CA2008342A1 - Methode de preparation de dinitrotoluene ou de mononitrobenzene - Google Patents
Methode de preparation de dinitrotoluene ou de mononitrobenzeneInfo
- Publication number
- CA2008342A1 CA2008342A1 CA002008342A CA2008342A CA2008342A1 CA 2008342 A1 CA2008342 A1 CA 2008342A1 CA 002008342 A CA002008342 A CA 002008342A CA 2008342 A CA2008342 A CA 2008342A CA 2008342 A1 CA2008342 A1 CA 2008342A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- nitric acid
- reaction
- toluene
- dinitrotoluene
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 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 abstract description 17
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title abstract description 21
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 78
- 230000000802 nitrating effect Effects 0.000 claims abstract description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 34
- 229910017604 nitric acid Inorganic materials 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 14
- 238000006396 nitration reaction Methods 0.000 claims description 13
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 238000005292 vacuum distillation Methods 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 5
- 238000005191 phase separation Methods 0.000 claims description 5
- 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 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 28
- 239000000543 intermediate Substances 0.000 abstract description 4
- 229920001228 polyisocyanate Polymers 0.000 abstract description 2
- 239000005056 polyisocyanate Substances 0.000 abstract description 2
- 238000006172 aromatic nitration reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 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 10
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 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
- GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical compound CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- INYDMNPNDHRJQJ-UHFFFAOYSA-N 3,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 INYDMNPNDHRJQJ-UHFFFAOYSA-N 0.000 description 1
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 1
- HNNYZRKJLZSYFR-UHFFFAOYSA-N 4-methyl-2-(nitromethoxy)phenol Chemical compound CC1=CC=C(O)C(OC[N+]([O-])=O)=C1 HNNYZRKJLZSYFR-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000839 emulsion 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
- 238000000605 extraction Methods 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type 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
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
-
- 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU38630/89A AU3863089A (en) | 1988-06-22 | 1989-06-14 | Process for the production of dinitrotoluene or mononitrobenzene |
| PCT/US1989/002635 WO1989012620A1 (fr) | 1988-06-22 | 1989-06-14 | Procede de production de dinitrotoluene ou de mononitrobenzene |
| CA000603642A CA1340073C (fr) | 1988-06-22 | 1989-06-22 | Methode pour la preparation de dinitrotoluene ou de mononitrobenzene |
| CA002008342A CA2008342A1 (fr) | 1988-06-22 | 1990-01-23 | Methode de preparation de dinitrotoluene ou de mononitrobenzene |
| CN90100885A CN1026583C (zh) | 1988-06-22 | 1990-02-22 | 制造二硝基甲苯的方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21054988A | 1988-06-22 | 1988-06-22 | |
| CA002008342A CA2008342A1 (fr) | 1988-06-22 | 1990-01-23 | Methode de preparation de dinitrotoluene ou de mononitrobenzene |
| CN90100885A CN1026583C (zh) | 1988-06-22 | 1990-02-22 | 制造二硝基甲苯的方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2008342A1 true CA2008342A1 (fr) | 1991-07-23 |
Family
ID=36754844
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000603642A Expired - Fee Related CA1340073C (fr) | 1988-06-22 | 1989-06-22 | Methode pour la preparation de dinitrotoluene ou de mononitrobenzene |
| CA002008342A Abandoned CA2008342A1 (fr) | 1988-06-22 | 1990-01-23 | Methode de preparation de dinitrotoluene ou de mononitrobenzene |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000603642A Expired - Fee Related CA1340073C (fr) | 1988-06-22 | 1989-06-22 | Methode pour la preparation de dinitrotoluene ou de mononitrobenzene |
Country Status (4)
| Country | Link |
|---|---|
| CN (1) | CN1026583C (fr) |
| AU (1) | AU3863089A (fr) |
| CA (2) | CA1340073C (fr) |
| WO (1) | WO1989012620A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4216416C1 (fr) * | 1992-05-18 | 1993-05-13 | Bayer Ag, 5090 Leverkusen, De | |
| CA2138391A1 (fr) * | 1992-06-17 | 1993-12-23 | Robert W. Mason | Methode pour l'obtention du dinitrotoluene |
| US8692035B2 (en) | 2008-11-10 | 2014-04-08 | Noram International Limited | Adiabatic process for making mononitrobenzene |
| CN102020567B (zh) * | 2009-09-11 | 2013-11-06 | 上海安赐机械设备有限公司 | 一种粗硝基苯精制方法及其装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2362743A (en) * | 1943-02-10 | 1944-11-14 | Hercules Powder Co Ltd | Manufacture of dinitrotoluene |
| US3928395A (en) * | 1972-10-05 | 1975-12-23 | Ciba Geigy Ag | Process for the nitration of aromatic compounds |
-
1989
- 1989-06-14 WO PCT/US1989/002635 patent/WO1989012620A1/fr not_active Ceased
- 1989-06-14 AU AU38630/89A patent/AU3863089A/en not_active Abandoned
- 1989-06-22 CA CA000603642A patent/CA1340073C/fr not_active Expired - Fee Related
-
1990
- 1990-01-23 CA CA002008342A patent/CA2008342A1/fr not_active Abandoned
- 1990-02-22 CN CN90100885A patent/CN1026583C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1054247A (zh) | 1991-09-04 |
| AU3863089A (en) | 1990-01-12 |
| WO1989012620A1 (fr) | 1989-12-28 |
| CA1340073C (fr) | 1998-10-06 |
| CN1026583C (zh) | 1994-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |