US20070261437A1 - Enhanced process for the purification of anhydrous hydrogen chloride gas - Google Patents

Enhanced process for the purification of anhydrous hydrogen chloride gas Download PDF

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Publication number
US20070261437A1
US20070261437A1 US11/433,809 US43380906A US2007261437A1 US 20070261437 A1 US20070261437 A1 US 20070261437A1 US 43380906 A US43380906 A US 43380906A US 2007261437 A1 US2007261437 A1 US 2007261437A1
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United States
Prior art keywords
gas
stream
hydrogen chloride
column
heat exchanger
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Abandoned
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US11/433,809
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English (en)
Inventor
Eric Boonstra
John Teepe
Renae Vandekamp
Anke Hielscher
Kaspar Hallenberger
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Bayer AG
Covestro LLC
Bayer US LLC
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Individual
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Priority to US11/433,809 priority Critical patent/US20070261437A1/en
Assigned to BAYER CORPORATE BUSINESS SERVICES, LLC, BAYER MATERIALSCIENCE LLC, BAYER TECHNOLOGY SERVICES GMBH reassignment BAYER CORPORATE BUSINESS SERVICES, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: VANDEKAMP, RENAI, TEEPE, JOHN M., BOONSTRA, ERIC F., HALLENBERGER, KASPAR, HIELSCHER, ANKE
Assigned to BAYER CORPORATE BUSINESS SERVICES, LLC, BAYER TECHNOLOGY SERVICES GMBH reassignment BAYER CORPORATE BUSINESS SERVICES, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: VANDEKEMP, RENAE M., TEEPE, JOHN M., BOONSTRA, ERIC F., HALLENBERGER, KASPAR, HIELSCHER, ANKE
Priority to JP2009508195A priority patent/JP5303453B2/ja
Priority to PL07724740T priority patent/PL2021275T3/pl
Priority to PT07724740T priority patent/PT2021275E/pt
Priority to EP07724740A priority patent/EP2021275B1/de
Priority to CN2007800172612A priority patent/CN101448738B/zh
Priority to PCT/EP2007/003813 priority patent/WO2007131623A2/en
Priority to RU2008148885/05A priority patent/RU2438970C2/ru
Priority to AT07724740T priority patent/ATE502898T1/de
Priority to KR1020087027568A priority patent/KR101332914B1/ko
Priority to DE602007013388T priority patent/DE602007013388D1/de
Priority to ES07724740T priority patent/ES2362019T3/es
Priority to TW096116733A priority patent/TWI387558B/zh
Publication of US20070261437A1 publication Critical patent/US20070261437A1/en
Assigned to BAYER BUSIENSS AND TECHNOLOGY SERVICES LLC reassignment BAYER BUSIENSS AND TECHNOLOGY SERVICES LLC MERGER (SEE DOCUMENT FOR DETAILS). Assignors: BAYER CORPORATE AND BUSINESS SERVICES LLC
Assigned to BAYER BUSINESS AND TECHNOLOGY SERVICES LLC reassignment BAYER BUSINESS AND TECHNOLOGY SERVICES LLC CORRECTIVE ASSIGNMENT TO CORRECT NATURE OF CONVEYANCE AND RECEIVING PARTY, PREVIOUSLY RECORDED AT REEL 021752 FRAME 0043. Assignors: BAYER CORPORATE AND BUSINESS SERVICES LLC
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/01—Chlorine; Hydrogen chloride
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/01—Chlorine; Hydrogen chloride
    • C01B7/07—Purification ; Separation
    • C01B7/0706—Purification ; Separation of hydrogen chloride
    • C01B7/0712—Purification ; Separation of hydrogen chloride by distillation
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/01—Chlorine; Hydrogen chloride
    • C01B7/07—Purification ; Separation

