822-06-0 Usage
Description
This diisocyanate compound is used in the manufacture
of various polyurethane products: elastic and rigid
foams, paints, lacquers, adhesives, bin ding agents,
synthetic rubbers, and elastomeric fibers.
Chemical Properties
Hexamethylene diisocyanate is a liquid with a volatility of the same order as
that of tolylene diisocyanate. It is respiratory irritant and also has powerful
effects on the skin and eyes.
Uses
Different sources of media describe the Uses of 822-06-0 differently. You can refer to the following data:
1. 1,6-Hexamethylenediisocyanate is a chemical intermediate used in the production of urethane products.
2. Cross-linking agent (hardener) in the
production of polyurethane materials such as
car paints, dental materials, and contact lenses
3. Hexamethylene diisocyanate (HDI) is one of the most common aliphatic disocyanates, It is a monomer used in the production of polyurethane foams and exceptionally high-quality coatings, and is found in some industrial paints and spray painting operations. It is a compound which reacts readily with water and alcohols (Von Burg 1993). It has a vapor pressure of 0.05 mm Hg at room temperature, but can be present in aerosol form allowing a potentially higher exposure to individuals. The HDI-BT trimer is often present for similar industrial uses. It would be expected to have a lower vapor pressure; however, the aerosol form can also be present, allowing potentially higher exposure of HDI-BT to individuals. Hexamethylene diisocyanate reacts slowly with water to form carbon dioxide (HSDB 1996). The base-catalyzed reaction of Hexamethylene diisocyanate with alcohols should be carried out in inert solvents; the reaction may occur with explosive violence in the absence of solvents (NFPA 1994).
Definition
ChEBI: A diisocyanate compound with the two isocyanates linked by a hexane-1,6-diyl group.
Preparation
Hexamethylene diisocyanate (HDI) is prepared by the phosgenation of hexamethylenediamine (section lO.2.2(b)): H2N-(CH2)6-NH2--COCl2-->OCN-(CH2)6-NCOHexamethylene diisocyanate is a liquid with a volatility of the same order as that of tolylene diisocyanate. It is respiratory irritant and also has powerful effects on the skin and eyes. Hexamethylene diisocyanate was one of the first diisocyanates utilized for making polyurethanes, being used to prepare fibres and moulding compounds. These applications are no longer of importance but hexamethylene diisocyanate now finds use mainly in coatings which are more light stable than those based on aromatic isocyanates.
Application
Hexamethylene diisocyanate is an aliphatic diisocyanate monomer typically used to produce oligomers and prepolymers that when combined with a polyol produce light-stable polyurethane.Highly reactive 1,6-hexamethylene diisocyanate (HMDI) was used to synthesize lactic acid polymers from oligomers by the addition of 2,2′-bis(2-oxazoline) (BOX) as chain extenders. Self-healing ability was rendered to polyurethane elastomer by synthesizing alkoxyamine-based diol and reacting it with tri-functional homopolymer of HMDI and polyethylene glycol (PEG). Plastic optical fiber (POF) was prepared by the bulk homopolymerization of HMDI catalyzed by Tin(II)-2 ethylhexanoate (SnOct).
General Description
A colorless crystalline solid. Toxic by ingestion and is strongly irritating to skin and eyes. 1,6-Diisocyanatohexane is used to make nylon.
Air & Water Reactions
Contact with moisture or temperatures over 399°F may cause polymerization. Soluble in water.
Reactivity Profile
1,6-Diisocyanatohexane reacts with water. Base-catalyzed reactions of 1,6-Diisocyanatohexane with alcohols may be explosively violent in the absence of diluting solvents. 1,6-Diisocyanatohexane is incompatible with strong bases, amines, acids and strong oxidizers. 1,6-Diisocyanatohexane is also incompatible with metal compounds and surface active materials. .
Health Hazard
HDI is moderately toxic by inhalation. Inhumans the acute toxic symptoms could bewheezing, dyspnea, sweating, coughing, dif-ficulty in breathing, and insomnia. In addition, this compound can produce irritationof the skin, eyes, nose, and respiratory tract.Chronic exposure may cause obstruction ofairways and asthma.
The lethal concentration for rats frominhalation of this compound for 4 hourswas 60 mg/m3. The oral toxicity of thiscompound was found to be low in testanimals. The toxicity order was much higherwhen given intravenously.
LD50 value, oral (mice): 350 mg/kg
LD50 value, intravenous (mice): 5.6 mg/kg
There is no report of any carcinogenic orteratogenic study for this compound.
