WO2022131737A1 - 염소화 반응의 hcl 제거방법 - Google Patents
염소화 반응의 hcl 제거방법 Download PDFInfo
- Publication number
- WO2022131737A1 WO2022131737A1 PCT/KR2021/018945 KR2021018945W WO2022131737A1 WO 2022131737 A1 WO2022131737 A1 WO 2022131737A1 KR 2021018945 W KR2021018945 W KR 2021018945W WO 2022131737 A1 WO2022131737 A1 WO 2022131737A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- chlorination reaction
- reactor
- hcl
- reaction
- hydrogen chloride
- Prior art date
Links
- 238000005660 chlorination reaction Methods 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 75
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 74
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 74
- 239000012467 final product Substances 0.000 claims abstract description 20
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000007864 aqueous solution Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/38—Steam distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/32—Other features of fractionating columns ; Constructional details of fractionating columns not provided for in groups B01D3/16 - B01D3/30
- B01D3/322—Reboiler specifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/005—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by heat treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/20—Halogens or halogen compounds
- B01D2257/204—Inorganic halogen compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/20—Halogens or halogen compounds
- B01D2257/204—Inorganic halogen compounds
- B01D2257/2045—Hydrochloric acid
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Definitions
- the present invention relates to a method for removing HCl in a chlorination reaction, and more particularly, to a method for efficiently removing HCl generated during the chlorination reaction of an aromatic compound.
- Chlorobenzene or chlorotoluene is a material used in various industrial fields, and is formed by the chlorination reaction of aromatic compounds such as benzene and toluene.
- monochlorotoluene such as o-chlorotoluene and p-chlorotoluene may be prepared by reacting toluene with chlorine in the presence of a catalyst such as FeCl 3 . Specifically, when toluene and chlorine are reacted in the presence of a catalyst, chlorine atoms are substituted, and monochlorotoluenes such as o-chlorotoluene and p-chlorotoluene are produced.
- a catalyst such as FeCl 3
- the present inventors intensified the study of an efficient HCl removal method that can significantly reduce the amount of wastewater discharged by removing hydrogen chloride gas without using a basic aqueous solution such as sodium hydroxide aqueous solution.
- the present invention is to provide a HCl removal method in the chlorination reaction with little loss of the final product and high HCl removal rate.
- the heating of hydrogen chloride may be performed by high-temperature steam supplied from a reboiler connected to the lower portion of the stripping column.
- the upper temperature in the stripping column is 10 to 30 ° C. and the pressure is 0.5 bar or less
- the lower temperature in the stripping column is 100 to 30 ° C. 150°C and pressure may be less than or equal to 1 bar.
- the high-temperature steam is supplied in an amount of 5 to 20 parts by weight per unit time based on 100 parts by weight of the reaction product supplied from the reactor located at the rearmost stage.
- the hydrogen chloride removal rate may be 99% or more.
- the raw material of the chlorination reaction may be an aromatic compound.
- chlorine gas is introduced into the lower part of each reactor in the same amount to perform the chlorination reaction in each reactor, and hydrogen chloride produced in each reactor Gas may be partially vented from each reactor.
- the reaction product generated in the front-end reactor is cooled by a heat exchanger located between the reactors to be quantitatively injected into the lower portion of the rear-end reactor.
- the wastewater discharged from the process can be significantly reduced.
- the HCl removal method of the chlorination reaction according to the present invention can remove HCl at a high removal rate without loss of the final product.
- the unit used without special mention is based on the weight, for example, the unit of % or ratio means weight % or weight ratio, and the weight % means any one component of the entire composition unless otherwise defined. It means % by weight in the composition.
- the numerical range used herein includes the lower limit and upper limit and all values within the range, increments logically derived from the form and width of the defined range, all values defined therein, and the upper limit of the numerical range defined in different forms. and all possible combinations of lower limits. Unless otherwise defined in the specification of the present invention, values outside the numerical range that may occur due to experimental errors or rounding of values are also included in the defined numerical range.
- 'comprising' is an open-ended description having an equivalent meaning to expressions such as 'comprising', 'containing', 'having' or 'characterized', and elements not listed in addition; Materials or processes are not excluded.