Definitions

  • the present invention relates to a process for purifying anhydrous hydrogen chloride gas (“aHCl”), and preferably the anhydrous hydrogen chloride gas recovered from an isocyanate production process.
  • aHCl anhydrous hydrogen chloride gas
  • the content of chlorinated organics may be reduced from up to 1000 ppm by volume to below 10 ppb by volume levels.
  • the process of the invention allows for chlorinated organic levels to be reduced to from 1 to 100 ppb, rendering the treated hydrogen chloride gas usable in a catalytic oxychlorination process or a Deacon process.
  • the treated gas is also suitable for absorption in water or dilute hydrochloric acid.
  • a number of important chemical processes generate aHCl as a byproduct. Examples of such processes include chlorination processes, silane production processes and phosgenation processes. Because large amounts of aHCl can not be disposed of, one of the challenges encountered with each of these processes is purification of the aHCl generated to obtain a usable technical product or raw material for other processes.
  • Several processes for purifying aHCl generated during production processes have been proposed. Thermal treatment of the aHCl at temperatures of up to 800 to 1600° C. is disclosed in U.S. Pat. No. 5,126,119. Full condensation and distillation under elevated pressure is disclosed in U.S. Pat. No. 4,935,220. The processes disclosed in these patents require high amounts of energy and expensive equipment.
  • Deacon process Another secondary process is the Deacon process, which produces chlorine and water by passing gaseous HCl and oxygen over a transition metal catalyst. This process is very sensitive to traces of some contaminants, such as sulfur and some organic compounds, which over time can lead to catalyst deactivation and/or plugging of reactors, which in turn can lead to unwanted by-product formation.
  • the present invention has several objects: i) a process for the removal of one or more contaminants from hydrogen chloride gas, ii) a process for separating small quantities of high boiling material, e.g., (chloro) aromatic compounds from large volumes of anhydrous HCl gas; and, iii) a process for reducing the concentration of contaminants such as (chloro)aromatic compounds in anhydrous HCl gas to ⁇ 100 ppb.
  • FIG. 1 schematically illustrates a flow diagram for the present invention.
  • FIG. 2 schematically illustrates a second embodiment of the present invention.
  • FIG. 3 schematically illustrates a preferred embodiment of the present invention.
  • the present invention is broadly directed to a cooling and distillation process to remove contaminants having boiling points higher than hydrogen chloride from a hydrogen chloride-containing gas comprising:
  • the gas is preferably compressed to a pressure of from 5 to 30 bars absolute.
  • the contaminants contained in the gas stream are preferably chlorinated aromatic compounds.
  • the gas stream also contains a contaminant with an intermediate boiling range between the hydrogen chloride boiling point and the chlorinated aromatic compound boiling point.
  • the intermediate contaminant is removed from the distillation column, is subsequently depressurized, and is discarded.
  • the intermediate contaminant is phosgene.
  • the incoming contaminated gas is cooled slowly.
  • the temperature difference between the cooling wall of the first heat exchanger and the inlet gas temperature is preferably between 0.5 and 40° C., and most preferably in the range of from 5 to 25° C.
  • the temperature of the compressed gas is preferably reduced to a temperature of from +10 to ⁇ 25° C. in the cooling step (step b)).
  • the condensate stream (of step b)) is fed to a separation vessel (or vessels) used to trap solids. If multiple vessels are used, one vessel can be used to collect solids while overflowing condensate from the vessel being fed to the distillation column at a point below the point where the first gas stream is fed, while the other vessel is depressurized to enable collected solids to be purged to waste.
  • a separation vessel or vessels used to trap solids. If multiple vessels are used, one vessel can be used to collect solids while overflowing condensate from the vessel being fed to the distillation column at a point below the point where the first gas stream is fed, while the other vessel is depressurized to enable collected solids to be purged to waste.
