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I Bg M Clbborneg Patented Nov NOV- 29, 1949 c. s. cARLsoN ETAL 2,489,619 ‘ RECOVERY OF NORMAL PROPYL ALCOHOL __./'FRQM OXYGENATED COHPOUNDS ' Filed Aug. 23, 1948 - H2O Ann MAKE UP Emrumak ——> 3 i {O WATER. Carl 6. Carlson ~ T2411 6.32.051: tson. {inventors Carter E.‘ orLer I bg M Clbborneg Patented Nov. 29, 1949 2,489,619 UNITED STATES ‘PATENT ' OFFICE RECOVERY OF NORMAL PROPYL ALCOHOL ' FROM OXYGENATED COMPOUNDS Carl S. Carlson, Elizabeth, N. J ., Nat C. Robertson,. Corpus Christi, Tex., and Carter E. Porter, Cranlord, N. J., assignors to Standard Oil De velopment Company, a corporation of Delaware Application August 23, 1948, Serial No. 45,724 11 Claims. (Cl. 202-42) - 1 ‘This invention relates to the puri?cation of n Bolling propyl alcohol, and particularly, to the puri?ca Boiling P omt- (H10 tion of an aqueous n-propyl alcohol fraction Ccmpound Poirétédry), Azeotropmy which is contaminated with other close-boiling l ' 0 C. oxygenated compounds, such as other alcohols, 5 ' Ethyl Alcohol ________________ __ ._ 78. 3 78. 1 esters, aldehydes and ketones. Isopropyl Alcohol ____________ __ _ 82. 4 80. 2 The drawing shows diagrammatically a train n-propyl Alcohol. _ _ 97. 2 87. 7 Ethyl Propionatc ___________________ _ _ 99. 1 81. 2 of apparatus for carrying out my process. Sec Butyl Alcohol. 99. 5 87. 7 Numerous processes are known in which an propyl Acetate 101. 6 82. 4 10 t amyl Alcoh ._ 102. 4 87. 2 aqueous solution of a mixture of oxygenated com Isobutyl Alcohol 108. 1 89. 8 pounds are produced. Typical of these processes sec-Butyl acetate . _ _ _ _ . _ _ _ __ 112. 0 y 87. Isobutyl Acetate- ___ 117. 2 ‘ 87. 4 are the well-known Fischer ‘synthesis, wherein . n-butyl Alcoh _ . _ 118. 92. 3 hydrocarbons and oxygenated compounds are Ethyl Butyrate__-__ 121. 6 87. 9 produced by the reaction between oxides of car Paraldehyde ______ _ _ 124 90. 4 bon and hydrogen in the presence of catalyst; 15 the numerous processes employed for the oxida It will be seen from the above range of boiling tion and partial oxidation of petroleum hydro points that the separation of an aqueous mixture carbons, particularly the lower aliphatic hydro of the above materials or any number'of them by carbons; and the so-called “0x0” process, where fractional distillation, would be a very di??cult in ole?ns are reacted with carbon monoxide and 20 procedure, demanding highly e?icient fraction hydrogen in the presence of a catalyst. ation. The presence of water during fractional A typical mixture consisting substantially of distillation is conducive to the formation of the n-propyl alcohol, which is to -be puri?ed accord binary aqueous azeotropes which boil so closely ing to the terms of this invention, has the follow that separation is practically impossible on an 25 economic basis. ing composition. ‘ This invention provides a means whereby'n propyl alcohol can be substantially freed from Component Amount other close-boiling components by distillation, by Wt. Percent the creation of other azeotropes in the system 2-6 Aldehydes _________________________________________ . 30 which make the separation'easier as a result of Esters . _ _ . _ _ . _ . _ _ _ _ _ . _ _ _ _ . _ _ _ _ _ _ _ _ _ _ . __ 0. 2-3 the increase in boiling point spread between the Water _________________________ _ _ _ 28~29 Alcohols (principally n-propyl) _ . _ _ _ 62-69. 8 azeotropes so produced and the azeotrope of n Ketones . _ _ _ _ _ _ _ _ _ _ _ _ . _ _ _ _ _ . _ _ _ _ _ _ _ _ _ . _ _ _ Trace propyl alcohol; According to the terms of this invention an The alcohols involved included ‘on an alcohol 35 aqueous “n-propyl cut” is puri?ed by an azeo basis, analyzed as follows: tropic distillation process wherein the harmful Volume per cent close-boiling impurities are removed overhead by an aliphatic ether entrainer. The aliphatic ether n-Propanol _____________________________ __ 90 employed according to the terms ofthis inventionv i-Propanol _____________________________ __ 6 40 is one boiling between 55° C. and 110° C., but pref Sec. BuOI-I _____________________________ __ 2 erably an aliphatic ether boiling in the range Ethanol ________________________________ __ 2 of 55° C. to '70 C. i-BuOH _____________________________ __ Trace The following ethers are suitable: The above analysis is typical of the so-called “n Boiling point ‘’ C. propyl cut” obtained from the water-soluble neu 45 tral products of the Fischer synthesis. Such a Diisopropyl ether ______________________ __ 67.5 out has a boiling range of 783° C. to 124° C., on Ethyl propyl ether _____________________ __ 64 an anhydrous basis, and a boiling range of 78.1° Chloro ethyl methyl ether ______________ __ 59.5 C. to 92.3" C., on a wet basis. Tertiary butyl ethyl ether _______________ __ 69 The following compounds are included among 50 Allyl ethyl ether ____'_ __________________ __ 67.6 those found in the “n-propyl cu.” The com Isobutyl methyl ether (at 741 mm) ______ __ 59 pounds are listed with their boiling points and Butyl methyl ether ____________________ __ 70 the boiling points of their aqueous azeotropes: Etc. 2,489,619 . 