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Aug. 29, 1967 Yoshi KAZU ITO ETAL 3,338,887 PREPARATION of NITROSYL CHLORIDE Filed Dec

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Aug. 29, 1967 Yoshi KAZU ITO ETAL 3,338,887 PREPARATION of NITROSYL CHLORIDE Filed Dec Aug. 29, 1967 Yoshi KAZU ITO ETAL 3,338,887 PREPARATION OF NITROSYL CHLORIDE Filed Dec. 26, 1962 INVENTORS YOSHIKAZU ITO FUMO NS-KAWA 2%-42.TAKAO WAMURA ATTORNEY 3,338,887 United States Patent Office Patented Aug. 29, 1967 1. 2 3,338,887 be taken out of the cyclic system in order to maintain PREPARATION OF NITROSYL CHLORIDE its material balance, or, alternatively, the water has to Yoshikazu to, Mizuho-ku, Nagoya, and Fumio Nishi be taken out of the cyclic system by distillation of the kawa and Takao Iwamura, Minami-ku, Nagoya, Japan, spent liquor under reduced pressure. assignors to Toyo Rayon Kabushiki Kaisha, Tokyo, Japan, a corporation of Japan While the spent liquor which has been taken out to Filed Dec. 26, 1962, Ser. No. 246,914 the outside of the system by the above method can be Claims priority, application Japan, Dec. 26, 1961, used for other purposes as sulfuric acid by being con 36/46,743 verted thereto by the conventional nitric oxide process 1 Claim. (Cl. 260-239.3) for sulfuric acid manufacture, the recovery of the oxides 10 of nitrogen which are formed in this instance is a dis This invention relates to a method of preparing nitro advantage from the commercial standpoint. Furthermore, syl chloride which makes it possible to prepare nitrosyl since a small amount of hydrochloric acid is contained chloride cyclically with advantage and effectiveness on in the cycling spent liquor, hydrochloric acid is also a commercial scale, and in which the liquid portion which contained in the sulfuric acid formed. Considerable re increases concomitantly as the reaction proceeds can be 5 strictions are also imposed as to the uses to which the directly utilized as the acid catalyst in the Beckmann re nitric acid formed can be employed. arrangement of the hydrochloride salts of cycloalkanone On the other hand, in the latter method consisting of oximes obtained by the photochemical reaction of cyclo taking out to the outside of the cyclic system of the alkanes. More particularly, the invention relates to a water produced as the by-product, although there is no method of preparing nitrosyl chloride which comprises 20 need of drawing off of the cycling spent liquor to the reacting a mixed gas comprising nitrogen monoxide and outside of the cyclic system for maintaining the material nitrogen peroxide with sulfuric acid to obtain a sulfuric balance thereof, it is an advantage from the operations acid solution of nitrosylsulfuric acid, reacting said sul management standpoint to draw off a part of the cycling furic acid solution with a primary hydrogen chloride gas spent liquor to the outside of the cyclic system on ac to generate primarily nitrosyl chloride, reacting a mixed 25 mount of the accumulation of such as metals in the gas comprising nitrogen monoxide and nitrogen perOX cycling spent liquor in the cyclic system. ide again with this spent liquor to set up a cyclic Sys Hence, the handling of the spent liquor taken out to tem for preparing nitrosyl chloride, taking out from the the outside of the cyclic system becomes a problem from aforesaid spent liquor the liquid portion which increases the commercial standpoint regardless of whether the concomitantly as the cyclic reaction proceeds, and then 30 former or the latter method is practiced. reacting this spent liquor with a secondary hydrogen chlo We have now found a cyclic method of preparing nitro ride gas to generate secondarily nitrosyl chloride until the syl chloride on a commercial scale and by means of which nitrosylsulfuric acid in the spent liquor is reduced to less the spent liquor may be utilized as an acid catalyst in than 3% by weight. the Beckmann rearrangement of the hydrochloride salts The spent liquor from which has been secondarily gen 35 of cycloalkanone oximes, obtained by the photochemical erated nitrosyl chloride after having been added, if neces reaction of nitrosyl chloride on cycloalkanes, to the cor sary, sulfuric acid or fuming sulfuric acid or without responding lactams of the cycloalkanes. such an addition can be directly utilized as the acid Accordingly, it is an object of the present invention catalyst when effecting the Beckmann rearrangement of to provide a method of preparing nitrosyl chloride where the hydrochloride salts of cycloalkanone oximes obtained 40 by the preparation of nitrosyl chloride by the cyclic by the photochemical reaction of cycloalkanes to the cor process can be carried into effect with advantage and responding lactams of said cycloalkanes. effectiveness on a commercial scale, and at the same time It is generally known to obtain nitrosyl chloride by the liquid portion of the spent liquor which increases obtaining a sulfuric acid solution of nitrosylsulfuric acid as the cyclic reaction proceeds can be directly utilized by causing a mixed gas comprising nitrogen monoxide as an acid catalyst in a related art, i.e., the Beckmann and nitrogen peroxide, such as a "nitrose' gas, to be ab rearrangement of the hydrochloride salts of cycloalkanone sorbed into sulfuric acid in accordance with the follow Oximes obtained by the photochemical reaction of cyclo ing Equation 1, and thereafter reacting as in Equation alkanes. 2 by blowing in hydrogen chloride gas into this solution. Another object of this invention is to provide a method 50 of preparing nitrosyl chloride conveniently by effecting (1) NO-2HSO->2HNOSO-H2O the generation of nitrosyl chloride in both the sulfuric acid solution of nitrosylsulfuric acid in the cyclic system (2) HCl--HNOSO->HSO--NOCI for preparing nitrosyl chloride and in the liquid portion However, this method of obtaining nitrosyl chloride of the aforesaid spent liquor produced in increasing from nitrosylsulfuric acid and hydrogen chloride gas had 55 amounts which is taken out of said system. been practiced hitherto only on a laboratory scale. Other objects and advantages of the present invention In order to carry out a similar method on a commercial will become apparent from the description which follows: scale, we have previously proposed a method of obtain The method of the invention comprises a method of ing nitrosyl chloride continuously by reacting the oxides preparing nitrosyl chloride which comprises, in combina of nitrogen with sulphuric acid to obtain a sulphuric 60 tion, the following steps: acid solution of nitrosylsulphuric acid, blowing hydro (a) reacting a mixed gas comprising nitric oxide and gen chloride gas into this solution and generating nitro nitrogen peroxide with a volume of sulphuric acid there syl chloride, then again blowing oxides of nitrogen into by preparing an increased volume of solution of nitrosyl the spent liquor from the nitrosyl chloride generation sulphuric acid in sulphuric acid; step in order to reproduce a nitrosylsulphuric acid solu 65 (b) reacting the solution obtained in (a) with hydro tion and in order to set up a cyclic system for preparing gen chloride, thereby generating nitrosyl chloride which the nitrosyl chloride by adding to the system only the is separated; oxides of nitrogen and hydrogen chloride. In this con (c) removing a volume of liquid from the spent liquor tinuous method water is produced constantly as indicated from step (b) substantially equal in volume to the vol in Equation 1 and the water formed has to be converted 70 ume of Sulphuric acid initially used in step (a) and re into sulphuric acid by means of fuming sulphuric acid acting this liquid in a subsequent step (a) with further or sulphur trioxide and a part of the spent liquor has to nitric oxide and nitrogen peroxide to regenerate a solu 3,338,887 3 4. tion of nitrosyl sulphuric acid in sulphuric acid which step (d), it is preferred to use a large excess of hydro is recycled for a subsequent operation of step (b) above; gen chloride over that theoretically required to react with and the nitrosylsulphuric acid in the spent liquor and then (d) reacting the remainder of the spent liquor from to use the mixed gas of hydrogen chloride and nitrosyl step (b) with hydrogen chloride thereby generating ad chloride as the source of hydrogen chloride in a subse ditional nitrosyl chloride which is separated, and continu quent operation of step (b). In order to reduce the con ing the treatment with hydrogen chloride until the con centration of nitrosylsulphuric acid in the spent liquor in centration of nitrosyl sulphuric acid in the liquor is re this step (d), the reaction with hydrogen chloride is duced to less than 3 weight percent. preferably at a temperature of 120 to 200 C. The mixed gas comprising nitric oxide and nitrogen The spent liquor which remains after step (d) has been peroxide may be obtained by mixing nitric oxide (NO) O carried out contains less than 3% by weight of nitrosyl and nitrogen peroxide (NO2) or nitric oxide (NO) (in Sulphuric acid and, as stated previously, this liquor may excess) and oxygen (O2) may be mixed and used since be utilized as an acid catalyst in the Beckmann rearrange the two react to form nitrogen peroxide. The preferred ment of cycloalkanone oxime hydrochlorides. When the gas mixture is "nitrose gas' which is that obtained by 5 nitrosylsulphuric acid content of a spent liquor exceeds the oxidation of ammonia with air. The presence of other 3% by weight, it cannot be used in the Beckmann re oxides of nitrogen, for example nitrous oxide (N2O) arrangement without causing adulteration of the lactam. which do not participate in the reaction, is also per The small amount, namely, less than 3% by weight, of missible, and it is also possible to use the spent gases nitrosylsulphuric acid present in the spent liquors pro of other industries so long as they contain nitric oxide 20 duced by the method of the invention is able to react (NO) and nitrogen peroxide (NO2).
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