  • step e) comprises:
  • step i) comprises i1) feeding liquid from the bottom portion of said column to a reboiler to generate stripping vapors for the bottom portion of the column, and wherein the reboiler heats the said liquid at low heat flux so as to prevent foaming action and i2) removing any remaining liquid from the reboiler to a collection vessel for disposal.
  • a reboiler Preferably, from 5% to 95% of the liquid reaching the reboiler is evaporated.
  • the reboiler design prevents the formation of foams and has a heat flux of from 500 to 20,000 BTU/hr/ft 2 as a lower limit and from 3,000 to 30,000 BTU/hr/ft 2 as a higher limit.
  • a portion of the liquid removed from the reboiler comprises hydrogen chloride and contaminants and is sprayed into the gas stream being fed to the first heat exchanger, most preferably in amount of from 1 to 25% by weight of the weight of the incoming gas stream.
  • the temperature of the gas being fed into the distillation column is preferably reduced to a temperature of from 0 to ⁇ 35° C. during the distillation step.
  • the purified hydrogen chloride gas from the first heat exchanger is further purified by treatment with activated charcoal.
  • the invention comprises
  • step g) the condensate stream (of step b)) can be fed to a separation vessel (or vessels) used to trap solids. If multiple vessels are used, one vessel can be used to collect solids while overflowing condensate from the vessel being fed to the distillation column at a point below the point where the first gas stream is fed, while the other vessel is depressurized to enable collected solids to be purged to waste.
  • step f) can comprise:
  • fog (or aerosol) formation is avoided by controlling the cooling rate of the incoming gas, and by the use of a condensate spray to promote more homogeneous cooling.
  • the present invention provides an enhanced method of purifying a contaminated hydrogen chloride stream by using a modified cooling and distillation process.
  • Small quantities of high boiling contaminants e.g. chlorinated aromatic hydrocarbons, can be removed down to a concentration of 10 ppb in the purified gas.
  • this process works well for purifying byproduct streams created by isocyanate production processes, which coproduce with the isocyanate, large volumes of anhydrous hydrogen chloride gas with contaminants including monochlorobenzene and dichlorobenzenes (ortho, meta and para isomers).
  • the contaminated hydrogen chloride gas (shown as stream A) enters compressor 1 , exits the compressor and enters the first heat exchanger 2 . As it passes through the first heat exchanger, the compressed gas is cooled to a temperature low enough to partially condense the contaminants and at a rate sufficiently low that fog formation is prevented.
  • Two streams flow from the first heat exchanger a first condensate stream C and a first gas stream B.
  • the first gas stream B is fed to a distillation column 3 at a point between the top and bottom of the column. In the distillation column, mass transfer occurs between liquid and gas, with the contaminants being concentrated in the bottom portion of the column, and hydrogen chloride gas being concentrated in the lower portion of the column.
  • the hydrogen chloride gas is fed (stream D) from the top portion of the column to a second heat exchanger 4 (that is provided with an appropriate coolant via stream shown in the figure as arrows entering one side of the exchanger and exiting on the other side) wherein the gas is partially condensed to form a second condensate stream E and a second gas stream F.
  • the second condensate stream E is fed back to the top portion of the column to provide reflux to the column.
  • the first condensate stream C is fed to the column at a point below the first gas stream B is fed.
  • the second gas stream F is fed back to the first heat exchanger as cooling medium.
  • Purified hydrogen chloride gas is recovered via stream G from the first heat exchanger and the liquid bottoms (that contain concentrated contaminants) of the column are fed via stream H to a collection vessel (not shown) for subsequent disposal.
  • FIG. 2 illustrates the process as if all the improvements were used. Of course, the artisan will recognize that not all the improvements must be used.
