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' ' T UNITED' STATES PATENT 'V OFFICE PatentedUNITED’ Apr.v22,_,>1947'-" STATES > PATENT' ‘ 'v TOFFICE ‘2,419,488 " PRODUCTION OF MoNocnLoRo DERIVA- ‘ ~ ' 'rrvns 0F UNSATUBATED NITRILES - ' Harris A. Dutcher, Borg'cr', ‘_Tex_., asslgnor 'to_ 4 Phillips Petroleum Company,.a corporation of ‘.Delaware> f . ' ' > v No Drawing. Application June 5,1944, I, > Serial No. 538,880 ‘ , ' 11 Claims. (01. zed-464$ , . 2 . The present invention relates to the production - Heretofore, a-chloroacrylonitrile has been pro of chlorine derivatives of unsaturated nitriles by ' duced as a by-product oi.‘ the direct substitutive the reaction of acetylene or acetylenic hydrocar- chlorination of acrylonitrile in the vapor phase bons with cyanogen chloride. More particularly over active carbon at a temperature between ap the invention relates to the production of 3- 5 proximately 200° and approximately 550° C. chloroacrylonitrile - ‘ . (Long, U. S. Patent No. 2,231,363). The process (Z-chloroviny] cyanide,‘ C1__CH___CH_CN) yields 2-chloroacrylonitrile as the principal prod uct. vNo other methods for the production of 3 rgldsl?ltlgfesmigoilxgr196ii?ggtggesagty‘gfgtg; chloroacrylonitrile or other monochloro deriva acetylenic hydrocarbons and cyanogen chloride 10 tives of unsaturatednitriles are known. ‘ ' ’ I have found that acetylene and acetylenic hy is 2281322232”; ‘13355;:ffgléetggesggtdilrgggi? . drocarbons may be reacted with cyanogen halides . I . v to produce.monohalogen-substituted unsaturated monochloro derivatives of unsaturated mtnles, . 1 such as 3-chloroacrylonitrile by there'action of- 1 mtr?es' The reactlon 1.5 facihtated ‘by certain ’ - » >15 catalysts which are referred to more speci?cally acetylene and cyanogen chloride. , hereinafter _ provideAnother a categlyst ob'ect (1201‘f thpfoggtiiirgtthevggg?lo?rg- e ‘n ' ' ‘ o Cyanogen' ‘ihlmd‘?. 157a readny.condens1ble. gas action of cyanogen chloride and acetylenic hydro- ' havmg a.memng pom? of approximately _6'5° Q‘ carbons and a boiling point within the range of approxi ‘ . mately 12.5 to 15.5“ C,‘ Itis very soluble in water, Other obJects- and advantages of the invention,. s alcohol and etherk Cyanogen chloride may‘ be‘ some of which are referred to-more speci?cally. readily prepared by the action‘ of chlorine on hy_ ‘ - ' ‘ hereinafter, will beapparent to thoseskilled 1n drogen cyanidek Investigations!“ methods for the art to which the invention pertains. , - . _ . Monochloro derivatives of unsaturatednitriles, ' the. preparatlon of .cya?nogen chlomde were de such as s_chlomacrylonitr?e : . 25 scribed by ‘T. Slater Price and Stanley-J. Green » - '- (J . ‘Soc. ,Chem.'Ind., 1920; vol. 39, pages 98-101T; <2-°h10r°vmy1 cyanide, 1-<>yan0-.2-"v . 11; ' Chem. Abs. 1920 vol. 14,-page‘ 2056). It has been chloroethylenei C1_CITI:CH,_CN)» reported that at 37°‘ C. cyanogen chloride ‘does 3-phenyl-3-chloroacrylonitrile _ - . not-react with ethylene (Ronald B. Mooney and ' (2-phenyl-2-chloro-vinyl cyanide, " I 30 Hugh G. Reich-J. Chem. Soc. (London), 1931, -- ' ;‘ _'_'._ ,-pase2597>-' ' I’ . CGHS 1 (in-CH1 CI?!) ' -: 1 Reactions similar to those of cyanogen chloride and z'chloro'l?'butadlenm cyatmvdevv ' ' occur with other- cyano'gengh'alides, such as 'cyé - (3-chloro-2,4-pentadienenitrile, > I ‘wan'ogen. bromide and cyanogen iodide, but the I_' CH2=CH__C(:¢1)=C I‘ 35 products are not at present of as‘v‘great industrial- interest as .the chloro' derivatives of unsaturated v1 and similar compounds, are products ofpoten-V * nitr?es , , I , , v v . tial industrial interest. They p'ossessrrmany of the ' . v I?aécordance withi*a[spe-ci?c'ém?bdinljent of ' I properties which make acrylonitrile desirable as the process of my invention-v'cyanog'e?'chloridé is. _ a material for copolymerization with 1,3,-,b_uta-' ,n voiatilized and’ passed,th;.ough"a; solution vof ; ' diene to form synthetic rubber. .Copolymersjof f1“- ace-tylene in an inert solventsuchhexane Orr butadienesaturated andmmles’ such withmonochloro Pr. without. derivatives apr'y 1091191111? of un_; 7' - v chloroacrylonitrilemaybeother saturated'hydm-carbens. separatedjfrorn _ The“ resulting the 1m}. 