Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1980-12-11
1983-11-29
Wiseman, Thomas G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564 57, 564134, 564138, 564 39, 260453A, 260453P, 260543A, 560115, C07C12715
Patent
active
044182112
ABSTRACT:
A process is disclosed for selectively making trans-cyclohexane-1,4-diisocyanate, trans-cyclohexane-1,4-diamine, a trans-cyclohexane-1,4-diurethane, a transcyclohexane-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 trans-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) 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.
REFERENCES:
patent: 3163675 (1964-12-01), Smith
patent: 3296303 (1967-01-01), Nemec et al.
patent: 3880925 (1975-04-01), Langer, Jr. et al.
patent: 4259258 (1981-03-01), Zengel et al.
Bergfeld Manfred
Zengel Hans
Akzona Incorporated
Green Robert F.
Pepper Frederick W.
Wiseman Thomas G.
Young Francis W.
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