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United States Patent 0 3,504,046 United States Patent 0 "Ice Patented Mar. 31, 1970 1 2 higher temperature would make such a difference in the 3 504,046 ALKYLATION OF NAPHTHALENE WITH PRO isomer product ratio. PYLENE IN THE PRESENCE OF PHOSPHORIC In accordance with the present invention the solid ACID CATALYST phosphoric acid catalyst and the naphthalene are charged Edward Jonathan Scharf, Somerville, and Herbert Ru into a suitable reaction vessel, such as an autoclave. The ‘dolph Kemme, Piscataway, N.J., assignors to American system is purged with nitrogen and then with propylene. Cyanamid Company, Stamford, Conn., a corporation of The mixture is then heated to the desired temperature, Maine agitation started and the reaction allowed to proceed un No Drawing. Filed Apr. 26, 1968, Ser. No. 724,626 der autogenous pressure. Upon completion of the reac Int. Cl. C07c 3/54 10 tion, the reactor is cooled, the product mixture with US. Cl. 260-671 2 Claims drawn and the catalyst separated. Any of the solid phosphoric acid catalysts disclosed ABSTRACT OF THE DISCLOSURE in US. Patent Nos. 2,575,457, 2,584,102, 3,183,233 and 3201,486 may be used in the invention. In general, The alkylation of naphthalene with propylene in the 15 they are comprised of phosphoric acid on an inert presence of solid phosphoric acid catalysts is conducted support, such as kieselguhr. They are used in the alkyla at temperatures above about 300° 0., whereby the ratio tion reaction in an amount, based on the total weight of beta- to alpha-isopropyl naphthalene in the product of naphthalene and proylene used, of at least about 1% is substantially increased. by weight. Although the reaction appears to be rela 20 tively insensitive to catalyst loading, it is preferred to used the catalyst in an amount of from about 5% to > 'This invention relates to an improved method for the about 20% by weight. The catalyst is insoluble in the production of isopropyl naphthalenes. More particularly, reaction medium and constitutes a separate, heavier it relates to an improved process for the preparation phase, which is easily separated after the reaction, such of isopropyl naphthalenes wherein a high ratio of beta 25 as by ?ltration. to valpha isomers is obtained. As aforeindicated, the ratio of beta to alpha isomer A number of processes have been employed or pro obtained in the reaction is substantially increased when posed for preparing alkylated napthalenes. In some the the reaction is conducted at temperatures above about yields are poor and in others the concentration or more 300° C., particularly above about 350° C. Thus, al than one isomer is signi?cant. The dit?culties of re 30 though other reaction parameters, such as the degree solving isomeric mixtures of alkylated naphthalenes is of conversion achieved and ratio of naphthalene to pro complicated by the fact that the isomers have very close pylene used, exert other effects, the beta to alpha isomer ly related boiling points. ‘In instances where the beta iso product ratio is critically dependent on the reaction tem mer is desired, for example where it is to be converted perature. For example, while longer reaction time gives into beta naphthol by subsequent oxidation and acidi 35 increased conversion of the naphthalene, the formation ?cation of the oxidized intermediate, it is important that of higher alkylates (di-, tri-, tetra-isopropyl naphtha the alkyl naphthalene be predominantly beta isomer in lenes) is increased also. However, this may be largely order to ensure the best possible yields of the desired overcome by operating the reaction at low conversions product. The presence of appreciable quantities of the and recycling the reactants. Also, the ratio of naphtha alpha isomer in the isomeric mixture of alkylate results 40 lene to propylene employed has an eifect on the amount in contamination of the ?nal product with. the alpha of higher alkylates formed in the reaction. Thus, While isomer. In view of the difficulties of separating the pure the reaction may be conducted using equimolar amounts isomers from isomeric mixtures of alkylated naphtha of propylene and naphthalene, and even slight excesses lenes, coupled with the dilfculties of oxidizing isomeric of propylene, it has been found that the formation of mixture thereof which contain signi?cant quantities of 45 monoalkylated product is favored by the use from 1 to the alpha isomer, there exists the need for improved about 10 moles of naphthalene per mole of propylene, methods of alkylation of naphthalene wherein the prod i.e., a mole ratio of naphthalene to propylene of from uct contains the beta-isomer in high ratio. 