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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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August 13, 2006

Six Chem-Geek Questions

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Posted by Derek

OK, some of this is going to sound like Sanskrit to my non-chemistry readership, but here goes:

1. When's the last time you held a paper copy of JACS in your hand? For me, I think it's been at least two years. They could be running swimsuit covers now and I wouldn't know about it.

2. Are ionic liquids actually good for anything, other than publishing papers about them?

3. To combine those first two, if you wrote up a paper about a ring-closing metathesis reaction to make a nanoscale structure in an ionic liquid, would the journals even bother sending it to a referee before immediately publishing it?

4. Are they ever going to hand out a chemistry Nobel for palladium coupling reactions? Or have the Swedes decided that credit is too tangled? (Not to mention the fact that not all the key early players are still alive). But if ring-closing metathesis deserves one (and I have no problem), doesn't the Suzuki reaction?

5. Weren't they promising us benchtop NMR machines back about twenty years ago? Does anyone expect to ever see the hypothetical personal benchtop LC/MS machine? Maybe we'll have them in our flying cars.

6. Will Chemical and Engineering News ever go a year without running a headline that says "Salaries for Chemical Engineers Still Higher". As far as I can tell, they haven't missed since about 1982.

Comments (45) + TrackBacks (0) | Category: Chemical News


COMMENTS

1. yepyep on August 14, 2006 3:42 AM writes...

1. Can't remember when but we are talking about years.
2. Don't know much about them but sounds to me a bit like solid-phase chemistry. People do all the 100-years-old reactions in it and get papers published, then after 10 years they'll start realizing it's not that useful after all.
3. Probably yes, especially if you manage to include one or more of the magic words in the paper: "cancer", "alzheimer's disease" or "HIV".
4. I don't know. I think the Swedes are a bit weird (I'm a Finn so it's my inherent right to think that).
5. Why would they bother when they can charge a lot of $s for the big ones?
6. Can't say but I know I would be a lot richer had I chosen the University of Technology instead of the plain old University...

Permalink to Comment

2. Jal-Frezi on August 14, 2006 3:51 AM writes...

Got a microwave reaction that stubbornly refuses to reach your desired temperature without the magnetron overheating? Put a drop or two of ionic liquid in there and Bob's your uncle...
Although Nick Leadbitter has been using these ceramic heating doodahs which seem less invasive.

Permalink to Comment

3. supercritical on August 14, 2006 6:08 AM writes...

Regarding ionic liquids - I agree they have become a bandwagon for many people.
I also think that just like in many other areas there has been a great deal of hype and exaggeration by some people which I think eventually leads to a bit of a back lash. However, if you can weed through the large amount of bad papers you will find that have many useful properties and have a great deal of potential to solve many problems and give advantages over existing methods.

The question of “will they ever be used commercially?� is often asked with scorn. But actually there a number of industrial processes already (some well publicised and some not so)! But what also must be remembered is that industry is slow to change and take up new technologies. They have only become very popular in the last 5 years or so – there are not many technologies that would be so quickly picked up and used by industry when it will involve re-design of plant equipment!

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4. RKN on August 14, 2006 6:21 AM writes...

  OK, some of this is going to sound like Sanskit

Maybe Sanskrit ;-)

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5. Derek Lowe on August 14, 2006 7:20 AM writes...

Dang it all, I thought I fixed that last night. It's OK now.

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6. Process Chemist on August 14, 2006 8:08 AM writes...

Re: nanoscale structures, ionic liquids, metathesis....

Here's another one for the list: Green chemistry.

There's a few research groups out there making a living of repeating 20 year old reactions without solvent and calling that "green chemistry". Of course, every single compound is purified dumping liters of hexane and ethyl acetate down silica gel columns.

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7. John Johnson on August 14, 2006 8:20 AM writes...

Sorry, doesn't sound like Sanskrit to me. I actually understand a little bit of Sanskrit. This, I do not. ;)

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8. Pd Couple on August 14, 2006 8:24 AM writes...

