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Nz Eisenlohr ET AL 3,415,742 RECOWERY of AROMATICS by EXTRACTION with SOLVENT MIXTURE of N-METHYL-PYRROLIDONE and GLYCEROL Filed Dec

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Nz Eisenlohr ET AL 3,415,742 RECOWERY of AROMATICS by EXTRACTION with SOLVENT MIXTURE of N-METHYL-PYRROLIDONE and GLYCEROL Filed Dec Dec. 10, 1968 KARL-Heinz Eisenlohr ET AL 3,415,742 RECOWERY OF AROMATICS BY EXTRACTION WITH SOLVENT MIXTURE OF N-METHYL-PYRROLIDONE AND GLYCEROL Filed Dec. 20, 1967 3. Sheets-Sheet l 32-24 || | | | | | | | | | | | 1z-LMasa | | | | as a -N | | | | | -1 N | | | | | -- acaya aa 1/ - CZZM-2. acadalay1/7 Ma17Za Mo-a o1 a 6d 2 a 3 12 as as 299 a 3 a. pes. Ze 9 ?o a sizzaT N vo, a N 26 N 4 H N Med s H -- 2 2 17-ases 2ag.9 e as 12 attes Zage 24 o-W 16 //W1a/WYears aaZ 1/a/MZazaa/YZ2/4. A Ca2az M-742 / ae, as1 2Ape-, 742 al-4 o Gille. , 177 701/Way/cs Dec. 10, 1968 KARL-Heinz Eisenlohr ET AL 3,415,742 RECOVERY OF AROMATICS BY EXTRACTION WITH SOLVENT MIXTURE OF N-METHYL-PYRROLIDONE AND GLYCEROL Filed Dec. 20, 1967 3. Sheets-Sheet 2 AAA || aO // F Mao 17III I// /o ao so 170 af2 72e2. -> 2.6462% // - sa/A27W7M//Y70/ea MMW1a/Yatars 122-1/a/M/.4% sa/WZaa/at e-A-HA-1-1a cata/a/ auty- MYeaaaas, and 6 a.s.leaa 1772/71axs Dec. 10, 1968 KARL-Heinz Eisenlohr ETAL 3,415,742 RECOWERY OF AROMATICS BY EXTRACTION WITH SOLVENT MIXTURE OF N-METHYL-PYRROLIDONE AND GLYCEROL Filed Dec, 20, 1967 3. Sheets-Sheet 3 /V\ /VVN /VVVN /VVVX7M /VVAX7VNAN/A/YYYYA /Ya7 VVVVN Z27 VVVVVVVN 7VVVVVVVVN t es ad Yade aaraaya 17aeata/77. //W1aaware/re 12a-a-Me.at/sa/WZoast a ca1%7 /76 Zaates United States Patent Office Patented Dec. 10, 1968 1. 2 3,415,742 On the other hand, the following disadvantages of the RECOVERY OF AROMATICS BY EXTRACTION addition of water must be taken into consideration: WITH SOLVENT MIXTURE OF N-METHYL (1) The solvent capacity for aromatics is reduced. TPYRROL DONE AND GLYCEROL (2) The water is vaporized azeotropically with the Karl-Heinz Eisenlohr, Buchschlag, and Eckart Miller, aromatics to be separated from the solvent which causes Bergen-Enkheim, Germany, assignors to Metallgesell Substantial increase in the heat energy required. schaft Aktiengesellschaft, Frankfurt am Main, Ger many (3) In many instances the water causes undesired Continuation-in-part of application Ser. No. 490,818, chemical reactions, especially hydrolysis. Sept. 28, 1965. This application Dec. 20, 1967, Ser. No. A number of non-aqueous solvent mixtures have also 692,019 O become known, such as, for example, mixtures of SO2, Claims priority, application Germany, Sept. 29, 1964, ethylene glycol and formamide or mixtures which con M 62,610 sist of a "primary solvent” which contains glycol deriva 1 Claim. (C. 208-323) tives and a "secondary solvent' such as methanol, etha nol and acetone. 5 These solvent mixtures, however, have the disadvan tage that a portion thereof has a lower boiling point than ABSTRACT OF THE DISCLOSUIRE the aromatics to be recovered whereas the other portion Aromatic hydrocarbons are extracted with solvent from has a higher boiling point. The separation of the aromatics hydrocarbon mixtures containing both aromatic and non from the solvent therefor requires substantial plant in aromatic hydrocarbon components using a mixture of N 20 vestment as well as high operation costs which in general methyl pyrrolidone and glycerol as the solvent. The ex are not compensated for by the advantages of the solvent tractions are conducted by liquid-liquid extraction. combinations. Further proposals for solvents include, for example, Hammunw"...wlu. (1) the combination of various glycol derivatives, (2) Cross-reference to related applications 25 mixtures of two solvents of which the first contains 1 This application is a continuation in part of copending or 2 hydroxyl groups and the second contains 2 or more application Ser. No. 490,818, entitled "Recovery of Aro hydroxyl groups, (3) ethylene carbonate with additions matics by Extraction or Extractive Distillation with Sol of glycerol, ethylene glycol, pentaerythritol, formamide, vent Mixtures,' and filed Sept. 28, 1965, now Patent formic acid, ethanol amine, monochlorohydrin, acetamide, 3,366,568, in the names of Karl-Heinz Eisenlohr and 30 resorcinol or hydroquinone as "diluent,” (4) alkane dini Eckart Muller. triles, dimethyl hydantoin, N-alkylpyrrolidones, B-buty rolactone, cyan ethers of diethylene glycol, tri- or tetra Background of the invention ethylene glycols or any desired mixtures of these solvents Field of the invention.