2855-13-2

Basic information

• Product Name: Isophorondiamine
• Synonyms: IPDA;ISOPHORONEDIAMINE;Isophorondiamine;1-AMINO-3-AMINOMETHYL-3,5,5-TRIMETHYLCYCLOHEXANE;3-AMINOMETHYL-3,5,5-TRIMETHYLCYCLOHEXYLAMINE;5-AMINO-1,3,3-TRIMETHYLCYCLOHEXANEMETHYLAMINE;5-amino-1,3,3-trimethyl-cyclohexanemethanamin;5-amino-1,3,3-trimethylcyclohexanemethanamine
• CAS NO: 2855-13-2
• Molecular Formula: C₁₀H₂₂N₂
• Molecular Weight: 170.25
• EINECS: 220-666-8
• Product Categories: Organics;Amines;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 2855-13-2.mol
• Article Data: 24

Chemical Properties

• Melting Point: 10 °C(lit.)
• Boiling Point: 247 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear/Liquid
• Density: 0.924 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.000538mmHg at 25°C
• Refractive Index: n20/D 1.490
• Storage Temp.: Store below +30°C.
• PKA: 10.57±0.70(Predicted)
• Explosive Limit: 1.2%(V)
• Water Solubility: miscible
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Isophorondiamine(CAS DataBase Reference)
• NIST Chemistry Reference: Isophorondiamine(2855-13-2)
• EPA Substance Registry System: Isophorondiamine(2855-13-2)

Safety Data

• Hazard Codes: C
• Statements: 21/22-34-43-52/53
• Safety Statements: 26-36/37/39-45-61
• RIDADR: UN 2289 8/PG 3
• WGK Germany: 1
• RTECS: GV5020833
• F: 10-21-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2855-13-2(Hazardous Substances Data)

Usage

Description

Isophorone diamine (IPD) is a clear to light-yellow, faintly yellow liquid that is highly soluble and slightly denser than water. It is widely used as an epoxy-resin hardener and is known to be a strong sensitizer, which can cause airborne contact dermatitis. It may be toxic by inhalation and skin absorption and is corrosive to the skin. Isophorone diamine is also used to make other chemicals.

Uses

Used in Epoxy Resin Industry:
Isophorone diamine is used as a hardener for epoxy resins, particularly in applications requiring low color, low odor, high flexural strength, and excellent chemical resistance of epoxy formulations. It is suitable for floor coatings, fillers, and paving mixes.
Used in Epoxy Network Formation:
Isophorone diamine is one of the three epoxy networks based on diglycidyl ether of bisphenol-A epoxy prepolymer cured with aliphatic amines, namely triethylenetetramine (TETA), 1-(2-aminoethyl) piperazine (AEP), and isophoronediamine (IPD). It plays a crucial role in the formation of these epoxy networks, which are essential for various industrial applications.
Used in Allergic Contact Dermatitis (ACD) Research:
Isophorone diamine's strong sensitizing properties make it a relevant compound in the study of allergic contact dermatitis (ACD), a common skin condition caused by exposure to certain allergens. Research on IPD can help in understanding the mechanisms behind ACD and developing effective treatments and preventive measures.
Used in Chemical Synthesis:
Isophorone diamine is utilized in the synthesis of various chemicals due to its unique chemical properties. Its reactivity and solubility make it a valuable component in the production of different chemical compounds, contributing to the chemical industry's growth and innovation.

Air & Water Reactions

Soluble in water. Flash Point 234 F. Melting point 50 F. Reacts with carbon dioxide from the air to form deposits around vents (Roger Patrick, DuPont Engineer).

Reactivity Profile

ISOPHORONE DIAMINE is an amine. Amines are chemical bases. They neutralize acids to form salts. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides (Roger Patrick, DuPont Engineer). Corrodes aluminum and steel in the presence of moisture and carbon dioxide [USCG, 1999].

Health Hazard

Inhalation of high concentrations of vapor causes irritation, coughing, and nausea. Eyes: May cause inflammation/burns. Skin: May cause burns. Ingestion: Nausea.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Contact allergens

Isophorone diamine is widely used in urethane and epoxy coatings for light-stable, weather-resistant prop- erties. It is used in water proofing and paving concret- ing, and in the manufacture of diisocyanates and polyamides as an epoxy resin hardener. It is a strong sensitizer and can cause airborne contact dermatitis.

