CA1154459A - Water removal in nitration of aromatic hydrocarbons - Google Patents
Water removal in nitration of aromatic hydrocarbonsInfo
- Publication number
- CA1154459A CA1154459A CA000375841A CA375841A CA1154459A CA 1154459 A CA1154459 A CA 1154459A CA 000375841 A CA000375841 A CA 000375841A CA 375841 A CA375841 A CA 375841A CA 1154459 A CA1154459 A CA 1154459A
- Authority
- CA
- Canada
- Prior art keywords
- gas
- reaction
- nitration
- water
- sulfuric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000006396 nitration reaction Methods 0.000 title claims abstract description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 17
- 230000008569 process Effects 0.000 claims abstract description 13
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 239000007789 gas Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 11
- 229910017604 nitric acid Inorganic materials 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 5
- 239000011261 inert gas Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229940032330 sulfuric acid Drugs 0.000 description 12
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- -1 nitronium ions Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 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 1
- 238000003915 air pollution Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical compound O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000126 substance Substances 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
- C07C201/02—Preparation of esters of nitric acid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J14/00—Chemical processes in general for reacting liquids with liquids; Apparatus specially adapted therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/14—Production of inert gas mixtures; Use of inert gases in general
-
- 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/10—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- 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
- Y02P20/141—Feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/143,372 US4331819A (en) | 1980-04-24 | 1980-04-24 | Water removal in nitration of aromatic hydrocarbons |
| US143,372 | 1980-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1154459A true CA1154459A (en) | 1983-09-27 |
Family
ID=22503788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000375841A Expired CA1154459A (en) | 1980-04-24 | 1981-04-21 | Water removal in nitration of aromatic hydrocarbons |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4331819A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0039556B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56167642A (cg-RX-API-DMAC7.html) |
| KR (1) | KR840001308B1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE11278T1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR8102405A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1154459A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3168254D1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK156512C (cg-RX-API-DMAC7.html) |
| ES (1) | ES8202782A1 (cg-RX-API-DMAC7.html) |
| IE (1) | IE51222B1 (cg-RX-API-DMAC7.html) |
| IN (1) | IN153701B (cg-RX-API-DMAC7.html) |
| MX (1) | MX159142A (cg-RX-API-DMAC7.html) |
| PT (1) | PT72906B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA812678B (cg-RX-API-DMAC7.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5313009A (en) * | 1990-01-04 | 1994-05-17 | Nrm International Technologies C.V. | Nitration process |
| DE69026590T2 (de) * | 1990-01-04 | 1996-10-31 | Nrm Int Tech | Nitrierungsverfahren |
| JPH04126224U (ja) * | 1991-04-30 | 1992-11-17 | タキロン株式会社 | 調光パネル |
| RU2167145C1 (ru) * | 2000-09-01 | 2001-05-20 | Старовойтов Михаил Карпович | Способ очистки технического нитробензола от серосодержащих, азот- и кислородсодержащих побочных продуктов |
| DE10047163A1 (de) * | 2000-09-22 | 2002-04-11 | Basf Ag | Verfahren zur Nitrierung aromatischer Kohlenwasserstoffe |
