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4098-71-9

Basic Information
CAS No.: 4098-71-9
Name: Isophorone diisocyanate
Article Data: 51
Molecular Structure:
Molecular Structure of 4098-71-9 (Isophorone diisocyanate)
Formula: C12H18N2O2
Molecular Weight: 222.287
Synonyms: Isocyanicacid, methylene(3,5,5-trimethyl-3,1-cyclohexylene) ester (7CI,8CI);1,3,3-Trimethyl-1-(isocyanatomethyl)-5-isocyanatocyclohexane;1-Isocyanato-3-(isocyanatomethyl)-3,5,5-trimethylcyclohexane;3,3,5-Trimethyl-5-(isocyanatomethyl)cyclohexyl isocyanate;5-Isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane;IPDI;Isophoronediisocyanate;Z 4770;Isophorone diisocyanate;
EINECS: 223-861-6
Density: 1.06 g/cm3
Melting Point: -60 °C
Boiling Point: 286.9 °C at 760 mmHg
Flash Point: 116 °C
Solubility: <0.1 g/100 mL at 25 °C in water
Appearance: colourless or slightly yellow liquid
Hazard Symbols: ToxicT,DangerousN
Risk Codes: 23-36/37/38-42/43-51/53-22
Safety: 26-28-38-45-61
Transport Information: UN 2290
PSA: 58.86000
LogP: 2.24300
Synthetic route
2855-13-2

3-aminomethyl-3,5,5-trimethylcyclohexylamine

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
99.9%
With Ni-Fe-Mg-Al-0 composite metal oxide In chlorobenzene at 135℃; under 12001.2 Torr; for 2h;85.2%
Multi-step reaction with 2 steps
1: phenol / 50 °C / Industry scale
2: 150 °C / 97.51 - 112.51 Torr / Industry scale
View Scheme
126249-14-7

3-(phenoxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid phenyl ester

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
at 220℃; under 97.5098 Torr; Industry scale;99.8%
at 150℃; Pyrolysis;99.8%
at 150℃; under 97.5098 - 112.511 Torr; Product distribution / selectivity; Industry scale;95%
75-44-5

phosgene

2855-13-2

3-aminomethyl-3,5,5-trimethylcyclohexylamine

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
at 300℃; under 1050.11 Torr; Product distribution / selectivity; Continuous process;98.5%
at 310℃; under 300.03 Torr; Inert atmosphere;98.6%
In chlorobenzene at 355 - 360℃; under 375.038 Torr; Inert atmosphere; Large scale;97.5%

1-(methoxycarbonyl)amino-3-(methoxycarbonylamino)methyl-3,5,5-trimethylcyclohexane

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
With 2-chloro-1,3,2-benzodioxaborole; triethylamine In toluene 1.) reflux, 5 min, 2.) 0.5 h;96%
1-ethyl-2,3-dimethylimidazolium tetrafluoroborate at 200 - 240℃; under 48.7549 Torr; for 1.66667h;81%
With boron trichloride; triethylamine In benzene for 0.5h; Heating; Yield given;
75-44-5

phosgene

IPDA hydrochloride

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
at 60 - 130℃; Irradiation;95%

1-(n-butoxy-carbonylamino)-3,3,5-trimethyl-5-(n-butoxy carbonylamino-methyl)-cyclohexane

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
1,2-dimethyl-3-butylimidazole perchlorate at 200 - 240℃; under 48.7549 Torr; for 1.66667h;93%
at 230℃; under 20.252 Torr; Product distribution / selectivity; falling film evaporator; Industry scale;
78632-23-2

3-ureidomethyl-3,5,5-trimethylcyclohexyl urea

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
at 380℃; Industry scale;90%
Multi-step reaction with 3 steps
1: 190 °C / Industry scale
2: dibutyltin dilaurate / 260 °C / 195.02 Torr / Industry scale
3: 230 °C / 3.75 Torr / Industry scale
View Scheme
Multi-step reaction with 2 steps
1: 210 °C / 150.01 Torr / Industry scale
2: 220 °C / 7.5 Torr / Industry scale
View Scheme

C28H38N2O4

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
With isocyanurate at 160 - 250℃; under 6000.6 Torr; for 200h; Inert atmosphere;90%

O,O'-diethyl 3,5,5-trimethylcyclohexane-1,3-dicarbamate

4098-71-9

isophorone diisocyanate

Conditions
ConditionsYield
zinc(II) oxide; 1-butyl-2,3-methylimidazolium tetrafluoroborate at 200 - 240℃; under 48.7549 Torr; for 1.66667h;86%
With boron trichloride; triethylamine In benzene for 0.5h; Heating; Yield given;
102-09-0

bis(phenyl) carbonate

2855-13-2

3-aminomethyl-3,5,5-trimethylcyclohexylamine

A

4098-71-9

isophorone diisocyanate

B

108-95-2

phenol

Conditions
ConditionsYield
In diphenylether at 20 - 240℃; for 3h; Inert atmosphere;A 86%
B n/a
Downstream Products
2855-13-2
113659-04-4
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Consensus Reports

EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 0.005 ppm (skin)
ACGIH TLV: TWA 0.005 ppm (skin)
DFG MAK: 0.01 ppm (0.092 mg/m3)
NIOSH REL: (Diisocyanates) 10H TWA 0.005 ppm; CL 0.02 ppm/10M
DOT Classification:  3; Label: Flammable Liquid; DOT Class: 6.1; Label: KEEP AWAY FROM FOOD (UN 2290)

Specification

The IUPAC name of Isophorone diisocyanate is 5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane. With the CAS registry number 4098-71-9 and EINECS 223-861-6, it is also named as Isophorone diamine diisocyanate. The product's category is Organics. It is colourless or slightly yellow liquid which may be sensitive to moisture and can react with all substances containing active hydrogen, such as acids, amines, water, phenols, mercaptans, amides, urea. When heated to decomposition, Isophorone diisocyanate emits toxic fumes of nitrogen oxides. So the storage environment should be well-ventilated, low-temperature and dry.

The other characteristics of  Isophorone diisocyanate can be summarized as: 
(1)ACD/LogP: 4.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.67; (4)ACD/LogD (pH 7.4): 4.67; (5)ACD/BCF (pH 5.5): 2077.62; (6)ACD/BCF (pH 7.4): 2077.62; (7)ACD/KOC (pH 5.5): 8247.27; (8)ACD/KOC (pH 7.4): 8247.27; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.519; (13)Molar Refractivity: 63.62 cm3; (14)Molar Volume: 209.4 cm3; (15)Polarizability: 25.22×10-24 cm3; (16)Surface Tension: 38.3 dyne/cm; (17)Enthalpy of Vaporization: 52.6 kJ/mol; (18)Vapour Pressure: 0.00257 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 222.136828; (21)MonoIsotopic Mass: 222.136828; (22)Topological Polar Surface Area: 58.9; (23)Heavy Atom Count: 16; (24)Complexity: 352.

Preparation of Isophorone diisocyanate: 
First, converting the acetone with a catalyst to produce isophorone. Secondly, reacting the isophorone with hydrogen cyanide to form isophorone nitrile. Thirdly, reacting the isophorone nitrile with ammonia, hydrogen and a catalyst, to form a mixture of isophorone diamine conformers (25/75 cis/trans). Fourthly, reacting the isophorone diamine with phosgene to form a crude mixture containing IPDI conformers (25/75 cis/trans). Finally, distilling the crude Isophorone diisocyanate to extract pure Isophorone diisocyanate.

Uses of Isophorone diisocyanate:
It is used in processing polyurethane plastics. It also can be used in enamel coatings which are resistant to abrasion and degradation from ultraviolet light. What's more, it can react with 4-nitro-7-piperazin-1-yl-benzo[1,2,5]oxadiazole to get C32H40N12O8. This reaction needs solvent CH2Cl2. The reaction time is 2 hours. The yield is 45%.


Safety information of Isophorone diisocyanate:
When you are using this chemical, please be cautious about it as the following:It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. And it is also toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. What's more, in case of insufficient ventilation, wear suitable respiratory equipment. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) So people should avoid release it to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure:
1. SMILES:O=C=N\C1CC(C\N=C=O)(CC(C1)(C)C)C
2. InChI:InChI=1/C12H18N2O2/c1-11(2)4-10(14-9-16)5-12(3,6-11)7-13-8-15/h10H,4-7H2,1-3H3 
3. InChIKey:NIMLQBUJDJZYEJ-UHFFFAOYAN

The following are the toxicity data of Isophorone diisocyanate:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 1mL/kg (1mL/kg)   National Technical Information Service. Vol. OTS0528418,
guinea pig LC50 inhalation 118mg/m3/1H (118mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0543418,
mouse LDLo oral 2500uL/kg (2.5mL/kg)   National Technical Information Service. Vol. OTS0528418,
rat LC50 inhalation 123mg/m3/4H (123mg/m3)   "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986Vol. 5, Pg. 334(86), 1986.
rat LD50 oral 4825mg/kg (4825mg/kg)   National Technical Information Service. Vol. OTS0530238,
rat LDLo skin 1mL/kg (1mL/kg)   National Technical Information Service. Vol. OTS0528418,