I am convinced that the true reason why people consider ionic liquids "green" is that they are so expensive you have to recycle them.

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9. Demosthenes by Day on August 14, 2006 8:34 AM writes...

1.) Not only JACS, but I haven't held a physical journal of any kind for well over three and maybe as long as five years.
2.) This is the same as when people sneezed on buckyballs and got a JACS paper. Exactly what its real use is still seems unclear to me.
3.)I'm guessing there would be a bidding war on that publication.
4.)I think you hit the nail on the head by asking the question who would get it for the Suzuki reaction? There are so many involved that I just have to believe the Nobel committee gets a headache every year trying to suss it out. Even RCM wasn't so clean in deciding who to honor but at least the group was much smaller than that for Pd-coupling.
5.)I'm totally happy with the walk-up simple instruments we have now. I don't need one on my bench and the automation for both our LC-MS and NMR are fine with me. Actually the ability to send the output to my computer doesn't even make me wish for one of these, anymore.
6.) No.

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10. yepyep on August 14, 2006 8:58 AM writes...

"...Of course, every single compound is purified dumping liters of hexane and ethyl acetate down silica gel columns."

And you can also find papers where the title screams "solvent free" and after the reaction they dilute it with CH2Cl2 (or some other not-so-green solvent). Of course, technically the reaction is solvent free but cmon...

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11. LNT on August 14, 2006 8:59 AM writes...

1.) 5 years ago (it's still common to read the paper version of Tett.Lett because the electronic one is so darn expensive for small companies)
2.) If ionic liquids can truely be economicly recycled on a large scale, then I'm all for them. But I've never heard of a medicinal chemist using them.
3.) Ha! Here's a great JACS paper waiting to be written: "Molecular docking studies of modified carbon nanotubes in an ionic liquid medium"
4.) Don't know enough about the history of Pd chemistry to comment
5.) I would love a benchtop LCMS. I can see it happening in 5-8 years. Here's what I would LOVE to see come down in price and complexity: HPLC-NMR. Imagine routinely separating compounds by HPLC and being able to click on a given fraction to see it's NMR spectra!
6.) Of couse chemists salaries are going to go up every year, the question is whether they are going up as compared to inflation and as compared to other industries. The real question is: When is the ACS going to admit that there are plenty of chemists already on the market and we don't have to encourage new people into the enter the field? There are already tremendous job shortages amoung PhD chemists -- why is the ACS trying to get more people interested in obtaining chemistry degrees?

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12. TheMatt on August 14, 2006 9:36 AM writes...

Well, I'm a physical chemist (the One True Branch), so I don't think I've ever held a paper copy of JACS. Now JPC:A and JCP...it's been a while due to the power of (Color online) which really helps with physchem plots.

As for Nobels, I'm actually a *theoretical* chemist, so every year I wonder where the prizes for theory are. I can recall maybe two in the last 20-30 years (Rudy Marcus and Pople & Kohn) and I'm pretty sure more has been done in the field.

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13. Don B. on August 14, 2006 10:09 AM writes...

Personally I could do without C&EN political cartoons (called "editorials").

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14. weirdo on August 14, 2006 10:14 AM writes...

1) Yesterday. I still like the smell. And I find I actually relax and BROWSE a paper copy, while on-line I always seem to be in a hurry.

2) Eventually, someone will stumble into something useful, the utility of which will be demonstrated by some process group at Merck or GSK, and the academic will get an ACS Cope Scholar Award for it, even though he/she didn't really recognize the potential.

3) Well, certainly the editors at Angewandte wouldn't.

4) No. This chemistry, at this point, is too "applied".

5) I think you'll see a bench LC/MS in about four years for about $75K. But the annual service contract will be ~$50K, and you'll need service monthly.

6) They will the same year you see the headline: "The U.S. is Training Too Many Scientists, Experts Warn".

