2855-13-2

Usage

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

• 79848-85-4 3-cyano-3,5,5-trimethylcyclohexaneimine 
• 4098-71-9 isophorone diisocyanate 
• 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 
• 72641-12-4 3-cyano-3,5,5-trimethyl cyclohexane 

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) 
• 4098-71-9 isophorone diisocyanate 
• 136210-28-1 IPDA/DEM 
• 66230-21-5 C₂₂H₄₂N₂ 
• 1027096-13-4 3-((3-methylbutyl)oxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid (3-methylbutyl) ester 
• 78632-23-2 3-ureidomethyl-3,5,5-trimethylcyclohexyl urea 
• 1338600-49-9 C₁₈H₂₆F₈N₂O₄ 
• 126249-14-7 3-(phenoxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid phenyl ester 

Relevant academic research and scientific papers

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 Amino Compounds From Nitrile Compounds

The present invention relates to a process for hydrogenating nitrile compounds to amino compounds, in which the cross-sectional loading of the reactor during the hydrogenation is less than or equal to 4.0 kg/m2*s, based on the liquid phase.

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.

A process for preparing isophorone diamine

The invention discloses a method for preparing isophorone diamine, and is characterized in that the method comprises the following steps: 1) under the condition of an organic amine catalyst, with isophorone and nitromethane as raw materials, synthesizing 3-nitromethyl-3,5,5-trimethylcyclohexanone, wherein the reaction temperature is 0 DEG C-150 DEG C, and the amount of the organic amine catalyst is 1-300% of the mass of the substance amount of isophorone; and 2) under conditions of liquid ammonia, hydrogen and a metal cobalt catalyst, allowing 3-nitromethyl-3,5,5-trimethylcyclohexanone to undergo a reaction to generate isophorone diamine, wherein the reaction temperature is 30-300 DEG C, the liquid ammonia amount is 1-50 times of the substance amount of 3-nitromethyl-3,5,5-trimethylcyclohexanone, and the hydrogen pressure is 0.1-10 MPa. The nitromethane with lower toxicity is used for replacing highly-toxic hydrogen cyanide or thiocyanate, and thus the method is a technical route which is safer in process and friendlier to the environment.

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

Isophoronediamine, is prepared by A) subjecting isophoronenitrile directly in one stage to aminating hydrogenation to give isophoronediamine in the presence of ammonia, hydrogen, a hydrogenation catalyst and an optional additive, and in the presence or absence of an organic solvent; or B) first converting isophoronenitrile fully or partly in at least two or more than two stages to isophoronenitrile imine, and subjecting the isophoronenitrile imine to aminating hydrogenation to give isophoronediamine as a pure substance or in a mixture with another component and/or isophoronenitrile, in the presence of at least ammonia, hydrogen and a catalyst.

A simple preparation process of isophorone diamine

The invention relates to a simple preparation method of isophorone diamine, and belongs to the technical field of chemical material processing. The preparation method comprises three steps including raw material pretreatment, hydrogenation and purification. The preparation method has the advantages that the process is simple, the implementation is easy, the cost is low, the conversion efficiency is high, and the like. The preparation method is suitable for being popularized and used in industry in a large scale.

A 3-aminomethyl -3, 5, 5-trimethyl method for preparing cyclohexylamine

The invention discloses a method for preparing 3-aminomethyl-3,5,5-trimethyl cyclohexylamine (IPDA). The method comprises the following steps: (a), reacting isophorone and halogenated isobutenyl magnesium to obtain 3-(2-methylpropenyl)-3,5,5-trimethyl cyclohexanone (IPA); (b), carrying out zonization reaction on the IPA and ozone to obtain 3-formyl-3,5,5-trimethyl-ring cyclohexanone (IPFM); (c) carrying out imidization reaction on the IPFM and ammonia to obtain 3-aminomethyl-3,5,5-trimethylcyclohexylimide (IPMI); and (d) carrying out catalytic hydrogenation reaction on the IPMI to obtain the IPDA. The method has the advantages that no HCN and hydrazine hydrate are used, no 3-amino-3,5,5-trimethyl-cyclohexanol (IPAA) which is difficult to separate is generated, the device cost is low, the reaction conditions are mild, the process chain is relatively complete and the yield of products are relatively high.

3-aminomethyl -3, 5, 5-trimethyl method for preparing cyclohexylamine (by machine translation)

The present invention provides a 3-aminomethyl -3, 5, 5-trimethyl method for preparing cyclohexylamine. 3-cyano -3, 5, 5-trimethyl cyclohexyl imine the inferior amination reaction material, in the subsequent steps, with the assistance of the circulating material in the 1st 1st-stage hydrogenation reaction by the hydrogenation reaction material, and can effectively inhibit the generation of HCN product, then in the heating can decompose under the action of the alkaline additive to 2nd stage hydrogenation reaction, then heating the alkaline additive decomposition, decomposition reaction material as circulation material part of a 1st-stage hydrogenation reaction to return as adjuvant, 3rd levels of the remaining part of the hydrogenation reaction, to obtain 3-aminomethyl -3, 5, 5-trimethyl cyclohexane, in the product can be effectively reduced 3-cyano -3, 5, 5-trimethyl cyclohexane and secondary amines the content of the product. (by machine translation)

METHOD FOR PREPARING 3-AMINOMETHYL-3,5,5-TRIMETHYL CYCLOHEXYLAMINE

The present invention provides a method for preparing 3-aminomethyl-3,5,5-trimethyl cyclohexylamine. The method comprises: a) reacting 3-cyano-3,5,5-trimethyl cyclohexanone with excess primary amine as well as removing the water generated from the reaction, so that IPN is substantially converted into imine compounds; b) in the presence of an ammonolysis catalyst, mixing the product of step a) with liquid ammonia, making the imine compound perform ammonolysis reaction to generate 3-cyano-3,5,5-trimethyl cyclohexylimine and the primary amine; and c) in the presence of hydrogen and a hydrogenation catalyst, hydrogenating 3-cyano-3,5,5-trimethyl cyclohexylimine obtained in step b) to obtain 3-aminomethyl-3,5,5-trimethyl cyclohexylamine. The method of the present invention avoids the generation of 3,5,5-trimethyl cyclohexanol and 3-aminomethyl-3,5,5-trimethyl cyclohexanol as the major by-products in the prior art, thereby improving the yield of 3-aminomethyl-3,5,5-trimethyl cyclohexylamine.