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United States Patent (19) 4,731,488

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United States Patent (19) 4,731,488 United States Patent (19) 11 Patent Number: 4,731,488 Shimasaki et al. 45) Date of Patent: Mar. 15, 1988 54, WAPOR-PHASE HYDROGEN TRANSFER 4,255,283 3/1981 Bartek et al. ........................ 502/202 REACTION OF CARBONYL COMPOUND 4,407,732 10/1983 Kehl .................................... 502/208 4,418,005 11/1983 Dodd et al. ..................... 502/340 X WTH ALCOHOL 4,471,070 9/1984 Siefert et al. ................... 502/341X (75) Inventors: Yuuji Shimasaki, Suita; Youichi Hino, Sakai; Michio Ueshima, FOREIGN PATENT DOCUMENTS Takarazuka, all of Japan 5549322 10/1978 Japan ................................... 502/.340 73 Assignee: Nippon Shokubai Kagaku Kogyo Co., 727209 8/1977 U.S.S.R. .............................. 502/.340 Ltd., Osaka, Japan OTHER PUBLICATIONS (21) Appl. No.: 873,447 . Selective Reduction of Unsaturated Aldehydes and Ketones by Vapor-Phase Hydrogen Transfer Reaction, (22 Filed: Jun. 6, 1986 Ballard et al., Shell Development Co., Emeryville, Related U.S. Application Data Calif., pp. 754-763, Mar. 16, 1956. 62 Division of Ser. No. 802,183, Nov. 25, 1985, aban Primary Examiner-J. E. Evans doned. Attorney, Agent, or Firm-Sherman and Shalloway 30 Foreign Application Priority Data (57) ABSTRACT Nov. 27, 1984 JP Japan ................................ 59-2486.50 A catalyst for vapor-phase hydrogen transfer reaction Apr. 8, 1985 JP Japan .................................. 60-72698 between a carbonyl compound having an alkenyl or aryl group and a primary or secondary alcohol, said 51 Int. Cl." .................... C07C29/136; CO7C29/14; catalyst having a composition represented by the fol C07C 33/03; CO7C 33/22 52 U.S. C. .................................... 568/648; 502/202; lowing general formula 502/242; 502/303; 502/341; 568/813; 568/814; 568/825; 568/881 MgaxiY-Od 58) Field of Search ............... 568/814, 880, 881, 846, 568/825, 813 wherein X represents at least one element selected from 56) References Cited the group consisting of boron, aluminum, silicon, phos phorus, titanium, vanadium, iron, yttrium, zirconium, U.S. PATENT DOCUMENTS niobium, tin, antimony, lead, bismuth, lanthanum and l,844,963 2/1932 Larson ............................ 502/243 X cerium, Y represents at least one element selected from l,866,246 7/1932 Beekley ........................... 502/242 X 2,369,074 2/1945 Pitzer ..... ... 502/25 X the group consisting of alkali metals and alkaline earth 2,633,475 3/1953 Mattern ...... a ... 502/340 X metals excepting magnesium, O represents oxygen, and 2,767,221 10/1956 Ballard et al. .................... 502/38 X a, b, c and d represent the atomic ratios of the individual 2,889,266 6/1959 Baker et al. ..................... 502/202 X elements, and when a is 1, b represents a number of 0.01 2,932,673 4/1960 Melik et al. ... 502/340 X to 0.5, c represents a number of 0 to 0.5, and d is a 3,551,497 12/1970 Wymore......... ... 568/814 X number determined by the atomic valences and atomic 3,901,947 8/1975 Enomoto et al. ... 502/304X ratios of the individual elements. 3,962,134 6/1976 Cobb .............. .502/202 4,072,727 2/1978 Vanderspurt ... ... 502/243 X 4,096, 193 6/1978 Vanderspurt ................... 502/340 X 8 Claims, No Drawings 4,731,488 1. 2 invention is disclosed, for example, in U.S. Pat. No. WAPOR-PHASE HYDROGEN TRANSFER 2,767,221. According to this method, acrolein is reacted REACTION OF CARBONYL COMPOUND WITH with ethanol using a catalyst comprising magnesium ALCOHOL oxide and zinc oxide to produce allyl alcohol (in a yield 5 of 71.7% based on the consumed acrolein) and acetalde This application is a division of application Ser. No. hyde. In this method, however, the conversion of the 802,183, filed Nov. 25, 1985, now abandoned. unsaturated aldehyde is low, and the primary or second This invention relates to a catalyst for use in a vapor ary alcohol must be used in a large excess relative to the phase hydrogen transfer reaction between a carbonyl unsaturated aldehyde. In addition, a tendency to a de compound having an alkenyl or aryl group and a pri 10 crease in yield is observed after this catalyst is used for mary or secondary alcohol, for example, schematically ten and several hours. Because of these disadvantages, shown below. the method of the above U.S. patent does not prove to be satisfactory from a practical viewpoint. Generally, the production of an alcohol by hydroge Ra-C=O + Re-CHOH-CR-CHOH + R-C=O 15 nating a carbonyl compound having an alkenyl or aryl k d k d group in the vapor phase has the following problems. (I) (II) (III) (IV) (1) Since the alkenyl group is more easily hydroge nated than the carbonyl group, a large amount of a wherein R and R both represent a substituent having saturated aldehyde or saturated alcohol forms as a by an alkenyl or aryl group, or one of them is a substituent 20 product. having an alkenyl or aryl group and the other is hydro (2) When an aldehyde having an aryl group is used as gen, and each of Re and R represents hydrogen, an the carbonyl compound, side reactions such as the hy alkyl, hydroxyalkyl, alkenyl, phenyl or substituted drogenation of the aryl group or the hydrogenolysis of phenyl group. 