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Sept. 4, 1962. MICHIJIRO AKABOSH ETAL 3,052,610 CONCENTRATION of ACETIC ACID Filed May 19, 1960

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Sept. 4, 1962. MICHIJIRO AKABOSH ETAL 3,052,610 CONCENTRATION of ACETIC ACID Filed May 19, 1960 Sept. 4, 1962. MICHIJIRO AKABOSH ETAL 3,052,610 CONCENTRATION OF ACETIC ACID Filed May 19, 1960 INVENTORS MCHIJIRO AKABOSH KK UJ U RAGAM: BY KENSUKE O KUMA AttoRNEY 3,052,610 United States Patent Office Patented Sept. 4, 1962 2 1. acetate. Some of the vinyl acetate from the upper phase 3,052,610 is returned to the top of the distillation zone as reflux, CONCENTRATION OF ACETIC ACD in accordance with conventional distillation technique, Michijiro Akaboshi, Toyonaka City, and Kikuji Uragaini and the remainder is withdrawn as product. and Kensuke Okema, Toyama City, Japan, assignors to Particularly suitable as a source of vinyl acetate for Kurashiki Rayon Co., Ltd., Okayama Prefecture, the distillation operation referred to above is the vinyl Japan, a corporation of Japan acetate-acetic acid mixture which is produced in the syn Fied May 19, 1960, Ser. No. 30,384 thesis of vinyl acetate from acetylene and acetic acid. 6 Claims. (C. 202-42) Prior to its use for the production of polyvinyl acetate This invention relates to the concentration of aqueous O by polymerization, the vinyl acetate must be separated Solutions of acetic acid and is more particularly concerned from the acetic acid. In accordance with the invention, With a process for concentrating aqueous acetic acid solu this operation is combined with the acetic acid dehydrat tions which is effectively integrated with the manufac ing and concentrating operation so that two normally ture of polyvinyl alcohol. independent processing steps are effectively and efficiently In accordance with conventional practice, polyvinyl 5 combined into a single operation which produces sub alcohol is formed by the saponification or "alcoholysis' stantially pure vinyl acetate suitable for the production of polyvinyl acetate which, in turn, is formed by the poly of polyvinyl acetate, and an effectively concentrated or merization of vinyl acetate. Vinyl acetate is conven dehydrated acetic acid suitable for use in the production tionally produced by the action of acetylene upon acetic of further quantities of vinyl acetate by reaction with acid, as described, for example, in the article by L. Wilson 20 acetylene. Greene in “Chemical Engineering, July 1947, 98-99. While the aqueous acetic acid to be dehydrated may in that process there is produced a mixture of vinyl come from any source, such as the rayon-manufacturing acetate and acetic acid which is generally separated by and pyroligneous liquor processing operations referred to distillation. Upon alcoholysis of polyvinyl acetate to above, a particularly suitable source, which permits even produce polyvinyl alcohol, methyl acetate is produced as 25 further integration with the production of polyvinyl alco a by-product, and this compound is hydrolyzed to pro hol, is the aqueous acetic acid produced by the distilla duce an aqueous mixture of methanol, acetic acid, and tion of the aqueous acetic acid-methyl acetate-methyl unreacted methyl acetate. The methanol and methyl alcohol mixture produced by the hydrolysis of methyl acetate are readily separated from the mixture by distilla acetate obtained as a by-product in the alcoholysis of tion, and there is obtained from the bottom of the distilla 30 polyvinyl acetate to produce polyvinyl alcohol. The tion column a Stream of aqueous acetic acid. Aqueous production of polyvinyl acetate and the subsequent alco acetic acid solutions are also produced in a number of holysis of this polymer to produce polyvinyl alcohol and other well-known chemical processes, e.g. the manufac methyl acetate are well-known procedures and are de ture of rayon by the acetate process, or the treatment of scribed, for example in Cline et al. U.S. Patent 2,610,360. pyroligneous liquor as described, for example, in Bright 35 A particularly effective integrated process for the pro U.S. Patent 2,290,157. duction of polyvinyl alcohol from polyvinyl acetate is The problem of concentrating or dehydrating such disclosed in the co-pending application of Tsuguo aqueous acetic acid solutions has been the subject of much Kominami, Serial No. 862,626, filed December 29, 1959. research, and many proposals have been brought forth. 