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(12) Patent Application Publication (10) Pub. No.: US 2014/0206897 A1 Allman Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0206897 A1 Allman Et Al US 20140206897A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0206897 A1 Allman et al. (43) Pub. Date: Jul. 24, 2014 (54) METHOD FOR MAKING METHYL Publication Classification METHACRYLATE FROM PROPIONALDEHYDE AND (51) Int. Cl. FORMALDEHYDE VIA OXDATIVE CD7C 67/44 (2006.01) ESTERIFICATION (52) U.S. Cl. CPC ...................................... C07C 6744 (2013.01) (71) Applicant: Saudi Basic industries Corporation, USPC .......................................................... 560/210 Riyadh (SA) (57) ABSTRACT (72) Inventors: James Malcolm Allman, Sugar Land, A process for forming methyl methacrylate can comprise: TX (US); James Kauffman, Katy, TX reacting ethylene, carbon monoxide, and hydrogen, in the (US) presence of a first catalyst comprising a metal carbonyl: removing a first reaction product comprising propionalde (73) Assignee: Saudi Basic industries Corporation, hyde; reacting the first reaction product with formaldehyde; Riyadh (SA) removing a second reaction product comprising methac rolein; reacting the second reaction product with oxygen and (21) Appl. No.: 14/159,032 methanol in the presence of a second catalyst to form a third reaction product comprising methyl methacrylate. Another (22) Filed: Jan. 20, 2014 process for forming methyl methacrylate can comprising: reacting ethylene with carbon monoxide to form propional Related U.S. Application Data dehyde; reacting the propionaldehyde with formaldehyde to (60) Provisional application No. 61/755,260, filed on Jan. form methacrolein; and reacting the methacrolein with 22, 2013. methanol and oxygen to form the methyl methacrylate. Patent Application Publication Jul. 24, 2014 US 2014/0206897 A1 100-Providing ethylene, carbon monoxide, and hydrogen 200- Providing a homogeneous catalyst comprising a metal carbonyl 300-Forming a first reaction product comprising propionaldehyde 400- Providing the first reaction product, formaldehyde, a secondary amine, and an organic acid 500- Forming a second reaction product comprising methacrolein FIG. 1 600- providing the second reaction product, methanol, and oxygen 700- providing a heterogeneous catalyst comprising palladium with at least one of lead, mercury, thallium, and bismuth 800-Forming a third reaction product comprising methyl methacryalte US 2014/0206897 A1 Jul. 24, 2014 METHOD FOR MAKING METHYL 0012. In the acetone cyanohydrin route (1) below, acetone METHACRYLATE FROM is reacted with hydrogen cyanide to form acetone cyanohy PROPIONALDEHYDE AND drin. The cyanohydrin is then hydrolyzed and dehydrated by FORMALDEHYDE VIA OXDATIVE various means, usually Sulfuric acid, and then reacted with ESTERIFICATION methanol or a methanol derivative to form methyl methacry late (MMA). CROSS-REFERENCE TO RELATED APPLICATION 0001. The present application claims the benefit of U.S. (1) Provisional Application Ser. No. 61/755,260, filed Jan. 22, O OH acid 2013, the contents of which is hereby incorporated in its us + HCN -> -- entirety by reference. CN COOH BACKGROUND OF THE INVENTION 1. + CH3OH -> 1. 0002. This disclosure relates to methods of manufacture of COOH COOCH methyl methacrylate. 0003 Methyl methacrylates are useful in the manufacture 0013. In the isobutylene oxidation process (2), illustrated of articles and components for a wide range of applications, below, isobutylene (or t-butyl alcohol) is oxidized via vapor from medical technologies to transparent glass Substitutes. phase oxidation to methacrolein, and the methacrolein is Because of their broad use, it is desirable to manufacture Subsequently oxidized to methacrylic acid, also via Vapor methyl methacrylates efficiently and economically. However, phase oxidation. The methacrylic acid is Subsequently esteri the existing processes Suffer from drawbacks, including com fied with methanol to form MMA. plex processing and expensive materials. 0004. There accordingly remains a need in the art for producing methyl methacrylate while reducing the amount of (2) processing required and improving economic competitive O CSS. 1. + O2 -> 1. - A - CHO SUMMARY OF THE INVENTION 0005 Disclosed herein are processes for making methyl methacrylate. 1. 