WO2023223192A1 - Système et procédé de préparation de mono-nitro benzo trifluorure (nbtf) - Google Patents

Système et procédé de préparation de mono-nitro benzo trifluorure (nbtf) Download PDF

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Publication number
WO2023223192A1
WO2023223192A1 PCT/IB2023/055013 IB2023055013W WO2023223192A1 WO 2023223192 A1 WO2023223192 A1 WO 2023223192A1 IB 2023055013 W IB2023055013 W IB 2023055013W WO 2023223192 A1 WO2023223192 A1 WO 2023223192A1
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reactor
nitro
benzo
nbtf
reaction
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PCT/IB2023/055013
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English (en)
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Ganesan Muruganandam
Rajendra Gajare
Ganesh Salunkhe
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Deepak Nitrite Limited
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/16—Separation; Purification; Stabilisation; Use of additives

Definitions

  • the present subject matter described herein in general, relates to a system and process to produce Mono-Nitro benzo trifluoride (NBTF).
  • NBTF Mono-Nitro benzo trifluoride
  • the invention relates to an improved, continuous process and system for production of 3 -nitro benzo trifluoride, 2-nitro benzo trifluoride, and 4-nitro benzo trifluoride.
  • nitrating benzo trifluoride is old and well known and has been commercially practiced for many years to yield mono-nitro compounds or generally nitro mass.
  • the produced nitro mass is used, in turn, in the production of corresponding amino compounds.
  • the manufacture of nitro mass comprises the batchwise, stepwise or continuous addition of nitric acid to the mixture of sulfuric acid and benzo trifluoride or addition of nitrating mixture to the benzo trifluoride.
  • the reaction rate and the reaction efficiency between the phases are largely limited by mass transfer; that is, by the ability to expose large interfacial areas of each of the phases to each other. As the interfacial areas are increased, the reaction rate between the phases is enhanced. In conventional nitro mass production facilities, these interfacial areas are normally created by reacting the two phases in one or more agitated vessels where high shear forces are applied to the liquids.
  • Perry Chemical Engineering Handbook
  • 6th Edition several methods are proposed to achieve intimate mixing or contact between liquids including, for example, in-line motionless mixers, mechanical agitation, gas agitation, jet mixers, injectors, orifice mixers and nozzle mixers.
  • NBTF mono nitro-benzo trifluorides
  • a system for continuous production of mono nitro-benzo trifluorides comprising a first reactor configured for mono-nitration of benzo trifluoride by 90-98% reaction conversion of reactants comprising BTF, H2SO4, and nitric acid.
  • the system may further comprise a second reactor configured for mono-nitration of benzo trifluoride with the remaining 2-10% reaction conversion of the reactants.
  • the system may further comprise a third reactor enabled for separation of spent acid and organic layer comprising nitrobenzo trifluoride by the water addition to maintain the desired strength of spent acid.
  • the reaction generates 84-85% strength spent acid in the nitro-mass which is diluted while layer separation of spent acid to 72% for the recycle and reuse other member of same family of benzo trifluorides.
  • the system may further comprise a washing unit for washing of organic layer and separation of 4- nitro benzo trifluorides (4-NBTF), 2-nitro benzo trifluorides (2 -NBTF), and 3 -nitro benzo trifluorides (3 -NBTF) in a specific % ratio.
  • the first reactor may comprise a modified agitator, a plurality of turbine blades, a vortex breaker device (which is configured for proper and uniform mixing of the reactants), one or more internal baffles, an internal cooling brine coil, a cooling jacket, an overflow outlet comprising a cleat enabled for transferring the reaction mass of the first reactor to the second reactor.
  • a process for continuous synthesis of mono-nitro-benzo trifluoride may comprise a step of addition of predetermined molar ratio of benzo trifluoride (BTF) and 98% sulfuric acid (H2SO4) in a first reactor.
  • the process may further comprise a step of addition (403) of a predetermined molar ratio of nitrating agent such as strong nitric acid (HN03) after cooling the first reactor (105) within a temperature range of 5-10°C.
