Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
1998-09-30
2001-02-20
Carr, Deborah (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S861000
Reexamination Certificate
active
06191321
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to the preparation of 1,3-propanediol. In one embodiment, the invention relates to a selective process for manufacturing 1,3-propanediol from ethylene oxide in which production of aldehyde intermediates is relatively low.
1,3-Propanediol is a starting material in the production of polyesters for fibers and films. It is known to prepare 1,3-propanediol in a two-step process involving (1) the cobalt-catalyzed hydroformylation (reaction with synthesis gas, H
2
/CO) of ethylene oxide to intermediate 3-hydroxypropanal (HPA) and (2) hydrogenation of the HPA to 1,3-propanediol. One disadvantage of this route involves the tendency of the HPA intermediate to react with itself, resulting in the formation of intermediate by-products which do not undergo hydrogenation to the desired 1,3-propanediol product.
An alternate route to 1,3-propanediol from ethylene oxide involves production of intermediate methyl 3-hydroxypropionate followed by hydrogenation of the methyl 3-hydroxypropionate to 1,3-propanediol. This route would have the advantage of eliminating HPA and the associated by-products; however, this route is typically very unselective for 1,3-propanediol because of the tendency of the methyl 3-hydroxypropionate to undergo hydrogenolysis in the presence of ester hydrogenation catalysts such as copper chromium oxide or Raney nickel.
It is therefore an object of the invention to provide a selective, efficient process for hydrogenating methyl 3-hydroxypropionate to 1,3-propanediol. It is a further object of a specific embodiment of the invention to provide a selective process for the preparation of 1,3-propanediol via methyl 3-hydroxypropionate intermediate.
SUMMARY OF THE INVENTION
According to the invention, methyl 3-hydroxypropionate is hydrogenated to 1,3-propanediol in the presence of a copper zinc oxide hydrogenation catalyst.
According to one embodiment of the invention, 1,3-propanediol is prepared in a process comprising the steps of:
(a) contacting ethylene oxide with carbon monoxide and methanol in the presence of an effective amount of a carbonylation catalyst under methoxycarbonylation conditions, to produce an intermediate product mixture comprising methyl 3-hydroxypropionate;
(b) separating the methyl 3-hydroxypropionate from the intermediate product mixture and passing the methyl 3hydroxypropionate to a hydrogenation zone;
(c) contacting the methyl-3-hydroxypropionate with hydrogen in the presence of a copper zinc oxide hydrogenation catalyst under hydrogenation conditions to produce a hydrogenation product mixture comprising 1,3-propanediol; and
(d) recovering 1,3-propanediol from the hydrogenation product mixture.
The process enables the production of 1,3-propanediol in good yield and high selectivity in a process which avoids the problems inherent in producing an HPA intermediate.
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Forschner Thomas Clayton
Powell Joseph Broun
Slaugh Lynn Henry
Weider Paul Richard
Carr Deborah
Shell Oil Company
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