DE2525374A1 - Verfahren zur mononitrierung von ortho-xylol - Google Patents
Verfahren zur mononitrierung von ortho-xylolInfo
- Publication number
- DE2525374A1 DE2525374A1 DE19752525374 DE2525374A DE2525374A1 DE 2525374 A1 DE2525374 A1 DE 2525374A1 DE 19752525374 DE19752525374 DE 19752525374 DE 2525374 A DE2525374 A DE 2525374A DE 2525374 A1 DE2525374 A1 DE 2525374A1
- Authority
- DE
- Germany
- Prior art keywords
- xylene
- nitro
- mol
- mercury
- mole
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 25
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 57
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 claims description 27
- 229940078552 o-xylene Drugs 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 claims description 24
- 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
- HFZKOYWDLDYELC-UHFFFAOYSA-N 1,2-dimethyl-4-nitrobenzene Chemical group CC1=CC=C([N+]([O-])=O)C=C1C HFZKOYWDLDYELC-UHFFFAOYSA-N 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 150000002730 mercury Chemical class 0.000 claims description 10
- 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 claims description 9
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 9
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- 238000006396 nitration reaction Methods 0.000 claims description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052753 mercury Inorganic materials 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- FJKFBLLIOVQLFS-UHFFFAOYSA-L dibenzoyloxymercury Chemical compound [Hg+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 FJKFBLLIOVQLFS-UHFFFAOYSA-L 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 8
- VLKYKLNZVULGQK-UHFFFAOYSA-N 1,2-dimethyl-3,4-dinitrobenzene Chemical group CC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1C VLKYKLNZVULGQK-UHFFFAOYSA-N 0.000 description 7
- 238000003822 preparative gas chromatography Methods 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000802 nitrating effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic monocarboxylic acid Mercury salt Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 3
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002884 o-xylenes Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- IOVKULGETAMPSV-UHFFFAOYSA-N [Fe].[Hg] Chemical compound [Fe].[Hg] IOVKULGETAMPSV-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000370 mercury sulfate Inorganic materials 0.000 description 1
- VYHBEEBFCKLRAZ-UHFFFAOYSA-M mercury(1+);propanoate Chemical compound [Hg+].CCC([O-])=O VYHBEEBFCKLRAZ-UHFFFAOYSA-M 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US478189A US3929916A (en) | 1974-06-11 | 1974-06-11 | Process for the mononitration of ortho-xylene |
| US478190A US3929917A (en) | 1974-06-11 | 1974-06-11 | Process for the mononitration of ortho-xylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2525374A1 true DE2525374A1 (de) | 1976-01-02 |
Family
ID=27045816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752525374 Ceased DE2525374A1 (de) | 1974-06-11 | 1975-06-06 | Verfahren zur mononitrierung von ortho-xylol |
Country Status (14)
-
1975
- 1975-01-01 AR AR258836A patent/AR206028A1/es active
- 1975-05-07 IL IL47244A patent/IL47244A/en unknown
- 1975-05-14 GB GB2039775A patent/GB1468484A/en not_active Expired
- 1975-05-26 IT IT49778/75A patent/IT1035886B/it active
- 1975-06-06 DE DE19752525374 patent/DE2525374A1/de not_active Ceased
- 1975-06-09 SE SE7506590A patent/SE7506590L/xx not_active Application Discontinuation
- 1975-06-09 DK DK257775A patent/DK257775A/da unknown
- 1975-06-10 AT AT440675A patent/AT341495B/de not_active IP Right Cessation
- 1975-06-10 NL NL7506892A patent/NL7506892A/xx unknown
- 1975-06-10 CH CH750375A patent/CH602559A5/xx not_active IP Right Cessation
- 1975-06-11 ES ES438437A patent/ES438437A1/es not_active Expired
- 1975-06-11 BR BR4736/75D patent/BR7503689A/pt unknown
- 1975-06-11 FR FR7518295A patent/FR2274601A1/fr active Granted
- 1975-06-11 JP JP50069790A patent/JPS518226A/ja active Pending
-
1978
- 1978-09-08 SE SE7809506A patent/SE7809506L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT341495B (de) | 1978-02-10 |
| IL47244A0 (en) | 1975-07-28 |
| ATA440675A (de) | 1977-06-15 |
| GB1468484A (en) | 1977-03-30 |
| BR7503689A (pt) | 1976-06-29 |
| CH602559A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-31 |
| IL47244A (en) | 1977-08-31 |
| SE7809506L (sv) | 1978-09-08 |
| NL7506892A (nl) | 1975-12-15 |
| IT1035886B (it) | 1979-10-20 |
| AR206028A1 (es) | 1976-06-23 |
| FR2274601B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-09-01 |
| ES438437A1 (es) | 1978-10-16 |
| DK257775A (da) | 1975-12-12 |
| SE7506590L (sv) | 1975-12-12 |
| FR2274601A1 (fr) | 1976-01-09 |
| JPS518226A (en) | 1976-01-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| 8131 | Rejection |