4098-71-9 Usage
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 4098-71-9 differently. You can refer to the following data:
1. Isophorone diisocyanate is a liquid with a vapour pressure which is significantly lower than that of tolylene diisocyanate.
2. colourless or slightly yellow liquid
Uses
Different sources of media describe the Uses of 4098-71-9 differently. You can refer to the following data:
1. Yields polyurethanes with high stability, resistance to light discoloration, and chemical resistance.
2. Isophorone diisocyanate (IPDI) is used in theproduction of high-quality coatings, polyurethane paints, and varnishes and as an elastomer for casting compounds..
3. 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.
Definition
ChEBI: A diisocyanate in which the two isocyanate groups are linked by an isophorone substituent.
Preparation
Isophorone diisocyanate (IPDI) is prepared by the phosgenation of isophorone diamine (l-amino-3-aminomethyl-3,5,5-trimethylcydohexane):
General Description
A clear to light-yellow liquid. Slightly denser than water and insoluble in water. Toxic by inhalation and skin absorption. Very irritating to skin. Used to make polyurethane coatings.
Air & Water Reactions
Insoluble in water. Isophorone diisocyanate may be sensitive to moisture.
Reactivity Profile
Isophorone diisocyanate reacts with all substances containing active hydrogen atoms such as water, alcohols, phenols, amines, mercaptans, amides, urethanes and ureas.
Hazard
A severe irritant, toxic by skin absorption.
Health Hazard
Different sources of media describe the Health Hazard of 4098-71-9 differently. You can refer to the following data:
1. Like most other isocyanates, IPDI exhibitsmoderate toxicity via inhalation. The acutetoxic symptoms are somewhat similar tothose of toluene-2,4- diisocyanate and diphenylmethane-4,4'-diisocyanate. Thus thetoxicity of such types is a characteristic ofthe -N=C=O functional group and to agreat extent is independent of the nature ofthe ring.Inhalation of its vapor can cause bronchitis, asthma, tightness of chest, and dyspnea in humans. Recovery from these effectsmay occur in a short period from a lowconcentration exposure.IPDI is an irritant to the skin and eyes.Exposure to this compound produces skinsensitization and eczema. Its oral toxicity isvery low.LC50 value, inhalation (rats): 123 mg/m3/4 hrLD50 value, skin (rats): 1060 mg/m3There is no report of its carcinogenic orreproductive effects in animals or humans.
2. Isophorone diisocyanate is highly toxic by inhalation and moderately toxic through the skin. (Non-Specific -- Isocyanates) People with skin or respiratory problems should avoid exposure.
Fire Hazard
When heated to decomposition, Isophorone diisocyanate emits toxic fumes of nitrogen oxides.
Environmental Fate
IPDI is a synthetic organic chemical, which does not occur
naturally in the environment. At room temperature, it is
a liquid. It is miscible with alcohol, diglycol, monoethyl
ether, ether, acetone, carbon tetrachloride, benzene, chlorobenzene,
kerosene, and olive oil. IPDI decomposes in
water producing CO2, which can produce significant pressure
in a closed container. Upon contact with water or
moist air, IPDI will react to form stable, insoluble polyurea
solids. This reactivity dramatically limits the mobility of
these products in the event of a spill (spills are localized
and have only transient impact), and the products will tend
to remain in, and react within, the environment to which
they are released. IPDI is not readily biodegradable. It reacts
with water forming solid insoluble polyurea, isophorone
diamine (IPDA), and CO2, thus the predominant removal
mechanism is expected to be hydrolysis. The rate constant
of the OH radical sensitized indirect photodegradation
of isophorone diisocyanate corresponds to a half-life of
1.8 days at a 24 h mean OH radical concentration of
500 000 molecules per cm3. A preliminary hydrolysis test
resulted in a dissipation half-life of 0.84 h (approximately
50 min) at 23 ℃. Polyurea is more or less inert and – due
to its molecular size – not bioavailable. No biodegradation
(0% degradation within 28 days) was observed in a manometric
respiratory test performed with domestic, nonadapted
activated sludge. As no degradation occurred in the
test on ready biodegradability, it is not expected that
a significant degradation would occur in a simulation test
(water and soil). The test substance is considered as
nonbiodegradable in surface water, sediment, and soil.