- the term 'substantially' means that other elements, materials, or processes not listed together with the specified element, material or process are unacceptable for at least one basic and novel technical idea of the invention. It means that it can be present in an amount or degree that does not significantly affect it.
- the HCl removal method of the chlorination reaction according to the present invention can remove HCl at a high removal rate without loss of the final product.
- the present invention is to remove HCl produced during the reaction in a chlorination reaction in which a plurality of column-type reactors are connected in series to produce a final product in which the ends are substituted with chlorine.
- the raw material may be an aromatic compound, specifically benzene or toluene.
- the end product may be, but is not limited to, chlorides thereof.
- o-chlorotoluene and p-chlorotoluene may be produced by supplying chlorine gas to toluene, which is an aromatic compound.
- the reaction product generated in the front-end reactor to which the raw material and chlorine gas are first supplied is transferred to the adjacent downstream reactor.
- the reaction product generated in the front stage may be supplied to the reactor located at the last stage sequentially through each reactor arranged in series.
- chlorine gas is injected into each reactor, and the raw material and the reaction product passing through the shear reactor can undergo a chlorination reaction in each reactor.
- chlorine gas is introduced into the lower part of each reactor in the same amount and the chlorination reaction is performed in each reactor, and the hydrogen chloride gas generated in each reactor may be partially discharged from each reactor.
- a foam is generated by an increase in the gas volume according to the lapse of reaction time, and it is possible to prevent a decrease in chlorination reactivity, thereby increasing the yield of the manufactured product.
- the conversion rate of the product is improved, the generation of hydrogen chloride, which is a reaction by-product, is fundamentally reduced, HCl removal may be more advantageous in the HCl removal method of the present invention.
- the chlorination reaction of the present invention is an exothermic reaction, and the temperature of the reaction solution increases as the reaction proceeds. Since the selectivity of chlorination reaction products of aromatic compounds, such as o-chlorotoluene and p-chlorotoluene, tends to decrease as the reaction temperature increases, when the reaction proceeds too much, a problem of decrease in selectivity may occur. . Accordingly, the reaction product generated in the front-end reactor by the heat exchanger located between the adjacent reactors may be cooled and quantitatively introduced into the lower part of the rear-end reactor.
- Cooling may be carried out at a temperature of 0 °C or higher and about 50 °C or lower, specifically 5 °C or higher and 30 °C, but cooling is not limited as long as chlorine is not liquefied. Specifically, depending on the supply pressure of the chlorine gas may be 25 °C at 7.81 bara, if the supply pressure of chlorine is 5.07 bara may be 10 °C. When the chlorine gas supply pressure is 3.7 bara, it can be cooled down to 0°C. However, in order to lower the temperature of the chlorine gas, a refrigerant having a temperature lower than the temperature at which the cooling is to be performed is required, and cooling more than necessary causes excessive investment cost. Therefore, in consideration of the chlorine liquefaction temperature and operating cost according to the operating pressure, the above range may be preferable. However, the present invention is not limited thereto.
- the present invention is to remove hydrogen chloride generated in the chlorination reaction, and includes the step of removing by heating hydrogen chloride in a stripping column connected to the last reactor.
- the stripping column is a multi-stage column, and may be provided in 10 to 20 columns, but is not limited thereto.
- the heating of hydrogen chloride can be made in a manner that can heat the reaction product supplied from the reactor in the stripping column, specifically, a method widely known in the art such as a heat exchanger, a heater, and the like.
- the heating of hydrogen chloride may be performed by high-temperature steam supplied from a reboiler connected to the lower portion of the stripping-column.
- the reaction product supplied to the stripping column from the last reactor contains the final product generated through the chlorination reaction and by-products including HCl.
- HCl can be separated by distillation from the reaction product by heating HCl by supplying high-temperature steam to the inside of the stripping column to which the reaction product is supplied.
- the method of heating and separating HCl by supplying high-temperature steam to the stripping column can greatly reduce the solubility of HCl in the reaction product, thereby increasing the HCl removal rate.
