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A 4. GAAPHAARO AO77 Maww April 7, 1970 - E. SMITH ET All 3,505,308 PRODUCTION OF AZODICARBONAMIDES UTILIZING BROMINE Filed Oct. 27, 1966 WATER HYDRAZINE HYDRATE HYDRAZINE AQUEOUS HYDROCHLORIC ACID HYDRAZINE HYDROCHLORIDE AQUEOUS UREA HYDRAZO DLCARBONAMIDE SLURRY AZO DICARBONAMIDE SLURRY (ACID) CAUSTC BROMIN AZO (MAKE-UP) DICARBONAMIDE SLURRY (NEUTRAL) Cl2 AZO AIR (N2) DICARBONAMIDE PRODUCT BROMINE BROMIDE STORAGE LIQUOR AIR (N2) HCl acq. INVENTORS." AAR/C SM)7A/ WOffW A. AAPAGA EA? a 4. GAAPHAARO AO77 MaWW AGEw7 3,505,308 United States Patent Office Patented Apr. 7, 1970 1. 2 U.S. Patent 3,190,873 of 1965 and equivalent Belgian 3,505,308 PRODUCTION OF AZOOCARBONAMIDES Patent 627,533 of 1963 disclose passing chlorine gas UTELIZING BROMINE into a suspension of hydrazodicarbonamide (hydrazo Eric Smith, Madison, John E. Pregler, Wallingford, and formamide) in concentrated HCl, containing a bromide, Gerhard F. Ottmann, Hamden, Conn., assignors to to produce azodicarbonamide (azoformamide) in 93% Olin Mathieson Chemical Corporation yield. Filed Oct. 27, 1966, Ser. No. 589,911 Belgian Patent 631,410 of 1963 discloses passing chlo nt. C. CO7 07/02 rine gas into an aqueous suspension of hydrazodicarbon U.S. C. 260-192 10 Claims amide containing minor proportions of bromine, or a IO bromide, to produce azodicarbonamide in yields of 93 99%. With chlorine alone, yields are 35-38%. ABSTRACT OF THE DESCLOSURE In these processes, the chlorine must be introduced Azodicarbonamide having particle size especially suit slowly, with careful control, to avoid extensive forma able as a blowing agent in plastics and rubber composi tion of by-products by side reactions and over-oxidation tions without the necessity of any grinding or sizing is of the desired product. Bromine reacts rapidly and does prepared in two steps by synthesizing hydrazodicarbon not react with or over-oxidize the desired product. The amide in an aqueous suspension by reacting hydrazine with damaging side-effects of chlorine, even in the presence of excess urea, adding bromine in excess to oxidize hydrazodi bromine, are avoided. carbonamide to azodicarbonamide and separating the Further, the azodicarbonamide product of the processes product. The mother liquor is suitably chlorinated to re 20 of the prior art has generally required grinding, sizing, re cover bromine which is recycled. grinding oversized particles, re-sizing, and re-working undersized particles to provide the plastic and rubber users with a product of the size suitable for the blowing art. It This invention relates to an improved method for is a particular and unexpected advantage of the process of preparing azodicarbonamide. More specifically it relates this invention that an azodicarbonamide product is pro to the process of producing azodicarbonamide by reacting duced directly from the process which is suitable for use hydrazine and urea, to form a slurry of hydrazodicarbon as a commercial blowing agent without any sizing or grind amide, oxidizing the hydrazodicarbonamide in the slurry 1ng. with bromine to form a slurry of azodicarbonamide in The median particle size is determined in one method bromide liquor and separating the azodicarbonamide prod 30 microscopically, by measuring the length of the major uct. In a further embodiment of the invention, chlorine axis of the particles, dispersed in mineral oil. Alterna is introduced into the resulting bromide liquor, bromine tively, median particle size is determined by measuring is recovered therefrom and recycled to the oxidation the change in electrical resistance of a dispersion of step. particles in a salt solution, as it is pumped through a nar Azodicarbonamide is a well known blowing agent, which row orifice (Coulter counter). By these methods of is commercially available. It is an organic compound, measurement, the azodicarbonamide produced by the which at temperatures between about 160 and 200° C. process of this invention has a median particle size in evolves gases which are principally nitrogen. the desired range of 7 to 9 microns (Coulter counter) and Chemical compounds which, like azodicarbonamide, 5 to 6 microns microscopically. evolve gases at suitably elevated temperatures are useful 40 The process of the present invention generally com as blowing agents. They are utilized in the manufacture of prises: various foams and sponges which are characterized by (1) Reacting hydrazine with a stoichiometric excess of their extensive cellular structure and low ratio of weight urea in acid aqueous solution to form a first slurry of solid to volume. Foam materials, especially plastic foams, have hydrazodicarbonamide in a first aqueous phase; wide application as thermal insulation, life jackets, seat (2) Adding a stoichiometric excess of elemental cushions, and package fillers. bromine to said first slurry at a temperature of 20° to Hydrazodicarbonamide (biurea) has been prepared by 60° C. to form a second slurry of solid azodicarbonamide the reaction of hydrazine and urea, for example, by the in a second aqueous phase; and processes of U.S. Patents 