17611-82-4

Usage

Uses

Used in Pharmaceutical Industry:
Ethylsuccinonitrile is used as a key intermediate for the synthesis of various pharmaceuticals due to its ability to undergo multiple chemical reactions, facilitating the production of a broad spectrum of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, ethylsuccinonitrile is utilized as a precursor in the development of insect repellents, leveraging its chemical properties to create effective pest control agents.
Used in Dye Industry:
Ethylsuccinonitrile is employed as a starting material in the production of dyes, contributing to the creation of a diverse range of colorants for various applications.
Used in Perfumery:
As a precursor in the perfume industry, ethylsuccinonitrile is used to synthesize fragrances, capitalizing on its capacity to form a variety of aromatic compounds.
Used in Organic Synthesis:
Ethylsuccinonitrile is used as a versatile building block in organic synthesis for the creation of a wide array of chemical compounds, highlighting its adaptability in chemical reactions.
Safety Note:
It is crucial to handle ethylsuccinonitrile with care, as it is classified as harmful if ingested, inhaled, or comes into contact with the skin. Adequate safety measures are essential when working with this chemical to prevent any adverse effects.

InChI:InChI=1/C6H8N2/c1-2-6(5-8)3-4-7/h6H,2-3H2,1H3

Upstream product

• 74-90-8 hydrogen cyanide 
• 592-51-8 4-Pentenenitrile 
• 16529-66-1 3-Pentenenitrile 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 4635-87-4 3-pentenenitrile 
• 25899-50-7 cis-2-pentenenitrile 
• 13284-42-9 2-pentenenitrile 

Downstream Products

• 41819-75-4 4-ethylpyrrolidin-2-one 
• 199851-83-7 4-ethyl-1-methylpyrrolidin-2-one 

Relevant academic research and scientific papers

HETEROGENEOUS HYDROCYANATION

The present invention relates to an improved process for addition of hydrogen cyanide across olefins and, in particular, to the use of a specific aluminum oxide to catalyze the reaction. The aluminum oxide catalyst must have total alkali metal and/or alkaline earth metal content, measured in the form of alkali metal oxide and/or alkaline earth metal oxide, of less than 3,000 ppm by weight.

METHOD FOR PRODUCING NITRILE COMPOUNDS FROM ETHYLENICALLY UNSATURATED COMPOUNDS

The present invention relates to a method for the hydrocyanation of organic ethylenically unsaturated compounds including at least one nitrile function. The invention specifically relates to a method for the hydrocyanation of a hydrocarbon compound including at least one ethylenic unsaturation by a reaction with hydrogen cyanide in a liquid medium and in the presence of a catalyst including a metal element selected from the transition metals and an organophosphorous ligand, the organophosphorous gaud including a compound of general formula (I), where R1 and R2, which are identical or different, are a linear or branched alkyl radical having 1-12 carbon atoms, which can include heteroatoms, or an optionally substituted aromatic or cycloaliphatic radical that can include heteroatoms, wherein the covalent bond between P and R1, and that between P and R2, are P—C bonds.

PROCESS FOR THE PRODUCTION OF NITRILE COMPOUNDS FROM ETHYLENICALLY UNSATURATED COMPOUNDS

A method is described for the hydrocyanation of organic ethylene-unsaturated compounds into compounds including at least one nitrile function. Also described, is a method for the hydrocyanation of a hydrocarbon compound including at least one ethylenic unsaturation by reaction in a liquid medium with hydrogen cyanide in the presence of a catalyst including a metal element selected from among the transition metals and an organophosphorous ligand including, in one embodiment of the invention, an organophosphorous compound. The described method can be used in particular for the synthesis of adiponitrile from butadiene.

ORGANOPHOSPHORUS COMPOUNDS, CATALYTIC SYSTEMS COMPRISING SAID COMPOUNDS AND METHOD OF HYDROCYANATION USING SAID CATALYTIC SYSTEMS

The present invention relates to organophosphorus compounds belonging to the phosphinite-phosphite family, catalytic systems comprising a metallic element forming a complex with said phosphinite-phosphite compounds and methods of hydrocyanation employed in the presence of said catalytic systems.

Stable fluorophosphines: Predicted and realized ligands for catalysis

Ligand maps lead to treasure! The activity of complexes of fluorophosphines (R2PF) in catalytic hydroformylation and hydrocyanation is predicted from a ligand map. However, the instability of R2PF to disproportionation is well-documented. Examples of R2PF ligands (see scheme) are described that are stabilized to such an extent that they can be used in catalysis and are shown to be highly effective.

