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Use of Catalysts Comprising N-Substituted Cyclic Imides

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Use of Catalysts Comprising N-Substituted Cyclic Imides (19) & (11) EP 1 338 336 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: B01J 31/02 (2006.01) C07C 27/12 (2006.01) 04.04.2012 Bulletin 2012/14 C07C 33/20 (2006.01) C07C 49/78 (2006.01) C07C 51/21 (2006.01) C07C 51/265 (2006.01) (2006.01) (2006.01) (21) Application number: 01996429.5 C07C 55/14 C07C 63/04 C07C 63/06 (2006.01) C07C 63/26 (2006.01) C07C 63/313 (2006.01) C07D 213/80 (2006.01) (22) Date of filing: 08.11.2001 C07D 215/54 (2006.01) (86) International application number: PCT/JP2001/009767 (87) International publication number: WO 2002/040154 (23.05.2002 Gazette 2002/21) (54) USE OF CATALYSTS COMPRISING N-SUBSTITUTED CYCLIC IMIDES FOR PREPARING ORGANIC COMPOUNDS VERWENDUNG N-SUBSTITUIERTERRINGFÖRMIGER IMID ENTHALTENDER KATALYSATOREN ZUR HERSTELLUNG ORGANISCHER VERBINDUNGEN UTILISATION DE CATALYSEURS CYCLIQUES COMPRENANT DES IMIDES POUR LA PREPARATION DE COMPOSES ORGANIQUES (84) Designated Contracting States: (74) Representative: Grünecker, Kinkeldey, DE FR GB Stockmair & Schwanhäusser Anwaltssozietät (30) Priority: 15.11.2000 JP 2000348787 Leopoldstrasse 4 22.02.2001 JP 2001046986 80802 München (DE) (43) Date of publication of application: (56) References cited: 27.08.2003 Bulletin 2003/35 EP-A- 0 879 812 EP-A- 1 331 215 DD-A- 112 431 DE-C- 135 836 (73) Proprietor: Daicel Chemical Industries, Ltd. JP-A- 9 087 215 JP-A- 10 057 814 Kita-ku, JP-A- 11 226 416 Osaka-shi Osaka 530-0001 (JP) • TASHIRO, YASUTAKA ET AL: "A new strategy for thepreparation of terephthalic acid by the aerobic (72) Inventors: oxidation of p-xylene using N- • ISHII, Yasutaka hydroxyphthalimide as a catalyst" ADVANCED Takatsuki-shi, Osaka 569-1112 (JP) SYNTHESIS & CATALYSIS , 343(2), 220-225 • NAKANO, Tatsuya CODEN: ASCAF7; ISSN: 1615-4150, 2001, Himeji-shi, Hyogo 670-0029 (JP) XP002296660 • IWAHAMA, Takahiro Himeji-shi, Hyogo 671-1262 (JP) Remarks: • HIRAI, Naruhisa Thefile contains technical information submitted after Himeji-shi, Hyogo 671-1226 (JP) the application was filed and not included in this specification Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 338 336 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 338 336 B1 Description [0001] The present invention relates to a catalyst that is useful for oxidation, nitration, carboxylation, reaction for the formation of a carbon-carbon bond, and other reactions and to a process for producing an organic compound using the 5 catalyst. [0002] An oxidation reaction is one of the most basic reactions in the field of organic chemical industry, and various oxidation processes have been developed. From the viewpoints of resources and environmental issues, a catalytic oxidation process, in which molecular oxygen or air is directly used as an oxidizing agent, is preferred. However, the catalytic oxidation process generally requires high temperatures and/or high pressures for activation of oxygen or, 10 alternatively, must be performed in the co-existence of a reducing agent such as an aldehyde to proceed the reaction under mild conditions. Accordingly, such a conventional catalytic oxidation process cannot easily and efficiently produce an alcohol or a carboxylic acid under mild conditions. [0003] Lower hydrocarbons such as methane and ethane are nitrated using nitric acid or nitrogen dioxide at high temperatures of from 250°C to 300°C. However, when a hydrocarbon having a large number of carbon atoms is nitrated 15 under the above condition, the substrate is decomposed, and a target nitro compound cannot be obtained in a high yield. To nitrate hydrocarbons, a method using mixed acid (a mixture of nitric acid and sulfuric acid) is widely employed. However, this method requires large amounts of a strong acid in a high concentration. [0004] Additionally, few processes are known for efficiently and directly introducing carboxyl groups into hydrocarbons under mild conditions. 20 [0005] A variety of processes are known for producing organic sulfur acids or salts thereof. For example, processes for producing a sulfonic acid include a process of oxidizing a thiol or disulfide with an oxidizing agent, a process of allowing an aromatic hydrocarbon to react with anhydrous SO3-pyridine or chlorosulfuric acid by using a Friedel-Crafts reaction, and a process of synthetically obtaining a sulfonic acid by subjecting an unsaturated compound to free-radical addition. These processes, however, require extreme reaction conditions or inevitably produce large amounts of by- 25 products. Additionally, no processes for directly and efficiently sulfonating non-aromatic hydrocarbons have been known. [0006] Processes are known in which a variety of compounds are added to unsaturated compounds each having a carbon-carbon double bond or heteroatom-containing compounds and thereby