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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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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.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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A Diamine-Oriented Biorefinery Concept Using Ammonia and Raney Ni as a Multifaceted Catalyst.

Xianyuan Wu1, Mario De Bruyn2, Katalin Barta1,2

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Chemie-Ingenieur-Technik
|January 12, 2023
PubMed
Summary
This summary is machine-generated.

Lignocellulose can be converted into valuable diamines using Raney Nickel. This process efficiently transforms diols derived from biomass into diamines through hydrogenation and hydrogen-borrowing reactions.

Keywords:
AmineCatalysisCelluloseLignin

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Area of Science:

  • Biomass Valorization
  • Green Chemistry
  • Catalysis

Background:

  • Diamines are crucial industrial chemicals with diverse applications.
  • Sustainable sourcing of chemical feedstocks is an ongoing challenge.
  • Lignocellulose represents an abundant and renewable biomass resource.

Purpose of the Study:

  • To investigate the feasibility of utilizing lignocellulose as a feedstock for producing diols.
  • To develop efficient methods for converting these lignocellulose-derived diols into diamines.
  • To explore the catalytic role of Raney Nickel in these biomass conversion processes.

Main Methods:

  • Raney Nickel-catalyzed hydrogenation and demethoxylation for diol formation from lignocellulose components.
  • Raney Nickel-catalyzed hydrogen-borrowing diamination of diols in the presence of ammonia (NH3).
  • Analysis of reaction yields and product purity for both diol and diamine formation.

Main Results:

  • Demonstrated the feasibility of converting lignocellulose into diol-containing molecules.
  • Achieved good to excellent yields for the transformation of diols into diamines.
  • Raney Nickel effectively facilitated both diol formation (via hydrogenation/demethoxylation) and diamine formation (via hydrogen-borrowing).

Conclusions:

  • Lignocellulose is a viable and sustainable source for producing diols.
  • The developed method offers an efficient route to synthesize diamines from biomass-derived diols.
  • Raney Nickel is a key catalyst enabling these valuable chemical transformations from renewable resources.