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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
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Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

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Preparation of Binary and Ternary Deep Eutectic Systems
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Is ethaline a deep eutectic solvent?

Vira Agieienko1, Richard Buchner2

  • 1Nanotechnology and Biotechnology Department, Nizhny Novgorod State University, n.a. R.E. Alekseev, Minina Str. 24, 603950 Nizhny Novgorod, Russian Federation. vera.n.ageenko@gmail.com.

Physical Chemistry Chemical Physics : PCCP
|February 16, 2022
PubMed
Summary
This summary is machine-generated.

Ethaline, a choline chloride (ChCl) and ethylene glycol (EG) mixture, is not a deep eutectic solvent. The true eutectic point is at a different composition, with a melting point only slightly lower than pure EG.

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Area of Science:

  • Physical Chemistry
  • Materials Science

Background:

  • Choline chloride (ChCl) and ethylene glycol (EG) mixtures are often studied as potential deep eutectic solvents.
  • Ethaline (1:2 ChCl:EG molar ratio) is commonly misidentified as the eutectic composition.

Purpose of the Study:

  • To accurately determine the phase behavior and eutectic point of ChCl-EG mixtures.
  • To re-evaluate the classification of ethaline as a deep eutectic solvent.

Main Methods:

  • Differential scanning calorimetry (DSC) was used to measure melting points.
  • Phase diagram analysis was performed for ChCl mole fractions < 0.333 and temperatures < 323 K.
  • Water content was controlled to < 300 ppm.

Main Results:

  • The commonly accepted ethaline (1:2 ChCl:EG) is in the ChCl-saturated region, not the eutectic point.
  • The actual eutectic point was identified at a 1:4.85 ChCl:EG molar ratio (xChCl = 0.171).
  • The eutectic mixture has a melting point of 244 K, only 16 K below neat EG.

Conclusions:

  • Ethaline does not meet the criteria for a deep eutectic solvent based on its composition and melting point depression.
  • The phase diagram of ChCl-EG mixtures resembles that of an ideal binary mixture, despite ChCl being an electrolyte.