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I want to run a reaction that needs diethyl ether as anti solvent in the last step (comes from articles). But I can't use it due to its harmful effects on the body. Is there any other solvent?

My reaction is about substitution of $\ce{-OH}$ of lignin with BiBB in THF and in other one in $\ce{EtOAc}$ as solvent.

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  • $\begingroup$ Welcome to Chemistry.SE! To acquaint yourself with this page, take the tour and visit the help center. Furthermore this tutorial shows you how math and chemical formulae can be nicely formatted on this site. Please include references to the articles you are referring to in your question and when you use "non-trivial" abbreviations such as BiBB it would also be nice to include a link to some site that shows what hides behind the abbreviation. $\endgroup$
    – Philipp
    Commented Dec 6, 2014 at 11:53
  • $\begingroup$ I've added a link for BiBB. If its not the correct compound please change it. $\endgroup$
    – Philipp
    Commented Dec 6, 2014 at 11:55

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It is strange that you are concerned about diethyl ether (which has been used as an anesthetic), but you are not concerned about THF. From the US Pharmacopoeia:

Permitted Daily Exposure
Tetrahydrofuran 7.2 mg/day
Diethyl Ether 50 mg/day
Ethyl Acetate 50 mg/day

If you dry the product thoroughly (above 120°C), you should not have any problems with residual solvents.

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    $\begingroup$ Thank you for your answer, but my professor have wanted me to change this solvent $\endgroup$
    – Seyed Amir Mousavian
    Commented Dec 8, 2014 at 10:30
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    $\begingroup$ I second this answer. THF is much more hazardous to human health than diethyl ether. I assume that this will be done using proper personal protective equipment, especially fume hood ventilation, then handling ether is not a problem if you can safely handle THF. $\endgroup$
    – Ben Norris
    Commented Jan 7, 2015 at 12:17
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    $\begingroup$ However, if you are worried about one of the other ways diethyl ether is more hazardous than THF, then we have a different scenario. Diethyl ether has a lower boiling point (ca. $35\ ^\circ \text{C}$), which means it is much more likely that you will be exposed to the 50 mg/day vapor. Also, in some parts of the world, especially if there is no air conditioning, diethyl ether might be a gas. Diethyl ether also is more flammable (due to its higher volatility), and forms peroxides more quickly (and more explosively). $\endgroup$
    – Ben Norris
    Commented Jan 7, 2015 at 12:21

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