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Hydroformylation process

A hydrogenation catalyst and catalyst technology, applied in chemical instruments and methods, organic chemistry, carbon monoxide reaction preparation, etc., can solve problems such as adverse economic effects

Active Publication Date: 2012-07-04
LYONDELL CHEM TECH LP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

C 3 The formation of by-products effectively represents another yield loss in the process, which can have serious adverse effects on process economics

Method used

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Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1: Preparation of diphosphine ligand

[0026] Diphosphine ligands of the general formula below were prepared as described below.

[0027]

[0028] A solution of 2,2-dimethyl-4,5-bis[(tosyloxymethyl)methyl]-1,3-dioxolane in dry / degassed THF under argon (1 equivalent, 1.73g, 3.7×10 -3A molar amount of dioxolane in 50 mL THF) was added dropwise to a solution of an appropriate amount of lithium diarylphosphine (see formula above) in dry / degassed THF (2.3 equivalents in 100 mL THF). The mixture was heated at reflux for 2 hours, then cooled, and the solvent was removed under reduced pressure. The remaining solid was redissolved in dichloromethane, filtered through a bed of silica, and the solvent was removed under reduced pressure to give 2,3-O-isopropylidene-2,3-dihydroxy-1,4- Bis(diarylphosphino)butane.

[0029] Diphosphine 1A: 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,5-dimethylphenyl)phosphino]butane.

[0030] Diphosphine 1B: 2,3-O-isopropylidene...

Embodiment 2

[0039] Example 2: Hydroformylation using a diphosphine ligand

[0040] Diphosphine ligands 1A-1J were used to hydroformylate allyl alcohol according to the following procedure:

[0041] The desired diphosphine (2 equivalents or 8.6×10 -5 mol) in dry degassed toluene (15 g) was added to [Rh(CO) in a 100 mL Parr autoclave 2 (acac)] (1 equivalent or 4.3×10 -5 Moore). Use 1:1 CO / H 2 The solution was rinsed three times with the CO / H 2 The mixture was pressurized to 180 psig. The autoclave was then heated to 65 °C with stirring, allyl alcohol (3.5 mL) was injected, and the CO / H 2 Mixture The autoclave was pressurized to 200 psig. The autoclave was maintained at a constant pressure of 200 psig and the reaction was monitored for gas uptake. When there was no further gas uptake, the autoclave was cooled and depressurized. The resulting solution was analyzed by gas chromatography to determine the product of the reaction. This reaction produces HBA, HMPA and C 3 Products (n-pr...

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Abstract

The invention describes a process for the production of 4-hydroxybutyraldehyde. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solventThe invention describes a process for the production of 4-hydroxybutyraldehyde. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solventand a catalyst system comprising a rhodium complex and a 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,5-di-n-alkylphenyl)phosphino]butane. The process gives high yield of 4-hydroxybutyraldehyde c and a catalyst system comprising a rhodium complex and a 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,5-di-n-alkylphenyl)phosphino]butane. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.ompared to 3-hydroxy-2-methylpropionaldehyde.

Description

field of invention [0001] The present invention relates to a process for the hydroformylation of allyl alcohol to produce 4-hydroxybutyraldehyde. The process yields an unexpectedly high ratio of 4-hydroxybutyraldehyde:3-hydroxy-2-methylpropanal (linear:branched) product. Background of the invention [0002] The hydroformylation of allyl alcohol is a well known and industrially practiced process. See, eg, US Patent Nos. 4,064,145, 4,215,077, 4,238,419, 4,678,857, and 5,290,743. In the hydroformylation reaction, allyl alcohol and CO / H 2 The gas mixture reacts in the presence of a catalyst to produce 4-hydroxybutyraldehyde (HBA). The HBA can then be separated from the catalyst, eg, by water extraction, and hydrogenated to produce 1,4-butanediol (BDO). See US Patent No. 5,504,261. [0003] Various catalyst systems have been developed for this hydroformylation reaction, most notably rhodium complexes with phosphine ligands (see, eg, US Patent Nos. 4,064,145, 4,238,419, and 4...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/49C07F9/655C07C47/19
CPCC07F9/65515C07C45/49C07C47/19C07F9/655C07F15/00
Inventor D·F·怀特W·S·达布纳
Owner LYONDELL CHEM TECH LP
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