5124-30-1

Usage

Uses

Used in the Production of Urethane Foam:
Methylene-bis(4-cyclohexylisocyanate) is used as a raw material for the production of urethane foam with color stability.
Used in the Manufacture of Polymers:
HMDI is used as a key component in the synthesis of various polymers due to its reactive isocyanate groups.
Used in the Production of High-Performance Materials:
Methylene-bis(4-cyclohexylisocyanate) is used as a precursor for the production of high-performance elastic bodies, water polyurethane resins, and UV resins. Its excellent light stability, weather resistance, and mechanical properties make it especially suitable for these applications.
Used in the Coatings Industry:
HMDI is used as a component in the formulation of coatings, benefiting from its light stability and weather resistance properties, which contribute to the durability and performance of the final product.
Used in the Automotive Industry:
In the automotive industry, HMDI is used in the production of polyurethane materials for applications such as flexible foams, coatings, and elastomers, where its mechanical properties and resistance to environmental factors are highly valued.
Used in the Textile Industry:
Methylene-bis(4-cyclohexylisocyanate) is used in the textile industry for the production of durable water-resistant coatings and finishes on fabrics, leveraging its weather resistance and mechanical properties.

Air & Water Reactions

Reacts with water to form CO2

Reactivity Profile

Isocyanates and thioisocyanates, such as Methylene-bis(4-cyclohexylisocyanate), are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].

Hazard

Strong skin and eye irritant. Respiratorysensitization and lower respiratory tract irritant.

Health Hazard

Studies on test animals indicate that methy-lene bis(4-cyclohexylisocyanate) is highlytoxic by an inhalation route and can causesevere skin reaction. Exposure to 20 ppmfor 5 hours produced irritation of the respiratory tract, tremor, convulsion, congestion oflungs, and edema in rats. The symptoms atlower levels were decreased as to respirationrate and pulmonary irritation.Contact with the skin can produce severeirritation, erythema, and edema. The oraltoxicity of Methylene-bis(4-cyclohexylisocyanate) is very low.LD50 value, oral (rats): 9900 mg/kgThere is no report of the compound’smutagenicity or carcinogenicity.

Fire Hazard

Flash point data for Methylene-bis(4-cyclohexylisocyanate) are not available. Methylene-bis(4-cyclohexylisocyanate) is probably combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by inhalation. Mildly toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and CN-.

Potential Exposure

A potential danger to those involved in the manufacture of Methylene-bis(4-cyclohexylisocyanate) or its use in the production of light-stable, nonyellowing polyurethane resins.

Environmental Fate

HMDI is a synthetic organic chemical which does not occur naturally in the environment. At room temperature, it is a liquid. HMDI hydrolyzes rapidly in water, producing methylene bis(4-cyclohexylamine). The half-life for HMDI is approximately 2 h. Due to its rapid hydrolysis, transport between environmental compartments is unlikely to occur. Because of the rapid hydrolysis, the assessment of the substance is based on the hydrolysis product methylenebis(cyclohexylamine) and not on HMDI. The hydrolysis product was not classified as a PBT (persistent, bioaccumulative, toxic) substance. These data indicate that HMDI is not readily biodegradable. However, due to its rapid hydrolysis, HMDI is neither persistent in the water compartment nor bioaccumulative. The calculated Koc-value indicates that HMDI may strongly adsorb to soil; however, any emission to the terrestrial compartment would be affected by humidity and, therefore, terrestrial accumulation is not expected to occur.

Shipping

UN2206 Isocyanates, toxic, n.o.s. or Isocyanate solutions, toxic, n.o.s., flash point .61C and boiling point ,300C, Hazard Class: 6.1; Labels: 6.1-Poisonous materials., Technical Name Required.

Toxicity evaluation

The toxicological properties of isocyanates are attributed to the –N=C=O group. Skin sensitization with HMDI is thought to be associated with the activation and proliferation of lymphocytes in lymph nodes draining the site of exposure. Analysis of the nature and kinetics of the cytokine production (which regulates lymphocyte production) postexposure to HMDI revealed that both interleukin-1 (IL-1) and IL-6 were induced in a biphasic manner. The ordered and transient pattern of cytokine production that occurs during the afferent phase of contact sensitization suggests that sequential cytokine signals may be involved in regulating the characteristics of the response generated within the draining lymph node.