yield useful organic compounds. For example, when an active methylene compound such as a malonic diester is allowed to react with an olefin having an electron attractive group, such as acrylonitrile, in the presence of a base, a carbon- carbon bond is formed as a result of 30 a nucleophilic addition reaction and thereby yields an addition product (Michael addition reaction). When two types of carbonyl compounds are treated in the presence of an acid or a base, one carbonyl compound is nucleophilically added to the other to form a carbon-carbon bond and thereby yields an aldol condensate. [0007] These processes, however, are generally performed in the presence of an acid or base and cannot be applied to compounds each having a substituent that is susceptible to the acid or base. In addition, these processes cannot 35 allow, for example, a hydroxymethyl group, an alkoxymethyl group, an acyl group or a tertiary carbon atom to directly combine with a carbon atom constituting an unsaturated boned of an unsaturated compound or with a methine carbon atom of a bridged cyclic compound. [0008] Addition reactions to a carbon- carbon double bond in accordance with a radical mechanism or coupling reactions to form a carbon-carbon bond are also known. However, there are few processes that can efficiently yield addition or 40 substitution reaction products or derivatives thereof by action of, for example, molecular oxygen under mild conditions. [0009] Some processes are known as production processes of hydroxy-y-butyrolactone derivatives. For example, European Patent Publication EP-A-2103686 discloses a process for synthetically obtaining pantolactone by allowing glyoxylic acid to react with isobutylene. Likewise, Japanese Unexamined Patent Application Publication No. 61-282373 discloses a process for synthetically obtaining pantolactone by allowing hydrated glyoxylic acid to react withbutyl t- 45 alcohol. Tetrahedron, 933 (1979) discloses a process for synthetically obtaining pantolactone. This process includes the steps of hydrolyzing. 4- hydroxy-2-methyl-5,5,5-trichloro-1-pentene to yield 2-hydroxy-4- methyl-4-pentenoic acid and cyclizing this compound in the presence of hydrochloric acid. In addition, The Chemical Society of Japan, Spring Con- ference Proceedings II, pp. 1015 (1998) reports that light irradiation to a mixture solution containing an α-acetoxy-α,β- unsaturated carboxylic ester and 2-propanol yields a corresponding α-acetoxy-γ,β-dimethyl-γ-butyrolactone derivative. 50 However, each of these processes employs a material that is not easily available or requires special conditions for the reaction. [0010] Japanese Unexamined Patent Application Publications No. 8-38909 and No. 9-327626 each propose an oxi- dation catalyst comprising an imide compound having a specific structure or the imide compound in combination with, for example, a transition metal compound as a catalyst for oxidizing an organic substrate with molecular oxygen. Japanese 55 Unexamined Patent Application Publication No. 11-239730 discloses a process, in which a substrate is allowed to react with at least one reactant selected from (i) nitrogen oxides and (ii) mixtures of carbon monoxide and oxygen in the presence of the imide compound and thereby at least one functional group selected from nitro group and carboxyl group is introduced into the substrate. PCT International Publication No. WO00/35835 discloses a process, in which two 2 EP 1 338 336 B1 compounds are allowed to react with each other in the presence of a specific imide compound and a radical generator with respect to the imide compound and thereby yield an addition or substitution reaction product or an oxidized product thereof in accordance with a radical mechanism. These processes using the imide compounds can introduce an oxygen- atom-containing group such as hydroxyl group, nitro group or carboxyl group into a substrate or can form a carbon- 5 carbon bond. [0011] DE-C-135836 relates to the reaction of hydroxyphthalic acid amide with acetic anhydride which results in an imide compound having an N-substituted cyclic imide skeleton. [0012] DD-A-112431 discloses a process for the preparation of N-benzoyloxyphthalimide. [0013] EP-A-1331215 discloses a method for separating a reaction product from an imide compound catalyst or an 10 altered derivative thereof. [0014] EP-A-0879812 relates to a process for produding a hydroxybenzoic acid derivative and other aromatic com- pound with oxygen in the presence of an imide compound as a catalyst. [0015] Tashiro, Yasutaka et al., "A new strategy for the preparation of terephthalic acid by the aerobic oxidation of p- xylene using N-hydroxyphthalimide as a catalyst", Advanced Synthesis & Catalysis, 343 (2), 220-225, discloses an imide 15 compound comprising a ring group having a tertiary carbon atom at the bonding site to an adjacent oxygen atom, which is not a hydrolyzable protecting group.
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