18715-38-3

Usage

Uses

Used in Pharmaceutical Industry:
(E)-hex-3-enedinitrile is utilized as a key intermediate in the synthesis of pharmaceuticals, playing a crucial role in the development of new drugs and medicinal compounds. Its unique chemical structure allows for versatile reactions and modifications, facilitating the creation of a wide range of therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, (E)-hex-3-enedinitrile serves as an intermediate for the production of various agrochemicals. Its involvement in the synthesis of these compounds contributes to the development of effective solutions for pest control and crop protection, thereby supporting agricultural productivity.
Used in Perfume Industry:
(E)-hex-3-enedinitrile is employed as a chemical intermediate in the perfume industry, where it is used in the creation of unique and complex fragrances. Its ability to undergo various chemical reactions enables the production of a diverse array of scent compounds, enriching the palette of available perfume ingredients.
Used in Polymer Production:
(E)-hex-3-enedinitrile contributes to the field of polymer science as a component in the synthesis of certain polymers. Its integration into polymer formulations can influence the properties of the resulting materials, such as their strength, flexibility, or chemical resistance, depending on the specific application requirements.
Used in Organic Synthesis:
As a chemical intermediate in organic synthesis, (E)-hex-3-enedinitrile is instrumental in the preparation of a multitude of organic compounds. Its reactivity and functional groups make it a valuable building block for the synthesis of various target molecules across different chemical domains.

InChI:InChI=1/C6H6N2/c7-5-3-1-2-4-6-8/h1-2H,3-4H2/b2-1+

Upstream product

• 764-41-0 1,4-dichloro-2-butene 
• 143-33-9 sodium cyanide 
• 74-90-8 hydrogen cyanide 
• 110-57-6 trans-1,4-dichlorobut-2-ene 
• 310447-99-5 3,4-dichlorobut-1-ene 
• 930-22-3 epoxybutene 
• 1615-70-9 penta-2,4-dienenitrile 
• 590-12-5 (E)-1,2-dibromoethene 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 7732-18-5 water 
• 106-99-0 buta-1,3-diene 
• 107-13-1 acrylonitrile 
• 821-06-7 (E)-1,4-dibromobutene 
• 4367-08-2 copper(II) cyanide 

Downstream Products

• 25129-30-0 trans-Δ²-Buten-1,4-dicarbonsaeure-diamid 
• 100142-28-7 3-phenoxy-adiponitrile 
• 111-69-3 hexanedinitrile 
• 5309-29-5 (E)-2,5-Bis-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylidene]-hex-3-enedinitrile 
• 5263-43-4 (E)-2,5-Bis-[(2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethyl-cyclohex-1-enyl)-undeca-2,4,6,8,10-pentaen-(Z)-ylidene]-hex-3-enedinitrile 
• 64520-53-2 (5-oxo-pyrrolidin-2-yl)-acetic acid 
• 88612-68-4 2-(5-oxo-1-phenylpyrrolidin-2-yl)acetic acid 
• 60307-25-7 (1-methyl-5-oxo-pyrrolidin-2-yl)-acetic acid 
• 6985-24-6 (E)-2,5-Bis-[(2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dien-(Z)-ylidene]-hex-3-enedial 
• 7089-93-2 (E)-2,5-Bis-[(2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dien-(Z)-ylidene]-hex-3-ene-1,6-diol 
• 71655-17-9 (E)-3-hexen-1,6-diol 
• 55-97-0 hexamethonium bromide 
• 1031379-05-1 (E)-N-(2,5-dicyano-1-phenylpent-3-enyl)-4-methylbenzenesulfonamide 
• 1031379-06-2 N-((1E,5E)-4,7-dicyano-1-phenylhepta-1,5-dien-3-yl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Preparation method 1,4-cyano -2-butene

The invention discloses a preparation method of 1,4-dicyano-2-butene, and belongs to the field of organic chemistry. Acetylene is used as a raw material; after twice addition with bromine, eliminationis performed to obtain trans 1,2-acetylene dibromide; then, under the catalysis of cuprous salt, the trans 1,2-acetylene dibromide and trimethylsilylacetonitrile take a coupling reaction to obtain 1,4-dicyano-2-butene. During the synthesis, the use of a highly toxic product of hydrogen cyanide is avoided; a novel method is provided for the compound synthesis.

Method of producing hexamethylene diamine from butadiene

The invention relates to the production of hexamethylene diamine from butadiene. The method comprises the successively performed stages of: (i) a catalytic epoxidation of butadiene to 1,2-epoxy-3-butene; (ii) a basically catalyzed addition of hydrogen cyanide to butadiene monoxide to form a reaction mixture containing 3-hydroxy-4-pentene nitrile (3HPN) and 2-hydroxymethyl-3-butene nitrile (2HMBN); (iii) an acidically catalyzed dehydration of the cyanohydrines 3HPN and 2HMBN of stage (ii) to cis/trans-pentadiene nitrile (PDN); (iv) a basically catalyzed addition of the products of stage (iii) to form cis/trans-1,4-dicyanobutene-1 and -2 (DCB); and (v) a catalytic hydrogenation of the isomeric cis/trans-1,4-dicyanobutene of stage (iv) to hexamethylene diamine.

The kinetics and mechanism of the phosphorus-catalysed dimerisation of acrylonitrile

Isopropyl diarylphosphinites (Ar2POPri) catalyse the dimerisation of acrylonitrile (AN) to a mixture of cis- and trans-1,4-dicyanobut-1-ene (cis,trans-DCB-1), trans-1,4-dicyanobut-2-ene (DCB-2) and 2,4-dicyanobut-1-ene (MGN). The kinetics and mechanism of the reaction, which is a potential source of hexamethylenediamine, are reported in detail and the factors which govern rate and selectivity to DCB-1 and DCB-2 rather than MGN are elaborated.

Process for producing 1,4-dicyano-2-butene and catalyst therefor

2-Butene-1,4-diol and/or 3-butene-1,2-diol are (is) reacted with hydrogen cyanide in the presence of a molten catalyst comprising a cuprous halide and a non-aromatic organic amine hydrohalide.

Process for producing 1,4-dicyano-2-butene

The object of the present invention is to provide a process for producing 1,4-dicyano-2-butene in a high yield and in an industrially advantageous way. The present invention relates to a process for producing 1,4-dicyano-2-butene which comprises reacting a butene derivative represented by the formula [1] or the formula [2] wherein each of R1 and R3 represents a hydroxy group, lower acyloxy group, lower alkoxy group or cyano group; and each of R2 and R4 represents a hydroxy group, lower acyloxy group or lower alkoxy group, with hydrogen cyanide in the presence of a catalyst comprising a product prepared from a cuprous halide, a non-aromatic amine hydrohalide and at least one member selected from the group consisting of Lewis acids and basic compounds.