Sterification with HCL

Greetings. 

Im aiming to make my own Jazmín alike fragance from benzyl alcohol and acetic acid ussing hcl as catalizer, i have been researching and almost all the proccedures uses sulphuric acid, but i cant use sulphuric acid in my country, because it use or storage is forbiden its called "drug initiator".

Havr anyone experienced making fisher sterification ussing hcl, does ussing hcl instead of sulphuric makes a Big yield difference?

Thanks you very much

Comments

  • I've done that reaction but only with sulphuric acid, you will have to try it for yourself.
    Cosmetic Brand Creation. Concept to name to IMPI search to logo and brand registration. In-house graphic design inc. Pantone specs. Cosmetic label and box design & graphics.
  • PharmaPharma Member, Pharmacist
    It is possible but you have one main problem, water! Esterification only works in anhydrous systems and HCl comes at <35% aqueous solutions. Trying to remove said water by evaporation will evaporate HCl first whilst chemical or adsorption strategies (such as anhydrous Epsom salt or molsieve) will turn HCl into a gas and then you've got to run. You may want to try phosphoric acid or acetic anhydride ;) . In the latter case, you have to gently neutralise the excess acetic acid before solvent extraction or distillation.
  • I just can't imagine the difficulties of using acetic anhydride for anything, if not wearing a complete biohazard suit.
    Cosmetic Brand Creation. Concept to name to IMPI search to logo and brand registration. In-house graphic design inc. Pantone specs. Cosmetic label and box design & graphics.
  • Pharma said:
    It is possible but you have one main problem, water! Esterification only works in anhydrous systems and HCl comes at <35% aqueous solutions. Trying to remove said water by evaporation will evaporate HCl first whilst chemical or adsorption strategies (such as anhydrous Epsom salt or molsieve) will turn HCl into a gas and then you've got to run. You may want to try phosphoric acid or acetic anhydride ;) . In the latter case, you have to gently neutralise the excess acetic acid before solvent extraction or distillation.
    Im thinking in use an aparatus like dean-stark water separator, but it would be awesome that i could use phosphoric acid, have you made an experimento ussing phosphoric? 
  • Belassi said:
    I've done that reaction but only with sulphuric acid, you will have to try it for yourself.
    HI belassi, como estas?. Thanks you very much
  • AzizAziz Member
    Belassi said:
    I've done that reaction but only with sulphuric acid, you will have to try it for yourself.
    HI belassi, como estas?. Thanks you very much
    What material is  ' como estas ' ? 
  • Haha it's Spanish. We both live in Latin America. I'm good, thanks. I have to close the lab temporarily because we are moving home.
    Cosmetic Brand Creation. Concept to name to IMPI search to logo and brand registration. In-house graphic design inc. Pantone specs. Cosmetic label and box design & graphics.
  • PharmaPharma Member, Pharmacist
    Im thinking in use an aparatus like dean-stark water separator, but it would be awesome that i could use phosphoric acid, have you made an experimento ussing phosphoric? 
    A Dean Stark won't really work with aqueous HCl solutions. You'd distil off water and HCl together ;) .

    No, I have not tried phosphoric acid but theory says it will work nearly as smoothly as sulphuric acid. There are a few reasons why it's not used, being not reactive enough ain't one of them.
    Did you try ordering the final product at Perfumer's Apprentice? Neglecting the fun part, this might be less hard on time and budget... Glassware is expensive!

    I don't see why using acetic anhydride would require a hazmat suit... It has a fairly low reactivity for an acid anhydride and it boils above acetic acid. Slowly dripping it into a chilled solution of benzyl alcohol and neutralisation of eventual residues with a bit of water just before liquid-liquid separation will result in vinegar (or just add bicarbonate solution -> careful, it will bubble like crazy). Also, you can avoid heating as well as strong mineral acids and that's already a huge advantage over acid catalysed esterification.
    Besides, esterification with acetic anhydride (making aspirin) is a school experiment you can do with 14-16 year olds ;) .
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