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United States Patent (19) (11) Patent Number: 4,769,500 Yui Et Al

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United States Patent (19) (11) Patent Number: 4,769,500 Yui Et Al United States Patent (19) (11) Patent Number: 4,769,500 Yui et al. (45. Date of Patent: Sep. 6, 1988 (54) PROCESS FOR PREPARATION OF 3,842,130 10/1974 Kawaguchi et al. ............... 568/772 2,3,5-TRIMETHYLHYDROQUINONE 4,018,833 4/1977 Miller et al. ........... ... 568/772 4,072,660 2/1978 Miller et al. ....................... 568/772 75 Inventors: Tomoyuki Yui, Nagareyama; Akira Ito, Kashiwa, both of Japan FOREIGN PATENT DOCUMENTS 73) Assignee: Mitsubishi Gas Chemical Company, 0091937 6/1982 Japan ................................... 568/772 Inc., Tokyo, Japan 535279 1/1977 U.S.S.R. .............................. 568/772 21 Appl. No.: 100,521 Primary Examiner-Werren B. Lone Attorney, Agent, or Firm-Frishauf, Holtz, Goodman & (22 Filed: Sep. 24, 1987 Woodward 30 Foreign Application Priority Data 57 ABSTRACT Oct. 16, 1986 JP Japan ............................... 61-244230 A process for preparation of 2,3,5-trimethylhydroqui 51) Int. Cl* ....................... C07C37/07; CO7C37/00 none (TMHQ) from 2,3,5-trimethylbenzoquinone 52 U.S. C. ..................................... 568/772; 568/766 (TMBQ) is disclosed, comprising reducing TMBQ with 58) Field of Search ........................ 568/772, 766, 799 hydrogen in the presence of a platinum group metal (56) References Cited catalyst with a silica alumina support containing an U.S. PATENT DOCUMENTS alkali metal component. This process permits prepara 2,229,573 1/1941 Jung .................................... 568/772 tion of TMHQ of purity as high as more than 99%. 3,723,541 3/1973 Schuster et al. ... 568/772 3,839,468 10/1974 Tamai et al. ........................ 568/772 19 Claims, No Drawings 4,769,500 1. 2 is more increased, thereby leading to a reduction in the PROCESS FOR PREPARATION OF yield. 2,3,5-TRIMETHYLHYDROQUINONE If the purity of TMHQ is sufficiently high, TMHQ can be used as the product without application of any BACKGROUND OF THE INVENTION 5 purification operation, and even in a case where the The present invention relates to a process for prepa purification is applied, the amount of energy is greatly ration of 2,3,5-trimethylhydroquinone (hereinafter re decreased. ferred to as "TMHQ") and more particularly to a pro Thus the reaction selectivity in hydrogenation of cess for preparing TMHQ from 2,3,5-trimethylben TMBQ is a very important factor exerting great influ 10 ences on the yield, purity and production cost of zoquinone (hereinafter referred to as "TMBQ') TMHQ, and it is of high industrial significance to de through its hydrogen reduction in the presence of plati velop a method whereby hydrogenation of TMBQ can num group metals deposited on an alkali metal-contain be carried out with high selectivity. ing silica alumina as a support. In practical use of catalysts, the catalyst life is impor TMHQ is an important material for preparation of 15 tant from an economic standpoint and also from a view Vitamin E (o-tocopherol), and its demand has been point of operation; that is, it is essential for industrial rapidly increased in recent years. The quality of Vita catalysts that not only the activity and selectivity at an min E varies depending on that of TMHQ as the start initial stage of use are high, but also the high activity ing material. Thus, from a viewpoint of the quality of and high selectivity are maintained over a long period the product Vitamin E and also from an economic 20 of time. Also in hydrogenation catalysts for TMBQ, the standpoint in the preparation thereof, it is required for catalyst life is important. TMHQ to have a high purity. As supports for platinum metals which are to be used As is well known in the art, TMHQ can be prepared in hydrogenation of TMBQ, active carbon (U.S. Pat. from various starting materials. Among these known No. 2,229,573), alumina (Japanese Patent Application methods is most predominant a method of preparing 25 Laid-Open No. 100430/1977) and silica, pumice and TMHQ through TMBQ. silicic acid (Japanese Patent Publication No. One of the known methods to prepare TMHQ from 23487/1976) are known. However, in hydrogenation of TMBQ as the starting material is a method in which TMBQ in the presence of catalysts comprising platinum TMBQ is reduced with reducing agents such as sodium group metals deposited on the above supports, side hydrogensulfite (Japanese patent application laid-open 30 reactions such as addition of hydrogen to carbon-car No. 108032/1974) and sulfur dioxide (Japanese patent bon double bonds will occur, thereby leading to a re publication No. 14455/1984). This method, however, duction in the selectivity of the desired product TMHQ. has disadvantages in that the reducing agents are expen High purification, therefore, is needed to obtain the sive, the yield is low, and impurities resulting from the product of high purity. reducing agent are readily incorporated in the product. 