InChI:InChI=1/C9H14O.2H3N/c1-7-4-8(10)6-9(2,3)5-7;;/h4H,5-6H2,1-3H3;2*1H3

Upstream product

• 7027-11-4 isophoronenitrile 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 97006-56-9 3-formyl-3,5,5-tris-methylcyclohexanone 
• 79848-85-4 3-cyano-3,5,5-trimethylcyclohexaneimine 
• 72641-12-4 3-cyano-3,5,5-trimethyl cyclohexane 
• 4098-71-9 isophorone diisocyanate 

Downstream Products

• 85213-49-6 N-trimethylsilyl-(3,5,5-trimethyl-3-trimethylsilylaminomethylcyclohexylamine) 
• 410090-46-9 N-tert-butyldimethylsilyl-(3,5,5-trimethyl-3-tert-butyldimethylsilylaminomethylcyclohexylamine) 
• 78632-23-2 3-ureidomethyl-3,5,5-trimethylcyclohexyl urea 
• 4098-71-9 isophorone diisocyanate 
• 61796-65-4 Undec-10-enoic acid (1,3,3-trimethyl-5-undec-10-enoylamino-cyclohexylmethyl)-amide 
• 126249-14-7 3-(phenoxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid phenyl ester 
• 112343-39-2 isophorone diformamide 
• 932742-30-8 C₄₄H₈₂N₂O₄ 

Relevant articles and documents

Method for preparing IPDI (isophorone diisocyanate)

The invention discloses a method for preparing IPDI (isophorone diisocyanate). The method comprises the following steps: (1) isophorone and hydrogen cyanide are subjected to a reaction in the presenceof a catalyst to obtain isophorone nitrile; (2) isophorone nitrile obtained in step (1), ammonia and hydrogen are subjected to a reaction in the presence of a catalyst to obtain isophorone diamine; (3) isophorone diamine is subjected to a phosgenation reaction to obtain IPDI, wherein the content of impurities containing secondary amine groups in isophorone diamine subjected to the phosgenation reaction in step (3) is smaller than or equal to 0.5wt%, preferably smaller than or equal to 0.3wt%, and more preferably smaller than or equal to 0.1wt%. By means of the method, content of hydrolyzed chlorine in the IPDI product can be effectively reduced, the yellowing resistance of the product is effectively improved, and the harm that downstream products are unqualified due to existence of hydrolyzed chlorine in the product is reduced.

Synthesis method of isophorone diamine

The invention relates to a synthesis method of isophorone diamine. The method includes the following steps that 1, in the presence of a catalyst, isophorone (IP) and nitromethane (NM) are subjected to addition reaction, and a nitromethyl-isophorone (NMIP) crude product is prepared; 2, the nitromethyl-isophorone (NMIP) crude product prepared in the step 1 is purified, and a nitromethyl-isophorone(NMIP) pure product is prepared; 3, the nitromethyl-isophorone (NMIP) pure product prepared in the step 2 is dissolved in a solvent, organic acid ammonia salt is added, reaction is conducted in the presence of a catalyst to generate isophorone diamine synthetic liquid, and finally, an isophorone diamine product is obtained through purification. According to the method, highly toxic hydrocyanic acid does not serve as necessary raw materials, high-pressure hydrogen and liquid ammonia are not used as raw materials for reaction, the technological process is safe and environmentally friendly, investments are saved, and the economic benefits are remarkable.

PROCESS FOR PREPARING 3 AMINOMETHYL-3,5,5-TRIMETHYLCYCLOHEXYLAMINE

Process for preparing isophoronediamine, characterized in that A) isophoronenitrile is subjected directly in one stage to aminating hydrogenation to give isophoronediamine in the presence of ammonia, hydrogen, a hydrogenation catalyst and possibly further additions, and in the presence or absence of organic solvents; or B) isophoronenitrile is first converted fully or partly in at least two or more than two stages to isophoronenitrile imine, and this isophoronenitrile imine is subjected to aminating hydrogenation to give isophoronediamine as a pure substance or in a mixture with other components and/or isophoronenitrile, in the presence of at least ammonia, hydrogen and a catalyst.