ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Aromatic hydrocarbons > Phthalonitrile
Phthalonitrile Chemical Properties
- Melting point:137-139 °C(lit.)
- Boiling point:227.54°C (rough estimate)
- Density 1.24
- vapor pressure <1 Pa (25 °C)
- refractive index 1.6231 (estimate)
- Flash point:162°C
- storage temp. Store below +30°C.
- solubility benzene: 50 mg/mL, clear
- form Crystals or Crystalline Powder
- color White to beige
- PH7 (H2O)
- Water Solubility 0.56 g/L (25 ºC)
- BRN 775028
- Stability:Stable. Incompatible with strong bases, strong acids, strong oxidizing agents, strong reducing agents.
- CAS DataBase Reference91-15-6(CAS DataBase Reference)
- NIST Chemistry ReferencePhthalonitrile(91-15-6)
- EPA Substance Registry System1,2-Benzenedicarbonitrile (91-15-6)
- Hazard Codes T
- Risk Statements 25-23/24/25
- Safety Statements 36/37/39-45-28A
- RIDADR UN 3439 6.1/PG 2
- WGK Germany 1
- RTECS TI8575000
- Autoignition Temperature>580 °C
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29269095
- Hazardous Substances Data91-15-6(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 85 mg/kg
Phthalonitrile Usage And Synthesis
- Chemical PropertiesPhthalonitrile is a crystalline powder having a faint grayish yellow color and a slighty aromatic odor, similar to benzonitrile. Phthalonitrile was first described in 1896 when it was isolated during the diazotization of 2-aminobenzonitrile. The compound is sparingly soluble in water (ca. 1 g/L) and soluble in acetone, nitrobenzene, and benzonitrile. It cannot be distilled and polymerizes if heated above the melting point. It is not explosive and is difficult to ignite, but the dust can explode.
- UsesPhthalonitrile is used as a starting material for producing phthalocyanine pigments (→ Phthalocyanines), fluorescent brightners, and photographic sensitizers.
- PreparationPhthalonitrile 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.
- ReactionsThe 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.
- Safety ProfilePoison 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 MethodsCrystallise 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.]
Phthalonitrile Preparation Products And Raw materials
- Ethyl isocyanoacetate 3-Nitrophthalonitrile 3,4,5,6-Tetrachlorophthalonitrile 1,3-Dicyanobenzene ETHYL 2-CYANOACRYLATE o-Phenylenediamine Methyl 4-cyanobenzoate 4-Aminophthalonitrile 2-Phenylacetoacetonitrile Potassium hydrogen phthalate Bis(2-ethylhexyl) phthalate Dibutyl phthalate O-Phthalimide Chlorothalonil Benzonitrile Phthalic anhydride Phthalic acid PHTHALAMIDE
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