CS207645B2 - Method of making the mononitrobenzene - Google Patents
Method of making the mononitrobenzene Download PDFInfo
- Publication number
- CS207645B2 CS207645B2 CS785136A CS513678A CS207645B2 CS 207645 B2 CS207645 B2 CS 207645B2 CS 785136 A CS785136 A CS 785136A CS 513678 A CS513678 A CS 513678A CS 207645 B2 CS207645 B2 CS 207645B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- reaction
- nitric acid
- mononitrobenzene
- nitration
- benzene
- Prior art date
Links
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 87
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 65
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 238000006396 nitration reaction Methods 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 239000012074 organic phase Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 16
- 239000000047 product Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 3
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/826,208 US4091042A (en) | 1977-08-19 | 1977-08-19 | Continuous adiabatic process for the mononitration of benzene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS207645B2 true CS207645B2 (en) | 1981-08-31 |
Family
ID=25245976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS785136A CS207645B2 (en) | 1977-08-19 | 1978-08-04 | Method of making the mononitrobenzene |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4091042A (de) |
| JP (1) | JPS5432424A (de) |
| AT (1) | AT357140B (de) |
| AU (1) | AU518647B2 (de) |
| BE (1) | BE867355A (de) |
| BR (1) | BR7803249A (de) |
| CA (1) | CA1083608A (de) |
| CH (1) | CH639936A5 (de) |
| CS (1) | CS207645B2 (de) |
| DD (1) | DD136960A5 (de) |
| DE (1) | DE2821571A1 (de) |
| EG (1) | EG13569A (de) |
| FR (1) | FR2400501A1 (de) |
| GB (1) | GB1597433A (de) |
| IN (1) | IN147796B (de) |
| IT (1) | IT1103488B (de) |
| MX (1) | MX148692A (de) |
| NL (1) | NL189757C (de) |
| PL (1) | PL113312B1 (de) |
| PT (1) | PT68105A (de) |
| TR (1) | TR19875A (de) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4241229A (en) * | 1979-08-08 | 1980-12-23 | American Cyanamid Company | Recovery of nitrated aromatic compounds from nitration wash liquors |
| JPS5785332A (en) * | 1980-11-17 | 1982-05-28 | Mitsui Toatsu Chem Inc | Ortho-alkylation of phenolic compound |
| DE3409719A1 (de) * | 1984-03-16 | 1985-09-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von dinitrotoluol |
| DE3409717C2 (de) * | 1984-03-16 | 1994-03-31 | Bayer Ag | Verfahren zur Herstellung von Nitrobenzol |
| US4973770A (en) * | 1988-12-15 | 1990-11-27 | C-I-L, Inc. | Manufacture of organic nitro compounds |
| US5313009A (en) * | 1990-01-04 | 1994-05-17 | Nrm International Technologies C.V. | Nitration process |
| TW236610B (en) * | 1992-11-13 | 1994-12-21 | Bayer Ag | Preparation of dinitrotoluene |
| DE4309140C2 (de) * | 1993-03-22 | 2001-09-20 | Bayer Ag | Verfahren zur Herstellung von Dinitrotoluol |
| DE4410417A1 (de) * | 1994-02-14 | 1995-08-17 | Bayer Ag | Verfahren zur adiabatischen Herstellung von Mononitrotoluolen |
| DE4411064A1 (de) * | 1994-03-30 | 1995-10-05 | Bayer Ag | Verfahren zur adiabatischen Herstellung von Mononitrohalogenbenzolen |
| DE4428459A1 (de) * | 1994-08-11 | 1996-02-15 | Bayer Ag | Verfahren zur Herstellung von Dinitrotoluol |
| DE4428462A1 (de) * | 1994-08-11 | 1996-02-15 | Bayer Ag | Verfahren zur Herstellung von Dinitrotoluol |
| DE4437047A1 (de) * | 1994-10-17 | 1996-04-18 | Bayer Ag | Verfahren zur Dinitrierung von aromatischen Verbindungen |
| US5763687A (en) | 1995-12-15 | 1998-06-09 | Mitsui Chemicals, Inc. | Preparation process for aromatic mononitro compounds |
