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(12) United States Patent (10) Patent No.: US 8,710,251 B2 Ozer (45) Date of Patent: *Apr

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(12) United States Patent (10) Patent No.: US 8,710,251 B2 Ozer (45) Date of Patent: *Apr US008710251B2 (12) United States Patent (10) Patent No.: US 8,710,251 B2 OZer (45) Date of Patent: *Apr. 29, 2014 (54) VAPORPHASE DECARBONYLATION USPC .......................................................... 549/506 PROCESS See application file for complete search history. (75) Inventor: Ronnie Ozer, Arden, DE (US) (56) References Cited (73) Assignee: E I du Pont de Nemours and U.S. PATENT DOCUMENTS Company, Wilmington, DE (US) 2.634,276 A 4, 1953 Carnah W - I aala (*) Notice: Subject to any disclaimer, the term of this 3.999; A 2.88. Sey patent is extended or adjusted under 35 35747 A 6/1966 Dunlop et al. U.S.C. 154(b) by 162 days. 3,663,295 A 5/1972 Baker 4,774,221 A 9, 1988 Medem This patent is Subject to a terminal dis- 4,780,552 A 10/1988 Wambach claimer. (21) 1 FOREIGN PATENT DOCUMENTS 21) Appl. No.: 13/392,541 RU 2027714 C1 1, 1995 (22) PCT Filed: Aug. 31, 2010 SU 1699601 A1 12, 1991 (86). PCT No.: PCT/US2010/0472.05 OTHER PUBLICATIONS S371 (c)(1) U.S. Appl. No. 13/122,740, filed Apr. 6, 2011, Inventor Ronnie Ozer. U.S. Appl. No. 13/392,550, filed Feb. 27, 2012, Inventors Ronnie (2), (4) Date: Feb. 27, 2012 Ozer and Ke Li. U.S. Appl. No. 13/392,556, filed Feb. 27, 2012, Inventors Ronnie (87) PCT Pub. No.: WO2011/026059 Ozer and Ke Li. PCT Pub. Date: Mar. 3, 2011 U.S. Appl. No. 13/124,574, filed Apr. 15, 2012, Inventors Ronnie Ozer and Ke Li. (65) Prior Publication Data Primary Examiner — Taofiq A Solola US 2012/O165560 A1 Jun. 28, 2012 57 ABSTRACT Related U.S. Application Data (57) A process is provided for the synthesis of furan and related (60) Provisional application No. 61/238.264, filed on Aug. compounds by vapor-phase decarbonylation of furfural and 31, 2009. derivatives, using a palladium/metal aluminate catalyst. The use of Such catalysts, which are inherently less acidic than (51) Int. Cl. alumina, results in improved lifetime and high productivity. CO7D 37/36 (2006.01) The compounds so produced can be used as starting materials (52) U.S. Cl. for industrial chemicals for use as pharmaceuticals, herbi CPC .................................... C07D 37/36 (2013.01) cides, stabilizers, and polymers Such as polyether ester elas USPC .......................................................... 549/506 tomers and polyurethane elastomers. (58) Field of Classification Search CPC ..................................................... CO7D 307/36 11 Claims, No Drawings US 8,710,251 B2 1. 2 VAPORPHASE DECARBONYLATION Co-pending U.S. Published Patent Application 2011/ PROCESS 0196126A1 hereby incorporated by reference in its entirety, provides a process for the vapor-phase decarbonylation of CROSS-REFERENCE TO RELATED furfural to furan using heating a Pd/alumina catalyst that has APPLICATIONS been promoted with an alkali carbonate. There remains a need for catalysts for the decarbonylation This application claims the benefit of U.S. Provisional of furfural to furan with improved lifetime and high produc Application No. 61/238,264, filed Aug. 31, 2009, which is tivity. incorporated in its entirety as a part hereof for all purposes. 10 DESCRIPTION FIELD OF DISCLOSURE The inventions disclosed herein include processes for the The disclosure relates to the manufacture of furan and preparation of furan and related compounds and for the related compounds, and to the industrial use thereof for the 15 preparation of products into which those compounds can be synthesis of other useful materials. converted. BACKGROUND Features of certain of the processes of this invention are described herein in the context of one or more specific Furan and related compounds are useful starting materials embodiments that combine various Such features together. for industrial chemicals for use as pharmaceuticals, herbi The scope of the invention is not, however, limited by the cides, stabilizers, and polymers. For example, furan is used to description of only certain features within any specific make tetrahydrofuran, polytetramethylene glycol, polyether embodiment, and the invention also includes (1) a Subcom bination of fewer than all of the features of any described ester elastomers, and polyurethane elastomers. embodiment, which subcombination may be characterized by Known transition metal catalyzed, vapor-phase processes 25 the absence of the features omitted to form the subcombina to produce furanby decarbonylation of furfural are limited by tion; (2) each of the features, individually, included within the either the selectivity or lifetime of the supported catalyst. The combination of any described embodiment; and (3) other conversion of furfural to furan is complicated by the tendency combinations of features formed by grouping only selected to form polymeric or carbonizing byproducts which foul the features taken from two or more described embodiments, catalyst