Olefine from amine - how to make?

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In summary: Essentially, the reaction can be carried out using a strong base and heat, or using a reagent like DBU. In summary, the conversation discusses the possibility of converting primary amines into olefins and the use of Hofmann elimination to achieve this. The individual is seeking guidance on the appropriate conditions for this reaction.
  • #1
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Hello! Can you please help me in my difficult situation. I ve already read much but found nothing.
So, I have primary amine (C16 and C18). I have to get the respective olefine. I watched the reaction deamination, but i ve read that it is impossible to get one product (one alcohol) from this reaction - because many isomer are appeared. If there are other way to deliver amine from amine group??
And then i have hexadecylsulfonate. Can i transfer this compound to olefine. I ve read that alkylsulfonate can be desulfonate by hydrolisis with RH as product. But it was describe for aromatic sulfonate. If this is suitable for aliphatic sulfonate?
Thank you for all help and hints. I m not organic but now i need olefine for my inorganic synthesis...
 
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  • #3
sjb-2812, thank you for help.
I ve read about this elimination, i have question - Have you done such reactions? Where can i get proper conditions for its realization?
Thank you.
 
  • #4
Helene87 said:
sjb-2812, thank you for help.
I ve read about this elimination, i have question - Have you done such reactions? Where can i get proper conditions for its realization?
Thank you.

I have not carried out the reaction, but there are a number of references at e.g. http://orgchem.chem.uconn.edu/namereact/hofmannelim.html or similar
 
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1. What is olefine and how is it related to amines?

Olefine, also known as olefin or alkene, is a type of hydrocarbon compound that contains at least one carbon-carbon double bond. Amines, on the other hand, are compounds that contain a nitrogen atom bonded to one or more carbon atoms. Olefines can be derived from amines through a process called dehydrohalogenation, where a hydrogen halide (such as HCl or HBr) is removed from the amine molecule to form a carbon-carbon double bond.

2. What are the common methods for making olefines from amines?

There are several methods for making olefines from amines, including dehydrohalogenation, elimination reactions, and oxidative cleavage. Dehydrohalogenation involves heating an amine with a strong base, such as potassium hydroxide or sodium hydroxide, to remove a hydrogen halide and form a carbon-carbon double bond. Elimination reactions, on the other hand, involve the removal of a small molecule, such as water or hydrogen chloride, from an amine to form an olefin. Oxidative cleavage involves the use of oxidizing agents, such as potassium permanganate or ozone, to break the double bond in an amine and form two olefin molecules.

3. What are the factors that affect the yield of olefines from amines?

The yield of olefines from amines can be affected by several factors, including the type of amine used, the strength of the base, the temperature and pressure of the reaction, and the presence of any impurities. The type of amine used can affect the stability of the intermediate formed during dehydrohalogenation, which can in turn affect the yield of olefin. The strength of the base and the reaction conditions can also affect the speed and efficiency of the reaction, thus impacting the yield of olefin. Lastly, impurities in the starting materials or reaction products can also affect the yield of olefines.

4. Are there any safety concerns when working with olefines and amines?

Yes, there can be safety concerns when working with olefines and amines. Amines can be corrosive and toxic, and some olefines can be flammable or explosive. It is important to handle these compounds with caution and follow proper safety protocols, such as wearing protective gear and working in a well-ventilated area. It is also important to properly dispose of any waste materials to avoid potential hazards.

5. How can the purity of the final product be determined?

The purity of the final product can be determined through various analytical techniques, such as gas chromatography, nuclear magnetic resonance spectroscopy, and mass spectrometry. These techniques can help identify the chemical composition and structure of the product and determine its purity by comparing it to known standards. Additionally, physical properties such as melting point and boiling point can also be used to assess the purity of the product.

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