40 It is a feature of the present invention that, except for Methods involving azeotropic distillation are described, for the small amount of reflux, the vinyl acetate does not re example, by D. F. Othmer (Ind. Eng. Chem..., 27, p. 250, cycle through the system and is not repeatedly used, as is 1935). As azeotropic agents there have been proposed the azeotropic agent in the conventional azeotropic acetic various alkyl acetates such as ethyl acetate, hydrocarbons acid-dehydrating operations, so that the fact that vinyl such as benzene and petroleum ether, and alkyl chlorides 45 acetate is a polymerizable compound is not a problem such as carbon tetrachloride and ethylene chloride. How and no difficulty from polymerization is experienced in ever, these azeotropic agents have both advantages and practice. disadvantages. For example, ethyl acetate has a high It is a further feature of the invention that dehydra azeotropic capacity but its solubility in water is high tion of acetic acid is effectively combined with the distill and this solubility further increases substantially when 50 lation of vinyl acetate-acetic acid mixtures produced in the ethyl acetate contains even small amounts of im the synthesis of vinyl acetate and the single operation purities such as alcohols, ketones, and aldehydes. As a which replaces two operations makes possible concurrent result, in most cases this azeotropic agent is used in com economies in operating costs and in apparatus. Substan bination with a hydrocarbon, as shown in H. M. Guinot tially the same apparatus normally used for the distill Japanese Patent 151,490 (1942). 55 lation of acetic acid-vinyl acetate mixtures alone can be It is an object of the present invention to provide an suitably used. improved process for the concentration or dehydration of Other objects and features of the invention will be aqueous solutions of acetic acid. readily apparent from the following detailed description It is a further object of the invention to provide a of the invention and from the accompanying drawing process of the character indicated which is efficiently and 60 wherein there is shown diagrammatically an apparatus effectively integrated with the production of polyvinyl system which can be suitably used for carrying out the alcohol. process of the invention. In accordance with the invention, the aqueous acetic There is shown at 1 a supply of crude vinyl acetate acid solution to be treated is distilled in the presence of solution obtained as product from the synthesis of vinyl vinyl acetate. The vinyl acetate and water form an 65 acetate by the reaction between acetylene and acetic acid, azeotrope of lower boiling point than acetic acid, and this and containing, for example, about 55% by weight of azeotrope is removed from the top of the distillation acetic acid. The introduction of the aqueous solution of zone. At the same time, acetic acid accumulates and is acetic acid to be concentrated is shown at 2. This acetic removed from the bottom of the distillation zone. Upon acid solution may be derived from any source and is suit condensation, the vinyl acetate-water azeotrope separates 70 ably obtained from the hydrolysis of methyl acetate ob into an upper vinyl acetate phase substantially free of tained by the alcoholysis of polyvinyl acetate in the pro water and a lower water phase substantially free of vinyl duction of polyvinyl alcohol. The two solutions are 3,052,610 3. 4. mixed and introduced into distillation column 3 having, acetic acid which comprises mixing said solution with for example, 30 theoretical plates, and being heated by vinyl acetate and distilling the resultant mixture in a distill steam coils or other convenient means known in the art. lation zone, recovering vinyl acetate and water from the In the distillation column, the water and vinyl acetate will top of said Zone, and recovering concentrated acetic acid vaporize as a low boiling azeotrope and the azeotrope from the bottom of said zone, separating said vinyl acetate vapors will move upwardly through the column and will from the water and withdrawing the vinyl acetate from be withdrawn at the top. These low-boiling vapors are the distillation system. condensed in a condenser 4 and the condensate passes 2. A process of concentrating an aqueous solution to a separator 5 wherein phase separation takes place. of acetic acid which comprises mixing said solution with The upper phase in the separator 5 is vinyl acetate and a 0 a mixture of vinyl acetate and actic acid, distilling the portion of it is returned through line 5a to the column combined mixture in a distillation zone, recovering vinyl as reflux to provide a reflux ratio of, for example, 10 to 1. acetate and water from the top of said zone, and re The remainder of the vinyl acetate in the separator 5 is covering concentrated acetic acid from the bottom of said removed as product through line 6. It may be further Zone, separating said vinyl acetate from the water and refined, if desired, by any convenient known procedure, 5 Withdrawing the vinyl acetate from the distillation system. before it is subsequently used, e.g. for the formation of 3. In the manufacture of polyvinyl acetate wherein polyvinyl acetate. The lower phase in the separator 5 acetylene and acetic acid are interacted to form a mixture is water containing a very small amount, e.g. 015 to 1.0 of acetic acid and vinyl acetate and said vinyl acetate is weight percent, of vinyl acetate. This lower phase is with polymerized to form said polyvinyl acetate, the steps of drawn from the separator through the line 9 and may be 20 combining said mixture of vinyl acetate and acetic acid treated, if desired, to recover the small amount of vinyl with an aqueous solution of acetic acid, distilling the acetate which it contains, by any known means.
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