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Process for coproduction of normal butanol and isobutyraldehyde

A technology of isobutyraldehyde and n-butanol, which is applied in the field of co-production of n-butanol and isobutyraldehyde, can solve the problems of increased manufacturing costs, low selectivity of straight-chain alcohols, and high manufacturing costs

Active Publication Date: 2009-09-02
MITSUBISHI RAYON CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, when the reaction is carried out using a conventional rhodium-organophosphorus compound catalyst, the selectivity of the target linear alcohol is low, and in the state where the reaction is forcibly completed, the linear alcohol and by-products The generation ratio of branched alcohols is about 2.5 (linearity = 71%), which is a low value
So the problem is that the remaining 29% of by-products are branched alcohols which have very low value as a product
In order to obtain isobutyraldehyde from isobutanol, a dehydrogenation reaction process is required, so this part of the production cost is additionally increased
[0015] On the other hand, there is an existing method of producing butyraldehyde from propylene by hydroformylation. Although this method obtains isobutyraldehyde in one step, in order to obtain n-butanol, it is necessary to convert the hydroformyl group of propylene into The n-butyraldehyde and isobutyraldehyde produced in hydrogenation are separated, and only n-butyraldehyde is hydrogenated, so as mentioned above, the production cost of this method is high

Method used

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  • Process for coproduction of normal butanol and isobutyraldehyde
  • Process for coproduction of normal butanol and isobutyraldehyde
  • Process for coproduction of normal butanol and isobutyraldehyde

Examples

Experimental program
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preparation example Construction

[0116] Next, a method for preparing the catalyst will be described.

[0117] The catalyst used in this embodiment can be added to the reaction zone after pre-preparation in an additional catalyst preparation zone, or can be added to the reaction zone separately, and the catalyst is prepared in the reaction zone.

[0118] As a preferred embodiment of the preparation method of the catalyst, after the co-production reaction of n-butanol and isobutyraldehyde, the product system and the catalyst system are separated, and the catalyst is recycled to the reaction zone. In this case, It is preferable to appropriately add a metal compound or an organophosphorus compound for supplementation according to the degree of deterioration and disappearance of the catalyst.

[0119] In a specific catalyst preparation method, each metal compound and each organophosphorus compound may be directly mixed to prepare the catalyst, or each component may be dissolved in an organic solvent or the like be...

Embodiment 1

[0169] Under nitrogen atmosphere, add Rh(acac)(CO) into the glass container for catalyst preparation 2 (11.2mg, 0.0434mmol), trioctylphosphine (64.3mg, 0.174mmol, relative to 1 mole Rh(acac)(CO) 24 moles), add ethanol (11.4ml, 83.6% by weight of the total weight of the reaction medium) and n-heptane (0.8ml) used as an internal standard for gas chromatograph analysis, and make it dissolve. Under nitrogen atmosphere, the solution Add it into a stainless steel autoclave with an inner volume of 50 ml prepared separately. After further pressing in propylene (1.15 g, 27.33 mmol), the autoclave was closed. After raising the temperature of the autoclave to 120° C., a mixed gas of hydrogen and carbon monoxide (mixing ratio: hydrogen / carbon monoxide=1 / 1) was injected so that the pressure in the system was 2.0 MPa, and the reaction was started. In addition, a mixed gas was introduced while bubbling into the reaction liquid through a feed pipe installed in the autoclave. Regarding stir...

Embodiment 2

[0173] In Example 1, the addition amount of trioctylphosphine was changed to 160.9 mg (0.434 mmol, relative to 1 mole of Rh(acac)(CO) 2 10 mol), except that, it reacted and analyzed similarly to Example 1. Furthermore, ethanol was 82.8% by weight of the total weight of the reaction medium.

[0174] Its result is as follows: n-butanol yield is 57.3%, isobutyraldehyde yield is 12.8%; The ratio of generation rate is as follows respectively: F NBA / F NBD =8.1, F NBA / F IBA =3.0, F IBD / F IBA =0.7. In addition, the ratio of the generation rate to the feed amount of raw material propylene to the reactor is as follows: F PPY / F IBD =7.8, F PPY / F NBA = 1.7.

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Abstract

The invention relates to a process for the coproduction of normal butanol and isobutyraldehyde by reacting propylene with hydrogen and carbon monoxide. The process comprises the step (A) of reacting propylene with hydrogen and carbon monoxide in a reactor (2) in the presence of a catalyst containing a compound of a Group 8, 9 or 10 metal element of the periodic table, the step (B) of withdrawing an overhead product containing normal butyraldehyde and so on and a sidestream containing isobutanol and so on from the reaction product stream with a separator (the first distilling column) (5), and the step (C) of separating the overhead product into normal butyraldehyde and isobutyraldehyde by fractional distillation with a separator (the second distilling column) (10) while separating the sidestream into isobutanol and normal butanol by fractional distillation with a separator (the third distilling column) (14), and withdrawing them separately.

Description

technical field [0001] The present invention relates to the coproduction method of n-butanol and isobutyraldehyde, more specifically, the present invention relates to the coproduction method of n-butanol and isobutyraldehyde taking propylene as raw material. Background technique [0002] The method of producing aldehydes by reacting olefinic compounds with hydrogen and carbon monoxide in the presence of a catalyst consisting of a transition metal belonging to Groups 8 to 10 of the periodic table and an organophosphorus ligand is a well-known process. Hydroformylation reaction. Generally, among the obtained aldehydes, aldehydes with relatively high linearity are useful, and various organophosphorus ligands have been developed in order to increase the linear selectivity thereof. [0003] The thus obtained highly linear aldehyde is usually converted into an alcohol by hydrogenation reaction or converted into an aldehyde with a large molecular weight by a condensation reaction,...

Claims

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Application Information

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IPC IPC(8): C07C27/24C07C29/44C07C31/12C07C45/50C07C45/82C07C47/02C07B61/00
CPCC07C29/44C07C45/82C07B61/00C07C29/80C07C45/50
Inventor 井上朋彦田中善幸
Owner MITSUBISHI RAYON CO LTD
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