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2,628,249 United States Patent Office Patented Feb. 10, 1953 2,628,249 UNITED STATES PATENT OFFICE 2,628,249 ESTERIFICATION PROCESS Anthony S. Bruno, Jr., Pittsburgh, Pa., assignor to Pittsburgh Coke & Chemical Company, Pitts burgh, Pa., a corporation of Pennsylvania. No Drawing. Application January 3, 1951, Serial No. 204,285 2 Claims. (C. 260-45) 2 This invention relates to new improvements in (3) The provision of new esterification catalysts esterification processes and is particularly con Which increase the speed of reaction to Such an Cerned with the production of discoloration-free extent that the tendency to produce color-form esters of high molecular weight and low vapor ing bodies is greatly reduced. preSSure from the corresponding alcohol and acid. Still further objects and the entire Scope of applicability of the present invention will be FIELD CE INVENTION come apparent from the detailed description Large quantities of esters are consumed each given hereinafter; it should be understood, how year as plasticizers in the formation of plastic ever, that the detailed description and specific Compositions, coating compositions, films, fila O examples, while indicating preferred embodi ments, and the like. One of the prime considera ments of the invention, are given by way of illus tions given to any ester for use in such manner tration. Only, since various changes and modifica is the purity of the product, i.e., the lack of con tions Within the Spirit and Scope of the invention taminating materials giving the product unde will become apparent to those skilled in the art Sirable color characteristics or acidic or similar from this detailed description. properties, which may cause the ester or the ma terials with which they are mixed to be unstable GENERA, DESCRIPTION or cause the products to be unusable for many These objects are accomplished according to purpoSeS. Accordingly, an extensive amount of the present invention by the production of esters Work has been carried out in an effort to devise 20 through the condensation of a carboxylic acid improvements in the existing procedures for ester With an alcohol in liquid phase contact with a production, so as to produce products having the catalyst comprising a mixture of (1) a sulfur highest possible degree of purity and freedom containing acid from the group consisting of sul from discoloration. furic and Sulfonic acids, and (2) activated carbon. In this regard, it has been known that certain is Sufficient of the catalytic mixture is used to have laterials, such as mineral acids, sulfonic acids, a catalytic effect upon the condensation of the ion exchange resins, or the like, can be used as alcohol and the acid. catalysts in esterifications. However, such mate The SucceSS Of the present invention is due pri rials, as the ion exchange resins, are costly and marily to the unique discovery that a mixture of difficulty of recovery from the reaction mixture activated carbon with sulfuric acid or an aryl and bulkiness make them generally unattractive. 3) Sulfonic acid can serve as a catalyst in esterifica On the other hand, the mineral acids and aryl tion procedures and that, when this catalytic Sulfonic acids possess the disadvantage that they mixture is employed, the resulting esters possess discolor the resulting esters. Although the such unpredictably high degrees of purity and lack discolored ester can be rendered colorfree, the of discoloration and are obtained in surprisingly treatments required are most involved and quite 35 high yields. This is in contrast to the results COstly. Consequently, the trade has been at obtained when the aryl Sulfonic acids, sulfuric tempting for SOme time to find new and better acid, or activated carbon per se are used as esterification catalysts and methods which do not esterification catalysts which, in the case of the pOSSess the detracting disadvantages referred to. acids, result in the formation of discolored esters 4) and Which generally require longer periods of OBJECTS time for completion. A principal object of this invention is the pro vision of new improvements in esterification pro EXAMPLES cedures, particularly, the methods used to form A more complete understanding of the pro high molecular weight esters. Further objects 4. cedures of this invention may be had by refer include: ence to the following illustrative examples of (1) The provision of new methods for forming actual operations in accordance with the inven plasticizer-type esters in very high yields, which tion, wherein all parts are by Weight. are Substantially free Cf discoloration and which pOSSeSS an extremely high degree of purity. 