3_ 01' “her unsaturatfid Mme’ Possess SOme ‘its-W1“ ‘ reacted acetylene and solyentby distinatiomprer-a- I ~ I ' advantages over simple copolymers of butadiene 45'_erab1y in the- presence.dfia.siibstancgiaapablé'pf . .. and acrylonitrile and over copolymers of buta-v _ - . an - ioXida-n't» {inhibitor-‘01:0 _ _> ." diene and dichloro' derivatives of acrylonitrile and ' friggélaiigg * t 1035,; a "1', “1y _' I‘ °V.er. 9011mm“ 0? blltt'diene and Styrene con" ' Insteadof'using the foregoing‘procedurej'soine-.'f’ - taming chloropropmmtrlles as comonomers. ~ ~ . what bet-ter- yieldis’are bbtainedr when catalysts These monochloro derivatives of unsaturated 5bxwhi‘ch prombte the additidn reaction‘ar-e used’ H nitriles may be hydrolyzed in' conventional‘ man ' -,Cuprous chloride issuchlas‘ a catalystand may1 ’ ner to produce the corresponding monochl'oroQun saturated acids,' for example, z-chloroac'rylic' "d; e-ujsea' asffol-lowsi' _Iknto_-ian__-agueous solution or" ' , and they may be hydrogenated to yield; ,c rolls-chloride qr'f‘examplego eicqnsistingior" ‘' chloro saturated nitriles, such asQ3'7-chlo 0'11; pionitrile, in the'presence'of catalysts such op _ er,v 15 cckoflconcentrated‘hydrochloric-‘acidand’ " 1,891,055) and Raney nickel (Winan's,,U._ff$;iPat-§ > ~- 51‘200cc', of‘water, are passed; streams ‘of acetylene - ent No. 2,334,140). The resulting hydrogenated . >_""and>cyai1ogen"chloride atsuch?owjrates'thatan beproduct, dehydrochlorinated for example, 3-chloropropionitrile,' to yield) acrylonitrile can 60'j approximatelymaintained. The‘ equimolecular'ratio catalyst solution o1 ismaintalned}; reactants is ' -(Pieroh, U. S. ‘g’atent No. 2,174 756). _‘ i v - _ ' ' preferably ata.temperatureof'approxiinately _ 2,419,488 3 . 4 to 210° F. The chloroacrylonltrile that is formed able for extensive investigation and since the re may collect as an oily layer or may be volatilized action products are rather complex and have not with the unreacted acetylene and cyanogenrchlo heretofore been identified in other reactions, so ride, depending on the reaction temperature. If . that their separation and identi?cation cannot be volatilized, it can be separated from the eiliuent readily accomplished. In the reaction of meth vapors by fractional condensation. The con ylacetylene and cyanogen chloride, for example, densed crude chioroacrylonitrile may then be sub it has not been established conclusively whether sequently puri?ed by fractional‘distillation, using ' the resulting product is a polymerization inhibitor in this operation. Al ternatively, the total effluent may be condensed CH:—C=OH—-CN ' and the chloroacrylonitrile recovered therefrom , l and from‘ other products formed in the reaction 8-chloro-3-methylacrylonitrile by fractional distillation. O1‘ - In accordance with another method for the CH:—O=CH_—C1 practice of my invention, which is preferred for 15 N certain purposes, cyanogen chloride and acetyl 3-ehloro-2-methylacrylonitrile ene, with or without a diluent gas such as nitro gen, are passed in approximately equimolecular because of the di?iculty of separation and iden proportions over a solid contact catalyst which ti?cation of the products. promotes the reaction at a temperature within 20 Although the foregoing description is directed the range of approximately 100° to 400° C. Solid particularly to the reaction of cyanogen chloride cuprous chloride or cuprous cyanide is a suitable with acetylene, in both vapor and liquid phase, catalyst, although barium cyanide, sodium cya to produce 3-chloroacrylonitrile, it will be obvious nide, potassium cyanide, and similar alkali and that by suitable conventional modification the alkaline-earth metal cyanides may be used. processes can be readily adapted to the produc Such solid contact catalytic materials, when used tion of other monochloro derivatives of unsat in the process of my invention, are preferably urated nitriles by the' reaction of cyanogen chlo deposited or coated on such adsorbent supporting ride and acetylenic hydrocarbons. Suitable acet or carrier materials as charcoal, bauxite, fuller’s ylenic hydrocarbons for use in such processes are earth and the like. Conventional methods may 30 methylacetylene (propyne, allylene), ethylacet be used for preparing'such supported catalytic ylene (l-butyne), dimethylacetylene (Z-butyne, materials. For example, a barium cyanide cata crotonylene), vinylacetylene (3-buten-l-yne) as lyst suitable for use in the process is prepared well as aromatic acetylenic hydrocarbons such by impregnating activated charcoal with an aque as phenylacetylene and the like. In connection ous solution of barium cyanide and thereafter with acetylenes containing a double bond in the I heating the resulting material to remove water; molecule, such as vinylacetylene, it is desirable such alternate impregnation and drying may be tovmaintain the reaction conditions within more repeated as often as necessary to obtain a cata critical limits in order to obviate any possible lytic material with the desired content of barium reaction of the double bond. However, a rather cyanide. ’ 40 Wide latitude is permitted between reaction con Wide variation is permissible in the proportions ditions which favor the reaction of a triple bond of the reactants which are used in the process. as in acetylene and those which promote sub These will largely be preselected with a view stantial reaction of a double bond. toward minimizing or obviating
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