JPS5819667B2 - 芳香族及び置換芳香族化合物の選択的ニトロ化法 - Google Patents
芳香族及び置換芳香族化合物の選択的ニトロ化法Info
- Publication number
- JPS5819667B2 JPS5819667B2 JP51049762A JP4976276A JPS5819667B2 JP S5819667 B2 JPS5819667 B2 JP S5819667B2 JP 51049762 A JP51049762 A JP 51049762A JP 4976276 A JP4976276 A JP 4976276A JP S5819667 B2 JPS5819667 B2 JP S5819667B2
- Authority
- JP
- Japan
- Prior art keywords
- nitration
- aromatic
- soluble anhydrite
- reaction
- compound
- 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
- 238000006396 nitration reaction Methods 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 33
- 125000003118 aryl group Chemical group 0.000 title claims description 18
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 61
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 26
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 22
- 229910017604 nitric acid Inorganic materials 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 11
- -1 alkyl aromatic compound Chemical class 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 3
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 7
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 6
- QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical class CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 239000010440 gypsum Substances 0.000 description 3
- 229910052602 gypsum Inorganic materials 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HFZKOYWDLDYELC-UHFFFAOYSA-N 1,2-dimethyl-4-nitrobenzene Chemical class CC1=CC=C([N+]([O-])=O)C=C1C HFZKOYWDLDYELC-UHFFFAOYSA-N 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 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 229910052925 anhydrite Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- BBUPBICWUURTNP-UHFFFAOYSA-N 2,4-dimethyl-1-nitrobenzene Chemical group CC1=CC=C([N+]([O-])=O)C(C)=C1 BBUPBICWUURTNP-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- VMMLSJNPNVTYMN-UHFFFAOYSA-N dinitromethylbenzene Chemical class [O-][N+](=O)C([N+]([O-])=O)C1=CC=CC=C1 VMMLSJNPNVTYMN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/02—Formation or introduction of functional groups containing nitrogen of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/574,131 US3957889A (en) | 1975-05-02 | 1975-05-02 | Selective nitration of aromatic and substituted aromatic compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51136626A JPS51136626A (en) | 1976-11-26 |
| JPS5819667B2 true JPS5819667B2 (ja) | 1983-04-19 |
Family
ID=24294821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51049762A Expired JPS5819667B2 (ja) | 1975-05-02 | 1976-04-30 | 芳香族及び置換芳香族化合物の選択的ニトロ化法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3957889A (enExample) |
| JP (1) | JPS5819667B2 (enExample) |
| BE (1) | BE841318A (enExample) |
| CA (1) | CA1066308A (enExample) |
| DE (1) | DE2619490A1 (enExample) |
| FR (1) | FR2309510A1 (enExample) |
| GB (1) | GB1510043A (enExample) |
| IT (1) | IT1059241B (enExample) |
| NL (1) | NL7604664A (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2632234C3 (de) * | 1976-07-17 | 1978-12-21 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Nitrotoluolgemischen mit einem überwiegenden Gehalt an Nitrotoluol |
| US4331819A (en) * | 1980-04-24 | 1982-05-25 | E. I. Du Pont De Nemours And Company | Water removal in nitration of aromatic hydrocarbons |
| US4361712A (en) * | 1980-05-19 | 1982-11-30 | Air Products And Chemicals, Inc. | Cyanide reduction in nitroaromatic process |
| US4431842A (en) * | 1982-12-01 | 1984-02-14 | The Dow Chemical Company | Catalytic preparation of nitroalkanes |
| US5001272A (en) * | 1988-06-22 | 1991-03-19 | Olin Corporation | Process for the production of dinitrotoluene |
| FR2645146A1 (fr) * | 1989-02-21 | 1990-10-05 | Rhone Poulenc Chimie | Procede de preparation de dinitrotoluenes |
| US5012019A (en) * | 1990-01-26 | 1991-04-30 | Olin Corporation | Process for purifying aromatic nitration products |
| FR2658188A1 (fr) * | 1990-02-09 | 1991-08-16 | Rhone Poulenc Chimie | Procede de preparation de dinitrotoluenes. |
| US5057632A (en) * | 1990-10-22 | 1991-10-15 | Olin Corporation | Process for preparing dinitrotoluene |
| US5099078A (en) * | 1990-12-21 | 1992-03-24 | Olin Corporation | Process for preparing dinitrotoluene |
| 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 |
| DE4225023A1 (de) * | 1992-07-29 | 1994-02-03 | Bayer Ag | Verfahren zur Herstellung von 2,3-Dichlor-nitrobenzol |
| US5391586A (en) * | 1992-08-04 | 1995-02-21 | Miles Inc. | Process for preparing flexible polyurethane foams and foams thus obtained |
| US5302763A (en) * | 1993-03-01 | 1994-04-12 | Olin Corporation | Process for preparing dinitrotoluene |
| CA2771396A1 (en) * | 2009-08-28 | 2011-03-03 | E.I. Du Pont De Nemours And Company | Process for the nitration of o-xylene and related compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3126417A (en) * | 1964-03-24 | Nitration of toluene with alkyl | ||
| NL103911C (enExample) * | 1958-02-11 | |||
| US3196186A (en) * | 1964-02-18 | 1965-07-20 | Allied Chem | Nitration of toluene in the presence of an aromatic sulfonic acid |
| FR1429519A (fr) * | 1964-02-18 | 1966-02-25 | Allied Chem | Procédé de préparation d'un mélange de mononitrotoluènes |
| JPS5114499B1 (enExample) | 1971-07-13 | 1976-05-10 | ||
| US3708546A (en) * | 1972-01-17 | 1973-01-02 | Stanford Research Inst | Preparation of dinitrotoluene |
| DE2249373A1 (de) * | 1972-10-09 | 1974-04-25 | Basf Ag | Verfahren zur nitrierung von aromatischen verbindungen |
| US3966830A (en) * | 1974-03-08 | 1976-06-29 | Teijin Limited | Process for the nitration of halogenated benzene derivatives |
-
1975
- 1975-05-02 US US05/574,131 patent/US3957889A/en not_active Expired - Lifetime
-
1976
- 1976-04-27 GB GB17117/76A patent/GB1510043A/en not_active Expired
- 1976-04-27 CA CA251,193A patent/CA1066308A/en not_active Expired
- 1976-04-28 FR FR7612543A patent/FR2309510A1/fr active Granted
- 1976-04-29 NL NL7604664A patent/NL7604664A/xx unknown
- 1976-04-30 IT IT22871/76A patent/IT1059241B/it active
- 1976-04-30 BE BE2055000A patent/BE841318A/xx unknown
- 1976-04-30 JP JP51049762A patent/JPS5819667B2/ja not_active Expired
- 1976-05-03 DE DE19762619490 patent/DE2619490A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1510043A (en) | 1978-05-10 |
| FR2309510A1 (fr) | 1976-11-26 |
| BE841318A (fr) | 1976-08-16 |
| US3957889A (en) | 1976-05-18 |
| IT1059241B (it) | 1982-05-31 |
| JPS51136626A (en) | 1976-11-26 |
| NL7604664A (nl) | 1976-11-04 |
| CA1066308A (en) | 1979-11-13 |
| FR2309510B1 (enExample) | 1982-09-10 |
| DE2619490A1 (de) | 1976-11-18 |
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