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Method for preparing aldehyde by alkene hydroformylation

An alkene hydroformyl and alkene technology, which is applied to the preparation of carbon monoxide reaction, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of catalyst loss, high cost, and difficulty in realizing industrialization. , to achieve the effect of easy separation, avoid deactivation and decomposition, and excellently promote catalytic acceleration.

Active Publication Date: 2009-01-21
QINGDAO SANLI BENNUO CHEM IND +1
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Problems solved by technology

[0004] Chinese patent CN1562932 discloses a method for preparing valeraldehyde by hydroformylation of butene in an ionic liquid of methyl butyl imidazolium tetrafluoroborate, although the method is easy to realize the separation of catalyst and product, but the ionic liquid Difficult to prepare, easy to cause environmental pollution, extremely high cost, difficult to realize industrialization
Chinese patent CN200410081352.0 discloses a Rh-TPP (triphenylphosphine)-phosphotungstic heteropolyacid supported on SiO 2 The heterogeneous catalyst above realizes the hydroformylation of butene to prepare valeraldehyde, but this method uses SiO 2 Supporting hydrocarbon-soluble triphenylphosphine-rhodium complexes, the oxidation of triphenylphosphine by trace oxygen in the reaction system and the leaching of olefins and aldehydes can easily lead to the loss of the catalyst
"Fine Petrochemical Progress 2003, 4 (2) 5-7 and 2004, 5 (6), 35-38 published the composition of water-soluble rhodium phosphine complexes and cationic surfactant cetyltrimethylammonium bromide The catalyst system is used in the hydroformylation reaction of butene in water-organic two-phase medium, but the amount of surfactant is relatively high, which is easy to cause emulsification of the solution and bring difficulties in the separation of the two phases
"Petrochemical Industry" 2000, 29 (9), 654-658 published a water-soluble phosphine ligand TPPTS (trisulfonated triphenylphosphine trisodium salt) and a rhodium complex catalyst HRh (CO) (TPPTS) 3 The hydroformylation reaction of butene in the water / organic two-phase system with the composite catalyst system composed of CTAB (cetyltrimethylammonium bromide) and disodium hydrogen phosphate, CTAB-Na 2 HPO 4 Although the introduction of increased the activity of the hydroformylation reaction, the selectivity of forming normal aldehydes was not high, and the basic Na 2 HPO 4 Introduced into the system, it is easy to cause the condensation of aldehydes

Method used

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  • Method for preparing aldehyde by alkene hydroformylation
  • Method for preparing aldehyde by alkene hydroformylation

Examples

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Effect test

example 1

[0024] Example 1, the rhodium complex [RhCl (COD)] 2 1 part, phosphine ligand TPPTS 20 parts, double long-chain surfactant [N(CH 3 ) 2 (C 8 h 17 ) 2 ] 0.01 part of Cl, 500 parts of deionized water were added into a reactor with a stirrer to completely dissolve it, and the reactor was replaced 5 times with synthesis gas (hydrogen: carbon monoxide = 1:1). Add 100 parts of 1-butene, then add synthesis gas pressure to 2MPa, keep the partial pressure of synthesis gas constant, react at a temperature of 110°C for 6 hours, take out the reactant after cooling, and analyze the product content by gas chromatography: butene The conversion rate is 90%, the selectivity of forming aldehydes is greater than 98%, and the ratio of normal aldehydes to isomeric aldehydes is 4.1.

example 2

[0025] Example 2, the rhodium complex [RhCl (COD)] 2 1 part, phosphine ligand TPPDS 30 parts, double long-chain surfactant [N(CH 3 )(C 4 h 9 )(C 10 h 21 ) 2 ] 0.02 parts of Cl and 1000 parts of deionized water were added into a reactor equipped with a stirrer to completely dissolve it, and the reactor was replaced 3 times with synthesis gas (hydrogen: carbon monoxide = 1:1). Add 200 parts of 1-butene, and then add synthesis gas to a pressure of 2 MPa. Keep the partial pressure of synthesis gas constant during the reaction. React for 6 hours at a temperature of 100°C. After cooling, take out the reactant and analyze the product content by gas chromatography: The conversion rate of butene is 92%, the selectivity of forming aldehyde is greater than 98%, and the ratio of normal aldehyde and isomeric aldehyde is 4.5.

example 3

[0026] Example 3, the rhodium complex [RhCl (COD)] 2 2 parts, phosphine ligand TPPMS 30 parts, double long-chain surfactant [P(CH 3 ) 2 (C 10 h 21 ) 2 ] 0.04 parts of Cl and 1000 parts of deionized water were added into a reactor with a stirrer to completely dissolve it, and the reactor was replaced 3 times with synthesis gas (hydrogen: carbon monoxide = 1:1). Add 100 parts of 1-butene, then add synthesis gas pressure to 2MPa, keep the partial pressure of synthesis gas constant, react at a temperature of 100°C for 6 hours, take out the reactant after cooling, and analyze the product content by gas chromatography: butene The conversion rate is 93%, the selectivity of forming aldehydes is greater than 98%, and the ratio of normal aldehydes to isomeric aldehydes is 5.5.

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Abstract

A method for preparing aldehyde through olefin hydroformylation is characterized in that compositions in portion by weight of 1 to 10 portions of rhodium complex, 10 to 1,000 portions of phosphine ligand, 0.01 to 1 portion of double long chain surface-active agent and 500 to 5,000 portions of deionized water are added in a reaction kettle with an agitator and a thermocouple, and are completely dissolved; synthetic gas in which the volume ratio of hydrogen to carbon monoxide is equal to 1to 1 is used to carry out substitution 3 to 5 times inside the reaction kettle; 100 to 2,000 portions of olefin is added through pressurization and then the pressure of the synthetic gas is increased to 1 to 6MPa so as to carry out reaction at a temperature of between 50 and 150 DEG C for 2 to 8 hours; and finally, reactants are taken out after cooling, and are separated to obtain the product aldehyde.

Description

Technical field: [0001] The invention relates to a method for preparing aldehydes by hydroformylation of olefins, belonging to the field of organic chemical synthesis. technical background: [0002] In the early 1980s, the National Cancer Institute of the United States released the news that di-isooctyl phthalate (DOP) was carcinogenic. People developed DOP substitutes one after another out of consideration for the safety of DOP carcinogenicity. Since the high-temperature performance of DOP cannot meet the needs of the development of cables, automotive interior decoration, and advanced PVC building materials, diisononyl phthalate (DINP), which is more excellent in volatility, migration resistance, and water extraction than DOP, Diisodecyl phthalate (DIDP) has been developed rapidly. [0003] Hydroformylation of butene to valeraldehyde, followed by condensation and hydrogenation to generate decanol is a new way to produce excellent plasticizers that is currently being develo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/49B01J31/24
Inventor 李贤均陈华李瑞祥黎耀忠陈骏如胡家元王晓光陈锴
Owner QINGDAO SANLI BENNUO CHEM IND
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