RU2106338C1 - Способ получения динитротолуола - Google Patents
Способ получения динитротолуола Download PDFInfo
- Publication number
- RU2106338C1 RU2106338C1 RU94046238A RU94046238A RU2106338C1 RU 2106338 C1 RU2106338 C1 RU 2106338C1 RU 94046238 A RU94046238 A RU 94046238A RU 94046238 A RU94046238 A RU 94046238A RU 2106338 C1 RU2106338 C1 RU 2106338C1
- Authority
- RU
- Russia
- Prior art keywords
- reaction
- nitric acid
- toluene
- dinitrotoluene
- nitration
- Prior art date
Links
- 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 27
- 238000000034 method Methods 0.000 title claims abstract description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 69
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006396 nitration reaction Methods 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 6
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 4
- GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical compound CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002699 waste material Substances 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
- 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
- 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
- 241000196324 Embryophyta Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 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
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- -1 nitrate aromatic compounds Chemical class 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 239000007858 starting material Substances 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
- 239000002351 wastewater Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90021392A | 1992-06-17 | 1992-06-17 | |
| US900,213 | 1992-06-17 | ||
| US900.213 | 1992-06-17 | ||
| PCT/US1993/005081 WO1993025503A1 (fr) | 1992-06-17 | 1993-06-01 | Procede de production de dinitrotoluene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU94046238A RU94046238A (ru) | 1996-10-10 |
| RU2106338C1 true RU2106338C1 (ru) | 1998-03-10 |
Family
ID=25412168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU94046238A RU2106338C1 (ru) | 1992-06-17 | 1993-06-01 | Способ получения динитротолуола |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0649400A1 (fr) |
| KR (1) | KR950701903A (fr) |
| AU (1) | AU665843B2 (fr) |
| BR (1) | BR9306554A (fr) |
| CA (1) | CA2138391A1 (fr) |
| RU (1) | RU2106338C1 (fr) |
| WO (1) | WO1993025503A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2295953C2 (ru) * | 2004-07-12 | 2007-03-27 | Тиберий Георгиевич Незбайло | Гидрофильная и гидрофобная композиции для лечения заболеваний инфекционного или вирусного характера и способ их применения |
| RU2330836C2 (ru) * | 2003-02-20 | 2008-08-10 | Байер Акциенгезельшафт | Способ двухстадийного получения динитротолуола |
| RU2356885C2 (ru) * | 2005-10-18 | 2009-05-27 | Йозеф Майсснер Гмбх Унд Ко. Кг | Способ удаления и регенерации смесей нитрующих кислот из процессов нитрования и промышленная установка для нитрования |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928395A (en) * | 1972-10-05 | 1975-12-23 | Ciba Geigy Ag | Process for the nitration of aromatic compounds |
| US4918250A (en) * | 1989-04-21 | 1990-04-17 | Olin Corporation | Process for the production of dinitrotoluene using an inorganic salt as a phase separation agent |
| US4935557A (en) * | 1984-08-07 | 1990-06-19 | Air Products And Chemicals, Inc. | Conitration of mixed aromatic hydrocarbons |
| US5001272A (en) * | 1988-06-22 | 1991-03-19 | Olin Corporation | Process for the production of dinitrotoluene |
| US5099079A (en) * | 1990-07-26 | 1992-03-24 | Olin Corporation | Process for separating acid from nitro substituted aromatics using a molten nitrate salt |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495372A (en) * | 1982-11-05 | 1985-01-22 | Uniroyal, Inc. | Preparation of mono-nitro aromatic compounds |
| AU3863089A (en) * | 1988-06-22 | 1990-01-12 | Olin Corporation | Process for the production of dinitrotoluene or mononitrobenzene |
| US5099080A (en) * | 1991-03-08 | 1992-03-24 | Olin Corporation | Process for preparing dinitrotoluene |
| US5245092A (en) * | 1991-03-15 | 1993-09-14 | Olin Corporation | Process for preparing dinitrotoluene with low by-product content |
-
1993
- 1993-06-01 EP EP93914223A patent/EP0649400A1/fr not_active Withdrawn
- 1993-06-01 AU AU43963/93A patent/AU665843B2/en not_active Ceased
- 1993-06-01 WO PCT/US1993/005081 patent/WO1993025503A1/fr not_active Ceased
- 1993-06-01 KR KR1019940704594A patent/KR950701903A/ko not_active Ceased
- 1993-06-01 RU RU94046238A patent/RU2106338C1/ru active
- 1993-06-01 BR BR9306554A patent/BR9306554A/pt active Search and Examination
- 1993-06-01 CA CA002138391A patent/CA2138391A1/fr not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928395A (en) * | 1972-10-05 | 1975-12-23 | Ciba Geigy Ag | Process for the nitration of aromatic compounds |
| US4935557A (en) * | 1984-08-07 | 1990-06-19 | Air Products And Chemicals, Inc. | Conitration of mixed aromatic hydrocarbons |
| US5001272A (en) * | 1988-06-22 | 1991-03-19 | Olin Corporation | Process for the production of dinitrotoluene |
| US4918250A (en) * | 1989-04-21 | 1990-04-17 | Olin Corporation | Process for the production of dinitrotoluene using an inorganic salt as a phase separation agent |
| US5099079A (en) * | 1990-07-26 | 1992-03-24 | Olin Corporation | Process for separating acid from nitro substituted aromatics using a molten nitrate salt |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2330836C2 (ru) * | 2003-02-20 | 2008-08-10 | Байер Акциенгезельшафт | Способ двухстадийного получения динитротолуола |
| RU2295953C2 (ru) * | 2004-07-12 | 2007-03-27 | Тиберий Георгиевич Незбайло | Гидрофильная и гидрофобная композиции для лечения заболеваний инфекционного или вирусного характера и способ их применения |
| RU2356885C2 (ru) * | 2005-10-18 | 2009-05-27 | Йозеф Майсснер Гмбх Унд Ко. Кг | Способ удаления и регенерации смесей нитрующих кислот из процессов нитрования и промышленная установка для нитрования |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0649400A1 (fr) | 1995-04-26 |
| WO1993025503A1 (fr) | 1993-12-23 |
| RU94046238A (ru) | 1996-10-10 |
| AU4396393A (en) | 1994-01-04 |
| AU665843B2 (en) | 1996-01-18 |
| CA2138391A1 (fr) | 1993-12-23 |
| BR9306554A (pt) | 1998-09-15 |
| KR950701903A (ko) | 1995-05-17 |
| EP0649400A4 (fr) | 1995-02-14 |
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