  • the inlet gas stream A enters compressor 1 exits the compressor and enters the first heat exchanger 2 .
  • the compressed gas is cooled to a temperature low enough to partially condense the contaminants and at a rate sufficiently low that fog formation is prevented.
  • Two streams flow from the first heat exchanger a first condensate stream C and a first gas stream B.
  • the first gas stream B is fed to a distillation column 3 at a point between the top and bottom of the column.
  • the condensate from the first heat exchanger flows (stream C′) into a solids trapping vessel 5 . If more than one vessel is used, they may be used interchangeably. In the separation vessel two streams result, a solids stream C′′ that can be collected and purged to waste and a third condensate stream C.
  • the third condensate stream (without solids) C is fed as a liquid feed to the distillation column at a point below the point where the first gas stream is fed.
  • the concentrated hydrogen chloride gas from the top portion of the column is fed via stream D to a third heat exchanger 9 .
  • the bottoms stream H from the distillation column can be split into two streams, H′ and H′′ which contain concentrated amounts of the contaminants.
  • the H′′ stream can be pumped via pump 10 back into the inlet of the HCl gas entering the first heat exchanger.
  • the H′ stream can be flashed against the concentrated hydrogen chloride gas entering the third heat exchanger.
  • This step can result in several streams—i) a gas stream J containing hydrogen chloride (at a lower pressure) and, in the case of a starting gas from an isocyanate production facility, phosgene (this stream can be collected and used again in another appropriate process), ii) a stream J′ containing mainly organic contaminants (that are then collected and disposed), iii) a gas stream D′ that is fed to the second heat exchanger 4 and iv) a condensate stream E′′.
  • Stream E′′ can be combined with the second condensate stream E and fed to the top portion of the column 3 to provide reflux to the column.
  • stream E′′ can be combined with the second condensate stream E and fed to a collection vessel 6 where solids are collected and discarded via stream E′′′ with the overflow condensate from the collection vessel being fed via stream E′ back to the top portion of the column 3 to provide reflux to the column.
  • the second gas stream F is fed back to the first heat exchanger as cooling medium.
  • FIG. 2 also shows a side draw-off stream I from the distillation column to remove intermediate boiling contaminants. This stream can be fed to an activated charcoal bed 8 to remove organics, resulting in stream I′ which is led off to disposal.
  • FIG. 2 also shows purified gas stream G being fed to an activated charcoal bed 7 , resulting in a stream G′ of purified hydrogen chloride gas.
  • FIG. 3 The embodiment shown in FIG. 3 is identical to that shown in FIG. 2 , except that the bottom liquids of the distillation column are fed via stream H to a reboiler 11 (that is provided with an appropriate coolant via stream shown in the figure as arrows entering one side of the exchanger and exiting on the other side) to generate stripping vapors that are fed via stream K to the bottom portion of the column.
  • the reboiler heats the bottoms liquid at low heat flux to prevent foaming action.
  • the condensate stream H′′′ from the reboiler can either be collected and discarded or can be sent to either the third heat exchanger (stream H′) or back to the inlet of the first heat exchanger (stream H′′).
  • the compressor A can be of any kind of equipment capable of increasing the pressure to from about of 5 to 30 bar absolute and preferably above 12 bar absolute.
  • Preferred compressors include piston compressors, screw compressors, optionally with oil injection, and centrifugal compressors.
  • the final pressure of the gas must be adjusted so as to overcome the pressure drop in overall system.
  • the gas enters the first heat exchanger at which point gas condensate spray mixes with the incoming gas in the amount of five to twenty-five weight percent of the total amount of incoming gas. Some condensation from this first heat exchanger can flow into solids collection vessel(s) to catch solids. The liquid condensate from these vessel(s) overflows and is fed to the distillation column.
