Preparation of butanone by oxidation

In summary, the experiment involved mixing butan-2-ol and sodium dichromate-2-water, then adding a few pieces of anti-bumping granules and conducting simple distillation. colourless distillate was obtained. Tests were conducted to determine the purity of butanone. Chromium (VI) can be pretty nasty and should be handled with care in this lab.
  • #1
KLscilevothma
322
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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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  • #2
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.
 
  • #3
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.
 
  • #4
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.
 

1. What is butanone and why is it prepared by oxidation?

Butanone, also known as methyl ethyl ketone, is a colorless liquid organic compound with a pungent odor. It is commonly used as a solvent in various industries. Butanone is prepared by oxidation because it is a key intermediate in the production of other important chemicals, such as plastics, adhesives, and coatings.

2. What is the process for preparing butanone by oxidation?

The process for preparing butanone by oxidation involves the reaction of n-butanol with oxygen in the presence of a catalyst, typically copper or silver. This reaction produces butanone and water as byproducts.

3. What are the main uses of butanone?

Butanone has numerous industrial applications, including being a solvent for resins, varnishes, and lacquers. It is also used in the production of plastics, rubber, and pharmaceuticals. Additionally, butanone is used in the synthesis of other chemicals, such as methyl isobutyl ketone and acetic acid.

4. Are there any safety concerns when working with butanone?

Butanone can be harmful if inhaled, ingested, or absorbed through the skin. It can also cause irritation to the eyes, skin, and respiratory system. It is important to handle butanone in a well-ventilated area and wear appropriate personal protective equipment, such as gloves and goggles.

5. Can butanone be prepared by methods other than oxidation?

Yes, butanone can also be prepared through the dehydrogenation of 2-butanol or the hydration of 1-butene. However, oxidation is the most common and commercially viable method for producing butanone.

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