PROCESS FOR PRODUCING COMPOUNDS COMPRISING NITRILE FUNCTIONS

The present invention relates to a process for producing compounds comprising at least one nitrile function by hydrocyanation of a compound comprising at least one non-conjugated unsaturation. The invention proposes a process for producing compounds comprising at least one nitrile function by hydrocyanation of an organic compound comprising at least one non-conjugated unsaturation, comprising from 2 to 20 carbon atoms, by reaction with hydrogen cyanide in the presence of a catalytic system comprising a complex of nickel having the oxidation state of zero with at least one organophosphorus ligand chosen from the group comprising organophosphites, organophosphonites, organophosphinites and organosphosphines and a cocatalyst of the Lewis acid type.

Cage phosphinites: Ligands for efficient nickel-catalyzed hydrocyanation of 3-pentenenitrile

The cage monophosphinites CgPOR {where CgP = 6-phospha-2,4,8-trioxa- adamantane and R = C6H5 (La); 2-C 6H4CH3 (Lb); 2,4,6-C 6H2(CH3)3 (Lc); 2,4-C6H3tBu2 (Ld); CH3 (Le); CH2CF3 (Lf)} and diphosphinites CgPZPCg {where ZH2 = 2,2′-biphenol (L g) or 1,2-benzenedimethanol (Lh)} have been made from CgPBr and the corresponding alcohol or phenol. The cage phosphinites are remarkably stable to water. All the ligands La-h have been tested for nickel(0)-catalyzed hydrocyanation of 3-pentenenitrile in the presence of Lewis acids (ZnCl2, Ph2BOBPh2, or iBu2AlOAliBu2), and tentative structure-activity relationships are suggested. The hydrocyanation activities obtained with catalysts derived from monophosphinite Lf (with iBu2AlOAliBu2) and diphosphinite Lh (with ZnCl2) are comparable with the commercial catalyst based on P(OTol)3. The complexes trans-[PtCl 2(L)2] where L = La (1a), Le (1e), and Lf (1f) and the chelate cis-[PtCl2(Lh)] (1h) are reported. From the νCO values for the complexes trans-[RhCl(CO)(La-f)2] (2a-f), it is concluded that ligand Lf is the most phosphite-like of the monophosphinites. Treatment of [Ni(cod)2] (cod = 1,5-cyclo-octadiene) with L h leads to a mixture of products, one of which was characterized as the binuclear [Ni2(Lh)2(μ-cod)] (3h). The crystal structures of Lh, 1a, 1e, 1f, 1h?2CH2Cl 2, and 3h?3C6H5CH3 are reported.

PREPARATION OF NITRILES FROM ETHYLENICALLY UNSATURATED COMPOUNDS

A process for the hydrocyanation of a hydrocarbon-based compound having at least one site of ethylenic unsaturation into a nitrile compound includes reaction thereof, in a liquid medium, with hydrogen cyanide in the presence of a catalyst containing a metal element selected from among the transition metals and an organophosphorus ligand, wherein the organophosphorus ligand is a mixture of at least one monodentate organophosphite compound and at least one monodentate organophosphine compound; the subject process is especially useful for the synthesis of adiponitrile from butadiene.

HYDROCYANATION OF PENTENENITRILES

The invention provides a hydrocyanation process to produce adiponitrile and other dinitriles having six carbon atoms, in the presence of catalyst composition comprising a zero-valent nickel and at least one bidentate phosphorus-containing ligand wherein the bidentate phosphorus-containing ligand gives acceptable results according to at least one protocol of the 2-Pentenenitrile Hydrocyanation Test Method.

HYDROCYANATION OF 2-PENTENENITRILE

The invention provides a process for hydrocyanation, comprising: contacting 2-pentenenitrile with hydrogen cyamide at a temperature in the range of about 0° C. to about 150° C. in the presence of at least one Lewis acid promoter and a catalyst precursor composition, wherein the catalyst precursor composition comprises a zero-valent nickel and at least one bidentate phosphite ligand selected from a member of the group represented by Formula I and Formula II, in which all like reference characters have the same meaning, except as further explicitly limited: wherein R1 and R5 are independently selected from the group consisting of C1 to C5 hydrocarbyl; and R2, R3, R4, R6, R7 and R8 are independently selected from the group consisting of H and C1 to C4 hydrocarbyl.