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(12) United States Patent (10) Patent No.: US 8.404,890 B2 Dumesic Et Al

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(12) United States Patent (10) Patent No.: US 8.404,890 B2 Dumesic Et Al USOO8404890B2 (12) United States Patent (10) Patent No.: US 8.404,890 B2 Dumesic et al. (45) Date of Patent: Mar. 26, 2013 (54) PRODUCTION OF 2.4-HEXADIENOIC ACID Barcardit et al., “Hydrogenations of Triacetic Acid Lactone, A New AND 1,3-PENTADIENE FROM Synthesis of The Carperter Bee (Xylocopa hirsutissima) Sex Phero 6-METHYL-5,6-DIHYDRO-2-PYRONE mone.” Tetrahedron Lett., 21:551-554 (1980). Casas et al., “Pentadiene production from potassium Sorbate by (75) Inventors: James A. Dumesic, Madison, WI (US); osmotolerant yeasts.” International Journal of Food Microbiology, Mei Chia, Madison, WI (US) 94(1):93-96 (2004). Fownes, G., “A Manual of Elementary Chemistry, 11" Ed.” Henry C. (73) Assignee: Wisconsin Alumni Research Lea, Philadelphia, PA, p. 632, 1872. Foundation, Madison, WI (US) Richardson et al., “Tolerance and Specificity of Recombinant 6-Methylsalicyclic Acid Synthase.” Metabolic Eng. 1: 180-187 (*) Notice: Subject to any disclaimer, the term of this (1999). patent is extended or adjusted under 35 Xie et al., Microbial Synthesis of Triacetic Acid Lactone, Biotech. U.S.C. 154(b) by 161 days. Bioeng, vol. 93, No. 4, pp. 727-736 (2006). (21) Appl. No.: 12/943,433 Zha et al., “Rational Pathway Engineering of Type I Fatty Acid Synthase Allows the Biosynthesis of Triacetic Acid Lactone from (22) Filed: Nov. 10, 2010 D-Glucose in Vivo..”.J. Am. Chem. Soc., 126:4534-4535 (2004). (65) Prior Publication Data * cited by examiner US 2012/O116119A1 May 10, 2012 Primary Examiner — Paul A Zucker (74) Attorney, Agent, or Firm — Joseph T. Leone, Esq.; (51) Int. Cl. Daniel A. Blasiole; DeWitt Ross & Stevens S.C. C07C 57/10 (2006.01) CD7C 45/60 (2006.01) (57) ABSTRACT CD7C5/48 (2006.01) (52) U.S. Cl. ......................... 562/601:568/386; 585/327 Described is a method of making Sorbic acid, pentadiene, or (58) Field of Classification Search ........................ None 3-penten-2-one. The method includes partially hydrogenat See application file for complete search history. ing 4-hydroxy-6-methyl-2-pyrone (HMP) to yield 5,6-dihy dro-4-hydroxy-6-methyl-2H-pyran-2-one (4-DHMMP). (56) References Cited Then, if 3-penten-2-one is desired, thermally decomposing the 4-DHMMP to yield 3-penten-2-one. If sorbic acid or U.S. PATENT DOCUMENTS pentadiene are desired, the 4-DHMMP is hydrogenated to 6,525,218 B2 2/2003 Kouno et al. yield 4-hydroxy-6-methyltetrahydro-2-pyrone (4-HMTHP). FOREIGN PATENT DOCUMENTS The 4-HMTHP is then dehydrated by contacting it with a JP 54-163516 12, 1979 solid acid catalyst to yield parasorbic acid (PSA). The PSA can then be ring-opened by contacting it with a solid acid OTHER PUBLICATIONS catalyst. The reaction conditions of the ring-opening reaction Takagaki et al. Chemistry Letters, Glucose to Value-added Chemi can be controlled to yield sorbic acid and/or pentadiene. cals: Anhydroglucose Formation by Selective Dehydration over Solid Acid Catalysts, 2009, 38(7), pp. 650-651.* 25 Claims, No Drawings US 8,404,890 B2 1. 2 PRODUCTION OF 2,4-HEXADIENOIC ACID sorbate solution is treated with activated carbon, neutralized, AND 13-PENTADIENE FROM and cooled to crystallize the purified sorbic acid. 6-METHYL-5,6-DIHYDRO-2-PYRONE See also U.S. Pat. No. 6.525,218, which describes a pro cess in which the intermediate polyester (the reaction product FEDERAL FUNDING STATEMENT between crotonaldehyde and ketene) is hydrolyzed with an aqueous hydrochloric acid solution having a concentration of This invention was made with Government support under from 3 to 10% by weight under a pressure greater than atmo 0813570 awarded by the National Science Foundation. The spheric pressure. United States Government has certain rights in the invention. These prior art processes for making Sorbates are less than 10 ideal because of the formation of by-products (tar, etc. formed FIELD OF THE INVENTION during the decomposition step), and yield losses during the Solid-liquid separation steps. The invention is directed to a method of making 2.4-hexa 1.3-Pentadiene (also known as piperylene) is a volatile, dienoic acid (i.e., Sorbic acid), 1,3-pentadiene, and related flammable, linear five-carbon hydrocarbon. It is widely used compounds via an acid-catalyzed, ring-opening of 6-methyl 15 as a monomer in the production of plastics, adhesives, and 5,6-dihydro-2-pyrone (i.e., parasorbic acid). resins. It is produced commercially as a by-product of ethyl ene production via the catalytic cracking of naphtha. There is BACKGROUND no other means known to produce 1,3-pentadiene in commer cial quantities. However, there have been efforts to geneti A. W. von Hofmann was the first to isolate sorbic acid cally engineer microorganisms such as yeast to produce 1.3- (2,4-hexadienoic acid) in 1859 (by