Fire Hazard
Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Flammability and Explosibility
Notclassified
Contact allergens
This diisocyanate compound is used in the manufac ture of various polyurethane products: elastic and
rigid foams, paints, lacquers, adhesives, binding
agents, synthetics rubbers, and elastomer fibers.
Safety Profile
Poison by inhalation
and intravenous routes. Moderately toxic by
ingestion and skin contact. Potentially
explosive reaction with alcohols + base.
When heated to decomposition it emits
toxic fumes of NOx. See also CYANATES.
Environmental Fate
HDI is not readily soluble (low mg l-1 range) in water.
However, upon contact with water, reactivity is rapid with
a half-life of 0.23 h at 23 ℃. This nonhomogeneous reaction is
expected to produce principally polyureas. In the occupational
environment, an aerosol can be formed by nebulization;
however, with a vapor pressure of 0.007 hPa, HDI is expected
to exist in the ambient atmosphere in its vapor state. As a vapor,
HDI is expected to degrade in the atmosphere by reaction with
hydroxyl radicals (half-life approximately 2 days). In direct
contact with water, its rapid hydrolysis reduces the likelihood
for HDI to bioaccumulate in the aquatic compartment or
transfer to groundwater. Therefore, the rapid hydrolysis in an
aquatic environment and relatively rapid degradation in
atmosphere limits the ability of this substance to be bioaccumulative
or persistent.
Toxicity evaluation
Toxicity predominantly results from direct interaction of HDI
with tissues or macromolecules at the portal of entry. HDI
reacts with biologic macromolecules containing nucleophilic
–NH, –SH, –OH, or –COOH groups, and these interactions
are thought to account for acute irritation to skin and mucus
membranes, sensory irritation, and dermal sensitization. Less
clear is the etiology of HDI-induced occupational asthma. A
number of mechanisms, including immunologic, neurologic,
and pharmacologic, have been postulated without a clear
resolution. Overall, these mechanisms account for the principal
effects associated with HDI that lead to toxicity at the
portal of entry with no evidence of primary systemic organ
toxicity.
Waste Disposal
Disposal is by chemical incineration of HDIsolution in a combustible solvent.
Check Digit Verification of cas no
The CAS Registry Mumber 822-06-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 2 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 822-06:
(5*8)+(4*2)+(3*2)+(2*0)+(1*6)=60
60 % 10 = 0
So 822-06-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H12N2O2/c11-7-9-5-3-1-2-4-6-10-8-12/h1-6H2
822-06-0Relevant articles and documents
Method for preparing isocyanate with low hydrolytic chlorine content by gas phase method
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Paragraph 0033-0036; 0041-0046, (2021/05/22)
The invention relates to a method for preparing isocyanate with low hydrolytic chlorine content by a gas phase method, which comprises the following steps of: carrying out phosgenation reaction on corresponding amine and stoichiometric excess phosgene in a reaction zone in the presence or absence of an inert medium; wherein the reaction conditions are selected such that at least the reaction components amine, isocyanate and phosgene are gaseous under these conditions, and feeding of at least one gas stream comprising amine and at least one gas stream comprising phosgene into the reaction zone, and introducing of a carbon dioxide stream in a quenching zone at the rear end of the reaction zone are carried out, and the molar content of the carbon dioxide stream is less than 60% of the molar weight of the phosgene stream, so that the isocyanate with low hydrolytic chlorine content can be obtained more easily, the product yield is improved, and the investment cost of the device is reduced.
Method for manufacturing pentamethylene diisocyanate
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Paragraph 0064-0065; 0066-0067, (2021/05/11)
The present invention provides a method for manufacturing pentamethylene diisocyanate. The method for manufacturing pentamethylene diisocyanate of the present invention manufactures intermediates by using dialkyl carbonate. By thermally decomposing the intermediates under a specific polymerization inhibitor, the method can manufacture the pentamethylene diisocyanate having excellent purity in a high yield.
METHOD OF PREPARING DIISOCYANATE COMPOSITION AND OPTICAL LENS
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Paragraph 0235-0238; 0243; 0290, (2021/06/11)
In the embodiments, an aqueous hydrochloric acid solution and an organic solvent instead of hydrogen chloride gas and solid triphosgene instead of phosgene gas may be used in the process of preparing a diisocyanate from a diamine through a diamine hydrochloride. In addition, the embodiments provide processes for preparing a diisocyanate composition and an optical lens, which are excellent in yield and quality with mitigated environmental problems by controlling the total content of metals, cations, or anions in a diamine hydrochloride composition.