Permalink to Comment

15. milo on August 14, 2006 10:35 AM writes...

1: Got to be at least 4 years...
2: I have heard that they will revolutionize the paper making industry. There was a letter not too long ago in Nature (16 February, 2006 pg 831-834) that talks about how ionic liquids can be distilled. They even have a picture of a *gasp* Kugelrohr...
3: As long as it has the word "nano" in the title you'd have your pick of journals.
4: Nope. Pd couplings are too useful and there have been too many people involved. Buckyballs on the otherhand...
5: I don't need a personal machine. I need the walk on ones to be treated with repect.
6: Nope.

Permalink to Comment

16. Atompusher on August 14, 2006 11:14 AM writes...

We have a group of chemists who do Hantzch dihydropyridine synthesis in ionic liquids on a regular basis. Nothing else works for them.

Permalink to Comment

17. MikeT on August 14, 2006 12:00 PM writes...

1. Not since I was in school.

2. Not yet.

3. Need a wikipedia type review for the masses.

4. See question 3.

5. At least you can see 'em on a computer screen now.

6. They also need to talk about inflation, which rises faster than saleries.

Permalink to Comment

18. Luke, I am your fungus! on August 14, 2006 1:03 PM writes...

actualy, ionic liquids are great solvents and they can become green if you add enough snot into them

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19. userlame on August 14, 2006 1:08 PM writes...

1. 6 yrs.
2. Heat baths (in some settings)
3. Even with those specific criteria, it would all depend on the institution you are publishing from and if you know an/the editor.
4. How about negative index of refraction for physics?
5. The benchtop NMR probably seemed reasonable then because we were cocky after making making gigantic strides toward high-Tc superconductivity.
6. Probably not.

Permalink to Comment

20. JB on August 14, 2006 1:42 PM writes...

1. Cannot even remember. As an aside, several years ago, when I called to cancel my subscription to JACS and Organometallics (this was before everything became availabe online), and was asked the reason why, I honestly told the operator "I’m running out of space". She actually laughed out loud.
2 and 3. Ionic liquids will go the way of single walled nanotubes (purification problems). Full scale industry application will not be feasible until they can make recycling the liquids economical.
3. I’m surprised. I wasn’t aware Prof. Suzuki had passed away. The Nobel committee must be afraid of opening a can of worms re this matter.
4. Don’t know much about LC/MS to comment on this.
5. And every year, I wonder to whom they send the questionnaires for their data.

Permalink to Comment

21. Derek Lowe on August 14, 2006 2:47 PM writes...

Oh, Suzuki's very much alive. I met him a couple of years ago, and he seemed to be doing just fine. I was thinking of Stille, for example, and you'd have a hard time leaving him out of the genesis of palladium-catalyzed couplings.

Permalink to Comment

22. Demosthenes by Day on August 14, 2006 3:08 PM writes...

Just wondering, Derek what famous chemist would be coverboy in a Speedo on your JACS swimsuit issue????
Actually I think I just put myself off my dinner with the thoought.
My apologies to everyone.

Permalink to Comment

23. scott on August 14, 2006 3:36 PM writes...

err... don't we already have benchtop LCMS machines? I don't get it.

I've heard of benchtop NMRs:

http://www.minispec.com/mq/index.html

I don't think the resolution is good enough to be practicle for structural determination, though.

Permalink to Comment

24. secret milkshake on August 14, 2006 4:24 PM writes...

Phil Baran in Speedos would be acceptable to wide audience I think, including the straight one

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25. supercritical on August 14, 2006 4:58 PM writes...

It CAN be economical to recycle ionic liquids, for example Eastman ran a process using one for 8 years!! It was discussed at COIL, and is mentioned here: Green Chem., 2006, 8, 411 - 414, DOI: 10.1039/b605378p

And depending on the type of ionic liquid they can be very easy to make very pure.

