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United States Patent Office Patented Apr 2,978,514 United States Patent Office Patented Apr. 4, 1961 1. 2 crude pentaerythritol in the solution is about 35-45%, the H2SO concentration is in the range of 0.2 to 0.6%. 2,978,514 Optimum results are attained at a pH of about 2.2. To SEPARATION OF PENTAERYTHRITOL AND facilitate subsequent recovery of the pentaerythritol and DIPENTAERYTHIRTOL FROM SOLUTION to minimize the size of the equipment and the amount of acid necessary, the concentration of the crude pentaeryth Arthur J. Poynton, Mount Royal, Quebec, Canada, as ritol in the solution should be rather high, e.g. in the signor to Canadian Chemical Company, Ltd., Montreal, range of about 35-45% previously mentioned, preferably Quebec, Canada, a corporation of Canada about 40%. The temperature at which this treatment. No Drawing. Filed Dec. 9, 1957, Ser. No. 701,361 10 is carried out is preferably in the range of about 95 or 100 to 105 C. It is most convenient to operate at about 3 Claims. (C. 260-615) the boiling point of the acidic solution being treated. The time of treatment should be above about 20 minutes, preferably about 30 to 120 minutes. This invention relates to pentaerythritol. 15 The charcoal treatment is preferably effected by mix Pentaerythritol is commonly produced by the reac ing powdered charcoal with the acidic pentaerythritol tion of formaldehyde, acetaldehyde and an alkali such solution during the sulfuric acid treatment. It is found as calcium hydroxide or sodium hydroxide. As a by that, surprisingly, the presence of the charcoal practically product there is obtained the formic acid salt of the alkali eliminates the tendency for the sulfuric acid to corrode employed, e. g. calcium formate or sodium formate. 20 the stainless steel (e.g. type 316 stainless steel) vessels in There are also obtained certain pentaerythritol deriva which such treatment may be carried out. However, the tives, such as dipentaerythritol and formals of pentaeryth charcoal may be added after the sulfuric acid treatment, ritol, and other organic compounds which are difficult and, if desired, the sulfuric acid may be neutralized prior to remove from the pentaerythritol. to the addition of the charcoal. The amount of charcoal It is an object of this invention to provide a novel 25 may be quite small, very good results having been at process for the purification of pentaerythritol. tained with the proportions in the range of about 0.2 to Other objects of this invention will be apparent from 0.5% based on the weight of the crude pentaerythritol. the following detailed description and claims. In this The solution is maintained hot during the treatment with description all proportions are by weight unless other charcoal, preferably in the range of about 95 or 100 to wise indicated, 30 105 C. It is most convenient to operate at about the According to one aspect of this invention crude pen boiling point of the solution. During the charcoal treat taerythritol containing pentaerythritol formals, such as ment it is desirable to agitate the mixture to promote dipentaerythritol formal, is treated, in aqueous solution, contact between the charcoal and all parts of the solution. with hot dilute aqueous sulfuric acid and with activated The time of contact of the charcoal and the solution may charcoal. The action of the hot sulfuric acid eliminates 35 be, for example, in the range of about 10 to 120 minutes. the pentaerythritol formals, hydrolyzing them to form At the conclusion of the treatment the charcoal may be pentaerythritoi and formaldehyde. The charcoal treat removed in any suitable manner, as by filtration. ment greatly improves the color of the product and de After the charcoal treatment the pentaerythritol sclu creases its color-forming tendencies. Surprisingly, it is tion is preferably cooled to effect recrystallization of the essential that the charcoal be in contact with the aqueous 40 pentaerythritol therefrom. One convenient method in solution of pentaerythritol during or after the treatment volves the use of the well known adiabatic crystallizer with sulfuric acid. If the aqueous solution of crude pen wherein the solution is placed under a subatmospheric taerythritol is treated with charcoal prior to the treatment pressure to cause evaporation of water therefrom to an with sulfuric acid, the desired results, i.e. improvement extent sufficient to reduce the temperature of the solu in color and the decrease in color-forming tendencies, 45 tion to the desired value. are not obtained. -- After the treatment with charcoal the acidic pentaeryth The crude pentaerythritol to which the process of this ritol solution may be neutralized, if desired, prior to invention is most usefully applied is one obtained by the cooling and crystallization. Thus, an alkaline material, condensation of formaldehyde (which is added in excess) such as sodium hydroxide or sodium carbonate, may be with acetaldehyde and sodium hydroxide in aqueous 50 added to raise the pH of the solution to about 5 to 