| AR027590A1 (es) | 2000-03-02 | 2003-04-02 | Dow Chemical Co | Reactor tubular, proceso para conducir las reacciones multifase de liquido/liquido en un reactor tubular, y un proceso para compuestos aromaticos denitracion de anillo en un reactor tubular |
| US20060078893A1 (en) | 2004-10-12 | 2006-04-13 | Medical Research Council | Compartmentalised combinatorial chemistry by microfluidic control |
| GB0307403D0 (en) | 2003-03-31 | 2003-05-07 | Medical Res Council | Selection by compartmentalised screening |
| GB0307428D0 (en) | 2003-03-31 | 2003-05-07 | Medical Res Council | Compartmentalised combinatorial chemistry |
| US20050221339A1 (en) | 2004-03-31 | 2005-10-06 | Medical Research Council Harvard University | Compartmentalised screening by microfluidic control |
| US7968287B2 (en) | 2004-10-08 | 2011-06-28 | Medical Research Council Harvard University | In vitro evolution in microfluidic systems |
| DE102005057555B3 (de) * | 2005-11-21 | 2007-05-16 | Meissner Gmbh & Co Kg Josef | Verfahren zur Herstellung von Salpetersäureestern einwertiger Alkohole |
| EP2363205A3 (de) | 2006-01-11 | 2014-06-04 | Raindance Technologies, Inc. | Mikrofluidische Vorrichtungen Und Verfahren Zur Verwendung Bei Der Bildung Und Kontrolle Von Nanoreaktoren |
| DE102006021857A1 (de) | 2006-05-09 | 2007-11-15 | Otto Bock Healthcare Ip Gmbh & Co. Kg | Verfahren zum Gießen eines Prothesenschaftes |
| EP3782722B1 (de) | 2006-05-11 | 2022-07-06 | Bio-Rad Laboratories, Inc. | Mikrofluidische vorrichtungen |
| US9562837B2 (en) | 2006-05-11 | 2017-02-07 | Raindance Technologies, Inc. | Systems for handling microfludic droplets |
| EP3536396B1 (de) | 2006-08-07 | 2022-03-30 | The President and Fellows of Harvard College | Fluorkohlenstoffemulsionsstabilisierende tenside |
| US8772046B2 (en) | 2007-02-06 | 2014-07-08 | Brandeis University | Manipulation of fluids and reactions in microfluidic systems |
| US8592221B2 (en) | 2007-04-19 | 2013-11-26 | Brandeis University | Manipulation of fluids, fluid components and reactions in microfluidic systems |
| DE102007059513A1 (de) | 2007-12-11 | 2009-06-18 | Bayer Materialscience Ag | Verfahren zur Herstellung von Nitrobenzol durch adiabate Nitrierung |
| WO2010009365A1 (en) | 2008-07-18 | 2010-01-21 | Raindance Technologies, Inc. | Droplet libraries |
| US12038438B2 (en) | 2008-07-18 | 2024-07-16 | Bio-Rad Laboratories, Inc. | Enzyme quantification |
| DE102008048713A1 (de) * | 2008-09-24 | 2010-03-25 | Bayer Materialscience Ag | Verfahren zur kontinuierlichen Herstellung von Nitrobenzol |
| HUE035115T2 (hu) | 2008-11-10 | 2018-05-02 | Noram International Ltd | Adiabatikus eljárás mononitrobenzol elõállítására |
| JP5602143B2 (ja) * | 2008-11-14 | 2014-10-08 | ノラム インターナショナル リミテッド | モノニトロベンゼンの生産における副産物ジニトロベンゼンの生成を低減する方法 |
| CN101759568A (zh) * | 2008-12-25 | 2010-06-30 | 南化集团研究院 | 硝基苯的绝热生产方法 |
| DE102009005324B4 (de) | 2009-01-16 | 2014-04-03 | Plinke Gmbh | Verfahren zur adiabatischen Nitrierung von Benzol |
| US9079822B2 (en) | 2009-02-26 | 2015-07-14 | Basf Se | Process for the preparation of nitrated aromatics and mixtures thereof |
| EP3415235B1 (de) | 2009-03-23 | 2025-11-12 | Bio-Rad Laboratories, Inc. | Manipulation von mikrofluidiktröpfchen |
| EP2486409A1 (de) | 2009-10-09 | 2012-08-15 | Universite De Strasbourg | Markiertes nanomaterial auf siliziumbasis mit verbesserten eigenschaften und seine verwendung |
| WO2011079176A2 (en) | 2009-12-23 | 2011-06-30 | Raindance Technologies, Inc. | Microfluidic systems and methods for reducing the exchange of molecules between droplets |
