38661-72-2

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

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

Downstream Products

• 391894-57-8 C₁₈H₂₈N₄O₁₀ 

Relevant academic research and scientific papers

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 OF PREPARING DIISOCYANATE COMPOSITION AND OPTICAL LENS

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.

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.

Synthesis method of 1,3-dimethyl isocyanate cyclohexane

The invention discloses a synthesis method of 1,3-dimethyl isocyanate cyclohexane. The method comprises the steps of pumping a metered inert solvent into reactor capable of performing stirring and with phosgene ingress pipe for bedding, performing cooling, beginning to continuously supply metered phosgene, dropwise adding a metered mixed solution of 1,3-hexamethylene dimethylamine and the inert solvent into a reaction system to form a mixture of 1,3-hexanaphthene dimethylamine hydrochloride and 1,3-hexanaphthene dimethylcarbamoyl chloride (a material in the reactor is slurry and the process isa cold photochemical reaction), after dropwise adding, heating to a reaction temperature (the process is a heat photochemical reaction), after the reaction, removing excessive phosgene and hydrogen chloride through nitrogen, and performing high vacuum rectification to form high-purity 1,3-dimethyl isocyanate cyclohexane. The method has the advantages that raw materials are easy to obtain, the solvent can be recycled, and the method is simple in technology, easy and simple to operate, higher in yield, mild in reaction condition and suitable for industrial production.

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.

Preparation method of hydrogenated xylylene diisocynate

The invention discloses a preparation method of hydrogenated xylylene diisocynate. The preparation method of the hydrogenated xylylene diisocynate comprises the following steps: (1) performing salt forming reaction on 1,3-cyclohexanol dimethylamine and concentrated hydrochloric acid in a two-phase reaction solvent to obtain amine salt, wherein the two-phase reaction solvent consists of water and an inert organic solvent insoluble in water ; (2) performing photochemical reaction on the ammonium salt obtained in the step (1) and phosgene in an inert solvent by taking N,N-dimethylformamide or N,N-dimethylacetamide as a catalyst to obtain reaction liquid, and performing aftertreatment on the reaction liquid to obtain the hydrogenated xylylene diisocynate. The preparation method of the hydrogenated xylylene diisocynate has the advantages of complete ammonium salt formation, small grain size of the ammonium salt, low viscosity of the ammonium salt, high space-time conversion rate of photochemical reaction, simple process, low cost and the like.

METHOD FOR PRODUCING CARBAMATE COMPOUND

PROBLEM TO BE SOLVED: To provide an industrially suitable method for producing a carbamate compound of quality suitable for producing an isocyanate compound by reacting a carbonate compound and an amine compound without requiring complicated operations. SOLUTION: There is provided a method for producing a carbamate compound, which comprises a step in which when a carbamate compound is produced by reacting an amine compound and a carbonate compound in the presence of at least one base selected from the group consisting of an alkali metal alkoxide and an alkaline earth metal alkoxide, the unreacted base is decomposed by adding water in an amount larger than the number of moles of the base used. COPYRIGHT: (C)2015,JPOandINPIT

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.

COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING A POLYMER BEARING JUNCTION GROUPS, AND COSMETIC TREATMENT PROCESS

The present patent application relates to a cosmetic or dermatological composition comprising, in a cosmetically or dermatologically acceptable medium, a polymer comprising: (a) a polymer backbone that may be obtained by reaction: of a polyol comprising 3 to 6 hydroxyl groups;of a monocarboxylic acid containing 6 to 32 carbon atoms;of a polycarboxylic acid comprising at least two carboxylic groups COOH, and/or of a cyclic anhydride such as a polycarboxylic acid and/or of a lactone comprising at least one carboxylic group COOH; and(b) at least one junction group linked to the said polymer backbone and capable of establishing H bonds with one or more partner junction groups, each pairing of a junction group involving at least three H (hydrogen) bonds. The patent application also concerns a cosmetic treatment process using the said composition.

Sensitizer/Initiator Combination for Negative-Working Thermal-Sensitive Compositions Usable for Lithographic Plates

The radiation-sensitive composition and the negative working imageable element include a cationic IR absorber with tetraarylborate counteranion and an onium initiator with tetraarylborate counteranion. The use of these components provides high imaging sensitivity, good shelflife and high print run length.