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United States Patent Office - 2,859,240 United States Patent Office Patented Nov. 4, 1958 2 or alcohol; a reaction which is typical of aliphatic alpha 2,859,240 hydro-alpha-hydroxy acids. This same decomposition to an aldehyde having one less carbon atom in the carbon PRODUCTION OF ACRYLATES BY CATALYTIC chain is also typical of procedures known to the prior DEHYDRATION OF LACT CACID AND ALKYL art in which lactic acid or the like is heated in the pres LACTATES ence of strong acids such as sulfuric or phosphoric acid. Reynold E. Holmen, White Bear Township, Ramsey In view of such prior art experience, it is not sur County, Milan, assignor to Minnesota Mining & Maiau prising that any methods for the preparation of acrylates facturing Company, St. Paul, Minn., a corporation of based on lactic acid or its esters as a raw material have Delaware 10 invariably involved the preliminary replacement of the No Drawing. Application January 12, 1956 alpha-hydroxy hydrogen (and the carboxyl hydrogen, Serial No. 558,607 when present) by some other radical whereby lactide formation and decomposition could be avoided, followed 4. Claims. (C. 260-486) by pyrolysis of the substituted lactate to the acrylate. 5 Typical of such methods is the -acetylation of methyl This invention is concerned with the production of lactate to methyl alpha-acetoxy propionate followed by acrylates, including acrylic acid as well as its lower alkyl pyrolysis to methyl acrylate and acetic acid. esters, from corresponding lactates by a direct catalytic Thus, despite the ready availability of lactic acid and process at an elevated temperature. the obvious advantages attendant upon its use, and fur This application is a continuation-in-part of my co 20 ther despite the very considerable efforts applied by re pending application Serial No. 319,185, filed November searchers toward a solution of the problem, the fact re 6, 1952, now abandoned. mains that no one, prior to the present invention, ever The acrylates comprise a class of materials which are succeeded in directly converting lactates to acrylates. of great industrial importance due to their ability to See, for example, the review by C. H. Fisher et al. en form polymers and copolymers having a wide range of 25 titled "Properties and Reactions of Lactic Acid' and applications. The relatively high cost of the acrylates published by the U. S. Dept. of Agriculture, No. A1C has, however, been a deterrent to their use in many 279, October 1950. applications for which their physical and chemical prop It has now been discovered, contrary to all previous erties are well suited. The high cost of these materials experience, that lactate material, i. e., lactic acid and has been in part a result of the methods of preparation 30 the lower alkyl esters thereof, may be converted in previously available, involving multiple-step processes, significant yields to acrylate material by direct catalytic use of large amounts of auxiliary reagents, and other dehydration at temperatures within the range of about inefficiencies. The development of new and more ef 200-600 C., or more particularly at temperatures with ficient processes for the production of acrylates has there in the more restricted and generally preferred range of fore long been an objective of those working in thus field. about 250-550 C. The oxidation of acrolein by means of silver oxide This is particularly surprising with respect to lactic acid was formerly employed in producing acrylic acid, from itself. Atwood, in his Patent No. 2,464,364, for exam which other acrylates could then be obtained. The ple, finds it necessary to remove all traces of lactic acid silver oxide reagent was expensive and was reduced to from his mixture of alkyl lactate and acetic anhydride the metal during the reaction, requiring reconversion 49 in order to prevent excessive coke formation in the to silver oxide prior to re-use. pyrolyzing furnace. Hydrolysis of ethylene cyanhydrin or of acrylonitrile Specific exampies will now be set forth in further ex provides much of the acrylates now produced com planation, but with no intent of limitation, of the inven mercially. Neither intermediate is low in cost. Con tion. siderable quantities of acidic reagents are required. EXAMPLE 1. Another method of preparation involves the pyrolysis of polymeric beta-lactone produced from ketene and A catalyst was made by pelleting NaH2POHO mixed formaldehyde. Several separate reactions are involved, with one-fourth its weight of graphite as a lubricant. cluding lactone formation, polymerization, and pyro Other lubricants, e.g., sodium stearate, are equally effec ySls. tive in providing coherent pellets. The amount of lub Acrylates have been synthesized from acetylene, car ricant may be much less than here indicated. bon mcnoxide and water or