16529-56-9

Usage

General Description

Clear yellow liquid.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Nitriles, such as 2-METHYL-3-BUTENENITRILE, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Fire Hazard

2-METHYL-3-BUTENENITRILE is flammable.

InChI:InChI=1/C5H7N/c1-3-5(2)4-6/h3,5H,1H2,2H3

Upstream product

• 544-16-1 n-Butyl nitrite 
• 759-35-3 diethyl (but-1-en-3-yl)malonate 
• 74-90-8 hydrogen cyanide 
• 106-99-0 buta-1,3-diene 
• 71-43-2 benzene 
• 590-18-1 (Z)-2-Butene 
• 111-69-3 hexanedinitrile 
• 4553-62-2 2-methylglutaronitrile 
• 188290-36-0 thiophene 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 22037-73-6 3-bromo-1-butene 
• 563-52-0 2-chloro-3-butene 
• 4894-61-5 trans-but-2-enyl chloride 
• 109-75-1 but-3-enenitrile 

Downstream Products

• 4403-61-6 2-methyl-2-butene nitrile 
• 16529-66-1 3-Pentenenitrile 
• 20068-02-4 (Z)-2-methyl-2-butenenitrile 
• 16545-78-1 (Z)-pent-2-enenitrile 
• 4635-87-4 3-pentenenitrile 
• 592-51-8 4-Pentenenitrile 
• 1130905-76-8 (S)-E-5-hydroxy-5-(3-methoxyphenyl)-2-methyl-hex-2-enenitrile 
• 26294-98-4 2-pentenenitrile 
• 30574-97-1 tiglonitrile 
• 25899-50-7 cis-2-pentenenitrile 
• 13284-42-9 2-pentenenitrile 
• 1380225-18-2 (R,E)-5-cyclohexyl-5-hydroxy-2-methylpent-2-enenitrile 
• 1380225-21-7 (S,E)-10-phenylmethoxy-5-hydroxy-2-methyldec-2-enenitrile 
• 1380225-15-9 C₁₄H₁₇NO 

Related news

The catalytic isomerization reactions of 2-METHYL-3-BUTENENITRILE (cas 16529-56-9) into 3-pentenenitrile in ionic liquids08/09/2019

The catalytic isomerization reaction of 2-methyl-3-butenenitrile (2M3BN) into 3-pentenenitrile (3PN) has been performed in the presence of Ni(0) and phosphine complexes and in biphasic ionic liquid/organic solvent. Several neutral and ionic phosphines and ionic liquids have been tested, the best...detailed

Theoretical and experimental study of the nickel-catalyzed isomerization of 2-METHYL-3-BUTENENITRILE (cas 16529-56-9) and the effect of a Lewis acid08/08/2019

A combined experimental and theoretical study was conducted to investigate the isomerization of 2-methyl-3-butenenitrile (2M3BN) to 3-pentenenitrile (3PN) and to 2-methyl-2-butenenitrile (2M2BN) catalyzed by nickel diphosphine complexes. Ni(1,4-bis(diphenylphosphino)butane) (dppb) was identified...detailed

Relevant academic research and scientific papers

A synthesis section of the mixed solution directly isomerization of 2-methyl-2-crotonization method

The invention discloses a method for synthesizing 2-methyl-2-butenenitrile through direct isomerization of alkene-nitrile mixed liquid. The method is characterized in that isomerization reaction occurs by adding calcium-containing inorganic base to the alkene-nitrile mixed liquid containing 2-methyl-3-butenenitrile and 3-pentenenitrile so as to generate a product containing the 2-methyl-2-butenenitrile. According to the method, the process of purifying the 2M3BN through reduced pressure rectification is omitted, the calcium-containing inorganic base is used as a catalyst and directly isomerizes the alkene-nitrile mixed liquid containing the 2M3BN and 3PN into the 2M2BN, and the reaction conversion rate and the selectivity are greater than 95% respectively. Compared with a conventional method, the method has the advantages that the rectification separation process of the alkene-nitrile mixed liquid is omitted, so that the whole process route is shortened, the technological process is simplified, the equipment cost and the production cost are reduced, the calcium-containing inorganic base is used as the catalyst, low in price and easy to obtain and can be recycled, and industrial wastewater, waste gases and residues are basically not generated in the whole technological process.

PROCESS FOR MAKING NITRILES

Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3- pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide. The catalyst for the reaction of 1,3-butadiene with hydrogen cyanide to make 3-pentenenitrile is recycled. At least a portion of the recycled catalyst is purified by an extraction process, which separates catalyst degradation products and reaction byproduct from the catalyst.

NICKEL METAL COMPOSITIONS AND NICKEL COMPLEXES DERIVED FROM BASIC NICKEL CARBONATES

Nickel-metal-containing solids for use in manufacturing nickel metal complexes are disclosed. The nickel-metal-containing solids are made by reducing basic nickel carbonates. By varying the molar ratios of carbonates and bicarbonates to nickel salts, the methods provide basic nickel carbonates that produce superior nickel metal-containing solids that react more effectively with phosphorous-containing ligands. The phosphorous containing ligands can be both monodentate and bidentate phosphorous-containing ligands.