| DE102010006984A1 (de) | 2010-02-05 | 2011-08-11 | Bayer MaterialScience AG, 51373 | Verfahren zur kontinuierlichen Herstellung von Nitrobenzol |
| US10351905B2 (en) | 2010-02-12 | 2019-07-16 | Bio-Rad Laboratories, Inc. | Digital analyte analysis |
| JP5934657B2 (ja) | 2010-02-12 | 2016-06-15 | レインダンス テクノロジーズ， インコーポレイテッド | デジタル検体分析 |
| US9399797B2 (en) | 2010-02-12 | 2016-07-26 | Raindance Technologies, Inc. | Digital analyte analysis |
| US9366632B2 (en) | 2010-02-12 | 2016-06-14 | Raindance Technologies, Inc. | Digital analyte analysis |
| DE102010038519A1 (de) | 2010-07-28 | 2012-02-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Nitrobenzol durch adiabate Nitrierung |
| US9562897B2 (en) | 2010-09-30 | 2017-02-07 | Raindance Technologies, Inc. | Sandwich assays in droplets |
| EP3859011A1 (de) | 2011-02-11 | 2021-08-04 | Bio-Rad Laboratories, Inc. | Verfahren zur bildung gemischter tröpfchen |
| EP2675819B1 (de) | 2011-02-18 | 2020-04-08 | Bio-Rad Laboratories, Inc. | Zusammensetzungen und verfahren für molekulare etikettierung |
| ES2633799T3 (es) | 2011-05-19 | 2017-09-25 | Josef Meissner Gmbh & Co. Kg | Aparato para la purificación de productos de nitración |
| EP3216872B1 (de) | 2011-06-02 | 2020-04-01 | Bio-Rad Laboratories, Inc. | Enzymquantifizierung |
| US8841071B2 (en) | 2011-06-02 | 2014-09-23 | Raindance Technologies, Inc. | Sample multiplexing |
| CN102311347B (zh) * | 2011-06-28 | 2013-08-14 | 江苏科圣化工装备工程有限公司 | 由焦化苯连续生产混二硝基苯的装置及方法 |
| US8658430B2 (en) | 2011-07-20 | 2014-02-25 | Raindance Technologies, Inc. | Manipulating droplet size |
| WO2013054181A1 (en) | 2011-10-14 | 2013-04-18 | Council Of Scientific & Industrial Research | Continuous two step flow synthesis of m-amino acetophenone |
| CN102516082B (zh) * | 2011-11-28 | 2013-11-06 | 万华化学集团股份有限公司 | 由苯与混酸反应制备硝基苯以及洗涤粗硝基苯产物的方法 |
| KR20140117474A (ko) | 2012-01-31 | 2014-10-07 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 니트로벤젠을 제조하기 위한 방법 및 시스템 |
| US8907144B2 (en) | 2012-03-22 | 2014-12-09 | Noram International Limited | Process for adiabatic production of mononitrotoluene |
| EP2877442B1 (de) | 2012-07-27 | 2016-11-16 | Covestro Deutschland AG | Verfahren zur herstellung von nitrobenzol durch adiabate nitrierung |
| WO2014016290A1 (de) | 2012-07-27 | 2014-01-30 | Bayer Materialscience Ag | Verfahren zur herstellung von nitrobenzol durch adiabate nitrierung |
| EP2877443B1 (de) | 2012-07-27 | 2016-05-11 | Covestro Deutschland AG | Verfahren zur herstellung von nitrobenzol durch adiabate nitrierung |
| JP6458006B2 (ja) * | 2013-04-29 | 2019-01-23 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | 断熱ニトロ化によるニトロベンゼン調製のためのプロセス |
| US11901041B2 (en) | 2013-10-04 | 2024-02-13 | Bio-Rad Laboratories, Inc. | Digital analysis of nucleic acid modification |
| US9944977B2 (en) | 2013-12-12 | 2018-04-17 | Raindance Technologies, Inc. | Distinguishing rare variations in a nucleic acid sequence from a sample |
| EP3090063B1 (de) | 2013-12-31 | 2019-11-06 | Bio-Rad Laboratories, Inc. | Verfahren zur detektion von latentem retrovirus |
| US10647981B1 (en) | 2015-09-08 | 2020-05-12 | Bio-Rad Laboratories, Inc. | Nucleic acid library generation methods and compositions |
| DE102017110084B4 (de) | 2017-02-03 | 2019-07-04 | Josef Meissner Gmbh & Co. Kg | Verfahren und Anlage zur adiabatischen Nitrierung von Aromaten |
| CN110573491B (zh) * | 2017-03-07 | 2022-11-11 | 科思创德国股份有限公司 | 制备硝基苯的方法 |
| WO2020011817A1 (de) | 2018-07-12 | 2020-01-16 | Covestro Deutschland Ag | Verfahren zur herstellung von nitrobenzol durch adiabatisch betriebene nitrierung von benzol |
