PL187688B1 - Sposób usuwania i odzyskiwania kwasu azotowego, kwasu siarkowego i tlenków azotu z surowego dwunitrotoluenu - Google Patents
Sposób usuwania i odzyskiwania kwasu azotowego, kwasu siarkowego i tlenków azotu z surowego dwunitrotoluenuInfo
- Publication number
- PL187688B1 PL187688B1 PL96313631A PL31363196A PL187688B1 PL 187688 B1 PL187688 B1 PL 187688B1 PL 96313631 A PL96313631 A PL 96313631A PL 31363196 A PL31363196 A PL 31363196A PL 187688 B1 PL187688 B1 PL 187688B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- dnt
- nitric acid
- mixture
- aqueous solution
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 33
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 title claims description 89
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title claims description 71
- 229910017604 nitric acid Inorganic materials 0.000 title claims description 71
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims description 17
- 235000011149 sulphuric acid Nutrition 0.000 title abstract description 3
- 239000001117 sulphuric acid Substances 0.000 title 1
- 238000006396 nitration reaction Methods 0.000 claims abstract description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 30
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000006286 aqueous extract Substances 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 61
- 238000000605 extraction Methods 0.000 claims description 39
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 230000000802 nitrating effect Effects 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 238000011084 recovery Methods 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 238000005406 washing Methods 0.000 description 25
- 239000002351 wastewater Substances 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 9
- GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical class CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 description 6
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002823 nitrates Chemical class 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000013505 freshwater Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002826 nitrites Chemical class 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 1
- XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 1
- KZBOXYKTSUUBTO-UHFFFAOYSA-N 2-methyl-1,4-dinitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O KZBOXYKTSUUBTO-UHFFFAOYSA-N 0.000 description 1
- IUOFDOCUNLJHFO-UHFFFAOYSA-N 2-methyl-3,4-dinitrophenol Chemical class CC1=C(O)C=CC([N+]([O-])=O)=C1[N+]([O-])=O IUOFDOCUNLJHFO-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- HIQCTHFRLRVNPP-UHFFFAOYSA-N 4-methyl-2,3-dinitrophenol Chemical compound CC1=CC=C(O)C([N+]([O-])=O)=C1[N+]([O-])=O HIQCTHFRLRVNPP-UHFFFAOYSA-N 0.000 description 1
- 229910003556 H2 SO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 239000012451 post-reaction mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Processing Of Solid Wastes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19512114A DE19512114C2 (de) | 1995-04-04 | 1995-04-04 | Rückgewinnung von Salpetersäure aus Nitrierprozessen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL313631A1 PL313631A1 (en) | 1996-10-14 |
| PL187688B1 true PL187688B1 (pl) | 2004-09-30 |
Family