  • the heat exchangers used in the present invention can be of any type. Shell and tube heat exchangers are preferred.
  • HCl offgas from isocyanate units containing monochlorobenzene, dichloro-benzene, and chlorinated methanes impurities are preferably used as the initial gas.
  • the gas is compressed to a pressure of 8 to 20 bar, preferably 12 bar.
  • the resulting compressed gas is fed to the first heat exchanger for cooling to between ⁇ 5 and ⁇ 20° C., preferably ⁇ 10° C., to partially condense impurities.
  • the condensed impurities are preferably first passed through a solids collection vessel to remove any solids and then led to the distillation column as liquid feed.
  • the gas stream from the first heat exchanger is fed to the distillation column as gaseous feed.
  • Overhead vapors from the distillation column pass through a second heat exchanger and are cooled to between ⁇ 18 and ⁇ 30° C. (preferably ⁇ 25° C.) to partially condense between 0.01 and 25%, preferably between 2 to 5%, of the inlet vapor stream to provide liquid reflux for the distillation column.
  • the purified HCl gas from the second heat exchanger are pumped back to the inlet gas stream to be injected like a spray to promote condensation in the inlet gas and to prevent the formation of an aerosol or fog.
  • the partially purified gas now has a concentration of from 0.1 to 100, and preferably 1 to 10 ppm organic impurities.
  • the partially purified HCl gas can then be fed to an activated charcoal adsorption column for final purification to reach a final organic impurities level of from 10 to 1000 ppb, preferably from 50 to 100 ppb.
  • the bottom stream of the distillation column contains most of the impurities and is allowed to flash to a lower pressure of between 1 bar and 10 bar, preferably 1.05 bar where much of the remaining HCl flashes off and is led off to an absorption step or to waste. The remaining residue, containing most of the impurities, is led off to incineration or other waste treatment.
  • the cooling effect of the bottoms stream flash can help to cool the vapors leaving from the top of the column.
  • a reboiler (preferable operation between ⁇ 10 and +8° C.) is provided to return most of the condensed HCl as vapor back to the column as stripping gas.
  • the design of the reboiler preferably uses a heat flux of between 1000 and 12000 BTU/hr/ft 2 and preferably between 2500 and 4000 BTU/hr/ft 2 .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Separation By Low-Temperature Treatments (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
  • Hydrogen, Water And Hydrids (AREA)
  • Detergent Compositions (AREA)
  • Treatment Of Water By Oxidation Or Reduction (AREA)
  • Catalysts (AREA)
US11/433,809 2006-05-12 2006-05-12 Enhanced process for the purification of anhydrous hydrogen chloride gas Abandoned US20070261437A1 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US11/433,809 US20070261437A1 (en) 2006-05-12 2006-05-12 Enhanced process for the purification of anhydrous hydrogen chloride gas
DE602007013388T DE602007013388D1 (de) 2006-05-12 2007-04-30 Verbessertes verfahren zur reinigung von wasserfreiem chlorwasserstoffgas
ES07724740T ES2362019T3 (es) 2006-05-12 2007-04-30 Procedimiento mejorado para la purificación de cloruro de hidrógeno anhidro gaseoso.
RU2008148885/05A RU2438970C2 (ru) 2006-05-12 2007-04-30 Улучшенный способ очистки безводного газообразного хлороводорода
AT07724740T ATE502898T1 (de) 2006-05-12 2007-04-30 Verbessertes verfahren zur reinigung von wasserfreiem chlorwasserstoffgas
PT07724740T PT2021275E (pt) 2006-05-12 2007-04-30 Processo melhorado para a purificação de cloreto de hidrogénio anidro gasoso
EP07724740A EP2021275B1 (de) 2006-05-12 2007-04-30 Verbessertes verfahren zur reinigung von wasserfreiem chlorwasserstoffgas
CN2007800172612A CN101448738B (zh) 2006-05-12 2007-04-30 用于无水氯化氢气体纯化的改进工艺
PCT/EP2007/003813 WO2007131623A2 (en) 2006-05-12 2007-04-30 Enhanced process for the purification of anyhydrous hydrogen chloride gas
JP2009508195A JP5303453B2 (ja) 2006-05-12 2007-04-30 無水塩化水素ガスを精製するための改良された方法
PL07724740T PL2021275T3 (pl) 2006-05-12 2007-04-30 Udoskonalony sposób oczyszczania gazów bezwodnego chlorowodoru
KR1020087027568A KR101332914B1 (ko) 2006-05-12 2007-04-30 증진된 무수 염화수소 기체 정제 방법
TW096116733A TWI387558B (zh) 2006-05-12 2007-05-11 提高無水氯化氫氣體之純化作用的方法

