Method for hydroformylation of olefinically unsaturated compounds, in particular the hydroformylation of olefin in the presence of cyclic carbonic acid esters
A technology for hydroformyl and cyclic carbonates, which is applied in the field of hydroformylation of ethylenically unsaturated compounds, especially olefins in the presence of cyclic carbonates, and can solve problems such as pollution and target product pollution
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example 1
[0082] Example 1 (transformation scheme A)
[0083] Into a 3 L stirred autoclave under nitrogen was charged 1070 g propylene carbonate, 0.22 g rhodium nonanoate and 3.4 g tris(2,4-di-tert-butylphenyl) phosphite. The rhodium concentration in the reaction mixture was 40 ppm and the molar ratio of phosphorus to rhodium was 10. After heating to 100° C. under an atmosphere of synthesis gas (hydrogen:CO molar ratio=1:1), 280 g of 1-octene were introduced. The hydroformylation reaction was carried out at a reaction pressure of 20 bar and a temperature of 100° C. with constant stirring.
[0084]After a reaction time of 50 minutes, the conversion of 1-octene was 76%. The selectivity to n-nonanal was 65%.
[0085] This corresponds to a yield of n-nonanal of 49.4%.
example 2
[0086] Example 2 (the comparative experiment of example 1)
[0087] Another experiment was carried out in a manner similar to Example 1, except that tetrabutane was used as solvent instead of propylene carbonate.
[0088] After the hydroformylation reaction was carried out for 50 minutes, the conversion rate of 1-octene was 92%, and the selectivity to n-nonanal was 34%.
[0089] This corresponds to a yield of 31.3% to n-nonanal.
[0090] A comparison of these two experiments shows that the selectivity and yield to linear aldehydes can be improved by using propylene carbonate.
example 3
[0091] Example 3 (transformation scheme B)
[0092] 1070 g of propylene carbonate, 0.26 g of rhodium nonanoate, 5.7 g of the bidentate phosphite ligand of general formula II and 273 g of n-decane were added to a 3 L autoclave under nitrogen. This corresponds to a rhodium concentration of 40 ppm and a phosphorus:rhodium molar ratio of 20. At syngas pressure (CO-H 2 After heating to 100° C. at a molar ratio of 1:1), 280 g of a mixture of internal octenes were introduced.
[0093] The hydroformylation reaction was carried out at a synthesis gas pressure of 20 bar and a temperature of 100°C. After the reaction was complete, the mixture was cooled to ambient temperature and the phases were separated. The hydrocarbon phase containing the active catalyst-complex remains in the reactor. The propylene carbonate phase, which contains most of the aldehyde, is drawn off from the reactor and worked up in a thin-film evaporator at 125° C. and 25 hPa, as a result of which crude aldehyde ...
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