8. medium, to produce (after suitable intermediate treat When the crude pentaerythritol contains less than ments, including addition of an acidic material to neu about 10% of polypentaerythritols, it is found that cool tralize the mixture, and distillation of excess formalde ing of solution resulting from the acid treatment, with hyde and of part of the water) a solution containing pen or without charcoal treatment, results in large bipyramid taerythritol and sodium formate, followed by crystal 55 crystals of pentaerythritol. It is also found that the di lization of the crude pentaerythritol from this solution. pentaerythritol present in the solution can be crystallized One suitable method of manufacture of this crude, un out in the form of much smaller crystals and that this recrystallized, pentaerythritol is disclosed in the U.S. difference in crystal size may be employed for recovering patent to Mitchell et al. No. 2,790,836. This crude pen the pentaerythritol and dipentaerythritol separately from taerythritol contains small amounts, e.g. up to 6% (on 80 the same solution. Thus, the mixture of crystals and a dry basis) of polypentaerythritols (including dipen solution resulting from the cooling step may be filtered taerythritol) as well as pentaerythritol formals. The through a screen whose apertures are of sufficient size sulfuric acid treatment may be applied to this crude pen to permit the fine dipentaerythritol crystals (which are taerythritol by incorporating the crude pentaerythritol mainly smaller than 10 microns in diameter) and solu into a hot aqueous solution containing the acid. This 65 tion to pass through, while retaining the crystals of mono may be done, for example, by dissolving the crude pen pentaerythritol. For example, a 100 to 325 mesh screen taerythritol in the water and then adding the acid or by may be employed, with the mixture being forced onto dissolving the crude pentaerythritol in hot acidulated the screen by centrifugal action, and the fine dipentaeryth water. The proportion of sulfuric acid should be in ritol crystals can then be recovered from the liquid by excess of one mole per mole of sodium formate present. 70 conventional elutriation procedures. This separation of Preferably, when the crude pentaerythritol contains less pentaerythritol and dipentaerythritol by conjoint crystal than about 1% sodium formate and the concentration of lization, after acid treatment, followed by crystal separa 2,978,514 3 4. tion, constitutes another aspect of my invention. It is lation zone, where unreacted formaldehyde and some particularly effective when applied to a mixture of pen water were stripped off, and then to an evaporator where taerythritol and dipentaerythritol containing about 2 to the solution was concentrated until its boiling point (at 5 or 6% dipentaerythritol. an atmospheric pressure of 710 mm. Hg) was 110° C. For many purposes, consumers of pentaerythritol de and the ratio of water to sodium formate therein was sire a so called "technical grade' product having a rela 100/55. The resulting concentrated solution was cooled, tively high polypentaerythritol content, e.g. about 12 to at the rate of 0.5° C. per minute, to a temperature of 5 20% polypentaerythritols, principally dipentaerythritols. C. to produce crystals, which were washed with 1 part For example, in the manufacture of certain oil-modified water at 5° C. per part of crystals, the washings being re alkyd resins using pentaerythritol as the polyhydric alco 10 cycled to the evaporator. These crude washed pentaeryth hol, an increase in the proportion of the polypentaeryth ritol crystals were dissolved in hot water to produce a ritol shortens the cooking time necessary to produce 40% solution to which H2SO4 was added, the amount of the alkyd resin. In accordance with another aspect of H2SO4 being 0.6% of the resulting solution. The acidic this invention, there are obtained from a single pen solution was heated for four hours at its boiling point taerythritol-forming reaction system two separate grades (105° C.) after which 0.5%, based on the weight of said of pentaerythritol, one having a low polypentaerythritol crude crystals, of powdered activated charcoal ("Norit') content (below 3% polypentaerythritol, based on dry was added, the mixture being stirred with said charcoal weight) and the other having a relatively high polypen for 15 minutes at 105 C. The charcoal was then re taerythritol content (about 12 to 20% polypentaerythri moved by filtration and the solution was cooled, at a rate tols or higher). This result is obtained by a modification 20 of 0.5 C. per minute, to 70 C. to produce a first corp of the reaction system described in the aforesaid of crystals, which was recovered in centrifuge preheated Mitchell et al. patent, and by a fractional crystallization to at least 70° C. followed by washing of said first crop of the product, either in the first crystallization or, pref with an equal weight of water at 70° C., the washings erably, in the recrystallization.
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