SK207990A3 - A connection of appparatuses for producing n-cyclohexylthiophthalimide - Google Patents

Abstract

The connection described in this patent is solved so that, the circulation cycle closed to the production of cyclohexylsulphenyl chloride is superposed before the circulation cycle of the condensation reactor created based on the circulation pump, heat exchanger and by the condensation reactor alone, being equipped with inlets for supplying of solution closed to cyclohexylsulphenyl chloride, potassium hydroxide solution, phtalimide, potassium chloride solution water and pure organic solvent, and the circulation cycle closed to the condensation reactor for the production of N-cyclohexylthiophthalimide is superposed before the filtration equipment with the subsequent water and organic phase separation, while this part continues directly or via intermediate reservoir to the point closed to product refining and in the subsequent step to the point responsible for product filtration together with solvent separation.

Description

The invention relates to the involvement of apparatuses for the production of N-cyclohexylthiophthalide.

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N-Cycloalkylthiothralimide can be prepared by the condensation reaction of a cyclohexylsulphenyl halide, preferably cliloride, with potassium phthalimide in an organic solvent, preferably non-polar, at temperatures of -15 to +50 ° C. The cyclohexylsulphenyl halide, generally chloride, is prepared by direct chlorination of cyclohexanethiol to dicyclohexyl disulphide followed by, for example, chlorination to cyclohexylsulphenyl chloride. Chlorination uses chlorine gas, rarely chlorine in solution in a perhalogenated nonpolar organic solvent. The solvent used to suspend potassium thalimide is preferably identical to the solvent used to prepare cyclohexylsulfenyl chloride. The yields of the thus prepared K -cyclohexylthiophthalimide are in the range of 58% of theory.

Another known preparation method is the reaction of a cyclohexylsulfenyl halide, preferably chloride, with phthalimidoin in a nonpolar organic solvent in the presence of an aprotic organic base e.g. trietylaraínu. The yields of the N-cyclohexylthiophthalicide thus prepared are also in the range of δο ^ χ 58%.

Another known method for the preparation of K-ClFFI is by direct chlorination of a mixture of Italimide potassium and the like. Italimide and dicycloboxy disulfide in a non-polar organic solvent environment. The yields obtained by this procedure do not exceed 30% of theory.

A disadvantage of the known processes for the production of N-cyclohexylthiophthalimide is that it requires the preparation of potassium phthalimide with high energy requirements, respectively. energy and handling requirements in the case of direct reaction of phthalicide with cyclohexyl halide to regenerate the organic base or low yields by direct chlorination of a mixture of potassium phthalimide and dicyclohexyldi sulfide.

The N-cyclohexylthiophthalimide production apparatus is discontinuous and consists of a portion for the production of potassium phthalimide, a portion for the production of cyclohexylsulfenyl chloride and a portion for conducting the reaction of cyclohexylsulfenyl chloride with potassium phthalimide. The device consisting of three basic units is bulky, since all three reactions work with concentrations of active substances up to 20 h hmtM. It requires increased energy and operating demands.

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The above disadvantages are solved by the invention.

the principle of which is the involvement of apparatuses for the production of N-cyclohexylthiophthalimide, eliminating the separate preparation of potassium phthalimide, wherein the N-CBTrl reactor system has a pre-circulation circuit for the preparation of cyclohexylsulphenyl chloride, phthaldehyde dosing and solutions of KOH, KCl, organic solvent and water. The circulation circuit of the N-CHTF1 reactor is upstream of the filtration apparatus followed by separation of the aqueous and organic phases, this part directly connected to the product separation node from the organic solvent, which is also upstream of the product refining node and subsequently the product separation node with solvent separation.