Incompatibilities

May form explosive mixture with air. Isocyanates are highly flammable and reactive with many compounds, even with themselves. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Reaction with moist air, water or alcohols may form amines and insoluble polyureas and react exothermically, releasing toxic, corrosive or flammable gases, including carbon dioxide; and, at the same time, may generate a violent release of heat increasing the concentration of fumes in the air. Incompatible with amines, aldehydes, alkali metals, ammonia, carboxylic acids, caprolactum, alkaline materials, glycols, ketones, mercaptans, hydrides, organotin catalysts, phenols, strong acids, strong bases, strong reducing agents such as hydrides, urethanes, ureas. Elevated temperatures or contact with acids, bases, tertiary amines, and acylchlorides may cause explosive polymerization. Attacks some plastics, rubber and coatings. Contact with metals may evolve flammable hydrogen gas. May accumulate static electrical charges, and may cause ignition of its vapors. May slowly polymerize if heated above 122F/50C. Contact with metals may evolve flammable hydrogen gas.

Waste Disposal

Methylene bis(4-cyclohexylisocyanate) isdissolved in acetone or any other combustible solvent and burned in a chemicalincinerator equipped with an afterburner andscrubber.

Synthetic route

phenyl N-[4-({4-[(phenoxycarbonyl)amino]cyclohexyl}methyl)cyclohexyl]carbamate (439680-99-6) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
at 170℃; Temperature; Pyrolysis;	99.9%
at 170 - 220℃; under 3.75038 - 757.576 Torr; for 240h; Product distribution / selectivity;	93.2%
With DURANATE TPA-100 In 1,2-dichloro-benzene at 250℃; under 6000.6 Torr; for 200h; Inert atmosphere;	84%
In 1,2-dichloro-benzene at 160 - 250℃; under 6000.6 Torr; Inert atmosphere;	83%
at 250℃; under 9.75098 Torr; Product distribution / selectivity; Industry scale;

phosgene (75-44-5) + 4,4'-diaminodicyclohexylmethane (1761-71-3) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
at 360℃; under 300.03 Torr; Product distribution / selectivity; Gas phase;	97.8%
at 360℃; under 300.03 Torr; Product distribution / selectivity; Inert atmosphere;	97.8%
In 1,2-dichloro-benzene at 355 - 360℃; under 375.038 Torr; Temperature; Inert atmosphere; Large scale;	97%
at 360℃; Inert atmosphere;	97.9 %Chromat.

dicyclohexylmethane-4,4'-diethylurethane (47460-66-2) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
1,2-dimethyl-3-ethylimidazole nitrate at 200 - 240℃; under 48.7549 Torr; for 1.66667h;	91%

4,4'-diaminodicyclohexylmethane (1761-71-3) + urea (57-13-6) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
Stage #1: 4,4'-diaminodicyclohexylmethane; urea In butan-1-ol at 135℃; under 760.051 Torr; for 8h; Stage #2: With butan-1-ol at 190 - 220℃; under 8250.83 - 10501.1 Torr; for 10.5h; Stage #3: tin(ll) chloride at 235 - 237℃; under 6.75068 - 7.50075 Torr; Product distribution / selectivity;	90%

dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate (99305-42-7) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
1-ethyl-2,3-dimethylimidazolium hexafluorophosphate at 190 - 240℃; under 48.7549 Torr; for 1.66667h;	88%
tin(ll) chloride at 232℃; under 6.75068 Torr;
With 2.6-dimethylphenol; dibutyltin dilaurate at 220℃; under 9.75098 Torr; for 13h; Product distribution / selectivity;
at 234℃; under 6.0006 Torr; Product distribution / selectivity; falling film evaporator; Industry scale;
With tin(ll) chloride at 236℃; under 6.75068 Torr; Product distribution / selectivity;

