Isophorone diisocyanate

Base Information

• Chemical Name: Isophorone diisocyanate
• CAS No.: 4098-71-9
• Deprecated CAS: 101701-80-8,102771-74-4,105439-02-9,110648-35-6,111093-75-5,124961-52-0,129212-17-5,146282-59-9,146665-38-5,149579-36-2,194936-84-0,26602-93-7,50974-99-7,52985-93-0,63793-40-8,66708-07-4,70936-97-9,74091-63-7,74520-92-6,88778-74-9,1186289-22-4,1199811-14-7,1211316-62-9,135454-41-0,1548444-15-0,158750-30-2,1899018-41-7,1973479-17-2,201046-13-1,102771-74-4,105439-02-9,111093-75-5,1186289-22-4,1199811-14-7,1211316-62-9,124961-52-0,129212-17-5,146282-59-9,146665-38-5,149579-36-2,194936-84-0,26602-93-7,50974-99-7,52985-93-0,63793-40-8,66708-07-4,70936-97-9,74091-63-7,74520-92-6,88778-74-9
• Molecular Formula: C12H18N2O2
• Molecular Weight: 222.287
• Hs Code.: 29291090
• European Community (EC) Number: 223-861-6
• ICSC Number: 0499
• UN Number: 2290
• UNII: 43B0856528
• DSSTox Substance ID: DTXSID0023826
• Nikkaji Number: J53.651B
• Wikipedia: Isophorone_diisocyanate
• Wikidata: Q415415
• Metabolomics Workbench ID: 58591
• ChEMBL ID: CHEMBL1509442
• Mol file: 4098-71-9.mol

Synonyms:isophorone diisocyanate

Chemical Property of Isophorone diisocyanate

Chemical Property:

• Appearance/Colour: colourless or slightly yellow liquid
• Vapor Pressure: 0.00257mmHg at 25°C
• Melting Point: -60 °C
• Refractive Index: n20/D 1.484(lit.)
• Boiling Point: 286.9 °C at 760 mmHg
• Flash Point: 116 °C
• PSA: 58.86000
• Density: 1.06 g/cm³
• LogP: 2.24300
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with esters, ketones, ethers, and aromatic and aliphati
• Water Solubility.: <0.1 g/100 mL at 25℃
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 222.136827821
• Heavy Atom Count: 16
• Complexity: 352
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

Isophorone Diisocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23-36/37/38-42/43-51/53-22
• Safety Statements: 26-28-38-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Diisocyanates
• Canonical SMILES: CC1(CC(CC(C1)(C)CN=C=O)N=C=O)C
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C on spraying.
• Effects of Short Term Exposure: The substance is corrosive to the skin. The substance is severely irritating to the eyes. The aerosol is irritating to the respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.
• Description: Isophorone diisocyanate (IPDI) (CAS No. 4098-71-9) is a clear to pale-yellow liquid with a camphorlike odor which is insoluble in water and miscible with most common organic solvents. IPDI exists in two conformers, cis and trans. Their reactivities are similar and each conformer is an asymmetrical molecule with the secondary isocyanate group being more reactive than the primary isocyanate group. Since the substance does not contain any groups that might oxidize or spontaneously ignite, it is not expected that IPDI would self-ignite, oxidize, or explode at ambient conditions. The water solubility is approximately 15 mg l-1 at 23 ℃, and hydrolysis with a half-life of about an hour leads to polymers or to the corresponding diamine.
• Uses: Yields polyurethanes with high stability, resistance to light discoloration, and chemical resistance. Isophorone diisocyanate (IPDI) is used in theproduction of high-quality coatings, polyurethane paints, and varnishes and as an elastomer for casting compounds.. Isophorone diisocyanate is used in the manufacture of polyurethane with high stability, resistance to light discoloration and chemical resistance; used in paints and varnishes for hardness, flexibility, abrasion, chemical resistance to chalking and weathering; as an elastomer applicable for casting compounds and mastics to highly flexible textile coatings; foams; hard industrial coatings; manufacture of contact lenses; curing.

Technology Process of Isophorone diisocyanate

There total 33 articles about Isophorone diisocyanate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.8%

3-(phenoxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid phenyl ester (126249-14-7) → isophorone diisocyanate (4098-71-9,101701-80-8,129212-17-5,149579-36-2,194936-84-0,26602-93-7,53895-32-2,66708-07-4,70936-97-9,74091-63-7,74520-92-6,102771-74-4,50974-99-7,52985-93-0)

Guidance literature:

at 220 ℃; under 97.5098 Torr; Industry scale;

Reference yield: 98.6%

phosgene (75-44-5) + 3-aminomethyl-3,5,5-trimethylcyclohexylamine (2855-13-2) → isophorone diisocyanate (4098-71-9,101701-80-8,129212-17-5,149579-36-2,194936-84-0,26602-93-7,53895-32-2,66708-07-4,70936-97-9,74091-63-7,74520-92-6,102771-74-4,50974-99-7,52985-93-0)

Guidance literature:

at 300 ℃; under 1050.11 Torr; Product distribution / selectivity; Continuous process;

Reference yield: 96.0%

1-(methoxycarbonyl)amino-3-(methoxycarbonylamino)methyl-3,5,5-trimethylcyclohexane → isophorone diisocyanate (4098-71-9,101701-80-8,129212-17-5,149579-36-2,194936-84-0,26602-93-7,53895-32-2,66708-07-4,70936-97-9,74091-63-7,74520-92-6,102771-74-4,50974-99-7,52985-93-0)

Guidance literature:

With 2-chloro-1,3,2-benzodioxaborole; triethylamine; In toluene; 1.) reflux, 5 min, 2.) 0.5 h;

DOI:10.1021/jo00106a044

upstream raw materials:

3-aminomethyl-3,5,5-trimethylcyclohexylamine

phosgene

3-((2,4-di-tert-amylphenyl)oxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid (2,4-di-tert-amylphenyl) ester

3-((3-methylbutyl)oxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid (3-methylbutyl) ester

Downstream raw materials:

C₄₀H₅₄N₂O₁₆

1-{N-[O-(N,N-dibenzylamino)carboxy]amino}-3-{N-[O-(N,N-dibenzylamino)carboxy]amino}methyl-3,5,5-trimethylcyclohexane

3-(hexyloxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid hexyl ester

C₄₄H₈₆N₂O₄

Refernces

• 1、 -. "Method for preparing isocyanate with low hydrolytic chlorine content by gas phase method". Paragraph 0037-0038. . Retrieved 2021/05/22.
• 2、 -. "Method for preparing polyisocyanate through photochemical reaction, and method for preparing waterborne polyurethane resin". Paragraph 0140-0148; 0175-0182. . Retrieved 2019/12/11.