DE1768748A1 - Verfahren zur Herstellung von 2,3-Dimethyl-2,3-bis(4-nitro-phenyl)-butan - Google Patents
Verfahren zur Herstellung von 2,3-Dimethyl-2,3-bis(4-nitro-phenyl)-butanInfo
- Publication number
- DE1768748A1 DE1768748A1 DE19681768748 DE1768748A DE1768748A1 DE 1768748 A1 DE1768748 A1 DE 1768748A1 DE 19681768748 DE19681768748 DE 19681768748 DE 1768748 A DE1768748 A DE 1768748A DE 1768748 A1 DE1768748 A1 DE 1768748A1
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- butane
- bis
- nitro
- phenyl
- 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
- 238000000034 method Methods 0.000 title claims description 11
- FHFAECPZWSCPOH-UHFFFAOYSA-N 1-[2,3-dimethyl-3-(4-nitrophenyl)butan-2-yl]-4-nitrobenzene Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C)(C)C(C)(C)C1=CC=C([N+]([O-])=O)C=C1 FHFAECPZWSCPOH-UHFFFAOYSA-N 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- JXMYUMNAEKRMIP-UHFFFAOYSA-N 1-nitro-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C([N+]([O-])=O)C=C1 JXMYUMNAEKRMIP-UHFFFAOYSA-N 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000007514 bases Chemical class 0.000 claims description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic tertiary alcohols Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JZRBCNLSIDKBMG-UHFFFAOYSA-N 1-butyl-4-nitrobenzene Chemical compound CCCCC1=CC=C([N+]([O-])=O)C=C1 JZRBCNLSIDKBMG-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000006025 oxidative dimerization reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768748 DE1768748A1 (de) | 1968-06-26 | 1968-06-26 | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-bis(4-nitro-phenyl)-butan |
| CH794169A CH514542A (de) | 1968-06-26 | 1969-05-23 | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-bis(4-nitro-phenyl)-butan |
| GB1225736D GB1225736A (https=) | 1968-06-26 | 1969-05-28 | |
| US831220A US3592863A (en) | 1968-06-26 | 1969-06-06 | Process for the preparation of 2,3-dimethyl-2,3-bis-(4-nitro phenyl)-butane |
| NL6909586A NL6909586A (https=) | 1968-06-26 | 1969-06-23 | |
| BE735151D BE735151A (https=) | 1968-06-26 | 1969-06-25 | |
| AT607769A AT289059B (de) | 1968-06-26 | 1969-06-26 | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-bis-(4'-nitrophenyl)-butan |
| FR6921543A FR2014272A1 (https=) | 1968-06-26 | 1969-06-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768748 DE1768748A1 (de) | 1968-06-26 | 1968-06-26 | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-bis(4-nitro-phenyl)-butan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768748A1 true DE1768748A1 (de) | 1971-12-09 |
Family
ID=5699846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768748 Pending DE1768748A1 (de) | 1968-06-26 | 1968-06-26 | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-bis(4-nitro-phenyl)-butan |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3592863A (https=) |
| AT (1) | AT289059B (https=) |
| BE (1) | BE735151A (https=) |
| CH (1) | CH514542A (https=) |
| DE (1) | DE1768748A1 (https=) |
| FR (1) | FR2014272A1 (https=) |
| GB (1) | GB1225736A (https=) |
| NL (1) | NL6909586A (https=) |
-
1968
- 1968-06-26 DE DE19681768748 patent/DE1768748A1/de active Pending
-
1969
- 1969-05-23 CH CH794169A patent/CH514542A/de not_active IP Right Cessation
- 1969-05-28 GB GB1225736D patent/GB1225736A/en not_active Expired
- 1969-06-06 US US831220A patent/US3592863A/en not_active Expired - Lifetime
- 1969-06-23 NL NL6909586A patent/NL6909586A/xx unknown
- 1969-06-25 BE BE735151D patent/BE735151A/xx unknown
- 1969-06-26 AT AT607769A patent/AT289059B/de not_active IP Right Cessation
- 1969-06-26 FR FR6921543A patent/FR2014272A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AT289059B (de) | 1971-04-13 |
| CH514542A (de) | 1971-10-31 |
| BE735151A (https=) | 1969-12-01 |
| FR2014272A1 (https=) | 1970-04-17 |
| GB1225736A (https=) | 1971-03-24 |
| NL6909586A (https=) | 1969-12-30 |
| US3592863A (en) | 1971-07-13 |
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