  • the process may further comprise a step of determining a level of reaction mixture in the first reactor reaching up to an overflow level, enabling simultaneous addition of 98% sulfuric acid (H2SO4), strong nitric acid (HNO3), and benzo trifluoride (BTF) in the first reactor.
  • the process may further comprise a step of maintaining the above reaction for about 45-90 minutes for a predetermined flow rate to obtain a nitro-mass comprising a mixture of mono-nitro benzo trifluorides (NBTFs).
  • the inlet and outlet flow rate from the second reactor is optimized for residence time of 45 mins to 2 hrs.
  • the process may further comprise a step of passing the said nitro-mass obtained in the second reactor to a third reactor for layer separation into aqueous and organic layers.
  • the process may comprise a step of passing the said organic layer separated in the third reactor to a washing and distillation unit to obtain pure 3- Nitro benzo trifluoride (3-NBTF), 2- Nitro benzo trifluoride (2-NBTF), and 4- Nitro benzo trifluoride (4-NBTF) in a specific % ratio.
  • Figure 1 depicts a system (100) for continuous production of mono nitro-benzo trifluorides (NBTF), in accordance with an embodiment of the present subject matter.
  • Figure 2 depicts a first reactor (105) enabled for mono-nitration of benzo trifluoride by 90-98% reaction conversion of reactants, in accordance with an embodiment of the present subject matter.
  • Figure 3 depicts a second reactor (106) configured for mono-nitration of benzo trifluoride with the remaining 2-10% reaction conversion of reactants.
  • FIG. 4 depicts a process (400) for continuous synthesis of mono-nitro-benzo trifluoride (NBTF), in accordance with an embodiment of the present subject matter.
  • the system (100) comprises a plurality of a continuous stirred tank reactors.
  • the said continuous stirred tank reactors of the system (100) may be connected in, but not limited by, series mode, cascade mode, or step-down mode.
  • the system (100) for continuous production of mono nitro-benzo trifluorides is disclosed herein.
  • the system may comprise a first reactor (105) configured for mono-nitration of benzo trifluoride by 90-98% reaction conversion of reactants.
  • the system (100) may further comprise a second reactor (106) configured for mononitration of benzo trifluoride with the remaining 2-10% reaction conversion of reactants.
  • system (100) may further comprise a third reactor (107) enabled for the water treatment of said nitro-mass to separate aqueous layer comprising spent acid and organic layer comprising nitro-benzo trifluoride.
  • the system may further comprise a washing (108) for washing of organic layer and separation of 4-nitro benzo trifluorides (4-NBTF), 2-nitro benzo trifluorides (2-NBTF), and 3-nitro benzo trifluorides (3-NBTF) in a specific % ratio.
  • the washing unit (108) may further transfer the 4-nitro benzo trifluorides (4-NBTF), 2-nitro benzo trifluorides (2-NBTF), and 3-nitro benzo trifluorides (3-NBTF) to distillation unit (not shown in figure).
  • An effluent obtained from the washing unit (108) may further be processed for acidic/alkaline effluent aqueous layer separation.
  • the effluent is then transferred to effluent treatment plant (not shown).
  • the system (100) may be enabled for feeding of benzo trifluoride (BTF) from a BTF feed tank (101).
  • BTF benzo trifluoride
  • benzo trifluorides employed may be acquired from any convenient source.
  • benzo trifluorides may be obtained from the reaction of benzene with other chloro- and Fluro- components.
  • the system (100) may be enabled for feeding nitrating agent from a nitrating agent feed tank (104).
  • the nitrating agent feed tank (104) is enabled for feeding strong nitric acid (72%) and 98% sulfuric acid to the first reactor (105).
  • the nitrating acid employed in the process of the invention is selected from strong 72% nitric acid and 98% nitric acid.