surface and hinder the rate and lifetime of the cata 30 optionally together with other features as disclosed elsewhere lyst. In the decarbonylation of furfural to furan, Pd has been herein. Some of the specific embodiments of the processes shown to be an excellent catalyst for the reaction in both the hereof are as follows: liquid and vapor phases. The challenge of this chemistry has been deactivation of the catalyst from fouling reactions that In one embodiment hereof, this invention provides a pro are thought to proceed primarily through acid catalyzed oli 35 cess for the synthesis of a compound as represented by the gomerization. Basic buffers have been added to the catalyst following structure of Formula (I) eitheras Surface treatments (vaporphase) or as Solid materials added to a liquid phase slurry reactor. Finding catalyst Sup ports which enhance decarbonylation activity while minimiz ing deactivation reactions such as carbon fouling is important 40 to the Success of a Pd based process. Treating Supports with basic buffers and base treatments has been shown to be effec tive in prior work, but a solid support that is active, stable and RI O high temperature capable would have high value in this tech nology. 45 Supported palladium catalysts are known to catalyze fur by providing a compound as represented by the following fural decarbonylation reaction with high selectivity but are structure of Formula (II) limited by short lifetime. For example, U.S. Pat. No. 3,007, 941 teaches a process for the production of furan from fur fural comprising heating a liquid phase consisting essentially 50 II of furfural in the presence of palladium metal and a basic salt of an alkali metal; the basic salt is not part of the catalyst per se but is continuously added to the liquid phase during the reaction. Also, U.S. Pat. No. 3,257,417 a process for produc tion of furan comprising contacting liquid furfural with a 55 palladium catalyst in the presence of calcium acetate. Both these processes Suffer from quick catalyst deactivation and difficult catalyst regeneration processes. U.S. Pat. No. 3.223, 714 teaches a continuous low pressure vapor phase decarbo in the form of a gas, heating a Pd/metal aluminate catalyst, nylation process for the production of furan comprising con 60 and contacting the Formula (II) compound and the catalyst to tacting furfural vapor with a Supported palladium catalyst. A produce a Formula (I) product; wherein R', R, and Rare preferred catalyst has about 0.3 wt % Pd supported on alu each independently selected from Hand a C to Ca hydrocar mina. The catalyst can be regenerated in situ but the lifetime byl group. of a running cycle for the catalyst is short and the production In another embodiment hereof, a process is provided for of furan per cycle is low. Catalysts which contain platinum 65 preparing a Formula (I) product, as described above, that and/or rhodium and to which cesium has been added are further includes promoting the Pd/metal aluminate catalyst preferably used. with an alkali carbonate. US 8,710,251 B2 3 4 In another embodiment hereof, a process is provided for In another embodiment of the processes described herein, preparing a Formula (I) product comprising providing a com the decarbonylation reaction is catalyzed by a Pd/metal alu pound as represented by Formula (II) in the form of a liquid, minate catalyst that has been promoted with an alkali carbon and heating the Formula (II) compound in a reactor in contact ate, such as sodium carbonate (Na2CO), potassium carbon with a Pd/metal aluminate catalyst. In another embodiment, ate (KCO), or cesium carbonate (CSCO). The alkali this process further includes promoting the Pd/metal alumi content of the catalyst is between about 1 and about 100 mg nate catalyst with an alkali carbonate. per g catalyst. In some embodiments, the alkali content is In another embodiment hereof, a process is provided for between and optionally including any two of the following preparing a Formula (I) product, as in any of the processes values: 1, 5, 10, 20,30,40, 50, 60, 70, 80,90, and 100 mg per 10 g catalyst. In one embodiment, the alkali carbonate is cesium described above, that further includes a step of subjecting the carbonate. furanto a reaction (including a multi-step reaction) to prepare The catalyst is promoted by immersing a palladium/metal therefrom a compound (such as that useful as a monomer), aluminate catalyst in the form of powder, pellets, rods, oligomer or polymer. spheres or any extruded or pressed form in an aqueous solu An advantageous feature of the processes hereof is the 15 tion of the alkali carbonate, with agitation. The concentration increased lifetime and productivity of the Pd/metal aluminate is the alkali carbonate solution not critical and is generally in catalyst and alkali carbonate-promoted Pd/metal aluminate the range of about 0.1 to about 20 wt %. Optimal immersion catalyst versus other catalysts used previously in the vapor time will depend on the surface area of the palladium/metal phase.
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