4,4'-methylene-di(cyclohexylcarbamate) dimethyl ester (63896-13-9) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
zinc(II) oxide; 1-(n-butyl)-3-methylimidazolium triflate at 200 - 240℃; under 48.7549 Torr; for 1.66667h;	81%

H12MDU + H12MDU + dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate (99305-42-7) → 2,2'-methylene-dicyclohexyldiisocyanate + 2,4'-methylene-dicyclohexyldiisocyanate + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
tin(ll) chloride at 230℃; under 7.50075 Torr;

dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate (99305-42-7) → 2,2'-methylene-dicyclohexyldiisocyanate + 2,4'-methylene-dicyclohexyldiisocyanate + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
tin(ll) chloride at 140 - 236℃; under 7.50075 Torr; for 8.5h;

4,4'-diaminodicyclohexylmethane (1761-71-3) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: phenol / ferrous acetylacetonate / 50 °C / Industry scale 2: 240 h / 170 - 220 °C / 3.75 - 757.58 Torr View Scheme
Multi-step reaction with 3 steps 1: tert-amylphenol / 100 °C / Industry scale 2: 200 °C / 525.05 Torr / Industry scale 3: 260 °C / 9.75 Torr / Industry scale View Scheme
Multi-step reaction with 3 steps 1: tert-amylphenol / 100 °C / Industry scale 2: 200 °C / 600.06 Torr / Industry scale 3: 250 °C / 6 Torr / Industry scale View Scheme

bis(2,4-di-tert-amylphenyl) 4,4'-methylene-di(cyclohexylcarbamate) (1027096-18-9) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
at 210℃; under 0.975098 Torr; for 11h; Product distribution / selectivity;

4,4'-methylenedi(cyclohexylcarbamate) bis(3-methylbutyl) ester (1027096-17-8) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
With dibutyltin dilaurate at 270℃; under 9.75098 Torr; Product distribution / selectivity; Industry scale;

C25H46N2O4 → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
dibutyltin dilaurate at 170 - 270℃; under 9.75098 Torr;

4,4'-methylenebis(cyclohexyl urea) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 200 °C / 525.05 Torr / Industry scale 2: 260 °C / 9.75 Torr / Industry scale View Scheme
Multi-step reaction with 2 steps 1: 200 °C / 600.06 Torr / Industry scale 2: 250 °C / 6 Torr / Industry scale View Scheme
Multi-step reaction with 2 steps 1: 220 °C / 450.05 Torr / Industry scale 2: 240 °C / 6 Torr / Industry scale View Scheme
Multi-step reaction with 2 steps 1: 230 °C / 262.53 Torr / Industry scale 2: 260 °C / 9.75 Torr / Industry scale View Scheme

N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (4-ethylphenyl) ester) (1266555-02-5) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
at 260℃; under 9.75098 Torr; Industry scale;

N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2-tert-amylphenyl) ester) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
at 260℃; under 9.75098 Torr; Industry scale;

N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2,4,6-trimethylphenyl) ester) (1266555-51-4) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
at 240℃; under 6.0006 Torr; Industry scale;

N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (4-ethoxyphenyl) ester) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
at 250℃; under 6.0006 Torr; Industry scale;

N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2-butyloxy)ethyl ester) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc diacetate / 200 °C / 150.01 Torr / Industry scale 2: 250 °C / 3.75 Torr / Industry scale View Scheme

N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2,6-dimethoxyphenyl) ester) (1266554-85-1) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
at 250℃; under 3.75038 Torr; Industry scale;

trimethyl hexamethylene diisocyanate (195456-49-6) + Hexamethylene diisocyanate (822-06-0) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

C15H24F2N2O2 → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; under 760.051 Torr; for 3h; Concentration;

carbon dioxide (124-38-9) + 4,4'-diaminodicyclohexylmethane (1761-71-3) → 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1)

Conditions	Yield
With phenylsilane; triethylamine; trichlorophosphate In toluene at 30℃; for 12h; Reagent/catalyst; Temperature;

