DE2227340C3 - Verfahren zum Durchführen der Nitrierung aromatischer Verbindungen - Google Patents
Verfahren zum Durchführen der Nitrierung aromatischer VerbindungenInfo
- Publication number
- DE2227340C3 DE2227340C3 DE2227340A DE2227340A DE2227340C3 DE 2227340 C3 DE2227340 C3 DE 2227340C3 DE 2227340 A DE2227340 A DE 2227340A DE 2227340 A DE2227340 A DE 2227340A DE 2227340 C3 DE2227340 C3 DE 2227340C3
- Authority
- DE
- Germany
- Prior art keywords
- nitration
- nitric acid
- inhibitor
- parts
- product
- 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 33
- 238000000034 method Methods 0.000 title claims description 7
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 44
- 229910017604 nitric acid Inorganic materials 0.000 claims description 44
- 239000003112 inhibitor Substances 0.000 claims description 29
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 13
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 238000005121 nitriding Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000061 acid fraction Substances 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 235000015097 nutrients Nutrition 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910002651 NO3 Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PEBDGSFQVVAAEU-UHFFFAOYSA-N 2-ethenylcyclohexa-2,5-diene-1,4-dione Chemical compound C=CC1=CC(=O)C=CC1=O PEBDGSFQVVAAEU-UHFFFAOYSA-N 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 244000236655 Diospyros kaki Species 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 1
- 239000003830 anthracite Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Inorganic materials [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000015598 salt intake Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH841371A CH563322A5 (en) | 1971-06-10 | 1971-06-10 | Nitration of organic cpds - with control of nitration rate by inhibitors, esp nitrites and phosphates |
| CH1458771 | 1971-10-05 | ||
| CH1535271 | 1971-10-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2227340A1 DE2227340A1 (de) | 1972-12-14 |
| DE2227340B2 DE2227340B2 (de) | 1976-11-18 |
| DE2227340C3 true DE2227340C3 (de) | 1981-01-22 |
Family
ID=27175993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2227340A Expired DE2227340C3 (de) | 1971-06-10 | 1972-06-06 | Verfahren zum Durchführen der Nitrierung aromatischer Verbindungen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3836547A (en, 2012) |
| JP (1) | JPS5654304B1 (en, 2012) |
| AR (1) | AR196074A1 (en, 2012) |
| BE (1) | BE784616A (en, 2012) |
| CA (1) | CA1019730A (en, 2012) |
| DD (1) | DD99988A5 (en, 2012) |
| DE (1) | DE2227340C3 (en, 2012) |
| FR (1) | FR2140602B1 (en, 2012) |
| GB (1) | GB1395347A (en, 2012) |
| IT (1) | IT956431B (en, 2012) |
| NL (1) | NL7207615A (en, 2012) |
Families Citing this family (7)
| 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 |
| DE2256644C2 (de) * | 1972-11-18 | 1983-10-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von reinem 1-Nitro-anthrachinon |
| DE2343977B2 (de) * | 1973-08-31 | 1978-10-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von reinem 1-Aminoanthrachinon |
| DE2704680A1 (de) * | 1977-02-04 | 1978-08-10 | Bayer Ag | Verfahren zur gewinnung von aromatischen dinitroverbindungen |
| DE2854427A1 (de) * | 1978-12-16 | 1980-06-26 | Bayer Ag | Verfahren und vorrichtung zur gewinnung von trockenem 1,5- und/oder 1,8- dinitroanthrachinon aus suspensionen, die festes 1,5- und/oder 1,8-dinitroanthrachinon und fluessiges nitrobenzol enthalten |
| CN109438246A (zh) * | 2018-09-27 | 2019-03-08 | 青岛海湾精细化工有限公司 | 一种蒽醌的处理方法及处理系统 |
| CN110343046A (zh) * | 2019-07-30 | 2019-10-18 | 安徽东至广信农化有限公司 | 一种提高对硝基氯苯纯度的生产方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1418624C3 (de) * | 1960-12-22 | 1973-01-04 | Ab Chematur, Stockholm | Verfahren zur kontinuierlichen Herstellung von Dinitrotoluol, Trinitrotoluol und deren Gemischen |
-
1972
- 1972-06-05 NL NL7207615A patent/NL7207615A/xx unknown
- 1972-06-05 GB GB2612272A patent/GB1395347A/en not_active Expired
- 1972-06-06 DE DE2227340A patent/DE2227340C3/de not_active Expired
- 1972-06-07 US US00260427A patent/US3836547A/en not_active Expired - Lifetime
- 1972-06-08 CA CA144,189A patent/CA1019730A/en not_active Expired
- 1972-06-08 JP JP5727272A patent/JPS5654304B1/ja active Pending
- 1972-06-08 BE BE784616A patent/BE784616A/xx not_active IP Right Cessation
- 1972-06-09 AR AR242473A patent/AR196074A1/es active
- 1972-06-09 FR FR7220765A patent/FR2140602B1/fr not_active Expired
- 1972-06-09 DD DD163581A patent/DD99988A5/xx unknown
- 1972-06-09 IT IT25505/72A patent/IT956431B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT956431B (it) | 1973-10-10 |
| DE2227340A1 (de) | 1972-12-14 |
| JPS5654304B1 (en, 2012) | 1981-12-24 |
| DD99988A5 (en, 2012) | 1973-09-05 |
| AR196074A1 (en, 2012) | 1973-11-30 |
| DE2227340B2 (de) | 1976-11-18 |
| CA1019730A (en) | 1977-10-25 |
| BE784616A (fr) | 1972-12-08 |
| FR2140602B1 (en, 2012) | 1977-12-23 |
| NL7207615A (en, 2012) | 1972-12-12 |
| US3836547A (en) | 1974-09-17 |
| GB1395347A (en) | 1975-05-21 |
| FR2140602A1 (en, 2012) | 1973-01-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |