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United States Patent [19] [11] 4,279,130 Finch Et Al United States Patent [19] [11] 4,279,130 Finch et al. [45] Jul. 21, 1931 [54] RECOVERY OF 1,3-BUTADIENE BY [5 7] ABSTRACT FRACTIONAL CRYSTALLIZATION FROM Freezing and melting techniques are described for sepa FOUR-CARBON MIXTURES rating 1,3-butadiene from a mixture of four-carbon com [75] lnvembrs; Ray N_ Finch; William 1)_ Nash, both > pounds by fractional freezing of the liquid mixture and of Odessa, Tex_ by fractional melting thereof. It has been discovered _ that when a frozen four-carbon mixture (BB) containing [73] Asslgnw El Paso Products Cmnvany, Odessa, about 36% 1,3-butadiene (ED) is initially frozen, the Tel‘- ?rst frozen fraction of up to about 30% of the mixture is [21] APPL No; 41308 enriched about 80% over the feed sample while the ?ltrate is decreased in BD about 36%. A second frac [22] piledl May 22, 1979 tional crystallization of the melt and of the ?ltrate [51] Int. cl.3 ............................................. .. B01D 9/04 shOws c‘mtinued enrichment and impc’verish’l‘m as t° [52] US. Cl. ...................................... .. 62/544; 62/538; BD content’ réspectlvely‘ It ha? also een discovered 585/812 thatwhen a solldly frozen BB mlxture is slowly thawed [58] Field of Search ............... .. 62/532, 538, 539, 544; and .the melt is pmgressivfaly rammed’ ‘.11? me" be‘ ,-‘ 585/812_817 comes markedly enriched 1n BD. A continuous frac tional crystallization process that uses these discoveries [56] References Cited for producing BD at purities greater than 99% is de us‘ P ATENT DOCUMENTS scribed. Utilizing lique?ed natural gas (LNG) as the -l _ cryogen source for this process is also suggested, so that 13; gl'nold ------------------------------- - the refrigeration need for fractional crystallization of i ’ rec" ' ' ' ' ' ' ' ' ' ' ' " BB can be combined with the heating need for LNG 2780 663 2/1957 Gunness ............................. .. 585/812 - - ’ ’ vaporization. Primary Examiner—Norman Yudkoff _ ' Attorney, Agent, or Firm—De Paoli & O’Brien 17 Claims, 5 Drawing Figures 2| f5; 29 . CRYOGEN 55 27 [ ’ é'ééiiélls 5|) 34" §-—25 FILTER TOP R FLUX PUMP __|3 . 7 55-FILTRATE Fl'umg >75 45 / AAIAAAA BB n..." /, FEEDSTOCK FEED 47 CHILLER s5\ PRE COOLER EcoNomzER BUTADIEIE PRODUCT 4 I V 7 —I7INSULATION VACUUM a LUX OVERHEAD US. Patent Jul. 21, 1981 Sheet 4 of5 4,279,130 F10 g. 4 Synthetic Crystallization of C4 Hydrocarbon Mixture I00 90 420 - - 8.5 75 7O 65 LEGEN D‘ 55 9!,3-Butodiene . Isobuiylene 45 v cis-Z- Butene u 1-Butene 35 I t-Z-Butene 30 A n-Butene 25 v Isobutane 2O 1 2 3 4 5 e 7 a no u l2 ,__ SAMPLE NUMBER ,_ g '2' E 5 L? E 1% 5 I00 66 1 1 1 7 5 4 4 2 1 1 (SAMPLE WT PERCENTAGES) 4,279,130 1 2 tion type of process rather than a fractional crystalliza RECOVERY OF 1,3-BUTADIENE BY FRACTIONAL tion process. CRYSTALLIZATION FROM FOUR-CARBON Crystallization processes from the melt utilize differ MIXTURES . ences in melting points of the components in a mixture. According to an article in Hydrocarbon Processing, BACKGROUND OF THE INVENTION Dec. 19, 1966, pages 97-102 by John E. Powers, com mercial separation and puri?cation processes using 1. Field of the Invention ' crystallization from the melt can be grouped according This invention relates to processes for purifying or to three basic procedural approaches: normal freezing, separating liquids and particularly relates to processes zone re?ning, and column crystallization in which there involving heating or cooling for separating speci?c is differential countercurrent contacting of crystals and liquids from a mixture. It especially relates to cryogenic melts. fractional crystallization and the application thereof to Zone re?ning or zone melting has had considerable four-carbon mixtures including 1,3-butadiene which usage in the production of high-purity materials for may hereinafter be referred to simply as butadiene. semiconductors, but this procedure has been limited as 2. Review of the Prior Art to size of equipment because the solid-liquid interfaces In recent years, hydrocarbon mixtures containing forming the zone are distorted ,by heat transfer from n-butenes and isobutylenes have been secondarily pro natural convection. Consequently, even though some duced in great quantities. An example thereof is the C4 organic materials of high purity have been produced by distillation fraction from the refining of petroleum 20 zone re?ning on a commercial basis, wide-spread appli naphtha. In this C4 fraction, the constituents include cation thereof has been signi?cantly hampered. isobutane, n-butane, isobutylene, l-butene, cis-Z-butene, Column crystallization appears to be well suited to trans-Z-butene, and 1,3-butadiene. These are all very commercial scale processing for hydrocarbons such as similar to one another in many of their