CA2248359A1 - Process for preparing 1,3-propanediol - Google Patents

Process for preparing 1,3-propanediol

Info

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
Application number
CA002248359A
Other languages
French (fr)
Other versions
CA2248359C (en
Inventor
Juan Pedro Arhancet
David Cleve Eubanks
Stephen Blake Mullin
Joseph Broun Powell
Paul Richard Weider
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij B.V.
Juan Pedro Arhancet
David Cleve Eubanks
Stephen Blake Mullin
Joseph Broun Powell
Paul Richard Weider
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US08/615,544 external-priority patent/US5770776A/en
Application filed by Shell Internationale Research Maatschappij B.V., Juan Pedro Arhancet, David Cleve Eubanks, Stephen Blake Mullin, Joseph Broun Powell, Paul Richard Weider filed Critical Shell Internationale Research Maatschappij B.V.
Publication of CA2248359A1 publication Critical patent/CA2248359A1/en
Application granted granted Critical
Publication of CA2248359C publication Critical patent/CA2248359C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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.
CA002248359A 1996-03-11 1997-03-06 Process for preparing 1,3-propanediol Expired - Fee Related CA2248359C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/615,544 1996-03-11
US08/615,544 US5770776A (en) 1994-09-30 1996-03-11 Process for preparing 1,3-propanediol
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)

Also Published As

Publication number Publication date
CA2248359C (en) 2006-10-24

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