5: Eacample I (2) The provision of new catalysts for use in This example illustrates the preparation of esterification reactions which may be employed dibutyl phthalate. in place of prior known esterification catalysts 200 parts of phthalic anhydride, 200 parts of without causing discoloration of desired products, butyl alcohol, one part of 95% sulfuric acid and and 5 5s 2.5 parts of activated carbon are charged into a 2,628,249 3 4. suitable reaction vessel fitted with a reflux Con DETAL LED DESCRIPTION denser, a reflux water separator, and an efficient One of the important reactants for use ill stirrer. With the contents of the vessel thor these new procedures is activated carbon which oughly agitated, they are heated up to a con may be derived from a number of different trolled reflux temperature of 145° to 150° C. and 5 sources. The exact form in which the activated retained there for five hours. During this period, carbon is used in the reaction is not critical, but water of reaction is removed and 90 parts of butyl most effective results are obtained when the car alcohol are added in 10 part portions to compen bon is used in an extremely finely divided form, sate for loss of alcohol dissolved in the removed e.g., a size where 85 to 95% Will pass a 325 mesh Water. O standard sieve. Most activated carbons appear At the end of five hours, the reflux condense!" to be more or less generally useful for this pur is shut off and the excess alcohol is allowed to pose, but equally desirable results are not ob distill off from the reaction vessel. The dibutyl tained with all activated carbons. It has been phthalate contained in the reaction vesselis. With discovered that activated decolorizing carbons drawn and passed to a mixing vessel where Sufi are most desirable. cient caustic soda is added to just neutralize the The other component of the catalytic mixture free mineral acid. The ester is then Washed. With for use with these new procedures is a sulfur an excess of water, after which it is passed containing acid, which may be either sulfuric through filters and collected. It is then blown acid or a sulfonic acid. Examples of Suitable with steam to insure complete removal of vola 20 aryl sulfonic acids include benzene, toluene, tiles, dried and filtered. naphthalene, or para-butylphenol Sulfonic acids. 354 parts of dibutyl phthalate having the foll Also alkane Sulfonic acids, such as petroleum oil lowing Specifications are obtained: sulfonic acids, may be used. Sulfuric acid is the Percent ester------------------------- 99.5% preferred material, and it is desirable to employ Percent acid (as phthalic acid).--------- 0.003% 25 a substantially concentrated Sulfuric acid, such Color APHA Scale--------------------- 10 to 15 as the commercial 95% acid. However, less con Specific gravity 20/20.---------------- 1.0474 centrated acid may be used. Percent Water------------------------ 0.05 The relative proportions of carbon to acid Refractive index 7p------------------ 1.4910 y in the catalytic mixture may be varied. However, U for best Tesults, it has been found that mixtures Eacample II containing about one part of the sulfur-contain The reaction of Example I is carried out in an ing acid for each one to 20 parts of activated identical manner, except that 50 parts of benzene carbon give the best esters with the greatest are added to the reaction mixture as an azeotropic speed. agent in order to effect a controlled temperature The quantity of the catalytic mixture of acti of 145° to 150° C. and obtain an efficient separa vated carbon and acid relative to the amounts of tion of water. The resulting product has the acid and alcohol used in the esterification reac same specifications as the product of Example I. tion can be varied and will be dependent to some extent upon the particular acid and alcohol used Eacample III in the process. Broadly, sufficient of the cata The reaction of Example I is carried out in an lytic mixture is employed to produce a catalytic identical manner, except that the activated car effect upon the condensation on the alcohol and bon is omitted. The resulting ester has an APFEA acid to form the ester. However, best results color of about 200. have been obtained using between 0.1 and 5% by Eacample IV 5 weight of the catalytic mixture in the esterifica tion, i.e., between about 0.05 and 2.5% H2SO4 and This example illustrates the preparation of di about 0.05 and 4.5% activated carbon. 2-ethylhexyl sebacate. The ability of the new catalytic mixtures of The following ingredients are charged into a this invention to form esters of high purity and reaction vessel equipped with stirrer, reflux con freedom from discoloration seems to be general denser, and refux water separator: for all esterification procedures, which form im 606 parts sebacic acid pure or discolored esters when mineral acids, such 859 parts 2-ethylhexanol as Sulfuric or aryl Sulfonic acids, are used as the 200 parts benzene catalysts. However, the invention is most use 1.5 parts sulfuric acid (95%) 5 5 fully applied in the formation of high molecular weight esters, such as those formed from poly 15 parts activated carbon carboxylic acids, of molecular weight greater The materials are heated to 125 to 130° C.
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