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9 WO 7/NFC Re Oct. 14, 1952 W. M. SMITH 2,614,070 HEAT TREATING AND DISTILLATION OF OXO ALCOHOLS Filed Nov. 16, 1949 COMAAM sa, a A42A Ayala 7aa 7O OCMAA2 A/ASA Ad S7Coa a GA 2 -pCOMADAM, CAE Ae 9 WO 7/NFC re - 15 2O HS 7aas/A/ZaAs, 7O UAE a (3) -o 22 7o s7 oadca /2 AFA2a C7 / C /ya 7/NG M6 Es 7O CL/AA /6 eas Cd/a Aa Patented Oct. 14, 1952 2,614,070 UNITED STATES PATENT OFFICE 2,614,070 HEATREATING AND DASALLATION OF OXO ALCOHOLS Warren M. Smith, Baton Rouge, La., assignor to Standard Oil Development Company, a corpo ration of Delaware Application November 16, 1949, Seria No. 2,628 5 Claims. (C. 202-5) 1. 2 This invention relates to improvements for the a large number of different types of reactions purification of crude alcohols, by a distillation take place to form a variety of products. The procedure. More specifically the invention re chief primary reaction products as Outlined lates to an improved distillation method for puri above are aldehydes. These aldehydes themselves fying higher boiling Oxo alcohols which contain 5 can undergo further reactions to yield other prod inpurities of the type tending to undergo de ucts. For instance, the aldehydes condense: With composition at the normal boiling point of the each other to yield aldols. At least a part of Oxo alcohol undergoing purification by distilla the aldols undergo dehydration to yield alpha-, tion. beta-unsaturated aldehydes. Some ketones are In practicing this invention, the crude Oxo 0 also formed under the reagtion conditions. A alcohols containing the impurities are subjected part of the aldehydes formed in the reaction Zone to a thermal treatment at elevated pressure for is hydrogenated to alcohols and the alcohols so a sufficient period of time to decompose and/or formed react with aldehydes and ketones present convert the higher boiling impurity compounds to give mixtures of acetals, hemi-acetals, and present in the crude OXO alcohols to Some other 5 ketals. These compounds can undergo further. materials, generally easily volatilizable materials, reactions, including dehydration, to give ethers, which are removed from the OXO alcohol prod particularly those of the unsaturated types. The ucts by distillation. The heat treatment is car alcohols can esterify the acids present to give ried out in One Zone and the materials Yinore esters. Hydrogenation of a part of the olefin volatile than the alcohol are removed from this 20 starting feed stock, as well as some deoxygena Zone as overhead while the bottoms product con tion of oxygenated intermediates, gives. Some hy taining substantially all the Oxo alcohol is dis drocarbons in the final Oxo product mixture. In charged to a second distillation Zone Operating addition, other more complex and less known re-- preferably at a lower pressure and slightly lower actions also occur between the various inter 25 mediates and products obtained thereby yielding temperature, from which zone the Oxo alcohol, a mixture of higher boiling impurities and con relatively free of both more volatile and higher taminants of the oxygenated type. - boiling impurities is taken off as overhead In the hydrogenation stage, the rinixtures of product, acids, Saturated and unsaturated aldehydes, A number of alcohols which are of great Com alcohols, ethers, aldol condensation products, mercial importance are prepared by Synthetic 30 glycols, acetals, ketals and esters are hydro processes and especially by the so-called OXO re genated in the presence of a suitable hydro action. The term "Oxo reaction' is a term used genating catalyst to yield more saturated prod to describe the preparation of oxygenated organic lucts containing a higher percentage of alcohols compounds by the reaction of carbon monoxide and non-Olefinic compounds. The product from and hydrogen with olefinic hydrocarbons in the 35 the hydrogenation stage is essentially alcoholic presence of a carbonylation catalyst. The in nature, with various impurities. Some of . method is used particularly for the manufacture these inpurities, especially the unsaturated of various primary alcohols, Specifically Octyl ethers, acetals, ketals, aldols and esters are quite alcohols, by operations involving interaction of unstable toward heat. For instance, in general, carbon monoxide, hydrogen, a hydrocarbon mix 40 the aldols, acetals, heini-acetals and ketals have ture containing substantial amounts of heptenes, a great tendency to undergo degradative decom and a cobalt carbonylation catalyst to form octyl position reactions whenever the alcohol is sub aldehydes, and subsequent reduction of these jected to a simple atmospheric distillation. In octyl aldehydes by catalytic hydrogenation to a many cases, thermally unstable esters are present mixture relatively high in Octyl alcohols. 