The dicyclohexyldisulphide solution cooler (DCHDS) provided with the DCHDii solution inlet line is connected to a cyclohexylsulfenyl chloride reactor (G'iioCl) which is connected to a circulation pump and a recycle cooler to a circulation circuit equipped with a chlorine inlet line, the C106 N8 circulation circuit connected to the reactor. -cyclohexylthiophthalimide, 1 ', which is provided with an inlet pipe of a solution of the Koes connected to a metering pump equipped with an inlet pipe of KOH and at the same time an N-CHTFI reactor is provided with an inlet pipe of phthalimide connected to the dosing device provided with an inlet pipe of phthalimide; the organic solvent piping, the water inlet piping and the KC1 solution inlet piping connected to the KC1 solution measuring cup, and the N-CliTFI reactor is connected by a piping to a circulation pump and a flow exchanger to the circulation circuit, is connected by a piping to a mixing boiler equipped with an outlet piping m connected to a reaction pump for the filter, provided with a filter cake outlet and a filtrate piping into a phase separator provided with an aqueous phase outlet pipeline connected to a water phase tank connected to a pump® outlet connected to a scoop upstream of N -CHTFI and at the same time the organic phase separator outlet piping after the filter is connected to the organic phase reservoir, which is connected via an outlet pipeline through a pump to an organic solvent recovery boiler, further equipped with a distillate outlet condenser connected condenser connected with a phase separator pipeline with a water outlet phase and an organic solvent outlet pipe connected to an optional device e.g. physical drying, which is connected via a pipeline to the regenerated solvent reservoir with a concurrently provided fresh solvent inlet pipeline and an organic solvent outlet pipeline connected to the pump further into the N-Cl 2 I reactor, while the organic phase recovery boiler is connected through a pipeline e.g. product melt with a dissolution boiler provided with an organic solvent inlet conduit, a condenser outlet conduit and a pump outlet conduit interconnected with a filter equipped with an outlet conduit connected to the dissolution boiler and a phase separator outlet conduit connected with the outlet conduit an aqueous phase and a product solution outlet pipe in an organic solvent connected to a crystallization boiler equipped with a product suspension outlet pipe connected through a pump to a filter provided by a filtrate outlet pipe e.g. for regeneration and an outlet path of the filter cake connected to an annealing device provided with an organic solvent outlet pipe, a water inlet pipe and an outlet pipe e.g. of the aqueous product suspension combined with the finalizing line.

The wiring according to the invention has the following advantages over the prior art devices: it allows to conduct the preparation reaction

N-CHTFI without the need for a plant for the production of potassium phthalimide, and in high yields and solectivity allows industrial production of N-CHTFI by reacting potassium phthalimide in situ. It ensures the removal of the heat of reaction of the exothermic reaction; 96% wt. suitable for application in the processing of rubber mixtures.

In the actual production process, a batch of dicyclohexyldisulphide (DCHDa) solution in an organic solvent to the reactor 4 for production of CIIIII is passed from the reservoir via route 1 through the cooler 2, further via route 3. The DCitPo coke circulates via pump 3, pump 11, with outlet path 12 to cooler 8, and then through path 2 to CHSC1 reactor 4. It enters the circulating solution via route 7 (dry / chlorine gas). The condensation reactor is fed via a route 20 with a portion of KCl solution, via a route 18 with a portion of the powdered thalimide (11) from an automatic weighing device 16 via a metering device 17. The slurry 11 from the reactor 23 is circulated via a line 24 via a circulation pump 25. The potassium hydroxide solution enters the condensation reactor 23 via line 14 from a metering pump 13 provided with an inlet line 86 of potassium hydroxide solution. At the same time, the preformed solution of Cl 2 Cl 2 passes through route 10 from the circulation circuit to the condensation reactor 23 (in a predetermined ratio with potassium hydroxide). Optionally, after the dispensing of the reaction components, the reaction mixture is supplemented with water 20 and the organic solvent route 20 from line 21, and the reaction mixture proceeds from reactor 23 via route 29 to the refiner boiler 30 where the crude reaction mixture is allowed to cool to the selected temperature. From the post-boiler the reaction mixture proceeds via route 31 to a pump from which route 33 leads to a filter device 34. from which route 35 the filter cake exits and at the same time via route 36 the filtrate is fed to the phase separation device 37. The water phase proceeds via route 38 to apparatus 40, from which it exits via route 41 to the pump 42 and then via route 43 is led back to the measuring cup 19 and to the measuring cup. route .66 for further processing. the organic phase solution proceeds from the phase separation apparatus 37 to the intermediate phase 44 of the organic phase. From the reservoir 44, the organic phase solution is passed via the pump 45 through the pump 46 and then via the route 47 to the recovery boiler 48. At the same time, a batch of organically contaminated or fresh water enters the recovery boiler via route 46. the degenerate organic solvent passes through route 59 to the heat exchanger system 60, from which route a1 passes to the phase separation apparatus 52. The aqueous phase passes through route 63 to the organically contaminated water system, the organic solvent passes through route 64 to the drying system and then route 65 to storage tank 66 of organic solvent, the degenerate organic solvent may alternatively proceed via routes 64, 87 and 65 directly to reservoir 86. From reservoir 66, the organic solvent flows via route 67 through pump 68 with outlet route 22 back to condensation reactor 23 or b. The product solution in the organic solvent passes through the pump 52 via the pump 54 with the discharge path 56 to the filter apparatus 57 with the outlet 58 back to the dissolution apparatus and simultaneously with the outlet 55 to the phase separation apparatus 59. 53 and 55 to the phase separation device 69. The aqueous phase proceeds from the phase separator via route 70 to the sewage treatment system, the organic phase proceeds via route 71 to the crystallization plant 72. The product suspension in the organic solvent proceeds via route 73, pump 74 and route. 75 to a filtering device 76 from which the filtrate passes through a route 77, for example, solvent recovery and a filter cake moist from the organic solvent, passes through a line 78 to the hot water dispenser TO, into which water suspends the cake. Solvent vapors and respiratory gases are passed through line 81 at normal or reduced pressure. as an azeotropic mixture to the heat exchanger system 82 from which they exit via route 83 and at the same time the organic solvent-free product, for example, as an aqueous suspension, passes through route 84 for finalization. The crude product, after regeneration of the organic solvent, proceeds from the recovery boiler 48 via route 50 to the dissolution boiler 51.

The invention is described in more detail below with reference to a specific embodiment.

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Example: ---------- ^{L -} To the cyclohexylsulphenyl chloride (CH 3 Cl) production chlorination reactor, 2 056 kg was fed through the exchanger inlet path

11.5% of a solution of dicyclohexyldisulfide (DC'h'ki) in carbon tetrachloride. The loaded DCHD5 solution, which was circulated through the tc-pla peripheral exchanger, was charged within 3 A hours. 76 kg of chlorine gas was supplied via the circulation pump suction route. A 13.4% C18SCl solution was obtained, which represented a 93% conversion of C18 to C18.

The contents of a 17x aqueous XC1 measuring cup were introduced into the condensation reactor with stirring, and 294 kg of ground lithium was seeded with a weighing device. The obtained suspension of the lithium azalide in aqueous KCl solution was cooled to -3 * 6 by circulation through a peripheral heat exchanger. Upon reaching this temperature, a 23% potassium hydroxide solution was metered into the condensation reactor via a metering pump. After a period of b min, the cyclohexylsulfenyl chloride solution prepared in advance was pumped into the condensation reactor so that the volume of CdClCl solution was evenly pumped over 25 minutes. min. The dosing of the 25% potassium hydroxide solution also took 25 min at a flow rate of 14.5 t / min. A temperature of -5 ° C to 3 ° C was maintained in the circulation circuit during the reaction. After dispensing of the reaction components, the reaction mixture was supplemented with 355% water and 1350 L of regenerated carbon tetrachloride. the reaction mixture reacted within 1 hour. Subsequently, the contents of the condensation reactor were pumped into a scrubber, where the contents were heated to 40-45 ° C with stirring over about 1 hour. The crude reaction mixture was then filtered to collect about 12 kg of the main cake. The product solution in carbon tetrachloride after separation of the aqueous phase was collected in an intermediate tank at 3,640 kg with an active ingredient content of 13.0%, which represents a 95% conversion calculated to the incoming cyclohexylsulphenyl chloride.

The obtained product solution in carbon tetrachloride was then pumped into a solvent recovery boiler in which 500 L of water was introduced. After distillation of the solvent, the product melt formed was subsequently dissolved in 3500 liters of cyclohexane, introduced in a dissolution collector at a temperature of 0 05 ° C. by filtration of the cyclohexane solution of the product, approximately S kg of insoluble fraction having a major phthalimide content was separated. The product solution in cyclohexane, after separation of the aqueous phase, was collected in crystallization boilers, where it was cooled to 8 - 10 ° C with stirring. The crystallized product was filtered, collecting 3,300 L of a 0.88% product filtrate, and then cyclohexane-moist filter cake was removed in a vacuum distillation apparatus. 1,300 kg of a 10.3 kg slurry were removed for finalization % of the product, representing J3, by X-n yield on the product obtained by the condensation reaction.