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + 1-aminooctadecane (124-30-1) → C51H100N4O2

Conditions	Yield
With Desmodur W In hexane for 1h; Reflux;	100%
In hexane for 1h; Reflux;	100%

6-chloro-1-hexanol (2009-83-8) + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → bis(6-chlorohexyl) (methylenebis(cyclohexane-4,1-diyl))dicarbamate

Conditions	Yield
With dibutyltin dilaurate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	91%

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + 12-Aminododecanoic acid (693-57-2) → C39H72N4O6

Conditions	Yield
In dimethyl sulfoxide at 20℃; Inert atmosphere;	80%

isostearyl Alcohol (41744-75-6) + 4,9-dioxa-1,12-dodecanediamine (7300-34-7) + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → C76H144N6O8

Conditions	Yield
Stage #1: isostearyl Alcohol; 4,4'-bis(diisocyanato)dicyclohexylmethane; dibutyltin dilaurate In hexane at 20 - 50℃; for 1h; Stage #2: 4,9-dioxa-1,12-dodecanediamine In hexane at 20℃; for 1h;	72%

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + 1,1-dimethylhydrazine (57-14-7) → 4,4'-bis(diimethylamino-urea)dicyclohexylmethane

Conditions	Yield
In toluene at 20℃; for 48h;	49%

N-acetylcystein (616-91-1) + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → 2-acetylamino-3-{4-[4-(2-acetylamino-2-carboxyethylsulfanylcarbonylamino)cyclohexylmethyl]cyclohexylcarbamoylsulfanyl}propionic acid

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.25h;	29%

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + N,N'-bis(2,6-diisopropylphenyl)carbodiimide (2162-74-5) → C65H90N6O2

Conditions	Yield
at 110℃; for 7h; Sealed tube;	0.96%

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → C44H68N6O5

Conditions	Yield
With water at 140℃;

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + poly(tetramethylene oxide)glycol of molecular weight 650 → 4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 650]

Conditions	Yield
at 80℃;

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + poly(tetramethylene oxide)glycol of molecular weight 1000 → 4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 1000]

Conditions	Yield
at 80℃;

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + poly(tetramethylene oxide)glycol of molecular weight 2000 → 4,4-methylene bis(cyclohexyl isocyanate) terminated [poly(tetramethylene oxide)glycol of molecular weight 2000]

Conditions	Yield
at 80℃;

4,4'-methylenebis-(2-chloroaniline) (101-14-4) + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; methylene-bis-ortho-chloroaniline

Conditions	Yield
In cyclohexanone; N,N-dimethyl-formamide at 80 - 90℃;

2,4-diamino-3,5-dimethylsulphanylchlorobenzene + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; 2,4-diamino-3,5-dimethylsulphanylchlorobenzene

Conditions	Yield
In cyclohexanone; N,N-dimethyl-formamide at 80 - 90℃;

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + ethylenediamine (107-15-3) → copolymer; monomer(s): 4,4\-methylene-dicyclohexyl-diisocyanate; ethylene diamine

Conditions	Yield
dibutyltin(II) dilaurate In cyclohexanone; N,N-dimethyl-formamide at 80 - 90℃;

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → C53H92N6O8

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 140 °C View Scheme

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + ethyl nitroacetate potassium salt (95848-28-5) → C23H34N4O10(2-)*2K(1+)

Conditions	Yield
In diethylene glycol dimethyl ether at 20 - 100℃; for 16h;
In 1,2-dimethoxyethane at 20 - 85℃; for 72h;

4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → Reaxys ID: 11465127

Conditions	Yield
Stage #1: 4,4'-bis(diisocyanato)dicyclohexylmethane; trihexyl(tetradecyl)phosphonium 1,2,4-triazolide at 30℃; for 3.5h; Stage #2: With dibutyl phosphate

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → Reaxys ID: 11465128

Conditions	Yield
zinc 2-ethylhexanoate at 120℃; for 6h;

N-methyl-1,1,2,2,3,3,4,4-nonafluoro-N-(2-hydroxyethyl)butane-1-sulphonamide (34454-97-2) + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → C22H30F9N3O5S