45 and undergo both thermal and hydrolytic decom Primary alcohols of this general type are of positions under distillation conditions. great economic importance and interest because To be more Specific, if a crude fraction of iso of their use as intermediates in the manufacture Octyl alcohol as produced by the oxonation of of piasticizers of di-ester type. Those considered Ci olefins, followed by hydrogenation, is distilled to be particularly valuable are the di-esters of 50 either in a batch or continuous manner and cuts phthalic and maleic acids. The Oxo reaction and removed according to increasing boiling point, subsequent hydrogenation have been found to then the following fractions can be isolated: comprise a highly economical and valuable 1. A fraction containing unconverted olefin hy method for manufacturing octyl alcohols from drocarbons, Saturated hydrocarbons, and unhy. cheap and readily available hydrocarbon ma 55 drogenated aldehydes. terials.In the Oxo or carbonylation stage of the process 2. A fraction containing principally iso-octyl 2,614,070 3 4. alcohol contaminated with decomposition prod additional and excessive purification prior to their ucts of aldols, hemi-acetals, acetals, ketals, esters, use aS plasticizers. ethers, and the like. It can thus be seen that it is highly desirable 3. A fraction containing higher boiling mate to have the alcohol products Such as those ob rials including esters and unsaturates of low vola tained in the Oxo reaction, as free of aldehydes, tility, higher alcohols, decomposition products of acetals, and other chemically reactive and ther acetals and undecomposed acetals, ethers, and mally unstable Substances as possible, particu ketals. larly if they are to be used later for the produc A mechanism which fits the facts in a general tion of plasticizer materials. fashion may beformulated in which it is assumed O This same type of problem of unstable impuri that decomposition reactions of various thermally ties also exists in connection with other alcohols and hydrolytically unstable materials proceed to made by the OXO reaction, particularly for alco an appreciable extent at the normal distillation hols of the range of C4 to C15 or higher. For ex temperature of the alcohol being purified, in this ample, the C9 alcohols, prepared by the reaction particular case, the iso-octyl alcohol. The de of C8 olefins such as diisobutylene with carbon composition reactions occurring produce Water, monoxide and hydrogen may be purified in the especially by aldol dehydration, and this water Same manner as that described herein for the probably contributes further to decomposition re purification of the C8 OXO alcohols. actions by its hydrolytic action, especially on such This novel distillation process can be used for inpurities as esters, ketals, acetals and unSat 20 purification of alcohols containing thermally un urated ethers. The more Wolatile of the deCOm Stable high boiling impurities obtained from any position products, including various Saturated and Source, and is especially applicable to treatment unsaturated aldehydes, Water, and alcohols (in Of alcohols having from 4 to 15 carbon atoms. It cluding both iso-octyl and other alcohols of lower finds particular application in purification of al boiling point), go overhead with the alcohol prod Cohols obtained by the so-called Oxo reaction uct and contaminate the latter since all these mentioned above and especially to alcohols of the products frequently boil within the same range. C8 and C9 class, although the process can also be Any aldehydes, which are usually quite volatile, applied advantageously for other alcohols con are distilled over With the alcohol fraction in this taining similar types of thermally unstable im manner and Subsequently combine very readily 30 purities, particularly alcohols obtained by hydro with the distilled alcohol product, reforming ac genation of carbonyl compounds. etals and henni-acetals, which are likewise subject A typical Ca Crude Oxo alcohol mixture such as to a second and Similar decomposition process can be employed as starting feed in this improved When a redistillation of the alcohol fraction is purification process has the following composi attempted for further purification. Aldehydes tion: and other low boiling decomposition products are objectionable because they lower over-all product Weight per cent purity, and, due to instability, cause difficulties in Alcohol as C8---------------------------- 65.0 the use of the alcohol especially When it is used as Aldehyde as C8--------------------------- 1.8 an esterification reactant. 40 Acetal as C24----------------------------- 3.7 It can readily be seen that it is difficult, if not Fister as Co------------------------------ 3.0 impossible, to remove
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