Yes i agree organic solvents are much easier to use in most cases. But the fact is solvents are one of the biggest source of waste, and there is increasing pressures to cut waste i hear. So i would argue there are a quite a drivers for alternative solvents.


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26. Anonymous on August 14, 2006 6:47 PM writes...

I'm of the opinion that Mizoruki or Heck should get the nobel for Pd couplings as to my knowledge they were the first to propose to do it, and in the case of Heck provide reasonable mechanisms. But I could be wrong, I wasn't born then.

Permalink to Comment

27. Greg Hlatky on August 14, 2006 8:11 PM writes...

1) Today, in fact. I prefer media I can take to the bathroom with me.

2) Hey, steady on there! I have a PCT application (WO20010181436) on doing polymerizations in ionic solvents. Truly a monument more enduring than bronze.

6) In re some of the comments above: "Shortage of scientists" = "Not enough cheap, easily exploitable labor for academics". Here's another question: does the ACS really give a damn about industrial chemists or is it an organization dedicated to (a) having national meetings and (b) handing out awards to professors?

Permalink to Comment

28. Yves on August 15, 2006 6:39 AM writes...

I think that the problem with Pd chemistry is that there are too many people involved, even only considering C-C formation. I guess that Suzuki and Heck (he is still alive) are clear candidates. The third gets a little complicated. There are a number to be considered. Any ideas?

Permalink to Comment

29. Thomas E. McEntee on August 15, 2006 7:19 AM writes...

1)JACS was pretty much off my radar screen after grad school.
2) For chemists of my era, ionic liquids were things like brine, hydrochloric acid, caustic solution...I date myself (see 1). Brined deep-fried turkey with a mango salsa and accompanied by a chilled Chardonnay is delicious.
3-5) No comment
6) The parade of notable chemists that have graced the pages of C&EN for decades are academic and industrial chemists. ACS exists to promote chemistry and the study of chemistry...this ensures a steady oversupply supply of eager chemists that provides the cheap grad student labor that the profs need to make their name, fills the ranks of industry, and keeps every chemist's salary down.

Permalink to Comment

30. Dr Toot on August 15, 2006 10:52 AM writes...

Looks like your # of geeks is getting bigger; well-deserved..

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31. MTK on August 15, 2006 3:15 PM writes...

I'm not entirely sure on all the history of organometallic chemistry, but if you were really going to put Pd couplings as Nobel-worthy, then one has to actually go back to the pioneering work of Kagan, who was one of the first to use transition metal catalysis for coupling reactions. Then on to Negishi with Ni catalysis before finally getting to Sonagashira, Tsuji, Trost, Suzuki, Stille, et al.

Permalink to Comment

32. MTK on August 15, 2006 3:47 PM writes...

Sort of off topic, but the Nobel discussion got me thinking...

a) The Nobel committee must love double bond formation given that olefin metathesis, Diels-Alder reaction, and Wittig reactions have all won Nobels.

b) The 1918 award to Fritz Haber is interesting. Not that Haber didn't deserve it, but becuase he supervised the German poison gas campaign of WWI. To win the Nobel in 1918 with that as a backdrop tells me that chemical warfare wasn't really viewed as the evil it is today. BTW, the gas war was a battle between two Nobel laureates, Haber and Victor Grignard.

c) The first recipient of the Nobel Prize in Chemistry was vant Hoff, but, unbelievably, not for the conceptualization of tetrahedral carbon, stereochemistry, and 3-D structure, but rather for his studies in chemical dynamics and osmotic pressure. I'm no physical chemist, but that must be some important stuff to push tetrahedral carbon to the side.

Permalink to Comment

33. gaussling on August 15, 2006 8:00 PM writes...

My comments are limited to the field of custom chemical manufacture. There may be pharma applications where the benefit of Ionic Liquids (IL's) are justified, where intermediates may be worth many 10's of thousands per kg. But in the fine chemical arena where chemicals sell for $5 to $1000 per kg for bulk quantities, IL applications are hard to justify.

