CA2248359A1 - Process for preparing 1,3-propanediol - Google Patents
Process for preparing 1,3-propanediolInfo
- Publication number
- CA2248359A1 CA2248359A1 CA002248359A CA2248359A CA2248359A1 CA 2248359 A1 CA2248359 A1 CA 2248359A1 CA 002248359 A CA002248359 A CA 002248359A CA 2248359 A CA2248359 A CA 2248359A CA 2248359 A1 CA2248359 A1 CA 2248359A1
- Authority
- CA
- Canada
- Prior art keywords
- water
- hydroxypropanal
- propanediol
- catalyst
- effective amount
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 title abstract 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 title abstract 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 4
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- 238000007037 hydroformylation reaction Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,3-Propanediol is prepared in a process in which ethylene oxide is reacted with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a catalyst promoter under reaction conditions effective to produce an intermediate product mixture comprising less than 15wt.% 3-hydroxypropanal.
The 3-hydroxypropanal is extracted in water from the product mixture in more concentrated form, with the majority of the cobalt catalyst remaining in the solvent phase for recycle to the hydroformylation reaction.
At least a portion of any residual catalyst in the water phase following extraction is removed by re-extraction with non-water-miscible solvent and recycled to hydroformylation. The 3-hydroxypropanal is then hydrogenated in aqueous solution to the desired 1,3-propanediol.
The 3-hydroxypropanal is extracted in water from the product mixture in more concentrated form, with the majority of the cobalt catalyst remaining in the solvent phase for recycle to the hydroformylation reaction.
At least a portion of any residual catalyst in the water phase following extraction is removed by re-extraction with non-water-miscible solvent and recycled to hydroformylation. The 3-hydroxypropanal is then hydrogenated in aqueous solution to the desired 1,3-propanediol.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/615,544 US5770776A (en) | 1994-09-30 | 1996-03-11 | Process for preparing 1,3-propanediol |
US08/615,544 | 1996-03-11 | ||
PCT/EP1997/001172 WO1997033851A1 (en) | 1996-03-11 | 1997-03-06 | Process for preparing 1,3-propanediol |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2248359A1 true CA2248359A1 (en) | 1997-09-18 |
CA2248359C CA2248359C (en) | 2006-10-24 |
Family
ID=37387463
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002248359A Expired - Fee Related CA2248359C (en) | 1996-03-11 | 1997-03-06 | Process for preparing 1,3-propanediol |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA2248359C (en) |
-
1997
- 1997-03-06 CA CA002248359A patent/CA2248359C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CA2248359C (en) | 2006-10-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO984111D0 (en) | Process for preparing 1,3-propanediol | |
AU3744595A (en) | Process for preparing 1,3-alkanediols and 3-hydroxyaldehydes | |
US5723389A (en) | Process for preparing alkanediols | |
JP3844781B2 (en) | Process for producing 1,3-propanediol | |
US3896047A (en) | Process for recycling a cobalt hydroformylation catalyst | |
US5545767A (en) | Process for preparing 1,3-propanediol | |
US5981808A (en) | Cobalt-catalyzed process for preparing 1, 3-propanediol from etylene oxide | |
EP0343819A1 (en) | Production of alcohols | |
CA2204133A1 (en) | Hydroformylation process | |
EP0642386A1 (en) | Stripper-reactor for volatile cobalt recovery | |
CA2248359A1 (en) | Process for preparing 1,3-propanediol | |
WO1993024227A1 (en) | Cobalt catalyst recovery using heavy olefin absorbent | |
AU688608B2 (en) | Process for preparing 1,3-alkanediols and 3-hydroxyldehydes | |
EP1122235A3 (en) | Process for preparing 1,3-alkanediol from epoxide derivative | |
CA1042470A (en) | Process for preparing diols | |
CA2235065A1 (en) | Process for preparing 1,3-propanediol | |
CA2201323A1 (en) | Process for preparing 1,3-alkanediols and 3-hydroxyaldehydes | |
KR920000587B1 (en) | Manufacture of butane dicar boxylic acid esters | |
CA2201304A1 (en) | Process for preparing 1,3-alkanediols and 3-hydroxyaldehydes | |
JPS6485937A (en) | Production of 1,5-pentanediol | |
MXPA98007262A (en) | Process for preparing 1,3-propanod | |
JPH0262304B2 (en) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |