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

PH

7 (H2O)

Water Solubility 

0.56 g/L (25 ºC)

BRN 

775028

Exposure limits

ACGIH: TWA 1 mg/m3

Stability:

Stable. Incompatible with strong bases, strong acids, strong oxidizing agents, strong reducing agents.

CAS DataBase Reference

91-15-6(CAS DataBase Reference)

NIST Chemistry Reference

Phthalonitrile(91-15-6)

EPA Substance Registry System

1,2-Benzenedicarbonitrile (91-15-6)

Safety Information

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 Data

91-15-6(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 85 mg/kg

MSDS

• Language:English Provider:o-Phthalodinitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Phthalonitrile Usage And Synthesis

Chemical Properties

Phthalonitrile 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.

Uses

Phthalodinitrile monomers can be polymerized thermally in the presence of small amounts of curing agents into thermosetting polymers. Phthalodinitrile is a precursor to phthalocyanine which is used as a dye or pigment.

Uses

Phthalonitrile is used as an intermediate for chemical synthesis in the production of building blocks for colorants and coatings, life science and agricultural chemicals. It is also used as a precursor to phthalocyanine pigments (which are precursors to the blue dye in jeans), fluorescent brighteners, and photographic sensitizers.

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

Not classified

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.]

Phthalonitrile(91-15-6)Related Product Information

• Diethyl phthalate
• Potassium hydrogen phthalate
• Bis(2-ethylhexyl) phthalate
• Dibutyl phthalate
• O-Phthalimide
• Chlorothalonil
• Benzonitrile
• Phthalic anhydride
• Phthalic acid
• PHTHALAMIDE
• ETHYL 2-CYANOACRYLATE
• o-Phenylenediamine
• Methyl 4-cyanobenzoate
• 4-Aminophthalonitrile
• Dimethyl phthalate
• Tetrachloroterephthalonitrile
• 3,4,5,6-Tetrachlorophthalonitrile
• 3-Nitrophthalonitrile