There are some spot applications that favor IL's, but due to their considerable cost, I don't anticipate that custom chemical manufacturers will start running many batch reactions in 1000 gal reactors full of IL solutions. If you generate ions in the reaction, you change the composition of the IL and then the question is, if we are going to re-use the IL for another batch, have we made a process change under PSM? Consequently, you have to monkey around with validating the fantastically expensive solvent for re-use in the batch processing campaign.

Having made a few custom IL's for for the market, it seems to me that IL's are a cure looking for a disease.

If you dispose of your waste by incineration, would your waste hauler knowingly jam a big load of IL's into their incinerator?

For now, most manufacturers would prefer to pay $3/kg for their solvent and learn to live with the flammability or other issues.

I know of a few patented continuous flow applications and have heard of some bang-up applications for narrow transformations. But as a "global innovation", IL's are not as green or economical as many acolytes in the field might suggest.

Permalink to Comment

34. supercritical on August 16, 2006 4:02 AM writes...

I agree ionic liquids are not going to solve all problems and they are not going to completely replace organic solvents - particularly in custom chemical manufacture.But that wasn’t the question that was raised.

If you have a process that will be run long term then they can be worth the investment. The Eastman process wasn’t making a particular expensive product.

It is the same way with supercritical carbon dioxide, it isn’t going to be used by everyone as it requires investment in plant equipment etc etc. But would anyone argue that using it instead of dichloromethane to decaffeinate coffee and tea in not a great step forward? And DuPont now prepare fluorinated polymers using carbon dioxide.

I also think ionic liquid / supercritical carbon dioxide biphasic systems are a cure for problems that do exist. These systems are an answer to the separation problems associated with homogeneous catalysis.
And these combined system have advantages over using use of both of these solvents individually. Carbon dioxide can extract products from the ionic liquid phase without the need for organic solvents to remove the product from the lower ionic liquid / catalyst phase (as the ionic liquid and catalyst doesn’t dissolve in the CO2). While ionic liquids enable polar catalysts and reactants to be used, which would not dissolve in carbon dioixde. They can be run as a continuous flow process.

These systems are an answer (cure) to the separation problems associated with homogeneous catalysis. And they have greater applicability than aqueous biphasic processes (eg Ruhrchemie/Rhone-Poulenc process) as aqueous biphasic systems can only be used effectively for reactions where the substrate is sufficiently water soluble. In the case of ionic liquid /carbon dioxide biphasic systems the ionic liquid can be designed to dissolve any substrate well.

Permalink to Comment

35. supercritical on August 16, 2006 4:02 AM writes...

I agree ionic liquids are not going to solve all problems and they are not going to completely replace organic solvents - particularly in custom chemical manufacture.But that wasn’t the question that was raised.

If you have a process that will be run long term then they can be worth the investment. The Eastman process wasn’t making a particular expensive product.

It is the same way with supercritical carbon dioxide, it isn’t going to be used by everyone as it requires investment in plant equipment etc etc. But would anyone argue that using it instead of dichloromethane to decaffeinate coffee and tea in not a great step forward? And DuPont now prepare fluorinated polymers using carbon dioxide.

I also think ionic liquid / supercritical carbon dioxide biphasic systems are a cure for problems that do exist. These systems are an answer to the separation problems associated with homogeneous catalysis.
And these combined system have advantages over using use of both of these solvents individually. Carbon dioxide can extract products from the ionic liquid phase without the need for organic solvents to remove the product from the lower ionic liquid / catalyst phase (as the ionic liquid and catalyst doesn’t dissolve in the CO2). While ionic liquids enable polar catalysts and reactants to be used, which would not dissolve in carbon dioixde. They can be run as a continuous flow process.