distilling oil pressed from pentadiene. See Casasa et al. (1 Jul. 2004) “Pentadiene the berries of mountain ash trees.). The distillation yields the production from potassium Sorbate by osmotolerant yeasts.” corresponding lactone, which Hofmann then converted to the International Journal of Food Microbiology, 94(1):93-96. acid by hydrolysis. Its antimicrobial properties were not extensively explored until after the close of World War II. 25 SUMMARY OF THE INVENTION Since the 1950s, sorbic acid (E200) has been used exten sively worldwide as a preservative in a vastarray of foods. For As noted above, described herein is a method of making example, sorbic acid has been used since the late 1950s as a 2.4-hexadienoic acid (i.e., Sorbic acid), 1,3-pentadiene (i.e., preservative in white wines. Sorbic acid and its salts (notably piperylene), and related compounds via an acid-catalyzed, potassium sorbate, E202) are also used as inhibitors of 30 ring-opening of 6-methyl-5,6-dihydro-2-pyrone (i.e., para Clostridium botulinum in processed meat products. Sorbic Sorbic acid). These products are commercially significant: acid and its salts are commodity products; worldwide produc sorbic acid as a food preservative; and 1,3-pentadiene as a tion of sorbates in 2008 was approximately 65,000 metric chemical intermediate for producing resins and adhesives. tons (i.e., tonnes; 71,650 US short tons). The sole commercial source of 1,3-pentadiene is from the Cs The benefits of sorbates as food preservatives are two-fold: fraction of naphtha cracking. A primary advantage and ben Sorbates inhibit a very wide spectrum of bacteria, yeasts, and efit of the method described and claimed herein is that the molds; and sorbates have extremely low toxicity (lower even parasorbic acid can be made from a renewable precursor, than table salt, NaCl). Sorbates are “generally regarded as 4-hydroxy-6-methyl-2-pyrone (HMP). safe” (GRAS) by the U.S. Food and Drug Administration. There are several known protocols for producing Sorbic A first version of the invention is directed to a method of acid and Sorbates. Commercial quantities are typically pro making Sorbic acid and pentadiene. Here, the method com duced by polymerizing crotonaldehyde and ketene to forman prises converting a renewable feedstock, 4-hydroxy-6-me intermediate polyester, decomposing the polyester to yield a thyl-2-pyrone (HMP) into parasorbic acid (PSA). The ring of crude Sorbic acid, and then Subjecting the crude Sorbic acid to the PSA is then opened by contacting the PSA with a solid a variety of purification steps to yield various grades of sorbic acid catalyst. This can be done with dehydration of the opened acid (e.g., food grade). The intermediate polyester is decom 45 ring to yield sorbic acid, or with decarboxylation of the posed by a number of means, including treating it with strong opened ring to yield pentadiene. The conversion of HMP to acid, strong base, or via heat. The required decomposition PSA is preferably accomplished via hydrogenating the HMP step is problematic because it yields unwanted, colored by in the presence of a catalyst comprising one or more noble products. To yield the highest grades of product (i.e., food metals, such as a catalyst comprising palladium or a mixture grade Sorbate or better) multiple purification steps are 50 of palladium and niobium. The conversion of HMP to PSA required. preferably takes place in a solvent selected from the group Japanese Examined Patent Application Publication No. consisting of C- to C-alcohols and C- to C-carboxylic 44-26646 discloses a process for producing Sorbic acid in acids. The conversion of HMP to PSA may take place in a which the polyester obtained by the reaction between cro single step, or in multiple steps, such as hydrogenating the tonaldehyde and ketene is decomposed with hydrochloric HMP to yield 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2- acid, followed by cooling and filtrating the resulting reaction 55 one (4-HMTHP), and then dehydrating the 4-HMTHP by mixture to yield crude sorbic acid. The crude sorbic acid is contacting it with a solid acid catalyst to yield PSA. The then dissolved in hot water to which is added activated car ring-opening reactions are preferably carried out in a polar, bon. The reaction mixture is filtered hot, and the filtrate is aprotic solvent, or a mixed solvent comprising water and a gradually cooled to yield crystalline Sorbic acid. polar, aprotic solvent. A related protocol is described in Japanese Unexamined 60 Another version of the method is directed to making sorbic Patent Application Publication No. 54-163516. Here, the acid and pentadiene in a more specific, three-step approach: polyester obtained from reacting crotonaldehyde and ketene (a) hydrogenating 4-hydroxy-6-methyl-2-pyrone (HMP) is decomposed with hydrochloric acid in the presence of a tO yield 4-hydroxy-6-methyltetrahydro-2-pyrone urea compound.
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