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A Process for Separating an Oxidation Reaction Product and an Oxidation

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A Process for Separating an Oxidation Reaction Product and an Oxidation Europäisches Patentamt *EP000825165B1* (19) European Patent Office Office européen des brevets (11) EP 0 825 165 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C07B 63/00, C07C 55/14, of the grant of the patent: C07C 51/48 16.01.2002 Bulletin 2002/03 // C07C31/12, C07C33/035, (21) Application number: 97113920.9 C07C35/22, C07C63/06, C07D213/807 (22) Date of filing: 12.08.1997 (54) A process for separating an oxidation reaction product and an oxidation catalyst Verfahren zur Trennung eines Oxidationsreaktionproduktes von einem Oxidationskatalysator Procédé pour la séparation d’un produit d’une réaction d’oxydation et d’un catalyseur d’oxydation (84) Designated Contracting States: (56) References cited: CH DE ES FR GB IT LI NL SE US-A- 5 030 739 (30) Priority: 20.08.1996 JP 21869396 • Y. ISHII ET AL: "Alkane oxidation with molecular oxygen using a new efficient catalytic system: (43) Date of publication of application: N-hydroxyphthalimide (NHPI) combined with 25.02.1998 Bulletin 1998/09 Co(acac)n (n = 2 or 3)" JOURNAL OF ORGANIC CHEMISTRY, vol. 61, no. 14, 12 July 1996, (73) Proprietor: DAICEL CHEMICAL INDUSTRIES, EASTON US, pages 4520-4526, XP000591064 LTD. • DATABASE WPI Section Ch, Week 9616 Derwent Sakai-shi, Osaka 590 (JP) Publications Ltd., London, GB; Class A41, AN 96-155414 XP002055654 & JP 08 038 909 A (72) Inventor: Hirai, Naruhisa (DAICEL CHEM IND) , 13 February 1996 Himeji-shi, Hyogo 671-12 (JP) (74) Representative: Grünecker, Kinkeldey, Stockmair & Schwanhäusser Anwaltssozietät Maximilianstrasse 58 80538 München (DE) Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 0 825 165 B1 Printed by Jouve, 75001 PARIS (FR) EP 0 825 165 B1 Description [0001] The present invention relates to a process for separating an oxidation reaction product or its salt, and an oxidation catalyst from a reaction mixture, the reaction mixture being obtained by oxidation of a substrate with using 5 an imide compound such as N-hydroxyphthalimide as the oxidation catalyst. [0002] N-hydroxyphthalimide and other imide compounds are known as oxidation catalysts, such oxidation being conducted by allowing a substrate such as a hydrocarbon, an alcohol, an aldehyde, a ketone, an amine and a hete- rocyclic compound to contact with molecular oxygen (Japanese Patent Application Laid-open No. 38909/1996 (JP-A- 8-38909)). An oxidation reaction by means of this catalyst, which can be conducted under mild conditions without any 10 exhaust gas treatment, can provide an oxidation reaction product including an alcohol, an aldehyde, a ketone and an organic acid at a high conversion rate and selectivity. Such an oxidation reaction product is separated from a reaction mixture commonly by distillation. [0003] Distillation, however, is not always an advantageous process for separation of an oxidation reaction product from a reaction mixture. When both of the oxidation reaction product and the substrate have low boiling points (e.g. 15 50 to 150°C), distillation results in deterioration of purity and yield owing to the substrate with a low boiling point. On the other hand, when the oxidation reaction product is a compound with a high boiling point (e.g. 150 to 500°C), the oxidation catalyst might be decomposed during distillation which is carried out at a high temperature with heating. The imide compound has a low decomposition temperature, for example, 230°C in the case of N-hydroxyphthalimide. Thus, distillation, as a process for separating a high-boiling-point oxidation reaction product, has a risk of thermal decompo- 20 sition of the oxidation catalyst, failing to reutilise the oxidation catalyst and raising the cost. Besides, the thermally decomposed product of the oxidation catalyst might degrade the quality of the reaction product. As mentioned above, it is not wise to choose distillation for separation of an oxidation reaction product having any boiling point from a reaction mixture without any consideration. [0004] US-A-5030739 discloses a process for the catalytic oxidation of an isoprenoid which has at least one allylic 25 hydrogen atom in the presence of a N-hydroxydicarboxylic acid imide. The oxidation catalyst can be separated by concentrating the reaction mixture, treating the concentrate with a non-polar solvent and then crystallizing the oxidation catalyst. Examples of the non-polar solvent include hydrocarbons such as hexane, and non-polar chlorinated hydro- carbons such as tetrachloromethane. The oxidation products obtained can be separated from the reaction mixture according to known methods. 