7517-76-2

Usage

Uses

Used in the Polymer Industry:
TRANS-1,4-CYCLOHEXANE DIISOCYANATE is used as a monomer for the synthesis of mixed aromatic/alicyclic polyimides. Its intermediate reactivity allows for the preparation of these polyimides through polycondensation reactions with other monomers such as PMDA, BTDA, and 6FDA. These polyimides are known for their high thermal stability and excellent mechanical properties, making them suitable for various applications in the polymer industry.
Used in the Production of Polyurethanes:
TRANS-1,4-CYCLOHEXANE DIISOCYANATE is also used as a key component in the production of polyurethanes. Its isocyanate functional groups react with other compounds, such as polyols, to form polyurethane polymers. These polymers are versatile and can be used in a wide range of applications, including foams, elastomers, coatings, and adhesives, due to their unique properties like flexibility, durability, and resistance to various environmental factors.

InChI:InChI=1/C8H10N2O2/c11-5-9-7-1-2-8(4-3-7)10-6-12/h7-8H,1-4H2/t7-,8-

Synthetic route

carbon dioxide (124-38-9) + trans-1,4-cyclohexyldiamine (2615-25-0) → trans-1,4-cyclohexane diisocyanate (7517-76-2)

Conditions	Yield
With triethylamine; trichlorophosphate 1.) acetonitrile, 1 atm., 2.) acetonitrile; Yield given. Multistep reaction;

trans-1,4-diaminocyclohexane (3114-70-3) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) → trans-1,4-cyclohexane diisocyanate (7517-76-2) + cis-1.4-diisocyanato-cyclohexane

Conditions	Yield
With 1,2-dichloro-benzene at 95℃; und Einleiten von Phosgen in eine Suspension der erhaltenen Carbamidsaeure,zuletzt bei 160grad;

4-tritylphenol (978-86-9) + trans-1,4-cyclohexane diisocyanate (7517-76-2) + 11'-(tert-butyl)-5',17',23',35',38',40'43',45'-octamethyldispiro[cyclohexane-1,2'-[7,15,25,33]tetraazaheptacyclo[32.2.2.2.2(3,6).2(16,19).2(21,24).1(3,13).1(27,31)]hexatetraconta[3,5,9,11,13(44),16,18,21,23,27,29,31(39),34,36,37,40,42,45]octadecaene..]. (169179-44-6) → C64H72N4O4*C58H50N2O4

Conditions	Yield
With triethylamine In dichloromethane Addition; Heating;	23%

pyridin-3-ylamine (462-08-8) + trans-1,4-cyclohexane diisocyanate (7517-76-2) → 1-pyridin-3-yl-3-[4-(3-pyridin-3-yl-ureido)-cyclohexyl]-urea

trans-1,4-cyclohexane diisocyanate (7517-76-2) + 2-(4-aminophenoxy)-2-methyl propionic acid (117011-70-8) → C28H36N4O8

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water Reflux;

C32H43N5O5 + trans-1,4-cyclohexane diisocyanate (7517-76-2) → C72H96N12O12

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 20℃;

histamine (51-45-6) + trans-1,4-cyclohexane diisocyanate (7517-76-2) → 1,1'-((1r,4r)-cyclohexane-1,4-diyl)bis(3-(2-(1H-imidazol-4-yl)ethyl)urea)

Conditions	Yield
In tetrahydrofuran; N,N-dimethyl acetamide; ethyl acetate at 120℃; for 0.25h; Temperature;

Upstream product

• 124-38-9 carbon dioxide 
• 2615-25-0 trans-1,4-cyclohexyldiamine 
• 3114-70-3 trans-1,4-diaminocyclohexane 
• 15719-64-9 methylammonium carbonate 

Relevant academic research and scientific papers

Isocyanates From Primary Amines and Carbon Dioxide: 'Dehydration' of Carbamate Anions

Carbamate anions, derived from primary amines CO2 and an added base (e.g.NEt3), undergo rapid reaction with electrophilic 'dehydrating agents' (e.g.POCl3, P4O10) to give the corresponding isocyanates in excellent yields.

Preparation of trans cyclohexane 1,4 diisocyanate

A process is disclosed for selectively making trans-cyclohexane-1,4-diisocyanate, trans-cyclohexane-1,4-diamine, a trans-cyclohexane-1,4-diurethane, a trans-cyclohexane-1,4-diurea and trans-cyclohexane-1,4-disulphonyl urea by reacting ammonia with a mixture of cis and trans-cyclohexane-1,4-dicarboxylic acid, a lower alkyl ester, a glycol ester, an oligomeric ester or a polyester to make a solid trans-dicarboxylic acid diamide in a first step. The diamide is chlorinated to form cyclohexane-1,4-dicarboxylic acid-bis-N-chloramide. The latter compound is then converted into a (a) trans-cyclohexane-1,4-diamine with an alkali metal hydroxide or alkaline earth metal hydroxide; or into a (b) a trans-cyclohexane-1,4-diurethane by reaction with an alcohol or glycol in a reaction mixture containing an alkali metal hydroxide or alkaline earth metal hydroxide; or into (c) a trans-cyclohexane-1,4-diurea by reaction with a primary or secondary amine in a reaction mixture containing an alkali metal hydroxide or alkaline earth metal hydroxide; or into a (d) trans-cyclohexane-1,4-sulphonyl urea by reaction with a primary sulphonamide in a reaction mixture containing an alkali metal hydroxide and dimethyl formamide and water. The diurea prepared in (c) may be converted into trans-cyclohexane-1,4-diisocyanate with gaseous hydrogen chloride in an inert solvent. The diurethane prepared in (b) and the disulphonyl urea prepared in (d) may be thermally decomposed into trans-cyclohexane-1,4-diisocyanate.

Process for the preparation of organic mono- and polyisocyanates

A process for the preparation of organic mono- and polyisocyanates is described, in which a hydrogen chloride adduct of a trisubstituted urea is thermally decomposed to form the isocyanate. The hydrogen chloride adduct at minimum contains the stoichiometric amount of HCl, and at maximum a 10 mole-% excess. The process is carried out in a closed system at a temperature between about 80° and 180° C.; the reaction is effected either in a melt or in the presence of an inert organic solvent.