Conditions	Yield
In n-heptane at 90 - 100℃;

C46H44F34O12S2 + 4,4'-bis(diisocyanato)dicyclohexylmethane (5124-30-1) → C105H106F68N2O26S4

Conditions	Yield
dibutyltin dilaurate In methylpentan-2-one, 4- at 55℃; for 4h; Michael Condensation; Heating / reflux;

Upstream product

• 99305-42-7 dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate 
• 1761-71-3 4,4'-diaminodicyclohexylmethane 
• 57-13-6 urea 
• 75-44-5 phosgene 
• 1027096-18-9 bis(2,4-di-tert-amylphenyl) 4,4'-methylene-di(cyclohexylcarbamate) 
• 439680-99-6 phenyl N-[4-({4-[(phenoxycarbonyl)amino]cyclohexyl}methyl)cyclohexyl]carbamate 
• 1027096-17-8 4,4'-methylenedi(cyclohexylcarbamate) bis(3-methylbutyl) ester 
• 63896-13-9 4,4'-methylene-di(cyclohexylcarbamate) dimethyl ester 
• 47460-66-2 dicyclohexylmethane-4,4'-diethylurethane 
• 1266554-85-1 N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2,6-dimethoxyphenyl) ester) 
• 124-38-9 carbon dioxide 
• 195456-49-6 trimethyl hexamethylene diisocyanate 
• 822-06-0 Hexamethylene diisocyanate 
• 1266555-51-4 N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2,4,6-trimethylphenyl) ester) 

Downstream Products

• 94113-65-2 4,4'-bis(diimethylamino-urea)dicyclohexylmethane 
• 109359-23-1 C₃₉H₅₀N₂O₁₀ 

Relevant academic research and scientific papers

METHOD FOR PRODUCING CARBAMATE AND METHOD FOR PRODUCING ISOCYANATE

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

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.

Preparation method of 4,4'-dicyclohexyl methane diisocyanate

The invention relates to a preparation method of 4,4'-dicyclohexyl methane diisocyanate. The method comprises the steps of firstly, adding a catalyst polyoxometallate and a solvent into a reaction vessel; then, adding a raw material of 4,4'-diamino dicyclohexyl methane, phenylsilane, an acid-binding agent and a dehydrating agent, and uniformly mixing the materials; finally, adding gaseous carbon dioxide and stirring the mixture for a thorough reaction through a magnetic force at a certain temperature to obtain a product. According to the method, M-Anderson type heteropoly acid is used as the catalyst, and the catalyst needs mild reaction conditions and is high in specific selectivity, recyclable and environmentally friendly; the cleanliness of an industrial reaction is improved, the economic efficiency of the process is improved, the manufacturing cost and the generation of three wastes are reduced, the environmental protection pressure is reduced, and industrial production is facilitated.

Method for preparing polyisocyanate through photochemical reaction, and method for preparing waterborne polyurethane resin

The invention especially relates to a method for preparing polyisocyanate through a photochemical reaction, and a method for preparing waterborne polyurethane resin, belonging to technical field of waterborne polyurethane resin. The method for preparing the waterborne polyurethane resin comprises a step of carrying out a polymerization reaction on raw materials containing polyisocyanate, oligomerpolyol, a chain extender and a hydrophilic agent to obtain the waterborne polyurethane resin, wherein the content of benzophenone impurities in the polyisocyanate is less than or equal to 0.045 wt%. By controlling the content of benzophenone impurities in the preparation process of polyisocyanate, the yellowing resistance of the waterborne polyurethane resin can be effectively improved, and harm to the qualified rate of downstream products caused by existence of the impurities in the waterborne polyurethane resin is also reduced.

