Panache
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n-propyl,2-chloro propionate
If anyone can readily access the boiling point and solubility/miscibility data on this ester i would appreciate it.
It is located in the bio-rad ester library but they won't let me in.
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Nicodem
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Before I waste time by searching about the wrong compound, please clarify exactly which compound are you interested (the name you gave is ambiguous):
A.) 2-chloropropyl propanoate = CH3-CHCl-CH2-O-CO-CH2-CH3
B.) propyl 2-chloropropanoate = CH3-CH2-CH2-O-CO-CHCl-CH3
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Panache
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| Quote: | Originally posted by Nicodem
Before I waste time by searching about the wrong compound, please clarify exactly which compound are you interested (the name you gave is ambiguous):
A.) 2-chloropropyl propanoate = CH3-CHCl-CH2-O-CO-CH2-CH3
B.) propyl 2-chloropropanoate = CH3-CH2-CH2-O-CO-CHCl-CH3 |
Its the second one, i downloaded the merck index from references but there's kind of this macintosh/PC compatability hitch, so essentially i
downloaded a useless .exe file. I appreciate it if you could do this Nicoderm as i'm quite perplexed and may have stumbled onto a novel way to
chlorinate propionic acid at the 2/alpha position and add a propyl ester simultaneously.
My CRC has many other alpha chlorine esters and but not the propyl.
oh just in case there's a long list of similar esters in front of you, my mystery fraction has a bp range of 166-168, which by deduction i figure to
be roughly where the propyl would be.
[Edited on 30-6-2008 by Panache]
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Nicodem
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The CAS is 1569-03-5.
Of the experimental properties in the Chemical Abstracts there is only the bp listed as 68°C at 23 torr (Leggetter, B. E. Canadian Journal of
Chemistry, 43 (1965) 1030-1035). Beilstein only gives that bp, but at least it also lists the density (1.0478 g/mL at 20°C), heat of combustion
at constant volume (813.25 kcal/mol) and refractive index (1.4218 at 20°C with 589nm). Nothing else, no NMR, no IR, no other spectroscopic data -
just another improperly characterized compound.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Panache
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Posts: 1290
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Many thanks for your time nicodem, i appreciate it.
Extrapolation of that reduced pressure bp to atmospheric places it close to it range, however those extrapolations are uncertain, guess i'll have to
try to get my digital vacuum gauge to work again to run the bp at 23mmHg, they get contaminated so easily, i usually don't bother.
Odd that in 2008 such a simple ester has not been characterised and published. I'm sure it has been characterized innumerable times and I'm
sure its in proprietary GC/MS libraries. Guess i'll have to pull a favour for a NMR for this one, if i feel the other measurements are not enough to
instill me with confidence, shit i hate those telephone conversations.
'Hey, yeah its Mark, how have you been since the last time i rang you to do something for me for nothing...'
Anyone in Melbourne offering??
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Nicodem
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The compound has been prepared and published. There are 18 references mentioning it, though most are in analytical journals in regard to
chromatographic properties. This situation where the NMR spectra for simple compounds is not published is actually quite common since most of them
were published in the pre-NMR era and since they are considered "known compounds" the editors don't push for the NMR characterization. It is however
still a bit unusual that the IR spectra has not been published.
There are always alternatives to spectroscopic verification. You can do like the good old chemists did, that is either independent synthesis or
derivatization.
For example, if you have lactic acid you can make 2-chloropropionyl chloride with SOCl2/pyridine (Monatshefte fuer Chemie, 88 (1957) 234-241)
and make the ester with 1-propanol. Then you compare their properties like bp and TLC comparison.
You can hydrolyze a sample in acidic media and isolate the putative 2-chloropropanoic acid or you can try to make a known compound from what you
suspect is propyl 2-chloropropanoate, for example via nucleophilic substitution...
But if you ask me it is much easier to ask a friend for a favor and have an 1H NMR done.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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