35 Moreover the service life of the above catalysts is not Another method is to reduce TMBQ with hydrogen sufficiently long. Thus various attempts to lengthen the in the presence of a catalyst (e.g., U.S. Pat. No. catalyst life have been made as in, for example, Japanese 2,229,573). This method is advantageous in that the Patent Publication No. 42964/1979, but with no satis reducing agent is inexpensive and is easy to separate factory results. because it is gas. Catalysts to be used in the method which have heretofore been known include catalysts SUMMARY OF THE INVENTION comprising activated metals such as Raney nickel and An object of the present invention is to provide a Raney cobalt, renium, and platinum group metals such process for preparing high purity TMHQ by hydroge as palladium, ruthenium and rhodium as deposited on a nation of TMBQ. support (Japanese Patent Publication No. 20285/1982). 45 Another object of the present invention is to provide These catalysts can be easily separated from TMHQ a hydrogenation method of TMBQ whereby TMHQ and the solvent by filtration after completion of the can be obtained with high selectivity. reaction because they are solid. As described above, the Still another object of the present invention is to hydrogenation method has advantages. provide a process for preparing TMHQ by hydrogena TMHQ to be used in preparation of Vitamin E which 50 tion of TMBQ by the use of a platinum group metal is to be utilized as a medicine or a food additive is re catalyst. quired to have a purity as high as more than 99%. If the A further object of the present invention is to provide purity of TMHQ is lower than 99%, it is necessary to a platinum group metal catalyst for hydrogenation of purify TMHQ. For this purification, for example, the TMBQ to prepare TMHQ, which can maintain its high following have been proposed: a method in which after 55 activity and high selectivity over a long period of time. completion of the reaction, a poor solvent is added to It has been found that the objects are attained by crystallize TMHQ from the reaction mixture (Japanese using platinum group metal catalysts using alkali metal Patent Publication Nos. 26424/1976 and 20285/1982), containing silica alumina as a support. and a method in which TMHQ once separated from the The present invention relates to a process for prepar reaction mixture is recrystallized from a suitable combi ing 2,3,5-trimethylhydroquinone by hydrogenation of nation of solvents (Japanese patent publication No. 2,3,5-trimethylbenzoquinone in the presence of a plati 20285/1982). These methods, however, have various num group metal catalyst using alkali metal-containing disadvantages: for example, a large amount of solvents silica alumina as a support. is used, the solvents used should be separated and re covered because they are mixed solvents, and if the 65 DETAILED DESCRIPTION OF THE purity of TMHQ is low, the amount of energy needed is INVENTION increased. Moreover, as the purity of TMHQ is lower, The process of the present invention is characterized the amount of TMHQabondoned along with impurities in that in preparation of TMHQ through hydrogenation 4,769,500 3 4. of TMBQ by the use of platinum group metals, silica ployed. For example, as the reducing agent, hydrogen, alumina containing alkali metals is used as a support. formalin, sodium formate, carbon monoxide and hydra The present invention produces various advantages. zine can be used. Preferred is a hydrogen reduction For example, since the process of the present invention method. permits hydrogenation of TMBQ into TMHQ in high The amount of the platinum group metal deposited selectivity, high purity TMHQ can be easily obtained on the support is usually 0.1 to 10% by weight, prefera without application of any additional post-treatment. bly 0.3 to 3% by weight based on the weight of the Since the catalyst for use in the process of the present Support. invention has a long service life, it is not necessary to The amount of the catalyst (metal--support) used is exchange frequently and thus the process of the present 10 usually 0.5 to 30% by weight, particularly preferably 1 invention can be carried out economically. to 10% by weight based on the weight of TMBQ. The present invention will hereinafter be explained in As the reaction solvent, solvents capable of dis detail. solving TMBQ, TMHQ and their adduct quinhydrone The ratio of silica to alumina in the support is not can be used. For example, as well as methanol and etha critical; preferably the silica/alumina ratio (weight) is 15 no which have been believed unsuitable because they from 90/10 to 40/60. Any of so-called low alumina in cause coloration, aliphatic alcohols such as propyl alco which the silica/alumina ratio (weight) is in the vicinity hol, butyl alcohol and amyl alcohol, aromatic alcohols of 87/13 and so-called high alumina in which the such as benzyl alcohol, ketones such as acetone and silica/alumina ratio (weight) is in the vicinity of 75/25, methyl ethyl ketone, organic acids such as acetic acid which are usually in industrial use, can be used in the 20 and propionic acid, organic acid esters such as methyl present invention.
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