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Synthesis of diphenyl oxalate

  1. Oct 3, 2014 #1
    How do I esterify phenol and oxalic acid to make diphenyl oxalate.
    P.S. My initial researches using google have yielded no results.
     
  2. jcsd
  3. Oct 3, 2014 #2

    Borek

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    I would start with Vogel's Textbook of Practical Organic Chemistry.
     
  4. Oct 4, 2014 #3

    DrDu

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    Once I prepared the dinitrophenyloxalic esters used in lightsticks, but I started from oxalylchloride. Usually Beilstein is a good starting point to find syntheses of standard organic compounds.
     
  5. Oct 4, 2014 #4
    I downloaded the fifth edition yesterday and it seems like a great general reference but I haven't found diphenyl oxalate anywhere. Perhaps you could tell me some other more focused references.
     
  6. Oct 4, 2014 #5
    The Beilstein database, right?
    P.S. I'm gonna use it for glow-science too!
     
  7. Oct 4, 2014 #6

    Borek

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    Vogel is more about finding general ideas and then trying by yourself.

    Unless you can find a specific synthesis described in literature - but using google is not a good approach, as DrDu suggested you will get better results using specialized databases (typically behind a paywall, but your school may have access).
     
  8. Oct 4, 2014 #7
    Well sadly I know that the school does not have access to any databases, but tell me do you have any other references, there is very little about esters in Vogel. Also is Beilstein not free?
     
  9. Oct 4, 2014 #8

    Borek

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    I am afraid you will not find a free and reasonably complete database.
     
  10. Oct 4, 2014 #9
    any other refrences?
     
    Last edited: Oct 4, 2014
  11. Oct 4, 2014 #10

    DrDu

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    Beilstein is not only a database but exists also as a shelf full of books, maybe at your local library.
    I think I followed the following article:
    http://pubs.acs.org/doi/pdf/10.1021/ed051p528
    Maybe you can locate it in some library as it is not free.
     
  12. Oct 4, 2014 #11
    Thanks for the link, but unfortunately I've just checked at the local library and they don't have Beilstein.
    Still I'll keep searching in other libraries, in the meanwhile do you have any other references which might have the reaction.
     
  13. Oct 6, 2014 #12

    DrDu

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  14. Oct 6, 2014 #13
    Yes, I found basically the same thing (the trichlorophenol variant though) here only in much better video form. It seems he also has a video where he prepares the TCPO. (he too uses toulene). Also I've been going through some books. (Including Morrison and Boyd.) I found some standard esterification methods and stuff but everywhere I looked I couldn't find anything which had two phenyl groups and 2 C double bonds. Still searching!
     
  15. Oct 7, 2014 #14

    DrDu

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    Watching NurdRage is always fun. Probably the hardest step is getting the oxalylchloride. To show the fluorescence, you can also use Rhodamin B, which is way cheaper and easier to obtain than Bis phenylethinylantracene, although the fluorescence is not as strong.
     
  16. Oct 7, 2014 #15
    UPDATE:- I was talking with a lot of chemical dealers today. One was promising (I still had to spell out oxalyl chloride for him though), he said he'll tell me tomorrow if he could get me the chemicals. (hope for the best.)
    Do you think sodium fluorescein (is usually used in highlighters I believe) will work ? The article you quoted said that almost all fluorescent dyes work and this says that it is slightly soluble in ethanol, though I'm not sure it'll work in ethyl acetate or diethyl pthalate.
     
    Last edited: Oct 7, 2014
  17. Oct 7, 2014 #16

    DrDu

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    Just take care in handling the oxalyl chloride. It is very toxic and volatile, comparable to phosgene. However, I was doing this as a high school project, too.
     
  18. Oct 7, 2014 #17

    epenguin

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    OMG I read it is still the best but that must go back a long way.
     
  19. Oct 10, 2014 #18
    I admit that I had no idea oxalyl chloride was so toxic, I had intended to go through the MSDS of each chemical after the dealer told me that the chemicals were available, but I ended up downloading the MSDS of each one just after reading this comment! But the dealers here are ridiculous, he has no idea what oxalyl chloride (maybe I'll buy that from sigma aldrich or something) is and tells me that I need a permit for buying toluene from him!

    Ahhh! so you have read my other posts! Funny how the number of people who read your other posts while conversating on one increases drastically on academic forums!
     
  20. Oct 10, 2014 #19
    Reduce phenyl-chloroformate with phenyl formate?
     
  21. Oct 10, 2014 #20
    Although I'm not sure if you can grignardize phenyl formate.
     
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