91-08-7

Usage

Uses

Used in the Footwear Industry:
2-METHYL-M-PHENYLENE DIISOCYANATE is used as a method for preparing breathable, sweat-absorbing Ethylene-Vinyl Acetate (EVA) foam shoe material. This application enhances the comfort and performance of the footwear by providing better breathability and moisture management.
Used in the Chemical Analysis Industry:
2,6-TDI, a related compound, may be used as a reference standard for the quantification of residual 2,6-TDI in foam samples using high-performance liquid chromatography coupled to coordination-ionspray tandem mass spectrometry (HPLC-CIS-MS/MS). This helps in ensuring the quality and safety of the foam materials.
Used in the Manufacturing Industry:
2-METHYL-M-PHENYLENE DIISOCYANATE is used in the manufacture of polyurethane foams, elastomers, and coatings. Its crosslinking properties make it a valuable component in the production of these materials, contributing to their durability and performance.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 257, 1995 DOI: 10.1021/jo00106a044

Reactivity Profile

2-METHYL-M-PHENYLENE DIISOCYANATE reacts violently with amines, alcohols, bases and warm water, causing fire and explosion hazards. [Handling Chemcials Safely 1980. p. 907]. Reaction with water to form Carbon Dioxide [Merck 11th ed. 1989].

Health Hazard

Classified as slightly toxic orally. Probable oral lethal dose in humans is 5 to 15 g/kg or between 1 pint and 1 quart for a 70 (l50 lb.) person. Particularly poisonous when breathed. This is among the most poisonous of isocyanates. Acute and chronic exposures to low concentrations may produce asthmatic attacks.

Fire Hazard

When heated to decomposition, 2-METHYL-M-PHENYLENE DIISOCYANATE emits toxic fumes of nitrogen oxides. Ventilation should be adequate. If polyurethane products are heated, protection against isocyanate release is necessary. Avoid decomposing heat.

Flammability and Explosibility

Nonflammable

Safety Profile

Confirmed carcinogen. Poison by ingestion and inhalation. Human systemic effects by inhalation: olfactory, eye, and pulmonary changes. Flammable liquid. When heated to decomposition it emits toxic fumes of NOx. See also CYANATES.

Purification Methods

It is purified by fractional distillation in a vacuum. Store it under N2 in sealed dark ampoules as it is water and light sensitive. Like the preceding 2,4-isomer, it has a sharp pungent odour, is TOXIC and is IRRITATING TO THE EYES. [Beilstein 13 IV 259.]

InChI:InChI=1/C9H6N2O2/c1-7-8(10-5-12)3-2-4-9(7)11-6-13/h2-4H,1H3

Upstream product

• 75-44-5 phosgene 
• 823-40-5 2,6-toluenediamine 
• 20913-18-2 toluene-2,6-bis(methyl) carbamate 
• 95-80-7 4-methylbenzene-1,3-diamine 
• 67-56-1 methanol 
• 108-71-4 3,5-diaminotoluene 
• 95-70-5 2-methyl-p-phenylenediamine 

Downstream Products

• 100246-43-3 4-bromomethyl-1,3-phenylene diisocyanate 
• 72672-88-9 1,3-bis-(3-ethyl-2-methyl-thiomorpholine-4-carbonylamino)-2-methyl-benzene 
• 20913-18-2 toluene-2,6-bis(methyl) carbamate 
• 823-40-5 2,6-toluenediamine 
• 188910-15-8 (S)-2-Amino-4-[(R)-2-{3-[(R)-2-((S)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanylcarbonylamino]-2-methyl-phenylcarbamoylsulfanyl}-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid 

Relevant academic research and scientific papers

Method for efficiently preparing toluene diisocynate compound by polyoxometallate

The invention discloses a method for preparing toluene diisocynate (TDI) by coupling 2,6-diaminotoluene and methanol under the catalysis of a polyoxometallate (wherein the polyoxometallate is one of six basic configurations of Keggin type, Wells-Dawson type, Anderson type, Lindeqvist type, Waugh type and Silverton type, and the Anderson type configuration is mainly adopted). The method comprises the specific implementation steps: putting a catalyst, a solvent methylbenzene, raw materials of 2,6-diaminotoluene, methanol and hydrogen peroxide, an acid-binding agent and a dehydrating agent into aclean reaction tube together, performing magnetic stirring for sufficient reaction in an air atmosphere under a certain temperature condition, and performing separation and purification to obtain a target product. According to the invention, the use of reagents with high corrosivity and easiness in poisoning and high-temperature and high-pressure reaction conditions in the traditional synthesis method are avoided, hydrogen peroxide is used as oxidizing agent, heteropolyacid taking Fe, Cu, Ni, Cr and other non-noble metals as central metals is used as a catalyst to catalyze and generate toluene diisocynate (TDI), the catalyst has extremely high reaction activity, and after the reaction is finished, the catalyst used by a sample subjected to simple treatment can be recycled, so that the method is environment-friendly, the cleanness of the reaction is improved, and the production and manufacturing cost is reduced.

