DE2317279A1 - Aufarbeitung von nitriergemischen - Google Patents
Aufarbeitung von nitriergemischenInfo
- Publication number
- DE2317279A1 DE2317279A1 DE2317279A DE2317279A DE2317279A1 DE 2317279 A1 DE2317279 A1 DE 2317279A1 DE 2317279 A DE2317279 A DE 2317279A DE 2317279 A DE2317279 A DE 2317279A DE 2317279 A1 DE2317279 A1 DE 2317279A1
- Authority
- DE
- Germany
- Prior art keywords
- nitration
- nitric acid
- ketones
- water
- cyclohexanone
- 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.)
- Pending
Links
- 238000006396 nitration reaction Methods 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 title description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 23
- 229910017604 nitric acid Inorganic materials 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000012074 organic phase Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- -1 aliphatic ketones Chemical class 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 22
- 150000002576 ketones Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000010626 work up procedure Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 3
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- QDYBCIWLGJMJGO-UHFFFAOYSA-N dinitromethanone Chemical compound [O-][N+](=O)C(=O)[N+]([O-])=O QDYBCIWLGJMJGO-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- SZNILIWUUKKNPE-UHFFFAOYSA-N 2-nitrocyclohexan-1-one Chemical compound [O-][N+](=O)C1CCCCC1=O SZNILIWUUKKNPE-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- SXOZDDAFVJANJP-UHFFFAOYSA-N cyclodecanone Chemical compound O=C1CCCCCCCCC1 SXOZDDAFVJANJP-UHFFFAOYSA-N 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- PWVHLUKAENFZIA-UHFFFAOYSA-N cyclohexanol;cyclohexanone Chemical compound OC1CCCCC1.O=C1CCCCC1 PWVHLUKAENFZIA-UHFFFAOYSA-N 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910001959 inorganic nitrate Inorganic materials 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical class O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 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
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/20—Nitrogen oxides; Oxyacids of nitrogen; Salts thereof
- C01B21/38—Nitric acid
- C01B21/46—Purification; Separation ; Stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2317279A DE2317279A1 (de) | 1973-04-06 | 1973-04-06 | Aufarbeitung von nitriergemischen |
| IT49690/74A IT1021532B (it) | 1973-04-06 | 1974-03-26 | Elaborazione di miscele di nitrazione |
| FR7410849A FR2224442A1 (en) | 1973-04-06 | 1974-03-28 | Nitroketone and nitric acid recovery - by dilution with aq. mineral salt soln. and extn. |
| NL7404405A NL7404405A (enrdf_load_stackoverflow) | 1973-04-06 | 1974-04-01 | |
| JP49037462A JPS505313A (enrdf_load_stackoverflow) | 1973-04-06 | 1974-04-04 | |
| DD177692A DD113525A5 (enrdf_load_stackoverflow) | 1973-04-06 | 1974-04-04 | |
| BE142896A BE813358A (fr) | 1973-04-06 | 1974-04-05 | Procede perfectionne pour traiter les melanges de nitration de cetones aliphatiques ou cycloaliphatiques |
| ES425039A ES425039A1 (es) | 1973-04-06 | 1974-04-05 | Procedimiento para la elaboracion de una mezcla de reaccionobtenida pro nitracion de cetonas alifaticas o cicloalifati-cas. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2317279A DE2317279A1 (de) | 1973-04-06 | 1973-04-06 | Aufarbeitung von nitriergemischen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2317279A1 true DE2317279A1 (de) | 1974-10-24 |
Family
ID=5877211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2317279A Pending DE2317279A1 (de) | 1973-04-06 | 1973-04-06 | Aufarbeitung von nitriergemischen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS505313A (enrdf_load_stackoverflow) |
