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Process for producing hydrogenated ester, hydrogenation catalyst for use therein, and processing for producing the catalyst

A technology of hydrogenation catalyst and production method, applied in metal/metal oxide/metal hydroxide catalyst, physical/chemical process catalyst, organic chemical method, etc., can solve problems such as undescribed

Inactive Publication Date: 2002-05-29
SHOWA DENKO KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has been pointed out that the problem in the process using this metal type catalyst is the hydrogenolysis of the ester containing unsaturated group as raw material
[0019] However, for example, the above-mentioned JP-A-194427 does not describe that when a nickel-type hydrogenation catalyst is used to produce a saturated ester from an ester containing an unsaturated group, the conversion rate of the ester containing an unsaturated group is 99.8% or higher. Achievement of selectivity factors of 98.0% or higher and 2.0% or lower for saturated esters and carboxylic acids, respectively

Method used

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  • Process for producing hydrogenated ester, hydrogenation catalyst for use therein, and processing for producing the catalyst
  • Process for producing hydrogenated ester, hydrogenation catalyst for use therein, and processing for producing the catalyst
  • Process for producing hydrogenated ester, hydrogenation catalyst for use therein, and processing for producing the catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1A-1

[0203] (dilute raw material with inert solvent)

[0204] according to figure 1Shown flow process, with 130ml loaded palladium catalyst (3mm-diameter ball, silica carrier, palladium content 0.5%, specific surface area 300m 2 / g, produced by NE-Chem Cat K.K.) as a hydrogenation catalyst was filled into a stainless steel cylindrical reactor 5 with an inner diameter of 20 mmφ to form a catalyst packing layer 6, and the pressure of the reactor 5 was adjusted to 2.0 MPa (gauge pressure) with hydrogen. . From the upper part of the reactor 5, a liquid mixture comprising recycled n-propyl acetate (hydrogenated ester): allyl acetate (unsaturated group-containing ester) = 12.9: 1 (wt / wt) was transferred from The feed pipe 1 of the ester containing the unsaturated group is added therein and circulated in the reactor 5 at a speed of 550ml / hr, and the hydrogen from the hydrogen feed pipe 2 is also in the reactor at a speed of 18.6Nl / hr. 5 internal circulation (fixed bed type, gas-liquid ...

Embodiment 1A-2

[0209] The unsaturated group-containing ester was hydrogenated in the same manner as in Example 1A-1, but with 130 ml of supported palladium catalyst (alumina carrier, a sheet of 3 mm in diameter × 3 mm in length, with a palladium content of 0.3%, and a specific surface area of ​​100 m 2 / g, produced by NE-Chem Cat K.K.) to replace the 130ml supported palladium catalyst used in Example 1A-1 (silicon oxide carrier, 3mm-diameter ball, palladium content 0.5%, specific surface area 300m 2 / g, produced by NE-Chem Cat K.K.) as a hydrogenation catalyst; the pressure inside the reactor is 0.9MPa (gauge pressure) instead of 2.0MPa (gauge pressure) used in Example 1A-1. The temperature at the outlet of the reactor (the bottom of the catalyst layer) was 97.5°C.

[0210] The reaction mixture from the outlet of the reactor was condensed and analyzed by gas chromatography (GC-14B manufactured by Shimazu Kagaku K.K.; hydrogen flame ionization detector) under the above conditions. The result...

Embodiment 1A-3

[0212] Hydrogenation of esters containing unsaturated groups in the same manner as in Example 1A-1, but with 130 ml of supported ruthenium catalyst (alumina carrier, a sheet with a diameter of 3 mm × length of 3 mm, a ruthenium content of 0.5%, and a specific surface area of ​​100 m 2 / g, produced by NE-Chem Cat K.K.) to replace the 130ml supported palladium catalyst used in Example 1A-1 (silicon oxide carrier, 3mm-diameter ball, palladium content 0.5%, specific surface area 300m 2 / g, produced by NE-Chem Cat K.K.) as a hydrogenation catalyst; replace the mixture containing allyl acetate and n-propyl acetate as a raw material in Example 1A-1 with a mixture containing methallyl acetate and isobutyl acetate Esters mixture. The temperature at the outlet of the reactor (the bottom of the catalyst layer) was 95.5°C.

[0213] The reaction mixture from the outlet of the reactor was condensed and analyzed by gas chromatography (GC-14B manufactured by Shimazu Kagaku K.K.; hydrogen fla...

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Abstract

A process for producing a hydrogenated ester by hydrogenating an unsaturated group-containing ester having a specific structure by using a hydrogenating catalyst so as to obtain a hydrogenated ester with a high selectivity. It is preferred that the unsaturated group-containing ester as the raw material is diluted with an inert solvent and / or the concentration of carboxylic acid contained in the raw material is made 1 wt % or less so as to effect a hydrogenation reaction. The hydrogenating catalyst to be used for the above hydrogenation may preferably be one comprising at least one metal selected from Group VIII elements, Group IX elements, and Group X elements in the periodic table, and preferably has an acidity of 1.0x10<-1> m mol / g or less.

Description

technical field [0001] The present invention relates to a method for the production of hydrogenated esters based on the hydrogenation of esters containing unsaturated groups; a catalyst suitable for the method, and a method for producing the catalyst. [0002] More specifically, the present invention relates to a production method of a hydrogenated ester, which uses a hydrogenation catalyst to hydrogenate an ester containing an unsaturated group to produce a hydrogenated ester corresponding to the ester containing an unsaturated group, wherein the hydrogenation reaction is a by- The amount of carboxylic acid produced by reaction hydrogenolysis is reduced, and the ester containing unsaturated group can be converted into the corresponding hydrogenated ester product with high conversion rate and high selectivity factor (or yield); it also relates to the method applicable to Catalyst, and the production method of this catalyst. [0003] The term "(corresponding) hydrogenated este...

Claims

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Application Information

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IPC IPC(8): B01J23/40B01J35/00C07C67/283
CPCB01J35/002B01J23/40C07C67/283B01J35/31B01J35/613B01J35/635C07C69/003C07C69/14C07C69/24
Inventor 大贺一彦藤本正幸内田博但马恒男
Owner SHOWA DENKO KK
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