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Isophthalonitrile

Isophthalonitrile structure

Isophthalonitrile 

structure
  • CAS No:

    626-17-5

  • Formula:

    C8H4N2

  • Chemical Name:

    Isophthalonitrile

  • Synonyms:

    1,3-Benzenedicarbonitrile;Isophthalonitrile;1,3-Dicyanobenzene;m-Dicyanobenzene;m-Benzenedinitrile;m-Cyanobenzonitrile;3-Cyanobenzonitrile;1,3-Benzodinitrile;IPN;1,3-Bis(cyano)benzene;Meta-dicyanobenzene;m-Dicyanobenzene;NSC 87880

  • Categories:

    Organic Chemistry  >  Nitrile Compound

Description

off-white to light brown solid


M-phthalodinitrile appears as white, crystalline or flaky solid with an almond-like odor. mp: 161-162°C (sublimes) Density 1.28 g/cm3 (at 25°C). Insoluble in water. Soluble in benzene and in acetone. Used as an intermediate in the manufacture of polyurethane paints and varnishes, pharmaceuticals, and agricultural chemicals.|DryPowder|COLOURLESS-TO-WHITE CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.|Needle-like, colorless to white, crystalline, flaky solid with an almond-like odor.


M-phthalodinitrile appears as white, crystalline or flaky solid with an almond-like odor. mp: 161-162°C (sublimes) Density 1.28 g/cm3 (at 25°C). Insoluble in water. Soluble in benzene and in acetone. Used as an intermediate in the manufacture of polyurethane paints and varnishes, pharmaceuticals, and agricultural chemicals.|Isophthalonitrile is a nitrile. It derives from an isophthalic acid.

Isophthalonitrile Basic Attributes

128.13

128.13

1072209

210-933-7

7G36N0292W

1583

87880

2811|3276

DTXSID7027259

NEEDLES FROM ALCOHOL|Needle-like, colorless to white, crystalline, flaky solid.

29269020

Characteristics

47.6

0.8

White to tan Flakes

4.42

162 °C

288 °C

288°C

1.566

H2O: 0.7 g/L (20 ºC)

2-8°C

1.33 Pa

Relative vapour density (air = 1): 4.42

Combustible Solid and a severe explosion hazard.

Almond-like odor.

No rapid reaction with air No rapid reaction with water Insoluble in water

Nitriles

m-PHTHALODINITRILE is a combustible solid. Emits toxic fumes of NOx and CN- when heated to decomposition. Incompatible with strong oxidizing agents.

Combustible Solid and a severe explosion hazard.

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

III

6.1(b)

2811

1

22-20/22

22-24/25-36/37/39-26

CZ1900000

Xn

Separated from strong oxidants and food and feedstuffs.

P260, P264, P270, P301+P312, P314, P330, P501

H302 + H332

Strong oxidizers (e.g., chlorine, bromine, fluorine).

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P301+P312, P304+P312, P304+P340, P312, P330, and P501|Aggregated GHS information provided by 138 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P301+P312, P314, P330, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)|Use water spray, powder, foam, carbon dioxide. In case of fire: keep cylinder cool by spraying with water.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|(See protection codes)

The worker should wash daily at the end of each work shift.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 mg/cu m.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

Separated from strong oxidants and food and feedstuffs.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.

The substance is irritating to the eyes.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST!

Avoid inhalation of dust.

Wear safety goggles.

Toxicity

5.62

NO REPORTS OF ADVERSE EFFECTS WERE REPORTED IN 15-YR REVIEW OF INDUSTRIAL EXPERIENCE WITH M-PHTHALODINITRILE. THE PROBABLE REASON FOR LACK OF SYSTEMIC EFFECTS OF IPN IS THAT AROMATIC, UNLIKE ALIPHATIC, NITRILES DO NOT LIBERATE CYANIDE IN THE BODY.

Drug Information

0.24 Days

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Headache, nausea, confusion Target Organs: Eyes, skin, central nervous system (NIOSH, 2016)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest.


Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

1,3-dicyanobenzene

inhalation, skin absorption, ingestion, skin and/or eye contact

headache, nausea, confusion; In Animals: irritation eyes, skin


Cough.


Redness.

Eyes, skin, central nervous system

Isophthalonitrile Use and Manufacturing

Methods of Manufacturing

The preparation method is meta-xylene ammoxidation method. That is, m-xylene, ammonia and air are reacted to obtain isophthalonitrile in the presence of a gas phase catalyst. The process is that m-xylene enters the vaporizer through a metering pump for gasification or is directly sprayed into the reactor in liquid form. Air enters the reactor from an air compressor through an oil separator, a filter, and a heat exchanger. The heat enters the reactor. The ammonia oxidation reaction generally uses a fluidized bed reactor with a heat-radiating tube bundle and the reaction temperature is 350-450°C. The catalyst uses silica gel as the carrier and V-Cr as the main component. After the reaction gas is separated by cyclone separator to remove solid particles and the heat exchanger is cooled down, it enters the trap, where the isophthalonitrile is condensed and discharged continuously. Excess ammonia is recovered from the tail gas or directly sent to the three wastes for treatment. The isophthalonitrile is centrifuged The crude isophthalonitrile product can be obtained by dehydration and drying, with a content of 94% to 98%. If high purity (≥98%) products are to be obtained, they must be refined. Methods such as vacuum distillation, water washing or solvent extraction can be used.

Uses

Used to prepare plastics, synthetic fibers, pesticides (chlorothalonil) and epoxy resin curing agents. It is the raw material for pesticide chlorothalonil and preservatives, and it is also used as a curing agent for polyurethane resin and epoxy resin. Packing: 25kg/plastic woven bag. Storage and transportation: Store in a cool, ventilated and dry place, and transport as general chemicals.


Intermediates

Production

1,000,000 - 10,000,000 lb|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1980) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Pesticide, fertilizer, and other agricultural chemical manufacturing|1,3-Benzenedicarbonitrile: ACTIVE|1,3-DICYANOBENZENE WAS AMONG COMPOUNDS PREPARED AND TESTED FOR ANTIINFLAMMATORY ACTIVITY.|THE RECOMMENDED MAXIMUM CONCENTRATION OF ISOPHTHALONITRILE IN WATER SUPPLIES IS 5 MG/L. THIS CONCN IS BELOW THE THRESHOLD FOR ODOR DETECTION (9 MG/L), WILL NOT AFFECT THE SELF-PURIFICATION OF THE STREAM, AND CORRESPONDS TO THE DOSE, 0.25 MG/KG, OBSERVED AS NON-TOXIC.

DETERMINATION OF PHTHALONITRILE IN WATER AND GEOLOGICAL SEDIMENTS BY GAS CHROMATOGRAPHY.

Environmental transformation -> Pesticide transformation products (metabolite, successor)

Isophthalonitrile is a known environmental transformation product of Chlorothalonil.

Computed Properties

Molecular Weight:128.13
XLogP3:0.8
Hydrogen Bond Acceptor Count:2
Exact Mass:128.037448136
Monoisotopic Mass:128.037448136
Topological Polar Surface Area:47.6
Heavy Atom Count:10
Complexity:180
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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