PDT

          [ Parent ]

      •  Like I said , many small but significant advances (0+ / 0-)

        I'd tip you but they cut off my tip box. "There is more stupidity than hydrogen in the universe, and it has a longer shelf life.” - Frank Zappa

        by OHdog on Mon Jul 09, 2012 at 12:24:43 PM PDT

        [ Parent ]

  •  You'll be pleased to learn about (1+ / 0-)
    Recommended by:

    the latest hair-brained scheme that's going to save the world: biochar fired steam locomotives.

    Even if you could sustainably generate enough biochar to replace all diesel locomotives, you'd still be left with a huge air pollution problem.

  •  I love this stuff, but I have a book by A S Ramadh (0+ / 0-)

    A S Ramadhas, Alternative fuels or something, and reading it made me lose my appetite for DME.
    The vapor pressure is too high & it'll go everywhere, and doesn't it boil at 4C?

    German Constitution, Article 1 (1) The dignity of man is inviolable. To respect and protect it is the duty of all state authority.

    by Mark B on Tue Jul 10, 2012 at 05:44:41 PM PDT

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