110-59-8 Usage
Description
Valeronitrile, also known as pentanenitrile, is a clear colorless to yellow liquid with chemical properties of a clear liquid. It is an organic compound that serves as a versatile building block in organic synthesis and has various applications across different industries.
Uses
1. Organic Synthesis:
Valeronitrile is used as a building block in organic synthesis for the creation of various chemical compounds. Its ability to act as a starting material allows for the development of a wide range of products.
2. Solvent:
Valeronitrile serves as a solvent in the chemical industry, facilitating various chemical reactions and processes. Its solvent properties make it a valuable component in the production of different substances.
3. Preparation of Valeric Acid:
Valeronitrile is used in the preparation of valeric acid, a significant organic compound with various applications in the pharmaceutical, flavor, and fragrance industries.
4. Enhancing Nitrilase Activity:
Valeronitrile is utilized to enhance the nitrilase activity in many strains, which is crucial for the biotechnological production of various chemicals and materials.
5. Industrial Applications:
Valeronitrile is employed as an industrial solvent and a chemical intermediate, playing a vital role in the manufacturing processes of numerous products.
Production Methods
Valeronitrile can be synthesized by dehydration of valeronamide. The nitrile is
also found in nature and is a constituent of coal gasification and oil shale
processing waste water, sewage wastewater
and tobacco smoke.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Nitriles, such as Valeronitrile, 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. Valeronitrile is incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents. .
Health Hazard
Valeronitrile is an irritant and may be harmful by inhalation, ingestion or skin
absorption .
Fire Hazard
Valeronitrile is combustible.
Metabolism
As with other aliphatic nitriles, valeronitrile is metabolized in vivo resulting in the
liberation of cyanide ion which is responsible for much of the observed toxicity of
this compound .
Biotransformation of valeronitrile presumably proceeds in a manner similar to that
of other aliphatic nitriles with an initial cytochrome P-450 catalyzed oxidation of
the nitrile to the cyanohydrin followed by release of the cyanide group from the
activated molecule. Cyanide formation was significantly reduced when
valeronitrile was incubated with mouse hepatic microsomes in the presence of
SKF-525A or carbon monoxide or when microsomes from mice pretreated with
chloroform were used . Ethanol pretreatment of mice markedly
increases the in vivo and in vitro microsomal oxidation of valeronitrile presumably as a result of increased levels of an ethanol inducible
cytochrome P-450 . As with other nitriles, the cyanide released
upon biotransformation of valeronitrile is readily converted to thiocyanate in vivo
and the latter ion was the major urinary excretion product observed with valero-nitrile in rats . From 18 to 31% of a daily 175 mg/kg dose of
valeronitrile was eliminated in the urine as thiocyanate during a 24 h period. In
another study , 43.2 and 27.5%, respectively, of an oral or i.p.
dose of 0.75 mmol/kg valeronitrile was excreted as thiocyanate in the urine of
male Sprague-Dawley rats over a 24 h period.
Purification Methods
Wash the nitrile with half its volume of conc HCl (twice), then with saturated aqueous NaHCO3, dry it with MgSO4 and fractionally distil it from P2O5. [Beilstein 2 H 301, 2 I 131, 2 II 267, 2 III 675, 2 IV 875.]
Check Digit Verification of cas no
The CAS Registry Mumber 110-59-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 110-59:
(5*1)+(4*1)+(3*0)+(2*5)+(1*9)=28
28 % 10 = 8
So 110-59-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3
110-59-8Relevant articles and documents
Regen et al.
, p. 2029 (1979)
A convenient procedure for the preparation of alkyl nitriles from alkyl halides. Acetone cyanohydrin as an in situ source of cyanide ion
Dowd,Wilk,Wlostowski
, p. 2323 - 2329 (1993)
A convenient preparation of alkyl nitriles from alkyl halides is described. Acetone cyanohydrin is employed as the source of cyanide ion.
Whitesides,G.M. et al.
, p. 5258 - 5270 (1972)
Deprotonation-alkylation of alkyl cyanides under sonochemical conditions
Berlan,Delmas,Duee,Luche,Vuiglio
, p. 1253 - 1260 (1994)
Deprotonation-alkylation of n-alkyl cyanides can be readily effected by an alkyl halide in the presence of sodium in a one pot procedure. Yields are generally better than in the usual methods, and the overall reaction conditions have important advantages
-
Tanner,D.D.,Bunce,N.J.
, p. 3028 - 3034 (1969)
-
Downie,Lee
, p. 855 (1967)
Zinc Oxide/Graphene Oxide as a Robust Active Catalyst for Direct Oxidative Synthesis of Nitriles from Alcohols in Water
Sarvi, Iraj,Zahedi, Ehsan
, (2021/08/30)
In this work, without using any linker or chemical modification of graphene oxide, a zinc oxide immobilized graphene oxide-based catalyst was used for the direct aerobic oxidative conversion of alcohols to the nitriles in water. In the first step, graphene oxide was prepared and then zinc ions were electrostatically adsorbed onto the surface of graphene oxide. In the following step, zinc oxide nanoparticles were generated via in-situ growth in presence of NaOH. It was illustrated that graphene oxide layers can control the size of in-situ generated zinc oxide nanoparticles. Various aromatic/aliphatic/heteroaromatic primary alcohols converted to the nitriles in high yields under O2 balloon with ZnO/GO catalyst. This catalyst can be used for 7 successful consecutive runs without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]
Method for preparing valeronitrile through hydrogenation of pentenenitrile
-
Paragraph 0032-0036, (2021/07/21)
The invention relates to a method for preparing valeronitrile through hydrogenation of pentenenitrile, and belongs to the technical field of chemical engineering. The method comprises the following steps: adding pentenenitrile, ethanol, a novel catalyst and an amorphous Fe-Mo-Ni-Al catalyst into a hydrogenation reaction kettle, starting stirring, carrying out nitrogen replacement for 3 times, then carrying out hydrogen replacement for 3 times, controlling the hydrogen pressure to be 0.2 Mpa, heating the reactants to 60 DEG C, and performing a reaction for 2 hours or determining that the hydrogen is not absorbed any more, continuously maintaining the hydrogen pressure, carrying out stirring reaction for half an hour, and then ending the reaction. The novel catalyst is a high-molecular palladium complex prepared from poly-gamma-(m-diphenylphosphinophenyl) propyl siloxane palladium with silicon dioxide as a carrier and sodium chloropalladite tetrahydrate through the interaction thereof.
NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature
Ahmed, Jasimuddin,Hota, Pradip Kumar,Maji, Subir,Mandal, Swadhin K.,Rajendran, N. M.
supporting information, p. 575 - 578 (2020/01/29)
Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study.