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United States Patent Office Patented Feb 3,644,476 United States Patent Office Patented Feb. 22, 1972 2 Hydrodimerizations have also been taught using alkali 3,644,476 metal amalgams but low yields and great inefficiencies PREPARATION OF ADPONTRLE have been major disadvantages. U.S. Pat. 3,215,726 seeks Olav T. Onsager, Waldwick, N.J., assignor to to provide an improvement by using beta-halopropioni Halcon International, Inc. No Drawing. Continuation-in-part of applications Ser. No. trile in combination with acrylonitrile in the alkali metal 801,757 and 801,758, both Feb. 24, 1969. This applica amalgam system but still shows high production of propio tion June 23, 1969, Ser. No. 835,722 nitrile and poor yields of adiponitrile despite the use of nt. C. C07c 121/26 expensive procedures and reagents. Electrolytic hydro U.S. C. 260-465.8 5 Claims dimerization procedures suffer from the problems in 10 herent in electrolytic cell usage-proportional capital cost for increase capacity insofar as the electrolytic cells are ABSTRACT OF THE DISCLOSURE concerned, and high power costs. A process for the reductive coupling of a compound The extension of carbon chains by the reductive having the formula coupling of two groups is well known in the art. Organic 15 coupling has been accomplished for example by the well R known Wurtz reaction wherein an organic halide is XCH-CH-A coupled in the presence of metallic sodium. Similarly, wherein X is Cl, Br, or I, R is H or lower alkyl, and A organic halo compounds activated by groups such allylic, is -CN, benzylic, gem di-halides and 1,2 dihalides have been 20 coupled. For example, in British Pat. 858,514 the coupling of -bor, - R chloro substituted allylic cyano compounds is shown. or -CONR2, using as reducing agent zero valent iron or However, the coupling of non-activated halo-compounds nickel or compounds thereof. The invention especially is not shown. relates to an overall process for the production of linear 25 RELATED APPLICATIONS dimers of compounds of the formula The present application is a continuation-in-part of co R pending applications, Ser. No. 801,757 filed Feb. 24, CH-)-A 1969 and Ser. No. 801,758 filed Feb. 24, 1969. by first hydrohalogenation to 30 SUMMARY OF THE INVENTION R In accordance with the present invention, an organic XCH-CH-A compound having the formula: followed by the reductive coupling. R 35 - x-CH-bh-A BACKGROUND OF THE INVENTION is coupled by reaction in the liquid phase at about 50'- 250 C. with nickel or iron or zero valent compounds This invention relates to a process for the reductive thereof to produce the coupled product. coupling of particular halo organic compounds and in particular provides a process for the preparation of valu 40 R R able compounds such as adiponitrile starting with inex A-du-CH-CH-CH-A pensive and readily available compounds such as acryloni A being -CN, trile. O O Adiponitrile is a chemical of very great potential im 45 portance since it is easily converted to hexamethylene -oR, -R diamine by straightforward procedures. Hexamethylene or -CONR, R being hydrogen or lower alkyl (1 to 4 diamine is, of course, a component of nylon 6,6. carbon atoms), and X being chloro, bromo, or iodo. In by Presently, the bulk of hexamethylene diamine is pre far the most preferred embodiment, adiponitrile is pre pared by the costly route of first preparing adipic acid 50 pared by the coupling of 3-halopropionitrile, especially and subsequently converting the adipic acid to hexa 3-bromopropionitrile. methylene diamine. In view of the high expenses as In a particular practice, the above coupled product is sociated with the adipic acid route, those skilled in this prepared from the unsaturated compound art have devoted much time and energy to devising other, less costly routes. 55 Acrylonitrile has become a cheap and readily available CH=C-A chemical and great efforts have been expended in order by the steps of reacting said unsaturated compound with to successfully prepare adiponitrile from acrylonitrile, HX to produce via linear dimerization of hydrodimerization procedures. R However, such methods have not proved completely suc 60 cessful since in linear dimerizations yields are very low XCH-CH-A and high amounts both of polymer and of the branched followed by the coupling of this latter product. The com dimer tend also to be produced. In U.S. Pat. 3,225,083, for example, linear dimerizations are taught using aro pounds matic tertiary phosphine catalysts but these produce at 65 R best only minor amounts of linear dimer. Hydrodimeriza CH=C-A tions produce better yields of adiponitrile but inevitably high amounts of propionitrile are also produced thus wherein R and A are as above indicated undergo anti rendering the process as economically unattractive. For Markownikoff addition of HX and this is essential in example, British Pat. 1,079,696 shows hydrodimerization 70 order to produce the halo-organic product which is using a ruthenium catalyst with yields of linear products coupled to form the saturated linear derivative of the less than 50% based on consumed acrylonitrile. above said unsaturated material. 