2304-58-7

Usage

Uses

Used in Polymer Industry:
5-Cyanopentanamide is used as a monomer for the production of nylon 66, a widely used synthetic polymer known for its strength, durability, and resistance to various environmental factors. The compound plays a vital role in the polymerization process, leading to the formation of the polymer chains that make up nylon 66.
Used in Chemical Synthesis:
5-Cyanopentanamide can be utilized as a building block in the synthesis of various other organic compounds and materials. Its unique structure allows for further chemical modifications and reactions, making it a versatile starting material for the development of new chemicals with potential applications in various industries.
Used in Pharmaceutical Industry:
Due to its structural similarity to certain biologically active molecules, 5-Cyanopentanamide may have potential applications in the pharmaceutical industry as a starting material for the development of new drugs. Its reactivity and functional groups can be exploited to design and synthesize novel drug candidates with potential therapeutic properties.
Used in Research and Development:
5-Cyanopentanamide can be employed as a research tool in various scientific studies, particularly in the fields of polymer science, organic chemistry, and materials science. Its unique properties and reactivity make it an interesting compound for exploring new reaction pathways, understanding molecular interactions, and developing innovative materials and applications.

Upstream product

• 111-69-3 hexanedinitrile 
• 628-94-4 adipamide 

Downstream Products

• 105-60-2 caprolactam 
• 373-04-6 6-aminocaproic amide 
• 68049-71-8 2-(2,4-dichloro-5-hydroxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-one 
• 68049-83-2 azafenidin 

Relevant academic research and scientific papers

5-Cyanovaleramide production using immobilized Pseudomonas chlororaphis B23

A biocatalytic process for the hydration of adiponitrile to 5- cyanovaleramide has been developed which can be run to higher conversion, produces more product per weight of catalyst, and generates significantly less waste products than alternate chemical processes. The biocatalyst consists of Pseudomonas chlororaphis B23 microbial cells immobilized in calcium alginate beads. The cells contain a nitrile hydratase (EC 4.2.1.84) which catalyzes the hydration of adiponitrile to 5-cyanovaleramide with high regioselectivity, and with less than 5% selectivity to byproduct adipamide. Fifty-eight consecutive batch reactions with biocatalyst recycle were run to convert a total of 12.7 metric tons of adiponitrile to 5-cyanovaleramide. At 97% adiponitrile conversion, the yield of 5-cyanovaleramide was 13.6 metric tons (93% yield, 96% selectivity), and the total weight of 5-cyanovaleramide produced per weight of catalyst was 3150 kg/kg (dry cell weight).

METHOD FOR PRODUCING epsilon-CAPROLACTAM

The present invention is a method of producing ε-caprolactam through adipamide as an intermediate, and characteristically includes a lactamization step of reacting adipamide, formed from a material compound, with hydrogen and ammonia in the presence of a catalyst containing: a metal oxide mainly containing an oxide(s) of one or more metallic elements selected from the group consisting of metallic elements of group 5 and groups 7 to 14 in the 4th to 6th periods of the periodic table; and a metal and/or a metal compound having a hydrogenation ability. The method can increase the selectivity of ε-caprolactam.

Hydration of nitriles using a metal-ligand cooperative ruthenium pincer catalyst

Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H2O to a wide variety of aliphatic and (hetero)aromatic nitriles in tBuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal-ligand cooperative binding of the nitrile.

Modulation of Nitrile Hydratase Regioselectivity towards Dinitriles by Tailoring the Substrate Binding Pocket Residues

The regioselective hydration of dinitriles is one of the most attractive approaches to prepare ω-cyanocarboxamides or diamides and such regioselectivity is often beyond the capability of chemical catalysts. The use of nitrile hydratase to biotransform dinitriles selectively would be highly desirable. Molecular docking of two aliphatic dinitriles and two aromatic dinitriles into the active site of a nitrile hydratase (NHase) from Rhodococcus rhodochrous J1 allowed the identification of proximal NHase substrate binding pocket residues. Four residues (βLeu48, βPhe51, βTyr68, and βTrp72) were selected for single- and double-point mutations to modulate the NHase regioselectivity towards dinitriles. Several NHase mutants with an altered regioselectivity were obtained, and the best one was Y68T/W72Y. Docking experiments further indicated that the poor binding affinity of aliphatic and aromatic ω-cyanocarboxamides to the NHase variants resulted in distinct regioselectivity between wild-type and mutated NHases.

A heterogeneous catalytic method for the conversion of nitriles into amides using molecular sieves modified with copper(II)

A heterogenous catalytic method is developed for the hydration of nitriles into amides with acetaldoxime. Copper(II) supported on 4 molecular sieves is an efficient catalyst for this reaction.

Optimization of adiponitrile hydrolysis in subcritical water using an orthogonal array design

A study of the hydrolysis of adiponitrile (ADN) was performed in subcritical water to research the dependence on experimental conditions. An L25(56) orthogonal array design (OAD) with six factors at five levels using statistical analysis was employed to optimize the experimental conditions for each product in which the interactions between the variables were temporarily neglected. The six factors were adiponitrile concentration (ADN c, wt%), temperature (T), time (t h), percentage of additives (reactant/additive, wt/wt%), additives (A), and pressure (p, MPa). The effects of these parameters were investigated using the analysis of variance (ANOVA) to determine the relationship between experimental conditions and yield levels of different products. The results showed that (ADN c) and T had a significant influence on the yields of adipamide, adipamic acid, and adipic acid at p0.05. Time was the statistically significant factor for the yield of 5-cyanovalermic acid at p0.05 and (ADN c) was the significant factor for the yield of 5-cyanovaleramide at p0.1. Finally, five supplementary experiments were conducted under optimized conditions predicted by the Taguchi method; the results showed that the yield obtained of each product was no lower than that of the highest in the 25 experiments. Carbon balance was calculated to demonstrate the validity of the experimental technique and the reliability of the results. Based on the experimental results, a possible reaction mechanism was proposed.

RhI-catalyzed hydration of organonitriles under ambient conditions

(Chemical Presented) New scoop on scope and selectivity: The hydration of organonitriles catalyzed by a RhI(OMe) species under nearly pH-neutral and ambient conditions (25°C, 1 atm) is chemoselective and high-yielding (93 to 99%), has a broad substrate scope, and may thus be complementary to enzymatic hydration methods for the introduction of a terminal amido group (CONH2) onto a carbon chain.