physical and C4 mixtures. In a column crystallizer, solid and melt are chemical properties. Accordingly, separation and puri 25 moved counter-currently in intimate contact so that ?cation of these constituents by conventional distilla there is adequate reuse of energy of crystallization and tion procedures are‘dif?cult so that producing four-car the possibility of operating a single crystallization unit bon materials of high purity is fairly expensive. Never under steady-state, continuous ?ow conditions without theless, there are numerous processes which‘ require handling any solids externally of the unit. Moreover, highly pure four-carbon compounds as a raw material, the products from column crystallizers are frequently in such as the production of 1,3-butadiene from n-butenes excess of 98 weight percent purity after a single pass and the production of methacrolein or methacryloni through the column. Column crystallizers can be center trile from isobutylene. Clearly, a method for isolating I fed or end fed. A suitablecenter-fed column crystallizer one or more speci?c compounds that is based upon is provided with a spiral-type conveyor, a freezing sec other properties than their boiling points is highly desir tion at its upper end, and a melting section at its lower able. end. An end-fed column crystallizer is suitably provided One possibility is to utilize the freezing points‘ of the with a melting section at its lower end and a chiller at its components of a C4 hydrocarbon mixture because n feed end to provide crystals to be packed into a bed above the melter with a circumannular?lter surround butane melts at — 135° C., isobutane melts at »~ 145° C., ing the upper end of the bed for removing mother liquor butene-l melts at —- 185° C., cis-Z-butene melts at — 138° ' therefrom. The high-purity product emerges from the C., trans-Z-butene melts at —- 106°C” and 1,3-butadiene melts at -— 109° C. No application of such separation by bottom beneath the melter. ' In order to consider the utilization of fractional crys melting points is known, however, although U.S. Pat. tallizers for processing the large quantities of C4 mix No. 2,622,115 discloses a process for purifying binary 45 tures that are available from the petroleum industry at mixtures by fractional crystallization, mentioning that the present time, it is necessary to have available large cis and trans-Z-butene are an eutectic pair and indicating quantities of refrigeration. However, there are numer that either component can theoretically be removed ous cryogenic processes which can supply the low-tem from the mixture in a pure state. U.S. Pat. No. 2,632,314 perature refrigeration which is needed, such as hydro- describes a fractional crystallization apparatus. 50 carbon cascade systems, multistage expansion systems, U.S. Pat. No. 2,912,469 describes a fractional crystal and the like. lization process which includes feeding an immiscible Excessive energy usage will not occur if adequate liquid with the multi-component composition. insulation is used and ef?cient heat exchangers are in U.S. Pat. No. 3,077,744 discloses a multi-stage frac stalled. High vacuum insulation, multiple-layer vacuum tional-freezing process for separating a highly puri?ed 55 insulation, and evacuated powder insulation are pre isoprene fraction from a mixture of C5 hydrocarbons. ferred, particularly with a vacuum of at least 10-4 mm This process utilizes a series of low-temperature ex Hg. change coolers in which the wall ?lm of solids is Moreover, low-level refrigeration can be obtained by scraped away by rotating scrapers having spring-loaded vapor-compression refrigeration of the BB stream, blades to form a solids-liquid mixture which ?ows to a using propane or ammonia for condensing and discharg solids-liquid separator (such as a ?lter or centrifuge). ing the heat therein to cooling water. The BB stream is Solids are removed, and liquid is sent to the next cooler. preferably at least pre-cooled by such a system for re The ?nal product contains about 70% isoprene. The frigerated storage or for direct combination with a cry process thus utilizes normal freezing of a liquid by ogenic process. contact with a cold surface. 65 In certain coastal areas, particularly where deep U.S. Pat. No. 3,264,363 discusses puri?cation of ?ve water port facilities are located close to an oil re?nery, carbon mixtures with liquid methane by direct contact there are receiving terminals for vaporizing lique?ed of the methane with the mixtures so that it is an extrac natural gas (LNG), which is being shipped on a large 4,279,130 3 4 scale in ocean-going tankers, for use by industrial and ?ltrate, comprising C4 hydrocarbon other than the C4 private consumers. In these terminals, LNG at —260° component product is removed from the freezing ?lter F.
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