PROCESS FOR MAKING AND REFINING 3-PENTENENITRILE, AND FOR REFINING 2-METHYL-3-BUTENENITRILE

The invention provides an integrated, continuous process for the production of 3-pentenenitrile, the refining of 3-pentenenitrile, and the refining of 2-methyl-3-butenenitrile, the process comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a butadiene-containing feed, and a catalyst composition, wherein the catalyst composition comprises a zero-valent nickel and at least one bidentate phosphorus-containing ligand selected from the group consisting of a phosphite, a phosphonite, a phosphinite, a phosphine, a mixed phosphorus-containing ligand, and combination thereof; (b) maintaining a residence time in the reaction zone sufficient to convert about 95% or more of the hydrogen cyanide and to produce a reaction mixture comprising 3-pentenenitrile and 2-methyl-3-butenenitrile, wherein the 2-methyl-3-butenenitrile concentration is maintained below about 15 weight percent of the total mass of the reaction mixture; (c) distilling the reaction mixture to obtain a first stream comprising 1,3-butadiene, a second stream comprising 3-pentenenitrile, 2-methyl-3-butenenitrile, (Z)-2-methyl-2-butenenitrile, and optionally 1,3-butadiene, and a third stream comprising the catalyst composition; (d) distilling the second stream to obtain a fourth stream comprising 1,3-butadiene, a fifth stream comprising 2-methyl-3-butenenitrile, (Z)-2-methyl-2-butenenitrile, and optionally 1,3-butadiene, and a sixth stream comprising 3-pentenenitrile; and (e) distilling the fifth stream to obtain a seventh stream comprising 1,3-butadiene, an eighth stream comprising (Z)-2-methyl-2-butenenitrile, and a ninth stream comprising 2-methyl-3-butenenitrile.

PROCESS FOR MAKING 3-PENTENENITRILE BY HYDROCYANATION OF BUTADIENE

The invention provides a continuous process for the production of 3-pentenenitrile, comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a 1,3-butadiene-containing feed, and a catalyst precursor composition, wherein the cata

PROCESS FOR MAKING 3-PENTENENITRILE BY HYDROCYANATION OF BUTADIENE

The invention provides a continuous process for the production of 3-pentenenitrile comprising: (a) contacting, in a reaction zone, a hydrogen cyanide-containing feed, a butadiene-containing feed, and a catalyst precursor composition, wherein the catalyst

Binaphthol-based diphosphite ligands in asymmetric nickel-catalyzed hydrocyanation of styrene and 1,3-cyclohexadiene: Influence of steric properties

A series of chiral (R)-binaphthol-based diphosphite ligands with different substituents was prepared and applied in the asymmetric nickel-catalyzed hydrocyanation of styrene and 1,3-cyclohexadiene to investigate the influence of their steric properties. The optimum steric properties for the hydrocyanation reaction lie within a narrow window. With the optimized ligand, hydrocyanation of styrene gave full conversion (Subs/Ni = 100) with 49% ee, the TON was determined to be 600. Hydrocyanation of 1,3-cyclohexadiene gave 50% conversion (Subs/Ni = 500) with an excellent ee of 86 %. This demonstrates that high ees are not only accessible for vinylarenes but also for conjugated dienes in the asymmetric nickelcatalyzed hydrocyanation.

Highly selective hydrocyanation of butadiene toward 3-pentenenitrile

A triptycene-based diphosphine ligand was synthesized in good yield following a new route. The corresponding Pt(II)- and Ni(0)-complexes were characterized. In butadiene hydrocyanation the tript-PPh2Ni(cod) catalyst leads to exceptionally high selectivities for the linear product 3-pentenenitrile, combining high activity for both hydrocyanation and isomerization. This one-step procedure could be the key toward process intensification. Copyright

Catayzed vapor-phase hydrocyanation of diolefinic compounds

A catalysed vapor-phase process for the hydrocyanation of acyclic diolefinic compounds to olefinic nitriles in which the olefinic double bond is not conjugated to the triple bond of the cyano group, wherein a supported catalyst composition comprising at least one multidentate phosphite ligand and zero-valent nickel is preferably used with specially selected or treated supports.

METHOD FOR THE PRODUCTION OF ADIPODINITRILE BY HYDROCYANATION OF 1,3-BUTADIENE

Disclosed is a method for the production of adipodinitrile by hydrocyanation of 1,3-butadiene on a catalyst, wherein in a first step 1,3-Butadiene is hydrocyanated to form 3-Pentene nitrile on at least one nickel(0) catalyst and, in a second step, 3-Pentene nitrile is hydrocyanated to form adipodinitrile on at least one nickel(0)-catalyst by adding at least one Lewis acid. At least one of the at least one nickel(0) catalysts used in the respective steps of the inventive method is converted in the other step.