Process for preparing TCD-diamine

A process for preparing 3(4),8(9)-bis(aminomethyl)tricycle-[5.2.1.02,6]decane by hydroformylating dicyclopentadiene with subsequent reductive amination, comprising reacting dicyclopentadiene, in a first hydroformylation stage in a heterogeneous reaction system using an aqueous solution of transition metal compounds, containing water-soluble organic phosphorus (III) compounds in complex-bound form selected from the group consisting of sulfonated triarylphosphines of the formula (I)

• in which Ar1, Ar2 and Ar3 are individually aryl groups of 6 to 14 carbon atoms, the substituents Y1, Y2 and Y3 are individually selected from the group consisting of alkyl and alkoxy of 1 to 4 carbon atoms, chlorine, bromine, hydroxyl, cyanide, nitro, and NR1R2 in which the R1 and R2 are individually hydrogen, or alkyl of 1 to 4 carbon atoms, in which m is selected from the group consisting of lithium, sodium, potassium magnesium, calcium and barium, m1, m2, and m3 are individually integers from 0 to 5, n1, n2, n3 are individually integers from 0 to 3, and at least one of n1, n2 and n3 equal to or treater than 1;
• sulfonated diphosphines of the formula (II)
• in which n4 and n5 are individually 0 to 1, and the sulfonated diphosphines of the formula (II) up to six SO3M groups, and M is selected from the group consisting of ammonium, a monovalent metal and an equivalent of a polyvalent metal and;
• sulfonated diphosphines of the formula (III)
• in which n6, n7, n8 and n9 are individually 0 or 1, and the sulfonated diphosphines of the formula (III) contain from four to eight SO3M groups, and M is selected from the group consisting of ammonium, a monovalent metal and an equivalent of a polyvalent metal;
• of group VIII of the Periodic Table of the Elements at temperatures of from 70 to 150° C. and pressures of from 0.5 to 10 MPa, with hydrogen and carbon monoxide to give 8(9)-formyltricyclo[5.2.1.02,6]dec-3-ene, then separating the organic phase from the aqueous phase and subsequently converting the thus obtained 8(9)-formyltricyclo[5.2.1.02,6]dec-3-ene, in a second hydroformylation stage in a homogeneous organic phase in the presence of transition metal compounds of group VIII of the Periodic Table of Elements at temperatures of from 70 to 140° C. and pressures of from 5 to 35 MPa by reacting with hydrogen and carbon monoxide, to 3(4),8(9)-bisformyltricyclo[5.2.1.02,6]decane and subsequently reductively aminating the thus obtained 3(4),8(9)-bisformyltricyclo-[5.2.1.02,6]decane to give 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.02,6]decane.