75719-23-2

Usage

Class of Compound

Pyrrolidinedione

Structure

Six-carbon chain attached to a five-membered ring containing two nitrogen atoms and one oxygen atom

Primary Use

Monomer in the synthesis of high-performance polymers, coatings, and adhesives

Building Block

Key building block in the production of specialty chemicals and pharmaceuticals

Properties

High thermal stability, excellent mechanical and chemical properties

Applications

Diverse and wide-ranging, used in a variety of industries.

Upstream product

• 108-30-5 succinic acid anhydride 
• 111-26-2 hexan-1-amine 
• 37912-62-2 sodium succinimide 
• 110-63-4 Butane-1,4-diol 
• 628-73-9 hexanenitrile 
• 5048-19-1 hex-5-enenitrile 
• 123-56-8 Succinimide 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 123-13-7 N-(1-hexyl) pyrrolidine 
• 110-63-4 Butane-1,4-diol 
• 111-26-2 hexan-1-amine 

Relevant academic research and scientific papers

Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines

A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding the formation of pyrrolidines, cyclic imides, and lactones.

Synthesis of Cyclic Imides by Acceptorless Dehydrogenative Coupling of Diols and Amines Catalyzed by a Manganese Pincer Complex

The first example of base-metal-catalyzed dehydrogenative coupling of diols and amines to form cyclic imides is reported. The reaction is catalyzed by a pincer complex of the earth abundant manganese and forms hydrogen gas as the sole byproduct, making the overall process atom economical and environmentally benign.

MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS

The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C-C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di- lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.

Method for preparation of amide and imide from alcohol and nitrogen Containing Compound

The present invention relates to a method for preparing amide and imide from alcohol and a nitrogen containing compound and, more specifically, to a method for preparing amide and imide by using: a catalytic composition obtained by reacting a mixture of a transition metal complex and an N-heterocyclic carbene precursor with base or by reacting an N-heterocyclic carbene precursor with a mixture of a transition metal complex and base; or a transition metal complex catalyst including an N-heterocyclic carbene.

Comparative study of chemically immobilized and conventional homogeneous ionic liquids as phase-transfer catalysts for the N -alkylation of heterocyclic compounds

Various ionic liquids (ILs) were screened for their phase-transfer catalytic (PTC) activity using the N-alkylation of nitrogen heterocycles as the model reaction. Immobilized ILs behaved extremely well and proved to be far better catalysts than conventional homogeneous PTCs in terms of their stability, easy recovery, and reusability. The investigation also demonstrated that quaternary tetraalkylammonium salts offer very high catalytic activity, whereas aromatic heterocyclic tetravalent nitrogen catalysts (imidazolium- and pyridinium-based salts) were poorly active.

Synthesis of cyclic imides from nitriles and diols using hydrogen transfer as a substrate-activating strategy

An atom-economical and versatile method for the synthesis of cyclic imides from nitriles and diols was developed. The method utilizes a Ru-catalyzed transfer-hydrogenation reaction in which the substrates, diols, and nitriles are simultaneously activated into lactones and amines in a redox-neutral manner to afford the corresponding cyclic imides with evolution of H2 gas as the sole byproduct. This operationally simple and catalytic synthetic method provides a sustainable and easily accessible route to cyclic imides.

PROCESS OF FORMING A CYCLIC IMIDE

A process is provided for the synthesis of a cyclic imide. A primary amine and a diol compound are contacted in the presence of a Ruthenium (II) complex. The Ruthenium (II) catalyst includes at least one of an alicyclic ligand, an aromatic ligand, an arylalicyclic ligand, an arylaliphatic ligand and a phosphine ligand.

Synthesis of cyclic imides from simple diols

There's something imide so strong: Cyclic imides were synthesized from simple diols with primary amines in a single step using an in-situ-generated ruthenium catalytic system. The atom-economical and operatively simple syntheses of succinimides, phthalimides, and glutarimides, which are important building blocks in natural products and drugs, was also demonstrated. Copyright

Heterocycles in Organic Synthesis. Part 42. Preparation of Azides, Phthalimides, and Sulphonamides from Primary Amines

N-Alkyl and N-benzyl substituents are displaced from 2,4,6-triphenylpyridinium cations by nucleophilic azide, phthalimide, succinimide, and sulphonamide anions.This enables the conversion of primary alkyl- and benzylamines into azides, and primary (with potential for inversion or labelling) and secondary amines.