0006. In an embodiment, a process for forming methyl methacrylate can comprise: reacting ethylene, carbon mon 1. COOH + CH3OH -- 1. COOCH oxide, and hydrogen, in the presence of a first catalyst com prising a metal carbonyl; removing a first reaction product comprising propionaldehyde; reacting the first reaction prod 0014. In a modification to the isobutylene oxidation pro uct with formaldehyde; removing a second reaction product cess, illustrated below (3) the last two steps are combined, comprising methacrolein; reacting the second reaction prod such that oxidation of methacrolein and esterification with uct with oxygen and methanol in the presence of a second methanol take place in the same reactor, in a reaction known catalyst to form a third reaction product comprising methyl as “oxidative esterification.” Not only does this improvement methacrylate. eliminate reaction and purification equipment by combining 0007. In another embodiment, another process for form steps, it specifically gets rid of the step of oxidizing methac ing methyl methacrylate can comprise: reacting ethylene with rolein to methacrylic acid, which has several challenges in carbon monoxide to form propionaldehyde; reacting the pro catalyst manufacture and performance. pionaldehyde with formaldehyde to form methacrolein; and reacting the methacrolein with methanol and oxygen to form the methyl methacrylate. (3) 0008. The above described and other features are exem plified by the following detailed description. 1. + O2 -- 1. CHO BRIEF DESCRIPTION OF THE DRAWINGS 1. + CH3OH + O2 -> 1. 0009 Refer now to the FIGURE, which is exemplary not CHO COOCH limiting. 0010 FIG. 1 is a schematic of an embodiment of the 0015. In the propionaldehyde formylation process, illus process disclosed herein. trated below (4), ethylene is first hydroformylated with CO and hydrogen to form propionaldehyde. Next, the propional DETAILED DESCRIPTION OF THE INVENTION dehyde is reacted with formaldehyde in analdol condensation 0011. There are several methods of manufacturing methyl to form methacrolein. The methacrolein is then oxidized to methacrylates. The routes include: acetone cyanohydrin, methacrylic acid, typically in a liquid-phase process. Finally, isobutylene oxidation, propionaldehyde formylation, propi the methacrylic acid is esterified with methanol to form onic acid formylation, and methyl propionate formylation. MMA. US 2014/0206897 A1 Jul. 24, 2014 ably priced. Also, compared with the other classes, the (4) amount of processing is not excessive (with the possible 21 + CO + H --> H2CO exception of the propionaldehyde formylation process). 21 2 CHO 0020. Among the ethylene-based processes, routes (4)–(6) above, it is expected that the methyl propionate formylation process is the most economical, as it involves the least pro 1. cessing. Propionic acid formylation is the next most economi CHOH cal, followed by propionaldehyde formylation, which + O. -- -e- involves the most processing. CHO COOH 0021. The problem with both of the two least expensive ethylene-based processes, methyl propionate formylation (6) and propionic acid formylation (5), is that these formylation 1so reactions are not favored by nature, and thus must be strongly assisted by catalyst, conditions, etc. The result is awkward 0016. In the propionic acid formylation process, illus and expensive processing, involving catalyst processing, high trated below (5), ethylene is first carbonylated to form propi formaldehyde concentrations, large recycles, etc. By con onic acid. The propionic acid is then reacted with formalde trast, the most expensive process in this class, propionalde hyde to form methacrylic acid. The resulting methacrylic acid hyde formylation (4), uses a formylation reaction that is is then esterified with methanol to form MMA. highly favored by nature, which is referred to as “aldol con densation.” Since this formylation produces methacrolein rather than methacrylic acid or MMA directly, it involves (5) more Subsequent processing, making it economically less desirable. CHO 21 + CO + H2O -- 1NcooH -- 0022. Without being bound by theory, it is believed that the favorable results obtained herein, e.g., an economical and efficient process for manufacturing methyl methacrylate, are 2. achieved through modification of the propionaldehyde formylation process to include the oxidation and esterifica 1. + CH3OH -- 1. tion of methacrolein. COOH COOCH 0023 The process can embody a combination of oxidation and esterification of methacrolein, which is ideally suited for use in the propionaldehyde formylation process. The combi 0017. In the methyl propionate formylation process, illus nation is believed to work better with propionaldehyde trated below (6), ethylene is carbonylated in the presence of formylation than with isobutylene oxidation, as the latter methanol to form methyl propionate. The methyl propionate involves a vapor-phase oxidation with associated inert gas, is then reacted with formaldehyde to form MMA directly. high temperatures, etc. By combining propionaldehyde formylation with oxidative esterification, a process can be (6) constructed that retains the raw material advantages of the CHO ethylene-based processes, retains the use of aldol condensa 21 + CO + CH-OH -- 1Noooch, He tion, and does not involve too much processing. 0024 “Methyl Methacrylate” means compositions
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