These systems are an answer (cure) to the separation problems associated with homogeneous catalysis. And they have greater applicability than aqueous biphasic processes (eg Ruhrchemie/Rhone-Poulenc process) as aqueous biphasic systems can only be used effectively for reactions where the substrate is sufficiently water soluble. In the case of ionic liquid /carbon dioxide biphasic systems the ionic liquid can be designed to dissolve any substrate well.

Permalink to Comment

36. TimTheToolMan on August 16, 2006 3:28 PM writes...

Pd coupling has been overdone and overrated.
Everytime I see another publish paper on Pd coupling of C to C bond or C to N bond i get sick.

Permalink to Comment

37. SJB on August 17, 2006 2:45 AM writes...

32. MTK on August 15, 2006 03:47 PM writes...

"c) The first recipient of the Nobel Prize in Chemistry was vant Hoff, but, unbelievably, not for the conceptualization of tetrahedral carbon, stereochemistry, and 3-D structure, but rather for his studies in chemical dynamics and osmotic pressure. I'm no physical chemist, but that must be some important stuff to push tetrahedral carbon to the side."

Wasn't the problem more at that stage that it (the tetrahedral model) couldn't be 'proved' - sure it explained a lot, but enough? A bit like Stephen Hawking's ideas in physics...?

S

Permalink to Comment

38. Dave E on August 18, 2006 2:30 AM writes...

There are some cool things you can do with ionic liquids vis-a-vis electrochemistry. I hope we can make them commercial, but that's as much as I can say...whether they will ever live up to green solvent hype, I don't know.

The paper journals are nice when you are kicked back and want to read some chemistry that you don't have to use in the lab in the next 20 minutes. I like mine over coffee. Where I work we circulate about 10 of the ACS journals in print form, with the distribution lists divided between the synthetic and analytical groups, with a little overlap. I love the online access to journals, but it is hard to beat the portability and existential pleasures of having the print version in hand.

Permalink to Comment

39. tom bartlett on August 18, 2006 8:20 AM writes...

"Will Chemical and Engineering News ever go a year without running a headline that says "Salaries for Chemical Engineers Still Higher"."

Come on; if YOU spent your career doing glorified plumbing, you'd want your ego massaged, too.

"err... don't we already have benchtop LCMS machines? I don't get it."

A pretty sad substitute.

"3. To combine those first two, if you wrote up a paper about a ring-closing metathesis reaction to make a nanoscale structure in an ionic liquid, would the journals even bother sending it to a referee before immediately publishing it?"

Stu Borman would have it written up in minutes.

Unrelated QOTD: How many famous chemists/med chemists/Chem E's have made it into Wikipedia? Bet you can get the complet history of Motley Crew, though.

Permalink to Comment

40. kevin on August 18, 2006 2:57 PM writes...

1)no clue. Must be at least 5 years.
2)no clue
3)near as I can tell (I work mainly with polymers) all you would need is the word nano
4)I have long given up trying to understand why the Nobel committee does anything...
5) no comment (work for an instrument manufacturer)
6) I always found those interesting as they never seem to match my or my friends experience. I thought the ACS worked mainly as a tool of companies to keep salaries low. And to give professors something to do twice a year.

Permalink to Comment

41. Steve on August 20, 2006 2:26 PM writes...

If the Nobel Committee waits until all but one contender is dead, they can award it to him. Think of it as a tontine. The others can be mentioned en masse without sorting them out in a footnote that reminds, a la what would have been Woodward's last Nobel, that there are no posthumous awards so only the surviving contenders can be recognized.

Permalink to Comment

42. Von Griescku on August 23, 2006 3:39 PM writes...

4. Heck-Stille-Suzuki-Negishi.
7. What about Teruaki Mukaiyama?

Permalink to Comment

43. gilbepeer on May 5, 2010 4:12 PM writes...

precipitation measurements majority tar

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44. attkinsben on May 5, 2010 4:12 PM writes...

india public contributed criticized economic records

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45. nashehrli on May 5, 2010 4:12 PM writes...

volcanic sun brightness north cannot processes

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