However, biodegradation is considered as irrelevant as
primary degradation step anyway because immediate hydrolysis takes place. Due to hydrolysis in water, bioaccumulation
of IPDI is not expected. The bioaccumulation
potential of the hydrolysis product IPDA is considered to
be low (log Kow = 0.99). There are no data on terrestrial
bioaccumulation available.
Toxicity evaluation
The toxicological properties of isocyanates are attributed to
the –N=C=O group. The consequence is that in the
hydrolysis of IPDI predominantly polyurea molecules are
formed with liberation of CO2. The polyurea molecules are
insoluble in water. Beside these insoluble main hydrolysis
products, there are minor amounts of other hydrolysis
products having a low to moderate molecular weight and
these are more or less water soluble (e.g., isophorone
diamine). The local toxic effect of the substance IPDI
is not related to metabolic mechanisms, because it is
a simple destruction of membranes due to corrosivity of the
substance.
Waste Disposal
Disposal is by chemical incineration of IPDIsolution in a combustible solvent.
Check Digit Verification of cas no
The CAS Registry Mumber 4098-71-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,9 and 8 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 4098-71:
(6*4)+(5*0)+(4*9)+(3*8)+(2*7)+(1*1)=99
99 % 10 = 9
So 4098-71-9 is a valid CAS Registry Number.
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
4098-71-9Relevant articles and documents
METHOD FOR PRODUCING CARBAMATE AND METHOD FOR PRODUCING ISOCYANATE
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Paragraph 0367; 0369-0379; 0399; 0402-0403, (2021/06/22)
The present invention provides a method for producing a carbamate that includes a step (1) and a step (2) described below: (1) a step of producing a compound (A) having a urea linkage, using an organic primary amine having at least one primary amino group per molecule and at least one compound selected from among carbon dioxide and carbonic acid derivatives, at a temperature lower than the thermal dissociation temperature of the urea linkage; and(2) a step of reacting the compound (A) with a carbonate ester to produce a carbamate.
ISOCYANATE PRODUCTION METHOD
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Paragraph 0419-0430; 0447-0451; 0454-0458; 0462, (2020/05/02)
An isocyanate production method according to the present invention is a method in which an isocyanate is produced by subjecting a carbamate to thermal decomposition, and includes: a step of preparing a mixture liquid containing the carbamate, an inactive solvent and a polyisocyanate compound; a step of conducting a thermal decomposition reaction of the carbamate by continuously introducing the mixture liquid into a thermal decomposition reactor; a step of collecting a low-boiling decomposition product by continuously extracting the low-boiling decomposition product in a gaseous state from the reactor, the low-boiling decomposition product having a boiling point lower than the polyisocyanate compound; and a step of collecting a high-boiling component by continuously extracting, from the reactor, a liquid phase component which is not collected in a gaseous state at the step of collecting the low-boiling decomposition product.
METHOD FOR PRODUCING ISOCYANATE
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Paragraph 0171-0172; 0176-0177, (2020/03/13)
PROBLEM TO BE SOLVED: To provide a method for producing isocyanate that suppresses a side reaction and continuously produces isocyanate. SOLUTION: The present invention provides a method for producing isocyanate by pyrolysis of carbamate, the method including: a pyrolysis step in which a liquid mixture containing carbamate and at least one compound (A) selected from a phenolic polymer having a repeating unit represented by general formula (4) and a phenol represented by general formula (5) is continuously introduced into a pyrolytic reactor for a pyrolytic reaction of carbamate; a low-boiling-point pyrolytic product recovery step in which a low-boiling-point pyrolytic product having a normal boiling point lower than that of the compound (A) is continuously extracted in a gas state from the pyrolytic reactor; and a high-boiling-point component recovery step in which a liquid phase component, which has not been recovered in a gas state in the low-boiling-point pyrolytic product recovery step, is continuously extracted as a high-boiling-point component from the pyrolytic reactor. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
