38661-72-2

Basic information

• Product Name: 1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANE
• Synonyms: 1,3-bis(isocyanatomethyl)-cyclohexan;1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANE;1,3-Bis(isocyanatomethyl)cyclohexane (cis and trans- mixture);1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANE, 99 % (MIXTURE OF CIS AND TRANS);1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANEPRE-POLYMER;CYCLOHEXANE,1,3-BIS(ISOCYANATOMETHYL)-;1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANE (CIS- AND TRANS- MIXTURE) 98+%;(1,3-Cyclohexanediylbismethylene)bisisocyanate
• CAS NO: 38661-72-2
• Molecular Formula: C₁₀H₁₄N₂O₂
• Molecular Weight: 194.23
• Product Categories: Isocyanate Monomers;Monomers;Polymer Science
• Mol File: 38661-72-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 294.4 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.101 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.4 mm Hg ( 98 °C)
• Refractive Index: n20/D 1.485(lit.)
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANE(38661-72-2)
• EPA Substance Registry System: 1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANE(38661-72-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 38661-72-2(Hazardous Substances Data)

Usage

Reactivity Profile

Isocyanates and thioisocyanates, such as 1,3-BIS(ISOCYANATOMETHYL)CYCLOHEXANE, 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)].

InChI:InChI=1/C10H14N2O2/c13-7-11-5-9-2-1-3-10(4-9)6-12-8-14/h9-10H,1-6H2

Synthetic route

phosgene (75-44-5) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2)

Conditions	Yield
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With hydrogenchloride In chlorobenzene at 30 - 45℃; for 3.5h; Large scale; Stage #2: phosgene In chlorobenzene at 60℃; Large scale;	96.5%
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With carbon dioxide In toluene at 25 - 30℃; for 1.33333h; Stage #2: phosgene In toluene at 25 - 90℃; for 23h;
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With hydrogenchloride In water; toluene at 20℃; for 0.5h; Stage #2: phosgene With N,N-dimethyl-formamide In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 5h; Solvent;
In 1,2-dichloro-benzene at 0 - 130℃; for 11h; Solvent; Temperature;

1,3-bis(methoxycarbonylaminomethyl)cyclohexane → 1-isocyanatomethyl-3-(methoxycarbonylaminomethyl)cyclohexane + 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2)

Conditions	Yield
With CARiACT Q50 at 150 - 375℃; under 9.976 Torr; for 0.5h;	A 11% B 84%

1,3-bis(methoxycarbonylaminomethyl)cyclohexane → 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2)

Conditions	Yield
With boron trichloride; triethylamine In benzene for 0.5h; Heating; Yield given;
In methanol at 50℃; for 8.5h;	157.2 g
With CARiACT Q50 at 150 - 350℃; under 9.976 Torr; for 0.5h;	157.2 g

1,3-bis(ethoxycarbonylaminomethyl)cyclohexane → 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2)

Conditions	Yield
With boron trichloride; triethylamine In benzene for 0.5h; Heating; Yield given;

1,3-bis(methoxycarbonylaminomethyl)cyclohexane (748708-85-2) + 1,3-bis(methoxycarbonylaminomethyl)cyclohexane → monoisocyanate + 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2)

Conditions	Yield
	A 14.2 g (73.1%) B n/a

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium methylate; water / methanol; acetone / 5.5 h / 50 °C 2: CARiACT Q50 / 0.5 h / 150 - 350 °C / 9.98 Torr View Scheme

1,4-cyclohexanedimethanol monoacrylate (23117-36-4) + 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2) → C21H32N2O5

Conditions	Yield
With dibutyltin(II) dilaurate at 60℃; for 1.5h;	99%

6-chloro-1-hexanol (2009-83-8) + 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2) → bis(6-chlorohexyl) (cyclohexane-1,3-diylbis(methylene))dicarbamate

Conditions	Yield
With dibutyltin dilaurate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	95%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + diethylamine (109-89-7) + 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2) → 1-[3-(3,3-Diethyl-ureidomethyl)-cyclohexylmethyl]-3-(2-morpholin-4-yl-ethyl)-urea

Conditions	Yield
With p-nitrophenyl(polystyrene)ketoxime 2.) CH2Cl2; 3.) toluene, 75 deg C; Yield given. Multistep reaction;

nitroacetic acid ethyl ester (626-35-7) + 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2) → C18H28N4O10 (391894-57-8)

N-methyl-1,1,2,2,3,3,4,4-nonafluoro-N-(2-hydroxyethyl)butane-1-sulphonamide (34454-97-2) + 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2) → C17H22F9N3O5S

Conditions	Yield
dibutyltin(II) dilaurate In hexane at 20 - 55℃;

6-chloro-1-hexanol (2009-83-8) + 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2) → bis(6-azidohexyl) (cyclohexane-1,3-diylbis(methylene))dicarbamate

Conditions	Yield
Multi-step reaction with 2 steps 1: dibutyltin dilaurate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: sodium azide / N,N-dimethyl-formamide / 80 °C View Scheme

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 2579-20-6 cis, trans-1,3-dimethylaminocyclohexane 
• 75-44-5 phosgene 
• 748708-85-2 1,3-bis(methoxycarbonylaminomethyl)cyclohexane 

Downstream Products

• 391894-57-8 C₁₈H₂₈N₄O₁₀ 

Relevant articles and documents

METHOD OF PREPARING DIISOCYANATE COMPOSITION

In the embodiments, an aqueous hydrochloric acid solution 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 size of the diamine hydrochloride composition, the b* value according to the CIE color coordinate of the diamine hydrochloride composition, or the content of water in the diamine hydrochloride composition within a specific range.

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.

The manufacturing method of the carbamate compounds

The present invention addresses the problem of providing a method for producing an industrially-suitable carbamate compound without requiring a complicated operation, wherein a carbamate compound of a quality suitable for producing an isocyanate compound is produced by reacting a carbonate compound and an amine compound. Said problem is solved by a method for producing a carbamate compound characterized by reacting an amine compound and a carbonate compound under the presence of at least one base selected from a group comprising alkali metal alkoxides and alkaline earth metal alkoxides, and then adding 0.01 to 0.5 moles of water to 1 mole of an amino group of the amine compound, and further reacting the amine compound and carbonate compound.