3,644,476 3. 4 Although the invention has wide applicability, in an Insofar as the coupling agent is concerned, by far the especially advantageous practice there is provided a pro most preferred practice of the invention involves the use cedure for producing adiponitrile i.e., of metallic iron as the coupling agent. Still further, it is preferred but not essential that the iron be added in NEC-CH-CH2-CH-CH-C=N finely divided form, for example, as iron powder. Iron from 3-halo propionitrile. It will, of course, be under in bulk form e.g., as sheets or large particles has also stood that the adiponitrile is readily converted to hexa been found effective in the process of the invention. The methylene diamine by known techniques. iron can be formed in situ as by decomposition of a pre DETAILS OF THE INVENTION cursor compound. O Metallic nickel which is the least preferred coupling (A) The halo organic compound agent in the inventive process, can be employed in finely The halo organic compound has the formula divided form as for example powder, or it may be pro vided in bulk form. R The coupling agent can also be composed of a zero X-CH-C-A valent nickel or iron moiety and a ligand or a nickel wherein X is chloro, bromo, or iodo, R is hydrogen or or iron carbonyl moiety and a ligand as set forth in co C1-C4 alkyl, and A is -CN, pending application Ser. No. 801,757 filed Feb. 24, 1969 O of which this application is a continuation in part. The ligand moiety of the coupling agent may be any -COR, -: R Lewis base such as phosphines, phosphites, phosphorous -CONR2. Examples are halides, amines, pyridines, o-phenanthrolines, arsines and 3-bromopropionitrile, stibines. 3-chloropropionitrile, The phosphines, arsines, stibines and phosphites may 3-iodopropionitrile, be suitably represented by the following general formulae: 3-bromo-2-methyl propionitrile, 25 RPH2----------- (R1).PH (Ri)2P-P(R:) 3-chloro-2-methyl propionitrile, (R)3P----------- (R1ASH2) -As(R1) a 3-iodo-2-methyl propionitrile, ((R)2ASH).------ (R1)3As 3-bromopropionic acid, 3-chloro-propionic acid, -As(R1)2 30 3-iodo-propionic acid, (RSbFI2)-------- ((R) SbF) R1 3-bromo methyl propionate, (Ri)3S)---------- (HO)2P(OR) 3-chloro methyl propionate, HOP (ORI) or P(OR1)3 -P 3-iodo methyl propionate, 3-bromo propionamide, 3-chloro propionamide, P(R) P(R1) 3-iodo propionamide, methyl (2-bromoethyl) ketone, The various R1 groups may be the same or different in methyl (2-iodoethyl) ketone, each ligand and may be an aliphatic, aromatic, ar-alkyl, methyl (2-chloroethyl) ketone. 40 alicyclic, phenoxy or phenylene group, both substituted (B) Preparation of the halo organic compound and unsubstituted. The aliphatic group may be an alkyl from 1-12 carbon atoms such as methyl, ethyl, butyl, The halo-organic compounds which are coupled in hepty, decyl and the like and may be substituted with a accordance with the present invention, are most suit group such as lower alkoxy, (methoxy, propoxy) hy ably prepared by hydrogen halide addition to the unsatu droxy and cyano. Preferably, the aliphatic group is a rated precursor, i.e., 45 lower alkyl group containing from 1-5 carbon atoms such as methyl, ethyl, butyl and the like. The aromatic I i group may be phenyl or a substituted phenyl such as CEI as C-A -- IX - XCH-CH-A. methoxyphenyl, hydroxyphenyl, cyanophenyl and the wherein X, R and A are as above described. Of course, like. The aralkyl group may be a benzyl, phenethyl, other methods are possible and could be used in carrying 50 phenylpropyl and the like or substituted aralkyl groups out the present invention. containing the substituents as indicated above. The ali The hydrogen halide addition is advantageously carried cyclic group may be a cycloalkyl or from 3-6 carbons, out by passing hydrogen halide into contact with liquid such as cyclopropyl, cyclohexyl and the like or a sub unsaturated precursor at moderate conditions, i.e., at 10 stituted alicyclic such as with a lower alkyl, a lower 100 C. for example. The hydrogen halide may be liquid 55 alkoxy and the like. The phenoxy or phenylene group may or vapor. be conveniently substituted with a cyano, hydroxy, lower All vapor phase techniques can be employed but these alkoxy and the like. are not preferred. The phosphorous halide reducing agent ligands may be Catalysts such as described in U.S.
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