1 to about 10, and particularly about 5-10. The reaction of propylene with naphthalene to pro Pressure is not a critical parameter of the reaction duce isopropyl nathphalene is well known. Various cata from the standpoint of producing a high beta/alpha lysts have been proposed or employed for use in this isomer ratio. The reaction is normally operated under reaction. |Solid phosphoric acid catalysts, such as phos autogenous pressure, although the reaction may be addi phoric acid on inert carriers like kieselguhr, have been tionally pressurized with propylene or an inert gas, reported in the alkylation of benzenes. Thus, US. 2,575, 55 such as. nitrogen. 457 and US. 2,584,102 disclose the preparation of such The alkylation may/be conducted either batchwise, for catalysts and their use for the alkylation of aromatic example, in an autoclave, or continuously, for example, compounds, including naphthalene. Similarly, lU.S. 3, using the catalyst in ?xed bed operation. Reaction times 201,486 discloses a process for the alkylation of alkyl in a continuous reaction system may be quite short, oper atable organic compounds, including naphthalene, using 60 ating at low naphthalene conversions and recycling the a solid phosphoric acid. A similar process is disclosed reactants. in US. 3,183,233. However, there is no disclosure in Although not preferred, the alkylation may be con these patents of the production of isopropyl naphtha ducted in the presence of a solvent which is inert with lene with a high beta-isomer content. respect to the reaction. Thus, such solvents as halogenated It has now been discovered that when the alkylation 65 hydrocarbons, for example, carbon tetrachloride, may be of naphthalene with propylene in the presence of the' used, if desired. solid phosphoric acid catalyst is carried out at a tem The invention is illustrated in the following example. perature above about 300° C., i.e., from about 300° C. to about 400° C., the ratio of beta to alpha isomer in EXAMPLE the isopropyl naphthalene product is markedly higher 70 A series of alkylation reactions (Runs 1-8) were car than that obtained at lower temperatures. This is a ried out according to the following procedure. The appro surprising result since it would be expected that the priate amount of solid phosphoric acid catalyst and naph 3,504,046 4 thalene were charged to an autoclave. The temperature As can be seen from the data in Table I, the ratio of was raised to about 80° C., to melt the naphthalene and 7 beta to alpha isomer obtained is markedly higher when the system was purged with nitrogen. The nitrogen was the reaction is conducted at 300-350° C. (Runs'3—8) as then purged with propylene. (The, amount of propylene compared to 200° C. (Runs 1 and 2). It will be seen, remaining in the autoclave at atmospheric pressure is in furthermore, that the higher reaction temperatures pro signi?cant and no reaction occurs under these conditions.) vide these higher ratios over a wide range of reaction The autoclave was then sealed, and heated to the indi times, pressures and mole ratios or naphthalene to propyl cated temperature. After pressurizing the system to the ene. Thus, even at short reaction times and low pressures desired pressure with propylene, agitation was started. the proportion of the beta isomer is substantially in Additional propylene was added as required to maintain 10 creased. It is thus seen that the obtainment of the higher this pressure as the reaction proceeded. The reactions ratios is most critically dependent on the temperature of were conducted under the conditions shown in Table I. the reaction. The cooled reaction mixtures, after ?ltering off the cata We claim: lyst, were analyzed by vapor phase chromatographic 1. In a process for the manufacture of isopropyl methods with the results shown in Table I. 15 naphthalene wherein naphthalene is reacted with propyl The solid phosphoric acid catalyst used in all of the ene in the presence of a solid phosphoric acid catalyst at runs consisted of a calcined mixture of about 21.5% by superatmospheric pressure, the improvement which com weight of kieselguhr as adsorbent support and about ‘ prises carrying out the reaction at a temperature above 78.5% by weight of phosphoric acid containing about ' about 300° C. ' 83% P205. The catalyst in this instance was in the form 20 2. The process of claim 1 wherein the reaction temper of a powder. However, it may suitably be in the form of ature is from about 300° C. to about 400° C. pellets, granules, or the like. TABLE I.—ALKYLATION OF NAPHTHALENE WITH PROPYLENE Analysis - Mole Ratio Catalyst, Pressure Temp. Time Ratio Percent 02 Percent 13 Percent {3/ Percent Percent (p.s.i.g.) (° C.) Quin.) N/P Percent N I IPN Percent 11 PIPN 15.0 200 200 63 2.5 63. 0 21. 3 7. 7 0.36 7. 1 15. 0 1, 000 200 3 l7. 0 93. 0 4. 2 2.
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