| DE102007059513A1 (de) * | 2007-12-11 | 2009-06-18 | Bayer Materialscience Ag | Verfahren zur Herstellung von Nitrobenzol durch adiabate Nitrierung |
| WO2013113651A1 (de) * | 2012-01-31 | 2013-08-08 | Bayer Intellectual Property Gmbh | Verfahren und anlage zur herstellung von nitrobenzol |
| CN103418318A (zh) * | 2013-08-09 | 2013-12-04 | 江苏淮河化工有限公司 | 芳烃类连续催化硝化的反应装置 |
| CN107106961B (zh) * | 2014-10-02 | 2020-08-07 | 科思创德国股份有限公司 | 用于连续生产二硝基甲苯的方法中的废气净化 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2007510A (en) * | 1931-11-30 | 1935-07-09 | Nat Aniline & Chem Co Inc | Control of temperatures in chemical reactions |
| US2135012A (en) * | 1934-11-28 | 1938-11-01 | Meissner Josef | Nitration of aromatic hydrocarbons |
| US2435314A (en) * | 1940-12-05 | 1948-02-03 | Autoxygen Inc | Method of nitrating organic compounds |
| SU73577A1 (ru) * | 1941-05-28 | 1947-11-30 | С.А. Рабинович | Способ мокрого обогащени каолинов |
| DE971523C (de) * | 1943-07-16 | 1959-02-12 | Dynamit Nobel Ag | Verfahren zum Nitrieren aromatischer Kohlenwasserstoffverbindungen |
| US2951877A (en) * | 1957-02-25 | 1960-09-06 | Hercules Powder Co Ltd | Process for the preparation of trinitrotoluene |
| DE1418624C3 (de) * | 1960-12-22 | 1973-01-04 | Ab Chematur, Stockholm | Verfahren zur kontinuierlichen Herstellung von Dinitrotoluol, Trinitrotoluol und deren Gemischen |
| NL133035C (cg-RX-API-DMAC7.html) * | 1966-02-03 | |||
| US3371122A (en) * | 1966-12-02 | 1968-02-27 | Du Pont | Continuous process for the nitration of xylene |
| US3928475A (en) * | 1974-08-09 | 1975-12-23 | Du Pont | Azeotropic nitration of benzene |
| US3957889A (en) * | 1975-05-02 | 1976-05-18 | Air Products And Chemicals, Inc. | Selective nitration of aromatic and substituted aromatic compositions |
| US4120905A (en) * | 1977-09-21 | 1978-10-17 | Eli Lilly And Company | Removal of nitrosating agents |
| US4123466A (en) * | 1977-12-12 | 1978-10-31 | The Upjohn Company | Process for nitrating aromatic hydrocarbons |
-
1980
- 1980-04-24 US US06/143,372 patent/US4331819A/en not_active Expired - Lifetime
-
1981
- 1981-04-21 JP JP5931381A patent/JPS56167642A/ja active Granted
- 1981-04-21 CA CA000375841A patent/CA1154459A/en not_active Expired
- 1981-04-22 IN IN428/CAL/81A patent/IN153701B/en unknown
- 1981-04-22 KR KR1019810001382A patent/KR840001308B1/ko not_active Expired
- 1981-04-22 BR BR8102405A patent/BR8102405A/pt not_active IP Right Cessation
- 1981-04-23 DE DE8181301797T patent/DE3168254D1/de not_active Expired
- 1981-04-23 DK DK182581A patent/DK156512C/da not_active IP Right Cessation
- 1981-04-23 ES ES501574A patent/ES8202782A1/es not_active Expired
- 1981-04-23 AT AT81301797T patent/ATE11278T1/de active
- 1981-04-23 PT PT72906A patent/PT72906B/pt not_active IP Right Cessation
- 1981-04-23 IE IE904/81A patent/IE51222B1/en not_active IP Right Cessation
- 1981-04-23 EP EP81301797A patent/EP0039556B1/en not_active Expired
- 1981-04-23 ZA ZA00812678A patent/ZA812678B/xx unknown
- 1981-04-23 MX MX186973A patent/MX159142A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR8102405A (pt) | 1981-12-29 |
| ZA812678B (en) | 1982-11-24 |
| DK182581A (da) | 1981-10-25 |
| KR840001308B1 (ko) | 1984-09-11 |
| EP0039556A2 (en) | 1981-11-11 |
| US4331819A (en) | 1982-05-25 |
| PT72906A (en) | 1981-05-01 |
| EP0039556B1 (en) | 1985-01-16 |
| PT72906B (en) | 1982-03-29 |
| DK156512C (da) | 1990-02-05 |
| IE810904L (en) | 1981-10-24 |
| IE51222B1 (en) | 1986-11-12 |
| MX159142A (es) | 1989-04-26 |
| DE3168254D1 (en) | 1985-02-28 |
| EP0039556A3 (en) | 1981-12-09 |
| JPS56167642A (en) | 1981-12-23 |
| JPH0233025B2 (cg-RX-API-DMAC7.html) | 1990-07-25 |
| DK156512B (da) | 1989-09-04 |
| KR830005103A (ko) | 1983-07-23 |
| ES501574A0 (es) | 1982-02-16 |
| ATE11278T1 (de) | 1985-02-15 |
| ES8202782A1 (es) | 1982-02-16 |
| IN153701B (cg-RX-API-DMAC7.html) | 1984-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |