91-15-6 Usage
Description
Phthalonitrile is an organic compound that serves as a crucial intermediate in the chemical synthesis process. It is known for its ability to form various building blocks for colorants, coatings, life science, and agricultural chemicals. Its unique structure allows it to be a versatile precursor to a range of products, including phthalocyanines, pigments, fluorescent brighteners, and photographic sensitizers.
Uses
Used in Chemical Synthesis Industry:
Phthalonitrile is used as an intermediate in the production of building blocks for colorants and coatings. Its chemical properties make it an essential component in the synthesis of these materials, contributing to their color, stability, and performance.
Used in Life Science and Agricultural Chemicals:
Phthalonitrile is used as a precursor to various life science and agricultural chemicals. Its ability to form different chemical structures allows it to be a key component in the development of pharmaceuticals, agrochemicals, and other related products.
Used in Pigment and Dye Manufacturing:
Phthalonitrile is used as a precursor to phthalocyanines, which are a class of pigments known for their intense color and stability. These pigments are widely used in various applications, such as inks, paints, and plastics.
Used in Fluorescent Brighteners Production:
Phthalonitrile is used in the production of fluorescent brighteners, which are compounds that enhance the brightness and whiteness of materials. These brighteners are commonly used in the textile, paper, and detergent industries.
Used in Photographic Sensitizers:
Phthalonitrile is also used as a precursor to photographic sensitizers, which are compounds that increase the sensitivity of photographic film or paper to light. This allows for the production of high-quality images with reduced exposure times.
Preparation
Phthalonitrile can be produced from phthalic acid, phthalic anhydride, phthalamide, or phthalimide by reaction with ammonia and elimination of water at 300–500°C in the gas phase in the presence of a catalyst.
In a single-stage continuous process, o-xylene is converted to phthalonitrile by reaction with ammonia and oxygen in the gas phase in a fluidized-bed reactor. Generally, metal oxide mixtures containing vanadium, antimony, chromium, and molybdenum, with further active components such as iron, tungsten, and alkali-metal oxides, on an alumina or silica support are used as catalysts.
Reactions
The route from o-phthalodinitrile can be represented 4C8H4N2 +M → MPc, where M is a bivalent metal, metal halide, metal alcoholate, or an equivalent amount of metal of valence other than two in a 4:1 molar ratio.
Flammability and Explosibility
Notclassified
Safety Profile
Poison by ingestion,
subcutaneous, and intraperitoneal routes.
Questionable carcinogen with experimental
tumorigenic data. When heated to
decomposition it emits toxic fumes of CN-
and NOx. See also NITRILES.
Purification Methods
Crystallise the nitrile from EtOH, toluene or *benzene. It has also been distilled under high vacuum. It is steam volatile. [Beilstein 9 H 815, 9 II 602, 9 III 4199, 9 IV 3268.]
Check Digit Verification of cas no
The CAS Registry Mumber 91-15-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 91-15:
(4*9)+(3*1)+(2*1)+(1*5)=46
46 % 10 = 6
So 91-15-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H
91-15-6Relevant articles and documents
Polyfunctionalized Cage Compounds by Pericyclic Domino Processes of 4,5-Dicyanopyridazine with Dienes: Applications and Limits
Giomi, Donatella,Nesi, Rodolfo,Turchi, Stefania,Mura, Elena
, p. 360 - 364 (2000)
The title compound 1 was found to behave as an attractive masked bis-diene to give 4-oxatricyclo-[4.3.1.03,7]dec-8-ene, 5-aza- and 5-silatricyclo[5.3.1.03,8]undec-9-ene, tricyclo[3.2.1.02,7]oct-3-ene, and tricyclo[5.3.1.03,8]undec-9-ene derivatives through purely pericyclic, three-step homodomino processes with diverse bis-dienophiles; whereas the reaction with myrcene (21) was characterized by a complete sitoselectivity affording compound 25, treatment of 1 with (R)-(-)-β-citronellene (26a) gave a 3:1 mixture of the homochiral diastereomers 30a and 31a. Some limits of this methodology, mainly arising from competitive side reactions upon the key cyclohexa-1,3-diene intermediates, are emphasized. The structures of the new compounds were established on the basis of spectral data.
Switchable activity of a Ru catalyst bearing an annulated mesoionic carbene ligand for oxidation of primary amines
Bera, Jitendra K.,Din Reshi, Noor U,Pal, Nilay Kumar,Pal, Saikat,Pal, Sourav,Yadav, Suman
, (2022/01/31)
The catalytic activity of a Ru complex 1, bearing a fused π-conjugated imidazo[1,2–a][1,8]naphthyridine-based mesoionic carbene (MIC) ligand, is examined for the oxidation of primary amines. Complex 1 affords nitrile or imine depending on the nature of th
An overview on the progress and development on the palladium catalyzed direct cyanation
Heydari, Somayyeh,Habibi, Davood,Reza Faraji, Ali,keypour, Hassan,Mahmoudabadi, Masoumeh
, (2020/10/02)
Generation of the positive CN ion and the corresponding direct cyanation are both extremely important for cyanation of aromatic compounds. Hereby, we would like to report the simultaneous use of the new Pd nano-catalyst as well as the three types of the N-arylsulfonyl cyanamides (A, B and C) as potent reagents for the in situ generation of the positive CN ion for the direct cyanation of phenylboronic acids in acetonitrile at reflux conditions.
A Versatile VMPO Catalyst Prepared In Situ for Oxidative Ammonolysis of Isomeric Picolines and Xylenes
Dutta, P.,Pathak, D. D.,Senapati, Rabinarayan
, p. 292 - 298 (2020/04/17)
Abstract: The V2O5–MoO3–P2O5 (VMPO) catalyst has been prepared in situ by thermal decomposition of vanado-molybdophosphoric acid (PMoV) on TiO2 support at 475°C. The TiO2 supported VMPO catalysts are characterized by FT–IR, XRD, BET surface area, NH3–TPD, and H2–TPR. Morphology of the catalyst has been studied by TEM. The accumulated data indicate decomposition of PMoV and presence of phosphate and pyrophosphate phases of molybdenum and vanadium after calcination. TPD and TPR studies exhibit the moderate acidity and presence of V4+ in the material, respectively. The VMPO catalyst has been used for ammoxidation of six different compounds including three isomeric picolines and three isomeric xylenes to the corresponding nitriles with the yield of 90–96%.