Claims (2)

1. Apparatus for the production of N-cyclohexylthiophthalimide characterized in that the circulation circuit of cyclohexylsulphenyl chloride is preceded by a circuit of a condensation reactor consisting of a circulation pump, a heat exchanger itself having a condensation reactor, which is also provided with cyclohexylsulphenyl chloride solution, of phthalimide, KCl solution, water and pure organic solvent and at the same time the circulation circuit of the condensation reactor for the production of N-cyclohexylthiophthalimide is upstream of the device for filtration followed by elongation of the aqueous and organic phases. which is simultaneously upstream of the product refining node and then the product filtering node with solvent separation. Wiring according to claim 1, characterized in that the exchanger (2) provided with an inlet pipe (1) is connected by a pipe (3) to the production of cyclohexylsulphenyl chloride which is connected to the circulation pump (11) and (11) and further along route (12) with exchanger (8), connected route (9) back to the cyclohexylsulfenyl chloride reactor, whereby inlet routes (6) and (7) of chlorine and at the same time circulation routes - the cyclohexylsulfenyl chloride production circuit consisting of the reactor (4), the pump (11) and the exchanger (8) is connected via a line (10) to a condensation reactor (23) connected by a line (24) and a pump (25) connected to a line (20) through a heat exchanger (27) connected by a conduit (28) with a condensation reactor, which is simultaneously connected by a conduit (18) to a metering device (17) of a storage tank (16) of a phthalitnide batch provided with an inlet (15) thalimide is provided with an inlet line (14) connected to the metering pump (13) of the potassium hydroxide solution provided with an inlet line (85) from the potassium hydroxide solution stock, a condensation reactor (23) is provided with an inlet line (14) associated with the metering pump 13) a potassium hydroxide solution provided by a tube (85) from a potassium hydroxide solution stock, a condensation reactor (23) is provided with an inlet pipe (7) of an inlet pipe (19) of a KCl solution (19), an inlet pipe (1l) of water; the inlet conduit (22) of the organic solvent and at the same time the condensation reactor (23) is connected by a conduit (28) to a post-reaction boiler (30), the outlet of which is connected by a conduit (31) to a pump (32) (34) equipped with an outlet path (35) of the filter cake and at the same time interconnected pipeline (36) with a system (37) of phase separation by interconnected pipeline (38) with a storage tank com / 40 / KC1 solution connected by piping © / 41 / with pump / 42 / connected © piping® / 43 / with ormerica / 16 / and at the same time pump (42) of KC1 solution is connected by piping / 66 / with system of another and the phase separation system (37) is connected via a line (39) to an intermediate tank (44) of the organic phase, which is connected via a line (45) to a pump (46) directly connected to a recovery boiler (46) and a recovery boiler (48) connected via a line (35) to a heat exchanger system (60) connected via a line (61) with a phase separator (62) directly connected via a line (63). (with an organically contaminated water system and at the same time a phase separator (52) is connected via a line (64) to an organic solvent drying system connected via a line (65) to a regenerated solvent tank (66) directly connected to the line The pump (68) is connected via a discharge line (22) to a condensation reactor (23) and at the same time the line (64) and (65) of the inlet and outlet of the regenerated organic solvent into of the drying system directly connected by a pipe (87) and at the same time the recovery boiler (48) is connected by trumpets (56) to the dissolution * boiler (51) of the product provided with solvent inlet pipe (68) and (54), which is connected via a line (56) to a filtering device (57) from an outlet connected via a line (58) with a dissolution boiler (31) and a line (55) to a phase separation system (89), Dissolving boiler (51) via line (33) directly connected via line (55) further to the phase separation system (69) with the outlet line (70) to the sewage treatment plant and at the same time the phase separation system (69) is connected via line (71) with the crystallization device / 72 / sp via a duct (73) with a pump (74) of the suspension connected from the discharge via a duct (75) to a filtering device (76) which is connected via a duct (77) to the organic solvent recovery system and at the same time with an incineration device (79) provided with a water supply line (80), an outlet conduit (81) of solvent vapor or an azeotrope pair with a heat exchanger system (82) connected to a vacuum system (83) and the incineration boiler (79) connected with a conduit 84 / output of, for example, a suspension of the N-cyclohexylthiophthalroid product for final processing.