ID=7758446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL96313631A PL187688B1 (pl) | 1995-04-04 | 1996-04-04 | Sposób usuwania i odzyskiwania kwasu azotowego, kwasu siarkowego i tlenków azotu z surowego dwunitrotoluenu |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5756867A (https=) |
| EP (1) | EP0736514B2 (https=) |
| CN (1) | CN1085656C (https=) |
| AT (1) | ATE202333T1 (https=) |
| CA (1) | CA2173381C (https=) |
| DE (2) | DE19512114C2 (https=) |
| IN (1) | IN187139B (https=) |
| PL (1) | PL187688B1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2767318B1 (fr) * | 1997-08-13 | 1999-10-29 | Rhodia Chimie Sa | Procede de recuperation d'acide nitrique compris dans un melange de composes aromatiques dinitres |
| US5963878A (en) * | 1998-07-30 | 1999-10-05 | Noram Engineering & Constructors Ltd. | Nitration process |
| US6288289B1 (en) † | 2000-01-27 | 2001-09-11 | Noram Engineering And Constructors Ltd. | Integrated effluent treatment process for nitroaromatic manufacture |
| DE10143800C1 (de) * | 2001-09-06 | 2002-08-22 | Plinke Gmbh | Verfahren zur Minimierung des Abwassers bei der Herstellung von DNT |
| DE10329303A1 (de) * | 2003-06-30 | 2005-02-03 | Bayer Materialscience Ag | Verfahren zur Aufarbeitung des bei der Herstellung von Dinitrotoluol anfallenden Abwassers |
| DE102004005913A1 (de) | 2004-02-05 | 2005-08-25 | Basf Ag | Verfahren zur Herstellung von Dinitrotoluol |
| DE102005050106B4 (de) * | 2005-10-18 | 2008-04-30 | Josef Meissner Gmbh & Co. Kg | Rückgewinnung von Nitriersäuregemischen aus Nitrienprozessen |
| CN100369885C (zh) * | 2006-01-17 | 2008-02-20 | 甘肃银光化学工业集团有限公司 | 连续制备二硝基甲苯的方法及其装置 |
| DE102006033722A1 (de) * | 2006-07-21 | 2008-01-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Dinitrotoluol |
| DE102006060572A1 (de) * | 2006-12-19 | 2008-06-26 | Bayer Materialscience Ag | Verfahren zur Herstellung von Toluylendiaminen durch katalytische Hydrierung von Dinitrotoluolen |
| US9115048B2 (en) | 2011-05-19 | 2015-08-25 | Josef Meissner Gmbh & Co. Kg | Method and apparatus for purifying nitration products |
| PL2841412T3 (pl) * | 2012-04-25 | 2016-10-31 | Sposób przemywania dinitrotoluenu | |
| US9249083B2 (en) | 2012-04-25 | 2016-02-02 | Basf Se | Process for scrubbing dinitrotoluene |
| PT106909B (pt) * | 2013-04-26 | 2017-06-01 | Cuf - Quim Ind S A | Processo e equipamento para remoção de impurezas de compostos aromáticos nitrados |
| WO2015032706A1 (en) * | 2013-09-05 | 2015-03-12 | Basf Se | Method for removing hcn from crude dinitro toluene |
| HUE040622T2 (hu) | 2013-10-22 | 2019-03-28 | Basf Se | Eljárás dinitrotoluol savas mosására hidrogéncianid jelenlétében |
| CN103714876B (zh) * | 2014-01-06 | 2016-09-14 | 中国原子能科学研究院 | 一种亚硝酸的脱除方法 |
| JP6661555B2 (ja) | 2014-06-24 | 2020-03-11 | 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 | ニトロベンゼンの製造方法 |
| DE102015106617B4 (de) | 2014-07-07 | 2017-09-21 | Josef Meissner Gmbh & Co. Kg | Verfahren zur Aufreinigung von Rohdinitrotoluolen |
| CN107986250B (zh) * | 2017-10-31 | 2020-08-04 | 湖北东方化工有限公司 | 一种硝基甲苯废硫酸处理低浓度稀硝酸的提浓装置 |
| CN107902634B (zh) * | 2017-10-31 | 2020-08-04 | 湖北东方化工有限公司 | 一种硝基甲苯废硫酸处理低浓度稀硝酸微成本提高浓度的生产装置 |
| CN107986249B (zh) * | 2017-10-31 | 2020-08-04 | 湖北东方化工有限公司 | 硝基甲苯废酸脱硝后稀硝酸去除硝基甲苯的方法 |
| 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 |
| CN113912470B (zh) * | 2020-07-09 | 2024-09-27 | 中国石化工程建设有限公司 | 一种回收硝酸的方法及装置 |