2,692,281 or 3,227,753. (3) Separating said solid azodicarbonamide from said Azodicarbonamide (azoformamide) has been prepared 50 Second aqueous phase. - by the method disclosed in B.I.O.S. Final Report No. 1150 In step (1), the reaction of urea with hydrazine in acid by oxidizing a hydrazoamide with an alkali metal solution to form hydrazodicarbonamide, the preferred chromate, specifically sodium dichromate. acid is hydrochloric acid. Other hydrohalogen acids, for In this prior art process, there are several disadvan example, hydrobromic acid, are suitable. Sulfuric and tages. Sodium dichromate is expensive, it has a high 55 phosphoric acids are useful in the process of this inven molecular weight and requires the use of large amounts tion but form difficulty soluble hydrazine salts. The sub of the compound to accomplish the oxidation. The rate of sequent reaction with urea is slower and more difficult reaction is relatively slow, taking several hours to produce to complete. Acetic acid is also suitable for use. Ap a batch of azodicarbonamide. Further, the deep green proximately two equivalents of acid per mole of hydrazine color of the chromate ions masks the orange colored 60 is appropriate and ordinarily Some excess acid is used. azo compound, to such an extent that it is difficult to The pH of the reaction mixture is not critical and suitably determine the end point of the reaction. In addition, varies from 1 to 7 without significant effect on overall chromium compounds are skin irritants and cause health yield or quality of product. problems if any chromium residues remain in the prod Advantageously, sufficient water is used in forming the 65 acid solution to result in a pumpable or stirrable slurry of uct. Serious and expensive waste disposal problems also the hydrazodicarbonamide formed. Conveniently, the re arise with use of chromium. sulting slurry contains about 20 percent solids, but this More recently, chlorine has been used to oxidize hy may vary from 5 to 30 percent by weight, depending on drazodicarbonamide to azodicarbonamide: equipment capability. Greater dilution limits the capacity U.S.S.R. Patent 138,930 of 1961 discloses the use of 70 of equipment. mixtures of chlorine and bromine for the oxidation of Stoichiometrically 2 moles of urea are required per hydrazodicarbonamide to azodicarbonamide. mole of hydrazine but an excess of up to 100 percent 3,505,308 3 4 increases the yield, shortens reaction time and produces It is appropriately washed with water and the washings a slurry of hydrazodicarbonamide in a first aqueous phase, are combined with the bromide liquor for bromine recov which in subsequent operations yields azodicarbonamide ery. Advantageously for drying, the azodicarbonamide is in finely divided form, suitable for use as a blowing agent washed with acetone, alcohol or isopropanol and then without the necessity of grinding and sizing. Preferably dried. the molar ratio of urea to hydrazine is from 3:1 to 4:1. Since the slurry of azodicarbonamide and the bromide Using the concentrations and proportions described, liquor are acid, it is advantageous to neutralize the slurry optimum results are obtained by refiuxing the slurry, before filtering or the liquor after filtering with caustic. after addition of the urea at atmospheric pressure, for This permits the use of cheaper equipment, not resistant about one to two hours. Unless the temperature of the to corrosive acids, in the filtration and recovery opera mixture is raised to reflux, the yield is decreased. Longer O tions. For this purpose 23 percent aqueous caustic is suit times appear to offer no advantage and unnecessarily able or any more or less concentrated alkali. Suitably occupy the equipment. neutralized to a pH of about 7, the slurry or liquor is Under the condition indicated above to be preferable appropriately handled in equipment not resistant to cor in the operation of step (1), yields of azodicarbonamide rosive acids. are usually from 90 to 95 percent of theory. In a particularly advantageous modification of the in It is a particular advantage of the process of this in vention, the bromine is recovered from the bromide vention that the slurry of hydrazodicarbonamide prepared liquor, whether neutralized or not, by introducing chlorine according to step (i) is especially suitable for oxidation thereinto. Chlorine gas, diluted if desired with air or with bromine to form a slurry of azodicarbonamide. The nitrogen, is most convenient. Other sources of chlorine presence of annonium chloride and urea in the aqueous active to liberate bromine from bromides are suitable phase is advantageous in producing azodicarbonamide including, for example, sodium hypochlorite solutions, of desirable particle size, without grinding or screening. bleach liquor or calcium hypochlorite solid or in solution. In addition, any possibility of forming the dangerously Appropriately the liquor is heated during or after addition explosive NCl3 from the NHCl present in the slurry is 25 of chlorine or both and bromine is distilled overhead.
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