  • the 72% /98% nitric acid is 1.0 to 1.10, preferably 1.05 to 1.15 times the theoretical amount of nitric acid required to nitrate all of the benzo tri fluoride present to mono nitro benzo trifluoride. It has been discovered that when the amount of nitric acid used for this continuous process is more than 1.15 times of theoretical value, the content of by-product spent acid having more nitric acid increases sharply, and when the amount of nitric acid is less than 1.00 times this theoretical value, the amount of unreacted benzo trifluoride increases.
  • the system (100) may be enabled for feeding sulfuric acid (H2SO4) from a FFSCfifeed tank (102).
  • the FFSCfifeed tank (102) is enabled for feeding of 98% FFSCfito the first reactor (105).
  • the sulfuric acid and nitric acid concentration may be selected such that the reaction could be carried out at a lower temperature without having a super-atmospheric pressure.
  • Contents of sulfuric acid and spent acid added in the reaction of the first reactor (105) are 22-24.0 % nitric acid (72%), and 74-77% sulfuric acid (98%).
  • the spent acid having 22.0-24.0 % nitric acid (72%), and 74-77% sulfuric acid (98%) may also be incorporated in the first reactor (105).
  • the ratio of nitric acid and sulfuric acid may be selected such that the nitric acid is preferably low and is substantially fully dissociated to nitronium ion, and commingling the benzo trifluoride with the nitronium ion solution so as to provide a fine emulsion, whereby the reaction can be carried out at a low temperature and at atmospheric pressure to lower the residence time within the first reactor (105) to provide NBTF product having no or low levels of impurities.
  • the first reactor (105) may comprise a modified agitator (204) having one or more turbine blades (205), a vortex breaker device (208) configured for proper and uniform mixing of the reactants.
  • a modified agitator (204) having one or more turbine blades (205), a vortex breaker device (208) configured for proper and uniform mixing of the reactants.
  • well-designed stirrer blades (205) are introduced in the first reactor (105) for high shear agitation.
  • FIG 2a is a top view of the first reactor (105) which depicts positioning of one or more baffles (206) with respect to the agitator (204).
  • the one or more baffles (206) are provided in the first reactor (105).
  • the width and thickness of baffles are adjusted in such a way that it breaks the vortexing generated due to agitation to ensure thorough mixing.
  • the residence time is kept between 60-90 minutes to achieve conversion between 90-98%.
  • the first reactor (105) may further comprise an overflow outlet (209) having a cleat (210) enabled for controlled transferring of the reaction mass without siphoning of the reaction mass from the first reactor (105) to the second reactor (106).
  • the second reactor (106) may be enabled for receiving and collecting the overflow of the reaction mass from the first reactor (106). The rest of the 2-10% reaction may take place in the second reactor (106) with a residence time of 45 to 60 mins. In one embodiment, the second reactor (106) may be configured for agitation of the reaction mass kept at high shear to achieve upto 100% conversion of the reaction mass within a predefined period of time achieving reduction in time of reaction.
  • the second reactor (106) may comprise an inlet (301) to receive and collect the overflow of the reaction mass from the first reactor (105).
  • the second reactor (106) may further comprise a simple stirrer unit (302) having one or more blades (303) selected from any of propeller blades, turbine blades, or paddle blades.
  • the second reactor (106) may further comprise a controlled cooling mechanism having a jacketed brine cooling (304) and a single internal cooling coil (305).
  • the second reactor (106) may further comprise a plurality of baffles (306) at the internal edge of the reactor.
  • an outlet (307) from the bottom of the second reactor (106) is configured for transfer of a nitro mass to a third reactor (separator) (107).
  • an outlet (307) from the bottom of the second reactor (106) is configured for transfer of a nitro mass to a third reactor (separator) (107).
  • the first reactor (105) and the second reactor (106) may comprise scrubber vent(s) (not shown in figure) to scrub out acid fumes for the reactors.
  • the reactors involved in preparation of NBTF may be continuous stirred tank reactors.
  • the respective raw materials with required flow rates are fed by means of a metering pump.
  • the reaction is highly exothermic, it is controlled by enabling circulation of lower temperature brine of water and methanol in the cooling brine jacket (207), (304) and the internal cooling coil (211), and (305).
  • the first reactor (105) may comprise a double internal cooling coil (211) along with the cooling brine jacket (207) and the second reactor (106) may comprise a single internal cooling coil (305) along with the cooling brine jacket (304).
  • temperature of the reaction was not optimized and often led to freezing of the reaction mass in the first reactor because of too low supply of utility temperature (-10°C) which further led to chocking of the overflow line. Therefore, to overcome this issue, in the present invention, temperature of the first and second reactor was maintained between 1-12°C and preferably 4 to 9°C by adjusting using combination of jacketed and internal circulation cooling brine at a predefined temperature and pressure conditions.
  • the system (100) may comprise a BTF and H2SO4 mixing chamber (103).
  • the mixing chamber (103) is configured for addition of pre-mix of BTF and H 2 SO 4 to the first reactor (105).
  • BTF and H2SO4 from the BTF feed tank (101) and H2SO4 feed tank (102), respectively, are added to the first reactor (105) before addition of nitric acid from the feed tank (104).
  • the first reactor (105) may comprise one or more reactant inlets such as 72% (or 98%) nitric acid inlet (201), nitro benzo trifluoride inlet (202), and 98% sulfuric acid inlet (203). All the reactants are fed into the first reactor using respective reactant inlets (201), (202) and (203).
  • the rate of flow of each of the raw material of benzo trifluoride, nitric acid and sulfuric acid components is controlled by adjusting the operating rates of metering pumps so that the reactants are delivered into the reaction chamber of the first reactor (105) in stoichiometric ratio of benzo tri-fluoride and the reaction temperature is maintained below 5°-7°C. The 90-98% conversion of the main reactant is being carried out in the first reactor (105).
  • a process (400) for continuous synthesis of mono-nitro-benzo trifluoride is disclosed. It may be understood that invention is in terms of the introduction of a reaction stream of mixed sulfuric acid with benzo trifluoride containing about 25-28% sulfuric acid, and from 13-16 % nitric acid.
  • the process (400) may comprise a plurality of steps.
  • the process (400) may comprise a step of addition (401) of predetermined molar ratio of benzo trifluoride (BTF) and 98% sulfuric acid (H2SO4) in the first reactor (105).
  • the process (400) may comprise a step of addition (402) of a predetermined molar ratio of nitrating agent such as strong nitric acid (HN03) after cooling the first reactor (105) within a temperature range of 5-10°C. The temperature of range of 5-10°C is maintained by the combination of jacketed and internal circulation brine cooling.
  • the strong nitric acid (HNO3) wherein the nitric acid is having a concentration between 72%-98%.
  • the process (400) may comprise a step of determining (403) a level of reaction mixture in the first reactor (105) reaching up to an overflow level of about 85% of the first reactor, enabling simultaneous addition of 98% sulfuric acid (H2SO4), 72% nitric acid (HNO3)/ 98% nitric acid, and benzo trifluoride (BTF) in the first reactor.
  • H2SO4 98% sulfuric acid
  • HNO3 72% nitric acid
  • BTF benzo trifluoride
  • 98% sulfuric acid and 72% nitric acid/98% nitric acid are fed continuously into the first reactor (105) through corresponding feed tanks (101, 102, 103, 104).
  • a state of complete emulsification throughout the mixture is created in the first reactor (105) by an agitating system as disclosed herein.
  • at step of determining (403) a level of reaction mixture in the first reactor (105) reaching up to an overflow level enables a short residence time (60-80 minutes) to the reaction mixture to obtain a nitro-mass comprising a mixture of mono-nitro benzo trifluorides (NBTFs).
  • NBTFs mono-nitro benzo trifluorides
  • the process (400) may comprise a further step of maintaining (404) the above reaction for about 45-90 minutes for a predetermined flow rate and continuously discharging the reaction mixture into a second reactor where rest 2-10% reaction is going to complete.
  • the process of the invention may be reversed, that is, benzo trifluoride may be delivered into a stream or body of mixed acid. It will also be understood that the process will be applicable to other nitration or other chemical reactions which are mass transfer limited.
  • the process (400) may comprise a step of passing (406) the said nitro mass obtained in the second reactor (106) to a third reactor (107) (hereinafter may be alternatively referred to as “separating reactor”) for layer separation of spent acid and organic layer.
  • a separating reactor 107 which is configured to dilute the mixture of organic products 3- nitro benzo trifluoride, 2- nitro benzo trifluoride and 4- nitro benzo trifluorides and separate from spent acid by means of water addition to such extent to keep the spent acid concentration from 84-85% to about 72%- 75% for recycle and reuse in nitration reaction for production other member of same family of benzo trifluorides.
  • the mixture of organic products comprising nitro mass then separated from the spent acid layer.
  • the collected nitro mass is further subjected for reaction workup and finally fed to fractionating columns to receive the pure compound 1 and compound 2,3 i.e., 3- nitro benzo trifluoride and 2- nitro benzo tri fluoride, 4- nitro benzo tri fluoride.
  • the spent mixed acid separated from the organic layer comprising the mixture of organic products comprising nitro mass may be recycled and reused.
  • the reaction is carried out under atmospheric pressure, and the spent acid contains 1.0-1.5 % nitric acid, 72.0-75.0 % sulphuric acid.
  • the process (400) may comprise a step of passing (407) the said organic layer separated in the third reactor to washing and distillation unit to obtain pure 3- Nitro benzo trifluoride (3-NBTF), 2- Nitro benzo trifluoride (2-NBTF), and 4- Nitro benzo trifluoride (4-NBTF) in a specific % ratio.
  • separation of mono nitro benzo trifluorides is possible by performing the distillation process.
  • the isomers like 3- nitro benzo trifluoride, 2- nitro benzo trifluorides and 4- nitro benzo trifluorides separated to each fraction is done in distillation column by means of adding some additives to reduce the distillation hazards.
  • a maximum overall yield of desired 3-Nitro BTF product was obtained up to 89-91%, 2-Nitro BTF product up to 7-8%, and 4- Nitro BTF product up to 2-2.5%.
  • Example 1 Production of mono nitro-benzo trifluorides (NBTF) in single reactor batch mode
  • a predetermined amount of benzo tri-fluoride from BTF feed tank is charged in reactor and predetermined amount of 98% H2SO4 is charged in reactor.
  • continuous addition of 72% nitric acid/98% nitric acid is charged keeping the temperature of the reaction between 4-7 degree centigrade.
  • the agitator RPM speed was maintained between 350-450.
  • the residence time in the first reactor was maintained as 45 min to 75 min to achieve maximum conversion of the BTF reactant.
  • the observations of batch type reaction are represented below in Table 1.
  • Example 2a Production of mono nitro-benzo trifluorides (NBTF) in continuous mode by using 72% nitric acid
  • NBTF mono nitro-benzo trifluorides
  • a predetermined amount of BTF from BTF feed tank at a flow rate of 35-45 kg/hr is mixed with a predetermined amount of 98% H2SO4 at a flow rate of 72.8- 94 kg/hr.
  • the mixture is added to a 100 Lit. first continuous stirred tank reactor comprising at least two baffles, vortex breaker at the bottom and an agitator having 3 turbine blades and a modified overflow line comprising opening/closing cleat component.
  • the agitator RPM speed was maintained at 550-600.
  • a predefined amount of 72% nitric acid at a flow rate of 22.3- 30 kg/hr is fed to the first reactor, wherein a molar ratio of BTF: 98% H2SO4: 72% HN03 is 1 :2.08: 1.02 to 1 :2.08: 1.10.
  • a simultaneous addition of all three reactants in initiated is initiated.
  • the reaction mass is transferred to second reactor to maintain the overflow limit, siphoning of the reaction mass and maximum conversion of the reaction mass.
  • the bottom valve of the second reactor, and the circulation line valve is opened.
  • the agitator RPM speed was maintained between 100-150.