| DE102018217955B4 (de) * | 2018-10-19 | 2020-06-04 | Plinke Gmbh | Verfahren zur Aufarbeitung von Mischsäure und Abwasser aus der Nitrierung von Aromaten sowie Vorrichtung zur Durchführung des Verfahrens |
| CN111393299A (zh) * | 2020-05-06 | 2020-07-10 | 沈阳感光化工研究院有限公司 | 一种使用微通道连续流反应器对硝基苯进行硝化的方法 |
| CN119451937A (zh) | 2022-06-28 | 2025-02-14 | 巴斯夫欧洲公司 | 生产硝基苯的方法 |
| WO2025045698A1 (en) | 2023-08-25 | 2025-03-06 | Covestro Deutschland Ag | Reactor for the nitration of aromatic compounds, production plant comprising said reactor and nitration process using said reactor |
| CN118221528A (zh) * | 2024-02-04 | 2024-06-21 | 清华大学 | 采用硝硫混酸制备单硝基芳烃的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087971A (en) * | 1953-12-07 | 1963-04-30 | Samuelsen Eirik | Method for trinitrotoluene manufacture |
| GB1081091A (en) * | 1964-01-08 | 1967-08-31 | Ici Ltd | Improvements in or relating to the preparation of dinitrotoluenes |
| US3928475A (en) * | 1974-08-09 | 1975-12-23 | Du Pont | Azeotropic nitration of benzene |
| US4021498A (en) * | 1975-12-09 | 1977-05-03 | American Cyanamid Company | Adiabatic process for nitration of nitratable aromatic compounds |
-
1977
- 1977-08-19 US US05/826,208 patent/US4091042A/en not_active Expired - Lifetime
-
1978
- 1978-04-15 IN IN418/CAL/78A patent/IN147796B/en unknown
- 1978-04-17 GB GB15064/78A patent/GB1597433A/en not_active Expired
- 1978-04-20 AU AU35299/78A patent/AU518647B2/en not_active Expired
- 1978-05-02 TR TR19875A patent/TR19875A/xx unknown
- 1978-05-08 MX MX173367A patent/MX148692A/es unknown
- 1978-05-08 CA CA302,819A patent/CA1083608A/en not_active Expired
- 1978-05-12 IT IT49331/78A patent/IT1103488B/it active
- 1978-05-17 DE DE19782821571 patent/DE2821571A1/de not_active Ceased
- 1978-05-18 NL NLAANVRAGE7805409,A patent/NL189757C/xx not_active IP Right Cessation
- 1978-05-21 EG EG325/78A patent/EG13569A/xx active
- 1978-05-22 BR BR7803249A patent/BR7803249A/pt unknown
- 1978-05-22 AT AT369978A patent/AT357140B/de not_active IP Right Cessation
- 1978-05-23 FR FR7815318A patent/FR2400501A1/fr active Granted
- 1978-05-23 JP JP6153578A patent/JPS5432424A/ja active Pending
- 1978-05-23 PL PL1978207037A patent/PL113312B1/pl unknown
- 1978-05-23 CH CH562278A patent/CH639936A5/de not_active IP Right Cessation
- 1978-05-23 BE BE187937A patent/BE867355A/xx not_active IP Right Cessation
- 1978-05-23 DD DD78205518A patent/DD136960A5/de unknown
- 1978-05-30 PT PT68105A patent/PT68105A/pt unknown
- 1978-08-04 CS CS785136A patent/CS207645B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD136960A5 (de) | 1979-08-08 |
| PT68105A (en) | 1978-06-01 |
| ATA369978A (de) | 1979-11-15 |
| BR7803249A (pt) | 1979-03-27 |
| NL189757B (nl) | 1993-02-16 |
| PL113312B1 (en) | 1980-12-31 |
| TR19875A (tr) | 1980-04-03 |
| IT7849331A0 (it) | 1978-05-12 |
| AU518647B2 (en) | 1981-10-15 |
| FR2400501B1 (de) | 1984-01-27 |
| US4091042A (en) | 1978-05-23 |
| DE2821571A1 (de) | 1979-03-01 |
| PL207037A1 (pl) | 1979-05-07 |
| NL189757C (nl) | 1993-07-16 |
| MX148692A (es) | 1983-06-02 |
| AT357140B (de) | 1980-06-25 |
| CA1083608A (en) | 1980-08-12 |
| BE867355A (fr) | 1978-11-23 |
| AU3529978A (en) | 1979-10-25 |
| NL7805409A (nl) | 1979-02-21 |
| FR2400501A1 (fr) | 1979-03-16 |
| JPS5432424A (en) | 1979-03-09 |
| CH639936A5 (de) | 1983-12-15 |
| GB1597433A (en) | 1981-09-09 |
| IT1103488B (it) | 1985-10-14 |
| EG13569A (en) | 1981-12-31 |
| IN147796B (de) | 1980-06-28 |
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