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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Preparation of Amines: Alkylation of Ammonia and Amines

Preparation of Amines: Alkylation of Ammonia and Amines

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...

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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.

Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions

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Published on: August 17, 2016

Methods to stabilize and destabilize ammonium borohydride.

Thomas K Nielsen¹, Abhi Karkamkar, Mark Bowden

¹Center for Energy Materials, Interdisciplinary Nanoscience Center and Department of Chemistry, Aarhus University, DK-8000 Aarhus, Denmark.

Dalton Transactions (Cambridge, England : 2003)

|September 15, 2012

Summary

This summary is machine-generated.

Ammonium borohydride (NH(4)BH(4)) shows promise for hydrogen storage but decomposes quickly. Applying back pressure stabilizes NH(4)BH(4), while nanoconfinement leads to faster hydrogen release from its decomposition product.

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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

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Published on: May 15, 2015

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Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production

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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Published on: May 15, 2015

Area of Science:

Materials Science
Chemical Engineering
Physical Chemistry

Background:

Ammonium borohydride (NH(4)BH(4)) possesses a high hydrogen content (24.5 wt%) and releases hydrogen below 160 °C.
The short ambient half-life (~6 h) of NH(4)BH(4) limits its practical application for hydrogen storage.
Investigating stabilization methods is crucial for advancing NH(4)BH(4) as a hydrogen storage material.

Purpose of the Study:

To explore pressure-mediated stabilization effects on ammonium borohydride (NH(4)BH(4)) decomposition.
To assess the potential of nanoconfinement in mesoporous silica (MCM-41) for stabilizing NH(4)BH(4).
To characterize the decomposition products and their properties, including potential phase transitions.

Main Methods:

Studied NH(4)BH(4) decomposition under variable hydrogen and argon back pressures.
Investigated nanoconfinement of NH(4)BH(4) within MCM-41 silica.
Utilized X-ray diffraction (XRD) and solid-state MAS (11)B NMR to analyze decomposition products and phase behavior.

Main Results:

Increasing hydrogen or argon back pressure reduced the hydrogen release rate of NH(4)BH(4) by ~16%, suggesting stabilization via a positive volume of activation.
Nanoconfinement in MCM-41 did not stabilize NH(4)BH(4); instead, it rapidly decomposed into [(NH(3))(2)BH(2)][BH(4)] (DADB).
Hydrogen desorption from nanoconfined DADB was enhanced (DSC peak temperature reduced by -13 °C), and DADB exhibited a reversible phase transition at temperatures below -30 °C.

Conclusions:

Positive back pressure can moderately stabilize ammonium borohydride (NH(4)BH(4)), offering a potential pathway for controlled hydrogen release.
Nanoconfinement in MCM-41 destabilizes NH(4)BH(4) but enhances hydrogen release from its decomposition product, DADB.
The discovery of a low-temperature polymorph of DADB opens new avenues for understanding and potentially controlling its properties.