US 7,541,486 B2
Method for producing 3-pentenenitrile
Jens Scheidel, Hirschberg (Germany); Tim Jungkamp, Kapellen (Belgium); Michael Bartsch, Neustadt (Germany); Gerd Haderlein, Grünstadt (Germany); Robert Baumann, Mannheim (Germany); and Hermann Luyken, Ludwigshafen (Germany)
Assigned to BASF Aktiengesellschaft, (Germany)
Appl. No. 10/586,007
PCT Filed Jan. 27, 2005, PCT No. PCT/EP2005/000774
§ 371(c)(1), (2), (4) Date Jul. 12, 2006,
PCT Pub. No. WO2005/073171, PCT Pub. Date Aug. 11, 2005.
Claims priority of application No. 10 2004 004 720 (DE), filed on Jan. 29, 2004.
Prior Publication US 2008/0227998 A1, Sep. 18, 2008
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 255/00 (2006.01); C07C 253/00 (2006.01)
U.S. Cl. 558—465  [558/303; 558/332; 558/435; 558/462; 558/463] 20 Claims
 
1. A process for preparing 3-pentenenitrile, characterized by the following process steps:
(a) reacting 1,3-butadiene with hydrogen cyanide over at least one catalyst to obtain a stream 1 which comprises 3-pentenenitrile, 2-methyl-3-butenenitrile, the at least one homogeneously dissolved nickel(0) catalyst which is stabilized with phosphorus ligands and the phosphorus ligands are selected from the group consisting of phosphines, phosphites, phosphinites and phosphonites, and 1,3-butadiene,
(b) distilling stream 1 in a column to obtain a high-1,3-butadiene stream 2 as the top product and a low-1,3-butadiene stream 3 as the bottom product which comprises 3-pentenenitrile, the at least one catalyst and 2-methyl-3-butenenitrile,
(c) distilling stream 3 in a column to obtain a stream 4 as the top product which comprises 1,3-butadiene, a stream 5 which comprises 3-pentenenitrile and 2-methyl-3-butenenitrile at a side draw of the column, and a stream 6 as the bottom product which comprises the at least one catalyst,
(d) distilling stream 5 to obtain a stream 7 as the top product which comprises 2-methyl-3-butenenitrile, and a stream 8 as the bottom product which comprises 3-pentenenitrile,
with the proviso that, in process steps (b) and (c), the bottom temperatures do not exceed 140° C. and the sum of the average residence times in the distillation apparatus in process steps (b) and (c) together is not more than 10 hours.