DE2549036C3 - Verfahren zur Herstellung von 4,4'-Dinitro-diphenylcarbonat - Google Patents
Verfahren zur Herstellung von 4,4'-Dinitro-diphenylcarbonatInfo
- Publication number
- DE2549036C3 DE2549036C3 DE2549036A DE2549036A DE2549036C3 DE 2549036 C3 DE2549036 C3 DE 2549036C3 DE 2549036 A DE2549036 A DE 2549036A DE 2549036 A DE2549036 A DE 2549036A DE 2549036 C3 DE2549036 C3 DE 2549036C3
- Authority
- DE
- Germany
- Prior art keywords
- diphenyl carbonate
- sulfuric acid
- dinitro
- carbonate
- nitric acid
- 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
- ACBQROXDOHKANW-UHFFFAOYSA-N bis(4-nitrophenyl) carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 ACBQROXDOHKANW-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 89
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 32
- 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
- 239000000203 mixture Substances 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 9
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006396 nitration reaction Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- -1 nitrate diphenyl carbonate Chemical compound 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XXYMSQQCBUKFHE-UHFFFAOYSA-N 4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1 XXYMSQQCBUKFHE-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VJAMBZRWYAAZSN-UHFFFAOYSA-N bis(2,4-dinitrophenyl) carbonate Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O VJAMBZRWYAAZSN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 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 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2549036A DE2549036C3 (de) | 1975-11-03 | 1975-11-03 | Verfahren zur Herstellung von 4,4'-Dinitro-diphenylcarbonat |
| IN1827/CAL/76A IN145558B (enExample) | 1975-11-03 | 1976-10-05 | |
| US05/735,715 US4101569A (en) | 1975-11-03 | 1976-10-26 | Process for the preparation of 4,4'-dinitrodiphenyl carbonate |
| CH1360476A CH605595A5 (enExample) | 1975-11-03 | 1976-10-28 | |
| BR7607286A BR7607286A (pt) | 1975-11-03 | 1976-10-29 | Processo para a preparacao de 4,4'-dinitro-difenilcarbonato |
| JP51130579A JPS5259132A (en) | 1975-11-03 | 1976-11-01 | Production of 4*4**dinitroo diphenyl carbonate |
| GB45284/76A GB1496108A (en) | 1975-11-03 | 1976-11-01 | Preparation of aromatic carbonate compound |
| DK496176A DK496176A (da) | 1975-11-03 | 1976-11-02 | Fremgangsmade til fremstilling af 4,4'-dinitrodiphenylcarbonat |
| NL7612149A NL7612149A (nl) | 1975-11-03 | 1976-11-02 | Werkwijze voor de bereiding van 4.4'-dinitrodi- fenylcarbonaat. |
| FR7633148A FR2329643A1 (fr) | 1975-11-03 | 1976-11-03 | Procede de preparation du carbonate de 4,4'-dinitrodiphenyle par nitration du carbonate de diphenyle |
| BE2055415A BE847881A (fr) | 1975-11-03 | 1976-11-03 | Procede de preparation du carbonate de 4,4'-dinitrodiphenyle par nitration du carbonate de diphenyle, |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2549036A DE2549036C3 (de) | 1975-11-03 | 1975-11-03 | Verfahren zur Herstellung von 4,4'-Dinitro-diphenylcarbonat |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2549036A1 DE2549036A1 (de) | 1977-05-05 |
| DE2549036B2 DE2549036B2 (de) | 1978-05-24 |
| DE2549036C3 true DE2549036C3 (de) | 1979-01-18 |
Family
ID=5960659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2549036A Expired DE2549036C3 (de) | 1975-11-03 | 1975-11-03 | Verfahren zur Herstellung von 4,4'-Dinitro-diphenylcarbonat |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4101569A (enExample) |
| JP (1) | JPS5259132A (enExample) |
| BE (1) | BE847881A (enExample) |
| BR (1) | BR7607286A (enExample) |
| CH (1) | CH605595A5 (enExample) |
| DE (1) | DE2549036C3 (enExample) |
| DK (1) | DK496176A (enExample) |
| FR (1) | FR2329643A1 (enExample) |
| GB (1) | GB1496108A (enExample) |
| IN (1) | IN145558B (enExample) |
| NL (1) | NL7612149A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5221798A (en) * | 1988-12-30 | 1993-06-22 | Amoco Corporation | Changing the regiopurity of mixtures containing 4,4'-disubstituted diphenyl carbonates |
| US5187294A (en) * | 1989-03-22 | 1993-02-16 | Amoco Corporation | Regioselective nitration of diphenyl compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB360883A (en) * | 1930-01-17 | 1931-11-11 | Franz Hofwimmer | Improved nitrating process |
| GB390556A (en) * | 1931-11-03 | 1933-04-13 | Ig Farbenindustrie Ag | The manufacture of nitro compounds of the diphenyl series |
| US2985688A (en) * | 1953-09-09 | 1961-05-23 | Bayer Ag | Production of substituted nitrophenols |
| DE1290148B (de) * | 1967-05-13 | 1969-03-06 | Bayer Ag | Verfahren zur Herstellung von 4, 4'-Dinitrodiphenylaether |
| US3715323A (en) * | 1971-02-25 | 1973-02-06 | Gen Electric | Nitration of aromatic ring-containing compositions |
-
1975
- 1975-11-03 DE DE2549036A patent/DE2549036C3/de not_active Expired
-
1976
- 1976-10-05 IN IN1827/CAL/76A patent/IN145558B/en unknown
- 1976-10-26 US US05/735,715 patent/US4101569A/en not_active Expired - Lifetime
- 1976-10-28 CH CH1360476A patent/CH605595A5/xx not_active IP Right Cessation
- 1976-10-29 BR BR7607286A patent/BR7607286A/pt unknown
- 1976-11-01 JP JP51130579A patent/JPS5259132A/ja active Pending
- 1976-11-01 GB GB45284/76A patent/GB1496108A/en not_active Expired
- 1976-11-02 DK DK496176A patent/DK496176A/da unknown
- 1976-11-02 NL NL7612149A patent/NL7612149A/xx not_active Application Discontinuation
- 1976-11-03 FR FR7633148A patent/FR2329643A1/fr not_active Withdrawn
- 1976-11-03 BE BE2055415A patent/BE847881A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2549036B2 (de) | 1978-05-24 |
| IN145558B (enExample) | 1985-01-05 |
| BE847881A (fr) | 1977-05-03 |
| NL7612149A (nl) | 1977-05-05 |
| DK496176A (da) | 1977-05-04 |
| DE2549036A1 (de) | 1977-05-05 |
| CH605595A5 (enExample) | 1978-09-29 |
| FR2329643A1 (fr) | 1977-05-27 |
| JPS5259132A (en) | 1977-05-16 |
| GB1496108A (en) | 1977-12-30 |
| BR7607286A (pt) | 1977-09-13 |
| US4101569A (en) | 1978-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |