Synthesizing Diphenyl Oxalate: Esterification of Phenol and Oxalic Acid

In summary: I'm not sure if I'll end up getting the chemicals or not.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.
  • #1
the_m-theorist
31
2
How do I esterify phenol and oxalic acid to make diphenyl oxalate.
P.S. My initial researches using google have yielded no results.
 
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  • #2
I would start with Vogel's Textbook of Practical Organic Chemistry.
 
  • #3
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.
 
  • #4
Borek said:
I would start with Vogel's Textbook of Practical Organic Chemistry.
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.
 
  • #5
DrDu said:
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.
The Beilstein database, right?
P.S. I'm going to use it for glow-science too!
 
  • #6
the_m-theorist said:
I haven't found diphenyl oxalate anywhere

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).
 
  • #7
Borek said:
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).
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?
 
  • #8
I am afraid you will not find a free and reasonably complete database.
 
  • #9
Borek said:
I am afraid you will not find a free and reasonably complete database.
any other refrences?
 
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  • #10
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.
 
  • #11
DrDu said:
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.
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
DrDu said:
I always thought thyat the young generation was smarter than I being an old guy in localizing everything on internet.
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!
 
  • #14
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.
 
  • #15
DrDu said:
Probably the hardest step is getting the oxalylchloride.
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.)
DrDu said:
To show the fluorescence, you can also use Rhodamin B
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.
 
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  • #16
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.
 
  • #17
Borek said:
I would start with Vogel's Textbook of Practical Organic Chemistry.
OMG I read it is still the best but that must go back a long way.
 
  • #18
DrDu said:
Just take care in handling the oxalyl chloride. It is very toxic and volatile, comparable to phosgene.
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!

DrDu said:
However, I was doing this as a high school project, too.
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!
 
  • #19
Reduce phenyl-chloroformate with phenyl formate?
 
  • #20
Although I'm not sure if you can grignardize phenyl formate.
 
  • #21
DrDu said:
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.
oxalylchloriden is to toxic and I am not allowed to work with this compound, does normal oxalic acid word to? (without chlorine)
 
  • #23
I've seen a paper that suggests that transesterfication of dimethyl oxalate over an SnO2 catalyst can be used to produce this compound with a ~22% conversion. I couldn't find the PDF of that paper, but I did find one on the production of SnO2 catalysts for transesterification here.

Presumably you could produce dimethyl oxalate with a Fischer Esterification of methanol and oxalic acid. This should make a mix of the mono-, di-, and tri-esters of oxalic acid. I'm unsure how you could separate these esters off the top of my head. Or you could just but dimethyl oxalate somewhere and use that to perform the transesterification.
 
  • #24
I did some reading: Apparently, the toxicity of Oxalylchloride had been overestimated. It is no longer classified as T but only as Xn. So if you have a fumehood in your school, it should be safe to operate with it. I don't see any reasonable alternative synthesis of TCPO or the like via other routes.
 
  • #25
thank you for your help , I tried the reaction with a Fischer Esterification but the result wasn't very clear. After a week at 50 degrees Celsius there were no visual changes
however the pH did change so mabey something did happen.

if I have a clear result I'll post the awnser so if more people have problems they can use it
 

1. What is the purpose of synthesizing diphenyl oxalate?

The purpose of synthesizing diphenyl oxalate is to produce a compound that is commonly used in the production of glow sticks. It is also used as a chemical intermediate in the synthesis of various pharmaceuticals and organic compounds.

2. What are the materials needed for the synthesis of diphenyl oxalate?

The materials needed for the synthesis of diphenyl oxalate include oxalic acid, phenol, sulfuric acid, and a solvent such as toluene or xylene. Additional equipment such as a round-bottom flask, condenser, and heating source are also required.

3. What is the process for synthesizing diphenyl oxalate?

The process for synthesizing diphenyl oxalate involves heating a mixture of oxalic acid, phenol, and sulfuric acid in a solvent. The reaction produces diphenyl oxalate, which can then be isolated and purified through techniques such as filtration and recrystallization.

4. Are there any safety precautions to take when synthesizing diphenyl oxalate?

Yes, there are several safety precautions that should be taken when synthesizing diphenyl oxalate. The chemicals used in the synthesis are corrosive and can cause irritation to the skin, eyes, and respiratory system. It is important to wear appropriate protective gear, work in a well-ventilated area, and handle the chemicals with care.

5. What are the potential uses for diphenyl oxalate?

In addition to its use in glow sticks and pharmaceutical synthesis, diphenyl oxalate can also be used as a photoinitiator in polymerization reactions and as a reagent in organic synthesis. It is also being researched for potential applications in solar energy conversion and as a fluorescent probe for detecting metal ions.

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