25 the starting aldehyde occur, and it is difficult to obtain Alcohols of formula (III) that can be produced by the desired alcohol in a high yield. this reaction have a wide range of applications, and are (3) In particular, when an alpha,beta-unsaturated useful, for example, as important raw materials or inter carbonyl compound is used as the starting material, the mediates in the fields of perfumes, medicines and poly selective hydrogenation of the carbonyl group becomes S. With regard to the production of alcohols (III) by 30 more difficult because of conjugation between its olefin selective hydrogenation of the carbonyl groups of car bond and the carbonyl group. To increase the selectiv bonyl compounds of formula (I), the Nagase et al. ity for an alphabeta-unsaturated alcohol, relatively method comprising hydrogenating the carbonyl com mild reaction conditions are required. This inevitably pound in ethanol using a catalyst prepared by adding a leads to a low conversion. Furthermore, even under the trivalent iron compound to a Raney-type catalyst com 35 mild reaction conditions, the amount of saturated alde posed of silver and zinc Chem. Lett, 1615, (1983)), and hyde and saturated alcohol as by-products are still a method comprising hydrogenating the carbonyl com large, and the yield of the desired alcohol is low. pound in the presence of a rhodium catalyst and an It is an object of this invention therefore to provide a amine Bull. Chem. Soc, Jap., 50 (8), 2148, (1977), for catalyst which can be used, without the inconveniences example, have been known heretofore. These methods of the prior art discussed above, in a reaction of selec are carried out under an elevated pressure of 50 to 80 tive catalytic hydrogenation of the carbonyl group of a kg/cm-G, and moreover, the resulting alcohols should carbonyl compound having an alkenyl or aryl group be separated from the solvent or the amine after the using a primary or secondary alcohol as a hydrogen reaction. Hence, these methods require many process source (vapor phase hydrogen transfer reaction). steps and much labor, and raise many problems in econ 45 The vapor-phase hydrogen transfer reaction is a reac omy and productivity from the viewpoint of industrial tion whereby the starting carbonyl compound is con production. verted to an alcohol by hydrogenation and the starting On the other hand, a method of selectively hydroge alcohol is converted to an aldehyde or ketone by dehy nating the carbonyl group of such a carbonyl com drogenation, and has the dual advantage that useful pound as that of formula (I) by vapor-phase hydrogena 50 aldehydes and ketones can be simultaneously produced tion reaction would be very advantageous in regard to by properly varying the type of the starting alcohol. productivity. Such a method is described in the prior Examples of suitable carbonyl compounds having an literature. For example, German Pat. No. 1,230,012 alkenyl or aryl group are shown below without any describes a method in which crotonaldehyde is con intention of limiting the invention thereto. Examples of verted to crotyl alcohol at a temperature of 200 C. and 55 a pressure of 15 atmospheres by using a catalyst com carbonyl compounds having an alkenyl group are unsat prising cadmium, copper and magnesium. U.S. Pat. urated aliphatic aldehydes or ketones having 3 to 10 Nos. 4,072,727 and 4,096,193 describe a method in carbon atoms such as (a) acrolein, (b) methacrolein, (c) which acrolein is converted to allyl alcohol at a temper crotonaldehyde, (d) methyl vinyl ketone, (e) seneci ature of 100 to 200 C. and a pressure of 250 psi to 2,500 oaldehyde, (f) 3-buten-1-one, (g) ethyl vinyl ketone and psi using a catalyst comprising silver and cadmium. (h) 5-hexen-2-one. They will respectively be converted These methods, however, require relatively high pres to the corresponding alcohols, i.e. (a) allyl alcohol, (b) sures. Furthermore, because the olefin bond portion of methallyl alcohol, (c) crotyl alcohol, (d) 3-buten-2-ol, the starting carbonyl compound is hydrogenated at a (e") 3-methyl-2-buten-1-ol, (f) 3-buten-1-ol, (g) 1-pent high ratio, the selectivity of the desired alcohol is insuf 65 en-3-ol and (h') 5-hexen-2-ol. ficient, and the method is far from being satisfactory. Examples of suitable carbonyl compounds having an One known method for hydrogen transfer reaction aryl group are aromatic aldehydes or ketones repre between an aldehyde and an alcohol as in the present sented by the following formula 3 4,731,488 4.
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