  • the residence time in the first reactor was maintained as 60-90 minutes and residence time in a 250 Ltr second reactor was maintained as 300-320 minutes.
  • the temperature of the first reactor was maintained at 5-7 degrees by jacketed and internal circulation of chilled brine.
  • the transferring valve was opened, and the nitro-mass was transferred from the second reactor to the separator reactor for dilution and separation process. While transferring to separator the sample from overflow line was analyzed for % BTF ⁇ 0.1- 0.8%, 3-NBTF ⁇ 88.5-89.5% in nitro-mass and %HN03 ⁇ 1.0-1.4% in Spent acid.
  • a predefined amount of water was added in a separator for dilution and stirring was carried out for 30 mins.
  • Example 2b Production of mono nitro-benzo trifluorides (NBTF) in continuous mode by using 98% nitric acid
  • a predetermined amount of BTF from BTF feed tank at a flow rate of 60 kg/hr is mixed with a predetermined amount of 98% H2SO4 at a flow rate of 66 kg/hr.
  • the mixture is added to a 100 Ltr first continuous stirred tank reactor comprising at least two baffles, vortex breaker at the bottom and an agitator having 3 turbine blades and a modified overflow line.
  • a predefined amount of 98% nitric acid at a flow rate 18.5-20 kg/hr is fed to the first reactor, wherein a molar ratio of BTF: 98% H2SO4: 98% HN03 is 1 : 1.10: 1.02 to 1 : 1.10: 1.05.
  • the agitator RPM speed was maintained between 550-650.
  • the residence time in the first reactor was maintained as 60-90 minutes and residence time in a 250 Ltr second reactor was maintained as 240 minutes.
  • the temperature of the first reactor was maintained at 5-7 degrees by jacketed and internal circulation of chilled brine.
  • the overall conversion of reactants in a continuous reactor mode was achieved about 98% in the first reactor and rest up to 2 % conversion was carried out in the second reactor.
  • the nitro-mass yield obtained from first and second reactor is disclosed in Table 2b as below:
  • NBTF mono nitro-benzo trifluorides

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Abstract

Système de fabrication continue de mono-nitro benzo trifluorures (NBTF). Le système comprend un premier réacteur configuré pour mono-nitrater du benzo trifluorure par conversion de réactifs de 90 à 98 % en réaction ; un deuxième réacteur conçu pour mono-nitrater du benzo trifluorure par le biais d'une conversion de réaction de 2 à 10 % résiduelle de réactifs ; un troisième réacteur qui peut séparer la couche organique, qui contient du nitro-benzo trifluorure, de la couche aqueuse, qui contient de l'acide sulfurique mélangé. Le système comprend également une unité de lavage pour laver la couche organique et séparer les 4-nitro benzo trifluorures (4-NBTF), les 2-nitro benzo trifluorures (2-NBTF) et les 3-nitro benzo trifluorures (3-NBTF) dans un rapport particulier. Le système permet une production à haut rendement, sans corrosion, rapide, compacte, à moindre coût et économiquement réalisable de NBTF par mono-nitration et met également en œuvre un acide usé de récupération réutilisable dans le procédé pour obtenir une efficacité environnementale et une efficacité de coût.
PCT/IB2023/055013 2022-05-16 2023-05-16 Système et procédé de préparation de mono-nitro benzo trifluorure (nbtf) WO2023223192A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111499517A (zh) * 2020-04-15 2020-08-07 北京格林凯默科技有限公司 一种间硝基三氟甲苯的制备方法
CN114014760A (zh) * 2021-10-25 2022-02-08 南通海晴医药科技有限公司 一种利用涡旋反应器合成3-氨基三氟甲基苯的方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111499517A (zh) * 2020-04-15 2020-08-07 北京格林凯默科技有限公司 一种间硝基三氟甲苯的制备方法
CN114014760A (zh) * 2021-10-25 2022-02-08 南通海晴医药科技有限公司 一种利用涡旋反应器合成3-氨基三氟甲基苯的方法

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