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(12) United States Patent (10) Patent N0.: US 8,222,011 B2 Fujikura (45) Date of Patent: Jul

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(12) United States Patent (10) Patent N0.: US 8,222,011 B2 Fujikura (45) Date of Patent: Jul US008222011B2 (12) United States Patent (10) Patent N0.: US 8,222,011 B2 Fujikura (45) Date of Patent: Jul. 17, 2012 (54) PROCESS FOR PRODUCING A RUBBER FOREIGN PATENT DOCUMENTS ANTI-AGING AGENT, A VULCANIZATION JP 2005-139239 A 6/2005 ACCELERATOR OR MODIFIED RUBBER BY JP 2006-152171 A 6/2006 MEANS OF A MICROORGANISM OTHER PUBLICATIONS (75) Inventor: Keitaro Fujikura, Kobe (JP) Humphrey and Deidoerfer, 1960; Microbiological Process Report, pp. 359-385.* (73) Assignees: Sumitomo Rubber Industries, Ltd., Huang and Tang 2007. Bioprocessing for value-added products from Kobe (JP); Research Institute of renewable resources: New Technologies and applicationsChapter 8iBacterial and yeast culturs-process characteristic, pr:oducts and Innovative Technology for the Earth, applications,, pp. 185-223.* KiZugawa (JP) Deidoerfer et al. 1961. Fermentatio process Report. Microbiological Process Report pp. 273-303.* ( * ) Notice: Subject to any disclaimer, the term of this Moore et al. 2002. Journal of Natural Products vol. 65 pp. 1956 patent is extended or adjusted under 35 1962* U.S.C. 154(b) by 296 days. Hertweck et al. Chembiochem (2001) No. 10, pp. 784-786.* Hertweck et al. Tetrahedron (2000) 56: 9115-9120.* (21) Appl.No.: 12/469,939 Lebel et al. Organic Lett. (2006) 8(25): 57l7-5720.* Arzoumanidis et al. J. Org. Chem. (1981) 46: 3930-3932.* (22) Filed: May 21, 2009 Translation of Of?ce Action dated Mar. 9, 2012 for German Appli cation No. 10 2009 024 402.6. (65) Prior Publication Data Organikum, 23. Auglage, Weinheim: Wiley-VCH Verlag, 2009, S. pp. 679-681. US 2009/0306431 A1 Dec. 10, 2009 * cited by examiner (30) Foreign Application Priority Data Primary Examiner * Susan Hanley Jun. 10, 2008 (JP) ............................... .. zoos-151413 (74) Attorney, Agent, or Firm * Birch, Stewart, Kolasch & Apr. 10, 2009 (JP) ............................... .. 2009-096016 Birch, LLP (51) Int. Cl. (57) ABSTRACT C12P 7/40 (2006.01) An object of the present invention is to provide processes for (52) US. Cl. .................. .. 435/136; 435/170; 435/252.35 producing a rubber anti-aging agent, a vulcanization accel (58) Field of Classi?cation Search ................ .. 435/136, erator and a modi?ed natural rubber converting glucose into 435/170, 252.35 benZoic acid or a benZoic acid derivative by a microorganism See application ?le for complete search history. or extracting benZoic acid or a benZoic acid derivative from a plant, converting the obtained benZoic acid or benZoic acid (56) References Cited derivative into aniline or an aniline derivative and then mak ing the rubber anti-aging agent, vulcanization accelerator or U.S. PATENT DOCUMENTS modi?ed natural rubber with the aniline or aniline derivative. 2008/0242823 A1 10/2008 Fujikura 2009/0155866 A1 6/2009 Burk et al. 6 Claims, No Drawings US 8,222,011 B2 1 2 PROCESS FOR PRODUCING A RUBBER The present invention also relates to a process for produc ANTI-AGING AGENT, A VULCANIZATION ing a modi?ed natural rubber, Which comprises: converting ACCELERATOR OR MODIFIED RUBBER BY glucose into benzoic acid or a benzoic acid derivative by a MEANS OF A MICROORGANISM microorganism or extracting benzoic acid or a benzoic acid derivative from a plant; converting the benzoic acid or ben TECHNICAL FIELD zoic acid derivative into aniline or an aniline derivative; and modifying a natural rubber by the aniline or aniline derivative. The present invention relates to a process for producing an antiaging agent, a vulcanization accelerator or a modi?ed DETAILED DESCRIPTION OF THE INVENTION natural rubber by means of a microorganism or a plant. More particularly, the present invention relates to a process for In the folloWing, the present invention is described in producing an antiaging agent, a vulcanization accelerator or a detail. modi?ed natural rubber by using benzoic acid or a benzoic In the present invention, glucose is used as carbon neutral acid derivative produced by a microorganism or extracted resources and is converted into benzoic acid or a benzoic acid from a plant. derivative by a microorganism. Alternatively, benzoic acid or a benzoic acid derivative is extracted from a plant; thereafter, BACKGROUND ART the obtained benzoic acid or benzoic acid derivative is con At present, antiaging agents used for a rubber, thiazole verted into aniline or an aniline derivative. An antiaging vulcanization accelerators and sulfenamide vulcanization 20 agent, a vulcanization accelerator or a modi?ed natural rub accelerators are synthesized from aniline Which is produced ber is produced from the thus obtained aniline or aniline from petroleum as a raW material. Assuming a rise in oil derivative. prices and exhaustion of oil in the future, a production process The production of the aniline or aniline derivative from a Which does not use oil is