30 [0005] It is an object of the present invention to provide a process for separating an oxidation catalyst such as N- hydroxyphthalimide or other imide compounds from a reaction mixture obtained by oxidation of a substrate such as a hydrocarbon in order to make effective use of the oxidation catalyst. [0006] It is another object of the present invention to provide a process for efficiently separating the imide compound to be reutilised while preventing decomposition thereof, even when the oxidation reaction product is a compound with 35 a high boiling point. [0007] It is yet another object of the present invention to provide a process for efficient separation of the oxidation reaction product and the oxidation catalyst from the reaction mixture obtained by oxidation of the substrate, the process not being affected by the boiling point of the reaction product. [0008] A further object of the present invention is to provide a process for separating the oxidation reaction product 40 and the oxidation catalyst from the oxidation reaction mixture by an easy operation under mild conditions. [0009] After intensive works for achieving the above objects, the inventor of the present invention has found that, in an oxidation reaction using an imide compound such as N-hydroxyphthalimide as the oxidation catalyst, use of an aqueous solvent at least containing water and a non-water-soluble solvent helps efficient distribution of the oxidation reaction product into an aqueous solvent layer and efficient distribution of the oxidation catalyst into a non-water-soluble 45 solvent layer, each solvent acting as an extracting solvent. The present invention is based on the above findings. [0010] The separation process of the present invention is a process for separating an oxidation reaction product and an oxidation catalyst from a reaction mixture obtained by oxidation of a substrate in the presence of an imide compound shown by the formula (1) as the oxidation catalyst, which process comprises using an aqueous solvent containing at least water and a non-water-soluble solvent separable from the aqueous solvent, thereby efficiently distributing the 50 oxidation reaction product into the aqueous solvent layer and the oxidation catalyst into the non-water-soluble solvent layer, 55 2 EP 0 825 165 B1 5 10 wherein R1 and R2 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cy- cloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group or an acyl group; R1 and R2 may together form a double bond, or an aromatic or nonaromatic ring; X stands for an oxygen atom or a hydroxyl group; and n denotes an integer of 1 to 3. [0011] The imide compound includes, for instance, N-hydroxyphthalimide and other N-hydroxyimide compounds. 15 As the substrates, there may be mentioned hydrocarbons, alcohols, aldehydes, ketones, amines and heterocyclic compounds. Use of the above substrate provides a corresponding oxidation reaction product (e.g. an alcohol, an al- dehyde, a ketone, a carboxylic acid). Water can be used as the aqueous solvent containing at least water (hereinafter it may be referred to as "hydrophilic solvent" or "aqueous solvent"). As the non-water-soluble solvent (hereinafter it may be referred to as "hydrophobic solvent" or "hydrophobic organic solvent"), use can be made of hydrocarbons, 20 ketones, esters and nitriles. [Imide Compound] [0012] In the compound of the formula (1), the halogen atom as the substituents R1 and R2 includes iodine, bromine, 25 chlorine and fluorine atoms. Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec- butyl, t-butyl, pentyl, hexyl, heptyl, octyl, decyl groups and other straight chain or branched chain alkyl groups each having 1 to 10 carbon atoms. A preferred alkyl group includes an alkyl group having 1 to 6 carbon atoms, and, in particular, a lower alkyl group having 1 to 4 carbon atoms. [0013] The aryl group includes, for example, a phenyl group and a naphthyl group. The cycloalkyl group includes 30 cyclopentyl, cyclohexyl, and cyclooctyl groups. As the alkoxy groups, there may be mentioned, for instance, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, t-butoxy, pentyloxy, hexyloxy and other alkoxy groups each having 1 to 10 carbon atoms. Among them, alkoxy groups each having 1 to 6 carbon atoms, in especial, lower alkoxy groups each having 1 to 4 carbon atoms are desirable. [0014] Examples of the alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopro- 35 poxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, t-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl and other alkoxycarbonyl groups each having 1 to 10 carbon atoms in the alkoxy moiety. A preferable alkoxycarbonyl group includes an alkoxycarbonyl group having 1 to 6 carbon atoms, above all, a lower alkoxycarbonyl group having 1 to 4 carbon atoms. [0015] As examples of the acyl group, there may be mentioned formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, 40 isovaleryl, pivaloyl and other acyl groups each having 1 to 6 carbon atoms.
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