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United States Patent (19) 11) 4,085,129 Semler Et Al

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United States Patent (19) 11) 4,085,129 Semler Et Al United States Patent (19) 11) 4,085,129 Semler et al. 45) Apr. 18, 1978 (54) PROCESS FOR THE PREPARATION OF 3,255,230 6/1966 Kurkjy et al. ....................... 260/463 CHLOROFORMICACDARYLESTERS AND CYCLC CARBONATES FOREIGN PATENT DOCUMENTS 75) Inventors: Ginther Semler, Kelkheim, Taunus; 2,007,804 1/1970 France ................................. 260/463 Georg Schaeffer, Hofheim, Taunus, OTHER PUBLICATIONS both of Germany Kirk-Othmer, Encyclopedia of Chem. Technology, 73) Assignee: Hoechst Aktiengesellschaft, 2nd ed., vol. 4, Interscience Publishers, N.Y. (1964), p. Frankfurt am Main, Germany 386. 21 Appl. No.: 727,332 Cotter et al., Chemistry & Industry, pp. 791-793, 5/8/65. (22 Filed: Sep. 28, 1976 Primary Examiner-Joseph Paul Brust Related U.S. Application Data Assistant Examiner-Robert C. Whittenbaugh Attorney, Agent, or Firm-Curtis, Morris & Safford 63 Continuation-in-part of Ser. No. 543,340, Jan. 23, 1975, abandoned, which is a continuation of Ser. No. 57 ABSTRACT 265,557, Jun. 23, 1972, abandoned. A process for the preparation of chloroformic acid (30) Foreign Application Priority Data aryl-esters and cyclic carbonates of aryl compounds containing at least two phenolic hydroxy groups Jun. 25, 1971 Germany ............................. 2131555 wherein aromatic compounds containing one or more Mar. 20, 1972 Germany ............................. 2213408 hydroxy groups linked to an aromatic nucleus, are re 51) Int. Cl. .............................................. C07C 68/02 acted with phosgene in the presence of catalytic 52 U.S. Cl. ................. amounts of N,N-disubstituted acid amide either under 58) Field of Search ......................................... 260/463 pressure or without pressure while removing the hydro gen chloride continuously from the reaction mixture. 56) References Cited This improved process results in almost quantitative or U.S. PATENT DOCUMENTS very high yields of pure products and avoids problems 3,170,946 2/1965 Kilsheimer et al. ................. 260/463 such as disposal of waste water. 3,211,774 10/1965 Stephens .............................. 260/463 3,211,776 10/1965 Stephens .............................. 260/463 11 Claims, No Drawings 4,085,129 1. 2 and hydrogen chloride by-product, from the reaction PROCESS FOR THE PREPARATION OF zone during the course of the reaction. After the reac CHLOROFORMICACD ARYL ESTERS AND tion has been completed under the aforedescribed con CYCLC CARBONATES ditions, the liquid phase is removed from the reaction This application is a continuation-in-part of copend zone and the chloroformic acid aryl esters are recov ing application Ser. No. 543,340 filed Jan. 23, 1975, now ered in high yields. abandoned, which was a continuation of application Substituted phenols or substituted naphthols are Ser. No. 265,557, filed June 23, 1972, now abandoned. herein meant to be, above all, compounds which con The present invention relates to a process for the prepa 10 tain one or more substituents being identical or different ration of chloroformic acid aryl esters and cyclic car which are chosen among the following groups: bonates of aryl compounds containing at least two phe halogen, such as fluorine, chlorine, bromine, nitro, nolic hydroxy groups. alkyl having from 1 to 18, preferably from 1 to 6 carbon The preparation is carried out by reacting aromatic atoms, phenyl optionally substituted, alkoxy having compounds containing phenolic hydroxy groups with 15 phosgene in the presence of catalytic amounts of a N,N- from 1 to 5 carbon atoms, phenoxy optionally substi disubstituted acid amide. tuted, aralkyl optionally substituted and containing al The preparation of chloroformic acid esters from kylene groups which have from 1 to 8 carbon atoms. alcohols or phenols and phosgene is known. While the Especially important starting materials, besides the reaction with alcohols already occurs at low tempera 20 phenol, are compounds which correspond to the gen tures and in the absence of a catalyst, the reaction of eral formula phenols with phosgene cannot be effected without the addition of hydrogen-chloride-binding substances. For this purpose, tertiary amines, such as N, N-dimethyl R R aniline (cf. Ullmann, Encyclopadie der technischen 25 Chemie, vol. 5, pages 380 et seq., 1954) or also aqueous alkali (cf. German Pat. No. 1,117,598) are generally R2 Gr (OH), used. This process has the drawback that the said basic R R6 auxiliaries have to be used in stoichiometric amounts n which is not economical and leads, furthermore, to the 30 formation of great amounts of organic and inorganic wherein R, R, R and Rare identical or different and salts thus raising big problems as to waste water. each represent hydrogen atoms, alkyl groups having It is, furthermore, known, that phenol reacts with phosgene at elevated temperature and under