desired. Further, processes of pro plant or a microorganism requires a nitrogen source; hoWever, duction of antiaging agents and vulcanization accelerators 25 since benzoic acid or a benzoic acid derivative is produced in cause global Warming since industrial production of aniline the present invention, it can be produced Without using a from petroleum resources emit a large amount of heat and nitrogen source. carbon dioxide. Therefore, based on an idea of utilizing natu In the case Where glucose is converted into benzoic acid or ral resources, a method is knoWn Wherein a vulcanization a benzoic acid derivative by a microorganism, the glucose accelerator is synthesized by the use of a naturally-derived 30 used is obtained from plants Which take in carbon dioxide in long-chain amine, as a material, Which is obtained by reduc the atmosphere. The examples thereof may include Waste tive amination of a saturated or unsaturated fatty acid Which is Wood, paddy straW, Weed and non-edible part of food crop obtained by hydrolysis of a natural fat and oil (Patent Docu (stem, root and xylem). Glucose can be obtained by adding an ment 1). acid to the materials and hydrolyzing them or carrying out a HoWever, acrylonitrile, mercaptobenzothiazoles and 35 hot-compressed Water treatment. In this process, since glu dibenzothiazolyl disul?de are used in the process of produc cose is converted into the benzoic acid or benzoic acid deriva ing vulcanization accelerators. There is no description that tive, it is not necessary to add a nitrogen source. these materials are produced from natural resources. Here, examples of the benzoic acid derivative may include Further, a production process is knoWn Wherein a modi?ed a compound in Which a substituent group, such as a hydroxyl natural rubber is produced by a graft polymerization or an 40 group and a carboxy group, is replaced on the benzene ring of addition of a compound containing a polar group under benzoic acid. Examples of a preferable benzoic acid deriva mechanical shear stress to a natural rubber raW material tive may include salicylic acid, and the like. (Patent Document 2). HoWever, it is not assumed that a natu Examples of the microorganism used When converting glu rally-derived material is used as a compound containing a cose into benzoic acid or a benzoic acid derivative by a polar group. 45 microorganism may include Streptomyces maritimus Patent Document 1: JP-A-2005-l39239 (EMBL AAF81726), Streptomyces coelicolor Patent Document 2: JP-A-2006-l52l7l (ATCC10147), and the like. Conversion of glucose into benzoic acid or a benzoic acid SUMMARY OF THE INVENTION derivative can be carried out in Water or a solvent Which is a 50 mixture of Water and an organic solvent. Examples of the It is an object of the present invention to provide processes organic solvent may include methanol, ethanol, dimethyl sul for producing an antiaging agent, a vulcanization accelerator foxide, diethyl ether, tetrahydrofuran and acetone. and a modi?ed natural rubber, Which are environmentally Temperature for conversion is preferably 200 C. to 42° C. If friendly and capable of making provision against a decrease the temperature is beloW 20° C., activity of the microorgan of petroleum resources in the future. 55 ism may be depressed. If the temperature is above 42° C., the The present invention relates to a process for producing an microorganism tends to be killed. Therefore, in both cases antiaging agent, Which comprises: converting glucose into yield decreases. It is more preferable that the loWer limit is benzoic acid or a benzoic acid derivative by a microorganism 25° C. and the upper limit is 30° C. or extracting benzoic acid or a benzoic acid derivative from a It is preferable that pH is betWeen 4 and 9 during the plant; and converting the obtained benzoic acid or benzoic 60 reaction. If pH is not Within the above range, production acid derivative into aniline or an aniline derivative. ef?ciency of benzoic acid may drop extremely. The present invention also relates to a process for produc Cultivation time may be 3 to 9 days, preferably 4 to 7 days. ing a vulcanization accelerator, Which comprises: converting The plants used upon extracting benzoic acid or a benzoic glucose into benzoic acid or a benzoic acid derivative by a acid derivative take in carbon dioxide in the atmosphere, and microorganism or extracting benzoic acid or a benzoic acid 65 examples thereof include Styrax benzoin (Order: Ericales, derivative from a plant; and converting the benzoic acid or Family: Styracaceae), Hypericum androsaemum (Order: benzoic acid derivative into aniline or an aniline derivative. Theales, Family: Guttiferae), and the like. The plants can be US 8,222,011 B2 3 4 obtained by re?ning the resin “benzoin”, Which is obtainable -continued by solidifying the sap obtained by scratching the trees of the Family Styracaceae. The benzoic acid orbenzoic acid derivative obtained by the use of a microorganism or a plant can synthesize aniline through the synthetic pathWay Without petroleum resources.
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