Process for the telomerization of a conjugated diene,...

Details Process for the telomerization of a conjugated diene,... Process for the telomerization of a conjugated diene,...

2002-11-04

2004-09-21

Dang, Thuan Dinh (Department: 1764)

Chemistry of hydrocarbon compounds

Plural serial diverse syntheses

To produce unsaturate

C585S259000

Reexamination Certificate

active

06794553

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a process for the telomerization of a conjugated diene, and a catalyst and bidentate ligand that can be used in this process.
BACKGROUND OF THE INVENTION
WO-A-9210450 describes a telomerization reaction wherein 1,3-butadiene is reacted with a compound containing an active hydrogen atom and having a formula R—H in the presence of a telomerization catalyst to form a 1-substituted-2,7-octadiene of formula CH
2
═CH—CH
2
—CH
2
—CH
2
—CH═CH—CH
2
—R, in which R represent the residue of the compound containing an active hydrogen atom. WO-A-9210450 describes telomerization catalysts such as the transition metals Fe, Co, Ni, Ru, Rh, Pd, Os, Ir and Pt (Group VIII transition metals) and compounds thereof, including those supported on an inert carrier, as well as ligand compounds including diphosphines.
However, it is desirable to provide a process for the telomerization of a conjugated diene, wherein the telomerization reaction can be carried out with an improved selectivity towards the linear telomerization product.
SUMMARY OF THE INVENTION
Accordingly, a process for the telomerization of a conjugated diene is provided, comprising:
reacting the conjugated diene with a compound containing an active hydrogen atom and having a formula R′—H in the presence of a telomerization catalyst based on:
(a) a source of group VIII metal,
(b) a bidentate ligand
wherein the bidentate ligand has the general formula I
R
1
R
2
M
1
—R—M
2
R
3
R
4
  (I)
wherein M
1
and M
2
are independently P, As or Sb;
R
1
, R
2
, R
3
and R
4
independently represent a monovalent aliphatic group;
or R
1
, R
2
and M
1
together and/or R
3
, R
4
and M
2
together independently represent an optionally substituted aliphatic cyclic group with at least 5 ring atoms,
wherein one ring atom in said cyclic group is M
1
or M
2
;
and R represents a bivalent organic bridging group.
In addition, a process for the preparation of 1-octene is provided, comprising:
a) reacting 1,3-butadiene with a compound containing an active hydrogen atom and having a formula R′—H in the presence of a telomerization catalyst based on:
(1) a source of group VIII metal,
(2) a bidentate ligand
wherein the bidentate ligand has the general formula I
R
1
R
2
M
1
—R—M
2
R
3
R
4
  (I)
wherein M
1
and M
2
are independently P, As or Sb;
R
1
, R
2
, R
3
and R
4
independently represent a monovalent aliphatic group;
or R
1
, R
2
and M
1
together and/or R
3
, R
4
and M
2
together independently represent an optionally substituted aliphatic cyclic group with at least 5 ring atoms,
wherein one ring atom in said cyclic group is M
1
or M
2
;
and R represents a bivalent organic bridging group; thereby producing 1-substituted-2,7-octadiene;
b) hydrogenating the 1-substituted-2,7-octadiene of step a), thereby producing 1-substituted octane;
c) decomposing the 1-substituted octane of step b), thereby producing 1-octene.
Also provided are catalyst systems and bidentate ligands useful in the processes of the present invention.


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U.S. patent application Ser. No. 10/669,916, Drent et al., filed Sep. 24, 2003.
Chemical Abstracts, vol. 96, No. 25, Jun. 21, 1982 Columbus, Ohio, US; Abstract No. 217253, Kuraray Co., Ltd. Japan: “Telomerization of Butadiene and Isoprene” XP002244618.
Karsch H. H. et al., “Funktionelle Trimethylphosphanderivate, XVIII [1] Methyl(Phosphinomethyl)Silanes and -Stannanes,” Zeitschrift Fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie., vol. 38b, No. 11, 1983, pp. 1399-1405 XP008018568.
Morimoto, T. et al., “A Convenient Method for the Synthesis of Bis(Trialkylphosphine)-Boranes Bearing Two Phospholanes,” Synlett (1996), (12), pp. 1211-1212, 1996 XP002244948.
International Search Report of Jul. 7, 2003.

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