Preparation of butanone by oxidation

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Discussion Overview

The discussion revolves around the preparation of butanone through the oxidation of butan-2-ol using sodium dichromate. Participants share their experimental procedures, safety concerns, and alternative oxidation methods, while also addressing the rationale behind reagent choice.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested
  • Experimental/applied

Main Points Raised

  • One participant outlines the experimental procedure for preparing butanone, including the use of sodium dichromate and the tests performed on the product.
  • Another participant criticizes the use of chromate oxidations, labeling them as outdated and environmentally harmful, suggesting alternative oxidation methods instead.
  • A participant expresses concern about the safety of the experiment, citing a lack of hazard warnings in their lab manual and recounting incidents of accidents during the experiment.
  • There is a discussion about the availability of reagents, with one participant suggesting that the choice of sodium dichromate may simply be due to what was available in the lab.
  • Concerns are raised about the toxicity of chromium (VI) and the necessity of proper safety measures, including the availability of Material Safety Data Sheets (MSDS).

Areas of Agreement / Disagreement

Participants express differing views on the safety and appropriateness of using chromate oxidations, with some advocating for their discontinuation due to toxicity, while others defend their use based on availability and adherence to lab protocols. The discussion remains unresolved regarding the best practices for oxidation in this context.

Contextual Notes

Participants highlight limitations in safety protocols and the potential hazards associated with the reagents used, as well as the dependency on the specific lab manual provided to students.

KLscilevothma
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I've done an experiment on preparing butanone by oxidation of butan-2-ol. Here are the simplified procedures.

1. Sodium dichromate-2-water were acidified by few cm^3 concentrated sulphuric acid, then the acidified dichromate and butan-2-ol were mixed.

2. Few pieces of anti-bumping granules were added and then simple distillation was carried out. Colourless distillate was obtained.

3. Add anhydrous calcium chloride to the distillate until the solid was in excess and the liquid was clear. Excess calcium chloride was then filtered. <purification of butanone>

4. Tests such as 2,4-dinitrophenylhydrazine solution test and Fehling's test were carried out.

In my lab report, I need to suggest a reason why sodium dichromate was used in the experiment in place of potassium dichromate. I can't think of a reason why since both potassium dichromate and sodium dichromate are strong oxidizing agents and both can react with butan-2-ol to form butanone.

Any help would be appreciated.
 
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Ugh. First off, I'd mention that all chromate oxidations suck and are antiquated. They're highly toxic and bad for the environment. You should be running TPAP, NMO, Swern oxidations, or even Dess-Martin Periodinane oxidations.

As for reasons why you used what you used, just say that was what was available. Often times chemists will use weird reagents because that's just what they happened to have on their shelves.
 
Originally posted by Chemicalsuperfreak
Ugh. First off, I'd mention that all chromate oxidations suck and are antiquated. They're highly toxic and bad for the environment.
I seems that you have a strong hatred towards chromate oxidation. There's no hazard warning in my lab manual telling us it is highly toxic and we weren't provided with gloves.

You should be running TPAP, NMO, Swern oxidations, or even Dess-Martin Periodinane oxidations.
I'm in high school and have to follow the lab manual. Also, I haven't learned the other oxidations that you mentioned.

In fact lots of accidents happened during this experiment, like in one group (4 persons in a group) after mixing butan-2-ol, sodium dichormate solution and concentrated suphuric acid, because the reaction is highly exothermic, the mixture started to boil and spilled out on a classmate's hands and lab garment. Also when doing simple distillation, a group's pear-shaped flask cracked and fireball was formed since a Bunsen burner was right under the pear-shaped flask.
 
Originally posted by KL Kam
I seems that you have a strong hatred towards chromate oxidation. There's no hazard warning in my lab manual telling us it is highly toxic and we weren't provided with gloves.

I'm in high school and have to follow the lab manual. Also, I haven't learned the other oxidations that you mentioned.

In fact lots of accidents happened during this experiment, like in one group (4 persons in a group) after mixing butan-2-ol, sodium dichormate solution and concentrated suphuric acid, because the reaction is highly exothermic, the mixture started to boil and spilled out on a classmate's hands and lab garment. Also when doing simple distillation, a group's pear-shaped flask cracked and fireball was formed since a Bunsen burner was right under the pear-shaped flask.

Chromium (VI) can be pretty nasty. Have you seen the movie Erin Brokovich? I'd be really careful in this lab, doesn't sound very safe. Make sure you've got all the proper MSDS available. It's required by law if you live in the US. Chromium oxidations have pretty much gone the way of the dodo in modern organic chemistry. Be safe.
 

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