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ChemicalBook CAS DataBase List CIS-2-BUTENE
590-18-1

CIS-2-BUTENE synthesis

13synthesis methods
-

Yield:590-18-1 40% ,624-64-6 60%

Reaction Conditions:

Stage #1:ethene with bis(1,5-cyclooctadiene)nickel (0);diphenylphosphane in 2,2,2-trifluoroethanol under 3375.34 Torr; for 0.0833333 h;Inert atmosphere;
Stage #2: with trifluoroacetic acid in 2,2,2-trifluoroethanol at 40; under 36978.7 Torr; for 0.25 h;Inert atmosphere;

Steps:

3
The reactor is purged with nitrogen for 5 minutes followed by addition of 48 mL of 2,2,2-trifluoroethanol, diphenylphosphine (1.0 mmol) and bis(1,5-cyclooctadiene)nickel(0) (0.275 g; 1.0 mmol). The reactor is sealed, purged with ethylene at least four times, and then pressured with ethylene to 0.45 MPa (50 psig) for 5 minutes. A solution of trifluoroacetic acid (0.1 14 g; 1.0 mmol) in 2 mL of 2,2,2-trifluoroethanol is added to the addition vessel using a syringe. The addition vessel is immediately sealed and pressured to 4.93 MPa (700 psig) with ethylene. The contents of the addition vessel (including ethylene) are transferred to the reactor at the end of the above mentioned 5 minute period through the addition valve. The reaction temperature is 40° C. by an external cooling water. The internal reactor pressure is about 700 psig and the reaction is continued for 10 minutes. GC analysis shows 90% wt of the C4 fraction which included 97% wt of the mixture 2-butenes (trans/cis=60/40).

References:

PIONEER ENERGY INC;Henri, John T;Zygmunt, Jan;Zubrin, Robert US2016/200645, 2016, A1 Location in patent:Page/Page column 4

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