3 In the distillation puri?cation process employ is an ether boiling in the range of 70° C. to 110° 6., ing an ether boiling between 55° C. and 70° C., the provided one uses such ethers in controlled n-propyl alcohol does not azeotrope with the amounts so as to remove from the “n-propyl alco aliphatic ether nor with the aliphatic ether and hol cut” only those contaminants other than water; hence, its e?ective boiling point remains 5 n-propyl alcohol, or in amounts such that only a the same, thus permitting its separation from the very limited amount of n-propyl alcohol is re other impurities whose boiling points are e?ec moved with the ether. tively lowered due to the formation of azeotropes, In batch operation, however, the advantage is thus allowing the separation to occur. In car unique in that employing entrainers within the rying out the invention, suiiicient ether is added 10 narrow boiling range of 55° C. to 70° C. none of to the crude aqueous n-propyl alcohol mixture to the n-propyl alcohol whatever is lost overhead cause its dehydration and its puri?cation due to during removal of the impurities. ' the formation of azeotropes between the con Examples of the higher boiling ethers which taminants and the aliphatic ether employed. may be employed are: This invention is particularly applicable to the 15 Boiling point °C. recovery of n-propyl alcohol from an aqueous Amyl methyl ether ___________________ __ 88. 5 mixture comprising n-propyl alcohol, ethyl al Butyl methyl ether ___________________ .._ 90-93 cohol, isopropyl alcohol, paraldehyde, and esters, Allyl ether ___________________________ __ 94. 3 such as ethyl propionate, n-propyl acetate, iso Propyl ether _________________________ .._ 91 butyl acetate, ethyl butyrate and secondary butyl 20 Ethyl isobutyl ether __________________ __ 80 acetate. When such a mixture is subjected to Dichloromethyl ether _________________ __ 105 fractional distillation in the presence of at least Etc. one aliphatic ether boiling in the range of 55° C. Although all of the ethers boiling in the range of to 110° C., and preferably, 55° C. to 70° C., an overhead distillate is produced containing sub 55° C. to 110° C. are operable under the conditions 25 stated, the unsaturated ethers are not preferred stantially all the ethyl alcohol, all of the isopropyl due to their tendency to undergo polymerization. alcohol, paraldehyde (in the form of acetalde Likewise, the chloroethers are not preferred due hyde produced by depolymerization) and all the to their tendencies to undergo hydrolysis during esters. The bottoms resulting from such an azeo tropic distillation consist substantially of n \distillation. The saturated ethers, among those propyl alcohol. 30 mentioned, are the preferred species according to When substantial amounts of the butyl alcohols the terms of this invention. are present, such as secondary butyl alcohol, The invention will be illustrated by the'puri? n-butyl alcohol, and isobutyl alcohol, and tertiary cation of a “n-propyl cut” from which secondary amyl alcohol, the “n-propyl cut” is ?rst subjected butyl alcohol, isobutyl alcohol and tertiary amyl to a water extractive distillation whereby sec 35 alcohol have been removed, such as by a water ondary butyl alcohol, isobutyl alcohol, tertiary extractive distillation process previously de amyl alcohol and some isopropyl alcohol are dis scribed. The crude n-propyl alcohol feed will tilled overhead. Such a normal propanol cut con then consist of a mixture of ethyl, isopropyl, taining substantial amounts of the butyl alcohols 40 n-butyl and n-propyl alcohols, paraldehyde, and and tertiary amyl alcohol, has the following typi esters, such as ethyl propionate, n-propyl acetate, cal analysis: secondary butyl acetate, isobutyl acetate and ethyl butyrate. The crude aqueous “n-propyl Weight per cent alcohol cut” of the above composition is led to Water _ _ _ _ _ _ . _ _ __ _ 30 n-Propanol 59 fractional distillation zone 2 through line I. An Iso-propanol _ ‘ 4 45 ether of the type described, such as diisopropyl ether, is added to the tower via line 3. Alter n-Butanol _____________________________ _. 1 natively, the ether entrainer could be added to Sec-butanol _._.. 3 the crude alcohol out prior to introduction of the Iso-butanol ____________________________ __ 2 same into the fractionation zone.
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