| CN111807963B (zh) * | 2020-08-07 | 2022-11-18 | 山东友道化学有限公司 | 间甲基苯甲酸的绿色硝化处理方法 |
| CN113184815B (zh) * | 2020-10-29 | 2023-08-15 | 江苏方圆芳纶研究院有限公司 | 一种利用氮氧化物制备硝化混酸的方法 |
| CN113371768B (zh) * | 2021-05-31 | 2023-04-18 | 湖北东方化工有限公司 | 一种tnt废酸-残液回收工艺及装置 |
| CN115893339B (zh) * | 2022-12-15 | 2025-04-25 | 万华化学集团股份有限公司 | 一种粗dnt中硝酸的回收方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB125140A (https=) † | ||||
| DE1418624C3 (de) * | 1960-12-22 | 1973-01-04 | Ab Chematur, Stockholm | Verfahren zur kontinuierlichen Herstellung von Dinitrotoluol, Trinitrotoluol und deren Gemischen |
| GB1081092A (en) † | 1964-01-08 | 1967-08-31 | Ici Ltd | Purification of dinitrotoluenes |
| CA1034603A (en) | 1973-10-05 | 1978-07-11 | Allied Chemical Corporation | Water washing of nitroaromatic compounds prior to catalytic reduction |
| US4257986A (en) * | 1979-02-02 | 1981-03-24 | Air Products And Chemicals, Inc. | Process for refining aqueous acid mixtures utilized in nitration of aromatics |
| JPS56142245A (en) * | 1980-04-09 | 1981-11-06 | Mitsubishi Chem Ind Ltd | Purification of crude dinitrotoluene |
| US4496782A (en) * | 1983-07-08 | 1985-01-29 | Air Products And Chemicals, Inc. | Nitric acid recovery by the adiabatic nitration of nitroaromatics with fortified spent acid |
| DE3409719A1 (de) * | 1984-03-16 | 1985-09-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von dinitrotoluol |
| US4650912A (en) * | 1985-03-26 | 1987-03-17 | Air Products And Chemicals, Inc. | Recovery of nitric acid from nitration spent acid by toluene extraction |
| DE3705091A1 (de) * | 1987-02-18 | 1988-09-01 | Bayer Ag | Verfahren zur abtrennung von schwefelsaeure und salpetersaeure aus bei der nitrierung von toluol erhaltenen dinitrotoluolgemischen |
| US5006325A (en) * | 1989-08-28 | 1991-04-09 | Air Products And Chemical, Inc. | Process for the recovery of nitric acid |
| US5057632A (en) | 1990-10-22 | 1991-10-15 | Olin Corporation | Process for preparing dinitrotoluene |
| WO1992011227A1 (de) | 1990-12-24 | 1992-07-09 | Hoechst Aktiengesellschaft | Verfahren zur kontinuierlichen nitrierung von nitrierbaren aromatischen verbindungen |
-
1995
- 1995-04-04 DE DE19512114A patent/DE19512114C2/de not_active Expired - Fee Related
- 1995-09-15 US US08/529,100 patent/US5756867A/en not_active Expired - Lifetime
-
1996
- 1996-03-16 AT AT96104233T patent/ATE202333T1/de active
- 1996-03-16 EP EP96104233A patent/EP0736514B2/de not_active Expired - Lifetime
- 1996-03-16 DE DE59607109T patent/DE59607109D1/de not_active Expired - Lifetime
- 1996-03-18 IN IN475CA1996 patent/IN187139B/en unknown
- 1996-04-03 CN CN96105960A patent/CN1085656C/zh not_active Expired - Fee Related
- 1996-04-03 CA CA002173381A patent/CA2173381C/en not_active Expired - Fee Related
- 1996-04-04 PL PL96313631A patent/PL187688B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN187139B (https=) | 2002-02-09 |
| PL313631A1 (en) | 1996-10-14 |
| EP0736514B1 (de) | 2001-06-20 |
| EP0736514A1 (de) | 1996-10-09 |
| DE19512114A1 (de) | 1996-10-10 |
| CA2173381A1 (en) | 1996-10-05 |
| ATE202333T1 (de) | 2001-07-15 |
| CN1145893A (zh) | 1997-03-26 |
| US5756867A (en) | 1998-05-26 |
| CN1085656C (zh) | 2002-05-29 |
| DE59607109D1 (de) | 2001-07-26 |
| EP0736514B2 (de) | 2010-10-13 |
| CA2173381C (en) | 2007-06-26 |
| DE19512114C2 (de) | 2000-04-27 |
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