Method for preparing isocyanate by using amine and carbonyl fluoride

The invention discloses an efficient synthesis method for preparing corresponding isocyanate by enabling carbonyl fluoride to directly react with amine. The efficient synthesis method mainly comprises the following two steps: carrying out acylation reaction on the amine and the carbonyl fluoride according to a preferable proportion in an anhydrous inertial organic solvent under a sealed environment and a proper reaction condition, thus generating an intermediate-carbamyl fluoride; (2) carrying out dehydrofluorination on the intermediate-carbamyl fluoride under normal pressure and the proper reaction condition, thus obtaining the target isocyanate. During a reaction process, addition of a catalyst is not needed, the reaction conditions are mild, excessive carbonyl fluoride and a used solvent during the reaction process can be efficiently recycled and reused, and a by-product HF can be commercially sold after being collected and refined.

Using carbon dioxide diarylbutadiene isocyanate production method (by machine translation)

PROBLEM TO BE SOLVED: To provide a method in which there are not various problems shown in a prior art when isocyanate is manufactured without using phosgene, and that can stably manufacture isocyanate for the long period of time in good yield. SOLUTION: The manufacturing method of isocyanate includes: a process in which diaryl carbonate and an amine compound are made to react in the presence of an aromatic hydroxy compound as a reaction solvent, thereby a reaction mixture that includes carbamic acid aryl having an aryl group originated from diaryl carbonate, an aromatic hydroxy compound originated from diaryl carbonate, and diaryl carbonate is obtained; a process in which the reaction mixture is transported to a thermal cracking reactor; and a process in which the carbamic acid aryl is subjected to a thermal decomposition reaction to obtain isocyanate, wherein a reactor in which the reaction of diaryl carbonate and an amine compound is performed and a thermal cracking reactor of carbamic acid aryl are different. COPYRIGHT: (C)2013,JPO&INPIT

LINEAR GLYCIDYL CARBAMATE (GC) RESINS FOR HIGHLY FLEXIBLE COATINGS

This invention relates to coating compositions comprising a linear glycidyl carbamate (GC) resin and a curing agent. The linear GC-resins were synthesized using linear and cycloaliphatic diisocyanates and a combination of diols and optional triols with glycidol. The combination of linear diisocyanates and diols introduces a more linear structure in the GC-resin compositions.

METHOD FOR PREPARING ALIPHATIC DIISOCYANATE

The present invention relates to a method for preparing an aliphatic diisocyanate by pyrolyzing an aliphatic dicarbamate in liquid phase, using a tin (II) or (IV) compound as a catalyst and a zwitterionic compound as a stabilizer, thereby remarkably inhibiting high-boiling by-products and providing the aliphatic diisocyanate with high yield.

PROCESS FOR PRODUCING ISOCYANATE

An object of the present invention is to provide a process that enables isocyanate to be produced stably over a long period of time and at high yield without encountering problems of the prior art during production of isocyanate without using phosgene. The present invention discloses a process for producing an isocyanate by subjecting a carbamic acid ester to a thermal decomposition reaction, including the steps of: recovering a low boiling point component in a form of a gaseous phase component from a thermal decomposition reaction vessel in which the thermal decomposition reaction is carried out; recovering a liquid phase component containing a carbamic acid ester from a bottom of the thermal decomposition reaction vessel; and supplying all or a portion of the liquid phase component to an upper portion of the thermal decomposition reaction vessel.

PROCESS FOR PRODUCING ISOCYANATES USING DIARYL CARBONATE

An object of the present invention is to provide a process that enables isocyanate to be produced stably over a long period of time and at high yield without encountering problems of the prior art during production of isocyanate without using phosgene. The present invention provides an isocyanate production process including the steps of: obtaining a reaction mixture containing an aryl carbamate having an aryl group originating in a diaryl carbonate, an aromatic hydroxy compound originating in a diaryl carbonate, and a diaryl carbonate, by reacting a diaryl carbonate and an amine compound in the presence of a reaction solvent in the form of an aromatic hydroxy compound; transferring the reaction mixture to a thermal decomposition reaction vessel; and obtaining isocyanate by applying the aryl carbamate to a thermal decomposition reaction, wherein the reaction vessel in which the reaction between the diaryl carbonate and the amine compound is carried out and the thermal decomposition reaction vessel for the aryl carbamate are different.