- the temperature of the top (Top) in the stripping column may be 10 to 30 °C, specifically, 15 to 20 °C, in this case, the upper pressure is 0.5 bar or less, specifically 0.1 bar It may be the following, but is not limited thereto.
- the temperature of the bottom in the stripping column to which the high-temperature steam is supplied is 100 to 150°C, specifically 120 to 140°C by the high-temperature steam, and the pressure may be 1 bar or less, specifically 0.6 bar or less, but limited thereto it doesn't happen However, in the above range, it is possible to effectively remove HCl while preventing deformation of the final product due to temperature and pressure.
- the high-temperature steam may be supplied without limitation as long as it is a supply amount that can remove HC with respect to the reaction product supplied from the reactor located at the rearmost stage, but preferably in units of 100 parts by weight. It may be supplied in an amount of 5 to 20 parts by weight, specifically 8 to 15 parts by weight per hour. In the above range, it is possible to efficiently heat the reaction product without wasting hot steam to heat and remove HCl.
- the ratio of hydrogen chloride removed to the generated hydrogen chloride that is, the hydrogen chloride removal rate is 99%, more specifically 99.9 or more, as it is possible to remove the chlorinated water with a high removal rate, to obtain the final product.
- the ratio of the remaining amount of the final product is also 99% or more, so that a high final product yield can be maintained.
- Toluene and chlorine gas are introduced into a reactor having an inner diameter of 13 cm and a height of 600 cm, but the chlorine gas has a linear speed of 5 to 10 m/sec, and the input speed of the raw material containing toluene is 10 to 40 m/sec. I adjusted the linear velocity of my aircraft.
- the molar ratio of toluene and chlorine was 2:1
- FeCl 3 was used as a catalyst
- S 2 Cl 2 was used as a co-catalyst
- concentrations of FeCl 3 and S 2 Cl 2 were 300 ppm and 150 ppm, respectively.
- Example 1 HCl was removed by spraying nitrogen gas without using high-temperature steam. Specific conditions are shown in Table 1 above.
- Example 1 only the chlorination reaction was carried out without going through the HCl removal step. Specific conditions are shown in Table 1 above.
- Example 1 the specific conditions of Example 1 and Comparative Examples 1 and 2, the amount of HCl removed, and the amount of loss of the final product were measured and described.
- the present invention has a HCl removal rate of 99% or more, and indicates that it has a final product yield of 99% or more.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
구분 | 실시예1 | 비교예1 | 비교예2 | |
Reactor Product(kg/h) | 6342.44 | 6313.89 | 6361.26 | |
HCl gas(kg/h) | 0.015 | 0.01 | 288.99 | |
Product 손실량(kg/h) | 18.82 | 47.37 | 0.00 | |
HCl gas 제거량(kg/h) | 288.98 | 288.99 | 0.00 | |
Column 총단수 | 14 | 15 | - | |
Temp.(°C) | Top | 19 | 17 | - |
Bottom | 126 | 15 | - | |
Press.(Barg) | Top | 0.1 | 0.1 | - |
Bottom | 0.6 | 0.6 | - | |
고온스팀 사용량(kg/h) | 644.757 | - | - | |
N2 사용량(kg/h) | 400 | - |
Claims (8)
- 복수개의 컬럼형 반응기가 상호 직렬 연결되어, 말단이 염소로 치환된 최종 생성물을 제조하는 염소화 반응에 있어서,상기 최후단에 위치하는 반응기와 연결된 스트립핑컬럼에서 상기 염소화 반응에서 발생된 염화수소를 가열시켜 제거하는 단계를 포함하는, 염소화 반응의 HCl 제거방법.
- 제1항에 있어서,상기 염화수소의 가열은 상기 스트립핑컬럼 하부와 연결된 리보일러(Reboiler)로부터 공급된 고온스팀에 의해 수행되는, 염소화 반응의 HCl 제거방법.
- 제2항에 있어서,상기 스트립핑컬럼 내 상부 온도는 10 내지 30℃및 압력은 0.5bar 이하이고,상기 스트립핑컬럼 내 하부 온도는 100 내지 150℃및 압력은 1bar 이하 인, 염소화 반응의 HCl 제거방법.