pressure in from 1 - 12, preferably from 1 - 10, most preferably the presence of catalytic amounts of tertiary amines or 35 from 1 - 6 carbon atoms, especially chlorine or bromine N,N-dialkylated acid amides. (cf. U.S. Pat. Nos. atoms, or wherein R and Rand/or RandR together 3,211,776 and 3,211,774). This process has the marked stand for a condensed benzene radical, RandR which drawback that the course of the reaction is not quantita may be identical or different, each represent chlorine tive and therefore, with relatively low yields, the sepa atoms, nitro groups or, preferably, hydrogen atoms, A ration of the chloroformic acid phenyl ester from the represents a direct linkage, an oxygen atom or a low unreacted phenol becomes very difficult. alkylene or cycloalkylene group having up to 6 carbon It has now been found, that these drawbacks can be atoms, preferably an alkylene group having from 1 - 3 avoided when the reaction of phenol, substituted phe carbon atoms, n is an integer from 1 to 3, perferably 1 to nols, unsubstituted and substituted naphthols and of 2 and m is zero, 1 or 2, preferably zero or 1. compounds containing in the vicinity a second hydroxy 45 group (in the preparation of cyclic carbonates), is ef If n is different from 1, the hydroxy groups can be fected with phosgene by adding catalytic amounts of a linked to the same or to different aromatic nuclei. All N,N-dialkylated carboxylic acid amide either pressure hydroxy groups are converted, according to the process less or under pressure and care is taken that the hydro of invention, into chloroformic acid ester groups if they gen chloride can escape continuously. Under these con 50 do not stand in ortho- or peri-position one to another, ditions, the reaction of the phenols and naphthols with such as, for example, in the pyrocatechin or in 2,3- or phosgene occurs practically quantitatively and the 1,8-dihydroxynaphthalene. In this case, the chlorofor chloroformic acid aryl esters or carbonates are obtained miates are transformed into the cyclic carbonates by in high yields and in pure state by simple distillation or intramolecular reaction. recrystallization. 55 Compounds in which hydroxy groups are linked to More specifically, it has been found that chlorofor more than one aromatic nucleus are, for example: 4,4'- mic acid aryl esters can be obtained in high yields in a dihydroxy-diphenyl, 4,4'-dihydroxy-diphenyl-methane, process wherein a liquid phase reaction mixture of a 2,2'-dihydroxy-3,3'-dicyclohexyl -5,5-dimethyl phenol or a naphthol and from 0.5 to about 20 mol percent of an N,N-dialkylacid amide catalyst is formed diphenylmethane, 2,2-(4,4'-dihydroxy-diphenyl)-pro and phosgene is introduced into that reaction mixture pane, 2,2-(3',3'-dimethyl-4,4'-dihydroxydiphenyl)- while maintaining the reaction temperature in the range propane, 2,2-(3',3'-diisopropyl-4,4'-dihydroxydi of from 30 - preferably of from 40 to 180° C and the phenyl)-propane, 2,2-(3',3'-di-tertiary-butyl-4,4'-dihy reaction pressure in the range of from atmospheric to droxydiphenyl)-propane, 2,2-(4,4'-dihydroxy about six atmospheres. A stoichiometric deficiency of 65 diphenyl)-butane or 1,1-(4,4'-dihydroxy-diphenyl)- phosgene with respect to the phenol or naphthol used is cyclohexane. maintained in the liquid phase reaction mixture by con Suitable catalysts are carboxylic acid amines disubsti tinuously venting gases, including unreacted phosgene tuted at the nitrogen atom of the general formula 4,085,129 4. ation is effected at a pressure of from about atmospheric R to about two atmospheres. N Products the melting point of which is above the N-CO-X reaction temperature are advantageously worked in R solution or in suspension, suitable solvents being those which are inert to phosgene, such as, for example, tolu wherein R and R' each represent low alkyl radicals ene, xylene, chlorobenzene or butyl acetate. having up to 4, preferably 1 or 2 carbon atoms which In all cases after the reaction has been completed, may also form, together, an alkylene group having from practically no starting product can be detected any 4 to 6 carbon atoms, preferably 5, and X represents a 10 more, for example, by gas chromatography. hydrogen atom, a low alkyl radical, preferably a methyl The reaction is advantageously carried out in such a radical, or a low molecular dialkylamino group the manner that phosgene is continuously passed through alkyl radicals of which may be identical or different, the reaction mixture the excess being formed in each preferably contain 1 to 2 carbon atoms, the radicals R or case escaping together with the hydrogen chloride. The R" each being able to stand together with X for an alkyl 15 phosgene escaping from the reaction mixture can easily group having from 3 to 5 carbon atoms, preferably for be condensed and introduced again into the reaction a 1,3-propylene group. mixture, while the hydrogen chloride which boils at Especially suitable catalysts for the process of the lower temperature escapes.
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