Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1996-07-12
1998-01-06
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568449, 568450, 568904, C07C 4752
Patent
active
057057079
DESCRIPTION:
BRIEF SUMMARY
This is the U.S. National Stage Application of PCT/EP94/0014 filed Jan. 12, 1995 now WO 95/19334 published Jul. 20, 1995.
The present invention relates to a process for the preparation of n-butyraldehyde and/or n-butanol.
n-Butyraldehyde and n-butanol are products which are produced on a large scale in the chemical industry and have varied uses. n-butyraldehyde, for example, is produced world-wide in amounts of more than 4 million t/yr and serves inner alia as starting material for the preparation of plasticizer alcohols. n-butanol is employed on a large scale as solvent, for example for coating compositions.
n-Butyraldehyde is prepared nowadays on an industrial scale virtually exclusively by the hydroformylation of propene, for which purpose various processes are used, which essentially make use of cobalt or rhodium hydroformylation catalysts, (Kirk-Othmer: Encyclopedia of Chemical Technology, 4th Edition, Vol. 4, pp. 741-746, John Wiley Sons, New York 1992).
n-Butanol is one of the quantitatively most important derivatives of n-butyraldehyde and is obtained therefrom by hydrogenation. Other processes for the preparation of n-butanol, such as the hydrogenation of crotonaldehyde, which is in turn produced by aldol condensation of acetaldehyde, are nowadays merely of historical interest or have only regional significance, such as in the case of the microbiological production of n-butanol by fermention of molasses, (Kirk-Othmer: Encyclopedia of Chemical Technology, 4th Edition, Vol. 4. pp. 694-696: John Wiley Sons, New York 1992). These processes, particularly the hydroformylation of propene, demand high investments, for example, for the construction of high-pressure plant for the cobalt-catalyzed hydroformylation or for the purchase of the expensive rhodium catalyst, the plant required for handling during hydroformylation and for working up the spent rhodium-containing catalyst solution. Furthermore the preparation of n-butyraldehyde by the hydroformylation process requires the presence of a synthesis gas plant for the preparation of the synthesis gas required for the hydroformylation. A further drawback of the process is the unavoidable formation of large quantities of the by-product isobutyraldehyde, which, on account of its restricted possibility of further usage in quantity, has a low economic rating.
1,3-Butadiene is a basic chemical which is produced in large amounts in steam crackers and is isolated, by extraction, from the C.sub.4 cut obtained in the cracker, for example, by means of N-methyl pyrrolidone. Although 1,3-butadiene is available in large amounts and is a very cheap raw material, no industrially usable process has been developed hitherto for the preparation of n-butyraldehyde or n-butanol on the basis of 1,3-butadiene. One reason for this is the tendency of 1,3-butadiene to undergo dimerization and polymerization reactions and the formation of mixtures of 1,2- and 1,4-adducts in addition reactions. The reason for this chemical behavior is the presence of two conjugated double bonds in the 1,3-butadiene molecule (Kirk-Othmer: Encyclopedia of Chemical Technology, 4th Edition, Vol. 4, pp. 676-683, John Wiley & Sons, New York 1992).
U.S. Pat. No. 2,922,822 and DE-A 2,550,902 disclose that alcohols react in the liquid phase with 1,3-butadiene in the presence of acid ion exchangers to form the corresponding unsaturated ethers. U.S. Pat. No. 2,922,822 carries out this reaction in the presence of a large excess of methanol, which leads to an increased formation of the undesirable dimethyl ether. According to the process described in DE-A 2,550,902 vinyl cyclohexene forms during this reaction as main product. In EP-A 25,240 the addition of alcohol to 1,3-butadiene is advantageously carried out in the presence of a polar, aprotic solvent, which must then again be removed, by distillation. In GB-A 943,160 the addition of alcohols is carried out by means of Bronsted acids in the presence of copper salts.
Transition metal complexes with phosphine ligands have also been used as catalysts for the additi
REFERENCES:
patent: 2922822 (1960-01-01), Beach et al.
patent: 4310709 (1982-01-01), Rebafka et al.
Kanand Jurgen
Paciello Rocco
Pinkos Rolf
Roper Michael
Thome Alfred
BASF - Aktiengesellschaft
Ivy C. Warren
Padmanabhan Sreeni
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