alcohol; but this process has A quantity of the catalyst pellets having an apparent not achieved commercial importance. Recovery of ex volume of about 65 ml. was used to pack a 10' sec pensive catalyst presents a major problem. tion of a 1%' O. D. "Pyrex' glass combustion tube passing through a "Hoskins' electrically heated tube The dehydration of hydracrylic acid (beta-hydroxypro furnace supported vertically. The furnace temperature pionic acid) or alkyl esters thereof to the corresponding was slowly raised so as to remove combined water with acrylate is a comparatively simple and economical proc out fusing the catalyst mass. A dropping funnel having ess, but the starting material is neither low in cost nor provision for admitting inert gas and for pressure equal readily available in quantity. Alpha-hydroxypropionic ization was attached to the top of the combustion tube by acid (lactic acid) is much more readily and potentially 60 means of a ground glass joint. The bottom end of the available, but this material, as such, has never been found combustion tube led directly to a water-cooled receiver, to be an effective source of acrylates. - from which non-condensed material passed through a When heated at moderate temperatures, lactic acid Dry-Ice trap and finally through a bubble counter. Oxy readily converts to polylactic acid or lactides. For ex gen-free nitrogen was fed into the system at the dropping ample, Whitmore, "Organic Chemistry,” in discussing the 65 funnel at a rate of about 0.1 cubic foot per hour in preparation of acrylic acid, states: "It is not obtained order to maintain an inert atmosphere and to assist from lactic acid or its esters which give a lactide in in sweeping the feed material and products through the stead.” At higher temperatures, lactic acid and its esters train. - - have been shown by Nef, and more recently by Fisher Methyl lactate was fed from the dropping funnel onto and Fiachione of the U.S. Dept. of Agriculture, to de 70 the dehydrated heated catalyst at a rate of about one - compose into acetaldehyde, carbon monoxide, and water drop per 4-5 seconds, and samples of the condensate were 2,859,240 3 withdrawn from the receiver at each of several furnace redistilled. A portion weighing 6.8 g., boiling from temperatures within the range of 270°-540° C. 70-77 C., and containing chiefly ethanol and ethyl In this as well as the following examples, the furnace acrylate, began to show polymerization after a few hours temperature was obtained by means of a thermocouple in the sunlight. The slightly viscous liquid was allowed which contacted the outer surface of the combustion to evaporate, leaving a film of clear polyethylacrylate. tube within the area of maximum temperature. The The identity of the polymer was confirmed by infrared temperature differential between such surface and the absorption analysis. center of the catalyst column was not more than about 25 °C. Temperatures were recorded in degrees Fahren EXAMPLE 7 heit and could be maintained at plus or minus about 5 0 In this experiment butyl lactate was passed over a F., but for convenience are here reported in degrees peileted catalyst which was prepared, in accordance with centigrade corresponding to the average recorded temper the procedure described under Example 1, from lithium ature. hydrogen phosphate mixed with some graphite. The The condensate contained methyl acrylate. After furnace temperature was 510 C. From 14 ml. of butyl standing at room temperature for about two weeks it was lactate there was obtained 6.2 g of nearly water-white found that polymerization of the methyl acrylate had pyrolysate. After adding a few granules of benzoyl peroxide and warming for thirty minutes on a water bath caused an increase in the viscosity of the samples, par the acrylate in the pyrolysate polymerized to give a vis ticularly those taken at 510-532 C. cous liquid. The clear solid isolated by evaporation of EXAMPLE 2 20 the volatile material was identified as chiefly polyacrylic A 9 inch section of the combustion tube of the ap acid, and butene was identified in the residue recovered : paratus described in Example 1 was packed with 6-10 in the Dry-ice trap, indicating that at the temperature mesh granules of a catalyst material prepared by mixing used the butyl acrylate first formed was further pyrolyzed a concentrated solution of Na2SO4 with finely divided to butene and acrylic acid. CaSO4 in a 1:25 mol ratio to form a stiff paste which 25 was dried in a thin layer, broken into small pieces, and EXAMPLE.8 screened. A short upper-section of the combustion tube In this experiment' lactic acid was directly dehydrated was filled with “Pyrex' glass helices for preheating the to acrylic acid. A solution of 70 ml. of 85% lactic acid feed. An aqueous 10% solution of lactic acid was fed in 30 ml.
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