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US11/433,809 US20070261437A1 (en) 2006-05-12 2006-05-12 Enhanced process for the purification of anhydrous hydrogen chloride gas

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US20070261437A1 true US20070261437A1 (en) 2007-11-15

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US11/433,809 Abandoned US20070261437A1 (en) 2006-05-12 2006-05-12 Enhanced process for the purification of anhydrous hydrogen chloride gas

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US (1) US20070261437A1 (de)
EP (1) EP2021275B1 (de)
JP (1) JP5303453B2 (de)
KR (1) KR101332914B1 (de)
CN (1) CN101448738B (de)
AT (1) ATE502898T1 (de)
DE (1) DE602007013388D1 (de)
ES (1) ES2362019T3 (de)
PL (1) PL2021275T3 (de)
PT (1) PT2021275E (de)
RU (1) RU2438970C2 (de)
TW (1) TWI387558B (de)
WO (1) WO2007131623A2 (de)

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US20080250924A1 (en) * 2007-04-10 2008-10-16 Bayer Materialscience Ag Regenerative adsorption processes for removing organic components from gas streams
US20080264253A1 (en) * 2007-04-26 2008-10-30 Bayer Materialscience Ag Processes for removing organic components from gases containing hydrogen chloride
US20120142959A1 (en) * 2009-08-11 2012-06-07 Basf Se Method for producing diisocyanates by gas-phase phosgenation
EP2559658A1 (de) * 2011-08-19 2013-02-20 Huntsman International LLC Verfahren zum Trennen von Phosgen und Chlorwasserstoff aus einem Flüssigkeitsstrom mit Phosgen und Chlorwasserstoff
EP2559659A1 (de) * 2011-08-19 2013-02-20 Huntsman International Llc Verfahren zum Trennen von Chlorwasserstoffgas aus einer Mischung von Chlorwasserstoff und Phosgen
KR20180022844A (ko) * 2015-06-29 2018-03-06 코베스트로 도이칠란트 아게 화학 반응을 위한 염화수소를 제공하는 방법
US10280135B2 (en) 2015-09-30 2019-05-07 Covestro Deutschland Ag Method for producing isocyanates
US10364214B1 (en) 2016-09-01 2019-07-30 Covestro Deutschland Ag Method for producing isocyanates
CN110642228A (zh) * 2019-07-04 2020-01-03 南通星球石墨设备有限公司 一种电石法pvc含汞废酸处理系统及利用该系统处理废酸的方法
US10577311B2 (en) 2015-09-24 2020-03-03 Covestro Deutschland Ag Method for producing isocyanates
US10611636B2 (en) 2015-08-10 2020-04-07 Showa Denko K.K. Method for producing hydrogen chloride
US11365172B2 (en) 2017-07-03 2022-06-21 Covestro Deutschland Ag Production plant for producing a chemical product by reacting H-functional reactants with phosgene, and method for operating same with an interruption to production
US20220194790A1 (en) * 2019-03-29 2022-06-23 Sgl Carbon Se Hcl recovery unit

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CN101817506B (zh) * 2010-03-22 2011-07-20 临沭县华盛化工有限公司 原甲酸三乙酯生产中所用氯化氢气体的纯化方法
MY156181A (en) * 2011-10-11 2016-01-15 Hong In Chemical Co Ltd Method and system for producing high-purity hydrogen chloride
WO2014064128A1 (de) * 2012-10-24 2014-05-01 Basf Se Verfahren zur herstellung von isocyanaten durch phosgenierung von aminen in flüssiger phase
EP2998270A4 (de) * 2013-05-15 2016-12-21 Asahi Glass Co Ltd Verfahren zur reinigung von wasserstoffchlorid
KR101470311B1 (ko) * 2013-07-24 2014-12-08 코아텍주식회사 공업용 암모니아 정제장치
EP2949622B1 (de) * 2014-05-27 2022-03-09 Covestro Intellectual Property GmbH & Co. KG Verfahren zur verarbeitung von chlorwasserstoff aus der isocyanatherstellung
US10252912B2 (en) 2015-03-12 2019-04-09 Basf Se Separation of a phosgene- and hydrogen chloride-comprising stream
CN107556215B (zh) * 2016-06-30 2022-04-19 科思创德国股份有限公司 从氯化氢液体混合物中分离和处理杂质的方法和系统
CN109110732A (zh) * 2018-09-11 2019-01-01 安徽东至广信农化有限公司 氯化苯生产工艺中用于降低副产物盐酸中有害物质的方法
WO2022131737A1 (ko) * 2020-12-14 2022-06-23 한화솔루션 주식회사 염소화 반응의 hcl 제거방법

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US11365172B2 (en) 2017-07-03 2022-06-21 Covestro Deutschland Ag Production plant for producing a chemical product by reacting H-functional reactants with phosgene, and method for operating same with an interruption to production
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