- 제2항에 있어서,상기 고온스팀은 상기 최후단에 위치하는 반응기로부터 공급된 반응생성물 100중량부에 대해 단위시간 당 5 내지 20중량부가 공급되는 염소화 반응의 HCl 제거방법.
- 제2항에 있어서,상기 염화수소 제거율은 99% 이상인 염소화 반응의 HCl 제거방법.
- 제1항에 있어서,상기 염소화 반응의 원료는 방향족 화합물인, 염소화 반응의 HCl 제거방법.
- 제1항에 있어서,상기 염소화 반응은 염소가스가 각 반응기 하부에 동일량으로 투입되어 각 반응기 내에 염소화반응 이루어지고, 각 반응기에서 생성된 염화수소가스는 각 반응기에서 일부 배출되는, 염소화 반응의 HCl 제거방법.
- 제1항에 있어서,상기 염소화 반응은 상기 반응기 사이에 위치하는 열교환기에 의해 전단 반응기에서 생성된 반응생성물은 냉각되어 후단 반응기 하부로 정량 투입되는, 염소화 반응의 HCl 제거방법.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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US18/256,940 US20240033654A1 (en) | 2020-12-14 | 2021-12-14 | Method for removing hcl in chlorination reaction |
EP21907041.4A EP4260923A1 (en) | 2020-12-14 | 2021-12-14 | Method for removing hcl in chlorination reaction |
CN202180084369.3A CN116600870A (zh) | 2020-12-14 | 2021-12-14 | 氯化反应的hcl去除方法 |
JP2023535655A JP2023553167A (ja) | 2020-12-14 | 2021-12-14 | 塩素化反応のHClの除去方法 |
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KR1020200174057A KR102666415B1 (ko) | 2020-12-14 | 염소화 반응의 HCl 제거방법 | |
KR10-2020-0174057 | 2020-12-14 |
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WO2022131737A1 true WO2022131737A1 (ko) | 2022-06-23 |
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US (1) | US20240033654A1 (ko) |
EP (1) | EP4260923A1 (ko) |
JP (1) | JP2023553167A (ko) |
CN (1) | CN116600870A (ko) |
WO (1) | WO2022131737A1 (ko) |
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KR20070067117A (ko) * | 2004-09-13 | 2007-06-27 | 바스프 악티엔게젤샤프트 | 염화수소와 포스겐을 분리하는 방법 |
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KR101773588B1 (ko) | 2016-04-19 | 2017-08-31 | 한화케미칼 주식회사 | o-클로로톨루엔 및 p-클로로톨루엔의 제조 방법 |
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2021
- 2021-12-14 WO PCT/KR2021/018945 patent/WO2022131737A1/ko active Application Filing
- 2021-12-14 US US18/256,940 patent/US20240033654A1/en active Pending
- 2021-12-14 JP JP2023535655A patent/JP2023553167A/ja active Pending
- 2021-12-14 CN CN202180084369.3A patent/CN116600870A/zh active Pending
- 2021-12-14 EP EP21907041.4A patent/EP4260923A1/en active Pending
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KR20070067117A (ko) * | 2004-09-13 | 2007-06-27 | 바스프 악티엔게젤샤프트 | 염화수소와 포스겐을 분리하는 방법 |
KR101332914B1 (ko) * | 2006-05-12 | 2013-11-26 | 바이엘 머티리얼싸이언스 엘엘씨 | 증진된 무수 염화수소 기체 정제 방법 |
WO2015014784A1 (en) * | 2013-08-01 | 2015-02-05 | Solvay Specialty Polymers Italy S.P.A. | Process for the dehydrochlorination of chlorinated hydrocarbons |
KR20170121159A (ko) * | 2014-12-22 | 2017-11-01 | 상하이 팡룬 뉴 머티리얼 테크놀로지 씨오., 엘티디. | 클로로포르밀 치환된 벤젠의 제조를 위한 청정 방법 |
KR101773588B1 (ko) | 2016-04-19 | 2017-08-31 | 한화케미칼 주식회사 | o-클로로톨루엔 및 p-클로로톨루엔의 제조 방법 |
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