--The present invention provides which are selective for aromatics or olefins. an improved process for the recovery of aromatic hydro 35 However, without exception, no advantages over the carbons, especially benzene, toluene and xylene, from use of a single solvent have been proved for these and hydrocarbon mixtures containing the same, by extraction many other proposals for the use of mixtures of various with water free solvent mixtures selective for aromatics Selective Solvents boiling above the aromatics to be re which as a whole boil over the boiling point range of the covered for the liquid-liquid extraction of aromatics, nor aromatics to be recovered. The extraction with the solvent 40 have any indications been given as to what quantity and mixtures concerned is by liquid-liquid extraction. in what proportions that various components of the Description of the prior art-The recovery of aromatic mixture should be used in order to attain advantages over hydrocarbons from hydrocarbon mixtures by liquid-liquid the use of single solvents. extraction with selective solvents has been practiced on a The state of the art concerning the possibilities of use commercial scale for several decades. However, from the of solvent combinations for the liquid-liquid extraction fact that again and again new solvents are Suggested and of aromatics can be summarized in that the effect of the patented for this purpose, it can be concluded that the addition of water to a solvent is known qualitatively, and ideal solvent has as yet not been found. that something is known concerning the properties of In addition to pure solvents, in many instances organic various combinations of glycol derivatives. However, solvent mixtures have been proposed as the selective 50 from which points of view, solvents may otherwise be solvents. Furthermore, widely spread practice is to add combined in order that they give good properties for certain quantities of water to the solvent. The addition liquid-liquid extraction of aromatics has neither been of water offers the following advantages: described in scientific literature nor in the patent literature. (1) The selectivity of the solvent is increased. 55 Summary of the invention.-The object of the present (2) The separation, especially of the higher aromatics, invention is to provide a process for the recovery of from the extract obtained is easily accomplished even aromatic hydrocarbons from hydrocarbon mixtures con with a small difference between the boiling point of the taining the same by means of a liquid-liquid extraction solvent and the aromatics because the aromatics distill azeotropically with the water at temperatures under process. 100° C. 60 The essence of the present invention lies in the use, (3) The sump temperature in the distillation column as the liquid extracting medium, of a water free solvent employed for separation of the aromatics from the sol mixture which boils above the boiling point range of the vent extract is lowered so that not only are losses en aromatics to be recovered and which consists of a mix gendered by thermal decompositions reduced but also the ture of N-methyl pyrrolidone and glycerol. heat energy required for heating the solvent to the sump 65 Brief description of the drawings.-In the accompany temperature is lowered. ing drawings: (4) With regard to liquid-liquid extractions a further FIG. 1 is a diagram showing the maximum quantity advantage is that the field of the existence of two phases of benzene in the heavy phase (solvent phase) with re is increased, so that larger quantities of aromatics may be 70 spect to the composition of the solvent mixture N-methyl contained in the feed stock without leaving the two pyrrolidone (hereinafter referred to as NMP) and glyc phase field. erol; 3,415,742 3. 4. FIG. 2 is a diagram showing the dependency of the sulfoxide with aromatics ranges between 35 and 50% selectivity of the composition of solvent mixture NMP especially are illustrative of the group of solvents with and glycerol; low aromatics range. FIG. 3 is a diagram in which the selectivity is plotted The solvents of group B with a high aromatic range, against the partition-coefficient in dependence on the 5 that is, solvents with an aromatic range of at least 50% composition of solvent mixture NMP and glycerol; in the maximum of the two-phase system belong to the FIG. 4 is a phase diagram for the 3 component Sys second group. They are therefore near the Solubility tem. NMP-glycerol-benzene; limit with aromatics, for example, so that they are mis FIG. 5 is a diagram showing the dependency of the cible in all proportions with benzene but not with Xylene. viscosity at 50° C. of solvent mixture NMP and glycerol O There are solvents of this group which have very high on its composition; and selectivity with good capacity, the latter, nevertheless, FIG. 6 schematically shows an apparatus for carrying being lower than that of the solvents of group A. As a out a liquid-liquid extraction according to the invention. consequence, solvents of group B would be the ideal Sol Description of the preferred embodiment.-According vents for the extraction of aromatics insofar as only to the invention, it was unexpectedly found that despite the selectivity and capacity is taken into consideration, the large number of solvents known for these purposes but remarkably they without exception possess other and despite their very different types of chemical struc physical properties of such unfavorable values that they ture, certain rules exist, the application of Which renders must be considered substantial disadvantages.
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