PROCESS FOR PREPARING ISOCYANATES

The invention relates to a process for preparing isocyanates by reacting the corresponding amines with phosgene in the gas phase, if appropriate in the presence of an inert medium, in which the amine and the phosgene are first mixed and converted to the isocyanate in a reactor, and in which a reaction gas which comprises isocyanate and hydrogen chloride and leaves the reactor is cooled in a quench space of a quench by adding a quench medium. The quench medium on addition to the quench space has a temperature above the condensation temperature or the desublimation temperature of the reaction gas.

PROCESS FOR THE PREPARATION OF ISOCYANATES

An isocyanate is produced by reacting an amine with a stoichiometric excess of phosgene in the gas phase. This reaction is carried out at a temperature above the amine's boiling point to obtain a liquid stream containing the isocyanate and a gas stream containing hydrogen chloride and phosgene. The gas stream containing hydrogen chloride and phosgene thus produced is separated into a gas stream containing hydrogen chloride and a liquid stream containing phosgene. At least part of the liquid stream containing phosgene is then converted to a gas stream containing phosgene which gas stream is then recycled. The gaseous phosgene stream is maintained at a higher pressure than the liquid phosgene stream.

PROCESS FOR PREPARING ISOCYANATES

The invention relates to a process for preparing isocyanates by reacting the corresponding amines with phosgene in the gas phase, if appropriate in the presence of at least one inert medium, the phosgene being passed into a reactor (21) through a first inlet and the amine through a second inlet of an ejector (1). The first inlet and the second inlet open into a mixing zone (17) in which the phosgene and the amine are mixed to give a reaction mixture. The mixing zone (17) is followed downstream by a diffuser (19) in which pressure and temperature of the reaction mixture composed of phosgene and amine are increased.

COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING A POLYMER BEARING JUNCTION GROUPS, AND COSMETIC TREATMENT PROCESS

The present patent application relates to a cosmetic or dermatological composition comprising, in a cosmetically or dermatologically acceptable medium, a polymer comprising: (a) a polymer backbone that may be obtained by reaction: of a polyol comprising 3 to 6 hydroxyl groups;of a monocarboxylic acid containing 6 to 32 carbon atoms;of a polycarboxylic acid comprising at least two carboxylic groups COOH, and/or of a cyclic anhydride such as a polycarboxylic acid and/or of a lactone comprising at least one carboxylic group COOH; and(b) at least one junction group linked to the said polymer backbone and capable of establishing H bonds with one or more partner junction groups, each pairing of a junction group involving at least three H (hydrogen) bonds. The patent application also concerns a cosmetic treatment process using the said composition.

PROCESSES FOR PREPARING LOW-CHLORINE ISOCYANATES

Processes comprising providing an amine reactant, and reacting the amine reactant with a stream of phosgene in a reaction zone to form a product comprising a corresponding isocyanate, wherein the phosgene stream has a CO content of 0.5% by weight or more.

Process for the production of aromatic discocyanates in the gas

Aromatic diisocyanates are produced by reacting in the gas phase the corresponding primary aromatic diamine with phosgene. The phosgene and the primary aromatic diamine are reacted within a mean residence time of from 0.05 to 15 seconds. The aromatic diamine used contains less than 0.05 mole % overall of aliphatic amine containing no keto groups, per mole of primary amino groups.

Process for the preparation of isocyanates in the gas phase

An isocyanate is produced by reacting a primary amine with phosgene in the gas phase above the boiling point of the amine over an average contact time of 0.05 to 15 seconds under adiabatic conditions.

Process for the preparation of isocyanates in the gas phase

Isocyanates are produced by reaction of primary amines with phosgene in the gas phase. In this process, the reaction is terminated by guiding the reaction mixture from the reaction chamber through a cooling stretch into which liquids are injected. Direct cooling takes place in the cooling stretch in one stage in two or more cooling zones connected in series.

Process for the production of the toluene diisocyanate

The invention relates to a process for the production of toluene diisocyanate, in which the crude toluenediamine obtained from the hydrogenation is purified and then phosgenated. The purification step reduces the total amount of cyclic ketones to less than 0.1 % by weight, based on 100% by weight of the toluenediamine.