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Hydroformylation process

A catalyst, phosphinomethyl technology, applied in the field of hydroformylation, can solve the problems such as the increase of the ratio of HBA:HMPA

Inactive Publication Date: 2012-04-25
LYONDELL CHEM TECH LP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

U.S. Patent No. 6,127,584 discloses that the use of trialkylphosphine ligands having at least 2 methyl groups results in an increased ratio of HBA:HMPA

Method used

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Embodiment 1

[0031] Embodiment 1: the preparation of diphosphine

[0032] 1A, 1B, 1C, 1D, and 1E : Diphosphines 1A, 1B, 1C, 1D and 1E of the general formula below were prepared as described below.

[0033]

[0034] 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 -3 moles 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 to 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(bisarylphosphine)butane.

[0035] Diphosphine 1A: 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,4-dimethylphenyl)phosphino]butane.

[0036] C...

Embodiment 2

[0042] Example 2: Hydroformylation using a diphosphine

[0043] Hydroformylation of allyl alcohol using diphosphine 1A-1E according to the following procedure:

[0044] The required diphosphine (2 equivalents or 8.6×10 -5 mol) in dry degassed toluene (15 g) was added to [Rh(CO)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. Then the autoclave was heated to 65°C under stirring, allyl alcohol (3.5ml) was injected, and the autoclave was heated with 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 reaction solution was analyzed by gas chromatography to identify the reaction product. This reaction produces HBA, HMPA, and C 3 Products (n-propanol and propiona...

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Abstract

A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst comprising a rhodium complex and a diphosphine. The diphoshine is a trans-1,2-bis(bis(3,4-di-n-alkylphenyl)phosphinomethyl)cyclobutane and / or a 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,4-di-n-alkylphenyl)phosphino] butane. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.

Description

technical field [0001] The invention relates to a method for preparing 4-hydroxybutyraldehyde by hydroformylation of allyl alcohol. Background technique [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 form 4-hydroxybutyraldehyde (HBA). The HBA can then be separated from the catalyst, for example by water extraction, and hydrogenated to 1,4-butanediol (BDO). See US Patent No. 5,504,261. [0003] A variety of catalyst systems have been used for this hydroformylation reaction, most notably rhodium complexes used with phosphine ligands (see, eg, US Pat. Nos. 4,064,145, 4,238,419, and 4,567,305). Commonly used phosphine ligands are trisubstituted phosphines such as triphenylphosphine. [0004] A disadvantage of the hydroformylati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/49C07C49/17C07F15/00B01J31/24
CPCB01J2531/0272B01J2231/321B01J2531/90C07C45/50B01J2531/822C07C45/49B01J31/2414C07C47/19B01J31/24C07C49/17C07F15/00
Inventor D·F·怀特
Owner LYONDELL CHEM TECH LP
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