| BE (1) | BE813358A (enrdf_load_stackoverflow) |
| DD (1) | DD113525A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2317279A1 (enrdf_load_stackoverflow) |
| ES (1) | ES425039A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2224442A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1021532B (enrdf_load_stackoverflow) |
| NL (1) | NL7404405A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH672397A5 (enrdf_load_stackoverflow) * | 1986-05-16 | 1989-11-30 | Max Zellweger |
-
1973
- 1973-04-06 DE DE2317279A patent/DE2317279A1/de active Pending
-
1974
- 1974-03-26 IT IT49690/74A patent/IT1021532B/it active
- 1974-03-28 FR FR7410849A patent/FR2224442A1/fr active Granted
- 1974-04-01 NL NL7404405A patent/NL7404405A/xx unknown
- 1974-04-04 JP JP49037462A patent/JPS505313A/ja active Pending
- 1974-04-04 DD DD177692A patent/DD113525A5/xx unknown
- 1974-04-05 ES ES425039A patent/ES425039A1/es not_active Expired
- 1974-04-05 BE BE142896A patent/BE813358A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7404405A (enrdf_load_stackoverflow) | 1974-10-08 |
| FR2224442B3 (enrdf_load_stackoverflow) | 1977-01-21 |
| ES425039A1 (es) | 1976-05-16 |
| FR2224442A1 (en) | 1974-10-31 |
| IT1021532B (it) | 1978-02-20 |
| BE813358A (fr) | 1974-10-07 |
| DD113525A5 (enrdf_load_stackoverflow) | 1975-06-12 |
| JPS505313A (enrdf_load_stackoverflow) | 1975-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE852993C (de) | Verfahren zur Herstellung von 2, 4, 4-Trimethylpentanal | |
| DE2317279A1 (de) | Aufarbeitung von nitriergemischen | |
| DE933149C (de) | Verfahren zur Herstellung von 6-Methyl-ª‡-jononen und 6-Methyl-ª‰-jonon | |
| DE2317277C3 (de) | Aufarbeitung von Nitriergemischen | |
| DE2548384A1 (de) | Verfahren zur herstellung von hydroxyphenylaethern | |
| DE2149821C3 (de) | Verfahren zur Herstellung aliphatischer und cycloaliphatischer alpha-Nitroketone | |
| DE573722C (de) | Verfahren zur Darstellung von ª‡-Dicarbonylverbindungen | |
| DE2317278A1 (de) | Aufarbeitung von nietrierungsgemischen | |
| DE2111196A1 (de) | Verfahren zur Gewinnung von Adipinsaeure | |
| DE2317277A1 (de) | Aufarbeitung von nitriergemischen | |
| DE1917132C3 (de) | Verfahren zur Herstellung von ß -Jonon | |
| EP0011281A2 (de) | Verfahren zur Herstellung von p-tert.-Butylbenzaldehyd und dessen am Kern durch Halogen substituierten Derivaten. | |
| DE2123989A1 (de) | Verfahren zur Herstellung von C tief 1bis C tief 10-Alkylestern der Chrysanthemsäure | |
| DE2317278C3 (de) | Verfahren zur Aufarbeitung von Nitrlerungsgemischen | |
| DE2540899C3 (de) | Verfahren zur Herstellung von m-Nitrobenzoesäure | |
| DE956950C (de) | Verfahren zur Herstellung von isomeren 1, 1, 6-Trimethyl-6-oxyoktahydronaphthalinen | |
| DE818492C (de) | Verfahren zur Herstellung von 6-Methyl-octa-3, 5, 7-trien-2-ol | |
| DE2405283A1 (de) | Thermolyse von styroloxid | |
| DE818349C (de) | Verfahren zur Darstellung von 6-Methyl-octa-3, 5-dien-7-in-2-ol | |
| DE942444C (de) | Verfahren zur Herstellung von aliphatischen und cycloaliphatischen Mononitrokohlenwasserstoffen | |
| AT218510B (de) | Verfahren zur Herstellung von 2, 6-Dichlorbenzalchlorid oder 2, 6-Dichlorbenzaldehyd | |
| DE1912405A1 (de) | Verfahren zur Herstellung von Alkoholen | |
| DE2540900A1 (de) | Verfahren zur herstellung von m-nitrobenzoesaeure | |
| DE640650C (de) | Verfahren zum Reinigen von aromatischen Sulfonsaeurechloriden | |
| DE1205531B (de) | Verfahren zur Herstellung von Oximen cycloaliphatischer Ketone |