IE44134B1 - Process for the preparation of n-phenyl-5-chloro-2-nitroaniline - Google Patents
Process for the preparation of n-phenyl-5-chloro-2-nitroanilineInfo
- Publication number
- IE44134B1 IE44134B1 IE2605/76A IE260576A IE44134B1 IE 44134 B1 IE44134 B1 IE 44134B1 IE 2605/76 A IE2605/76 A IE 2605/76A IE 260576 A IE260576 A IE 260576A IE 44134 B1 IE44134 B1 IE 44134B1
- Authority
- IE
- Ireland
- Prior art keywords
- aniline
- salt
- component
- pts
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 11
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 claims description 9
- FPKHZBVGKMTUHB-UHFFFAOYSA-N 5-chloro-2-nitro-n-phenylaniline Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1NC1=CC=CC=C1 FPKHZBVGKMTUHB-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract 6
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- 229920001971 elastomer Polymers 0.000 abstract 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 229920000459 Nitrile rubber Polymers 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 238000005299 abrasion Methods 0.000 abstract 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 229920002379 silicone rubber Polymers 0.000 abstract 1
- 239000004945 silicone rubber Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic amines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylphenylamine Natural products CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LFGKJWSNSRNZLY-UHFFFAOYSA-N 1,3,6,8-tetrachlorophenazine Chemical compound C1=C(Cl)C=C(Cl)C2=NC3=CC(Cl)=CC(Cl)=C3N=C21 LFGKJWSNSRNZLY-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- NWAQHIWGPITNGK-UHFFFAOYSA-N 2,7-dichlorophenazine Chemical compound C1=C(Cl)C=CC2=NC3=CC(Cl)=CC=C3N=C21 NWAQHIWGPITNGK-UHFFFAOYSA-N 0.000 description 1
- QVQSOXMXXFZAKU-UHFFFAOYSA-N 4-chloro-1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1[N+]([O-])=O QVQSOXMXXFZAKU-UHFFFAOYSA-N 0.000 description 1
- GYOVQZDXSHTPBS-UHFFFAOYSA-N 4-chloro-2-nitro-n-phenylaniline Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1NC1=CC=CC=C1 GYOVQZDXSHTPBS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BATIQQWMBZSQEP-UHFFFAOYSA-N bis(2,4-dichlorophenyl)diazene Chemical compound ClC1=CC(Cl)=CC=C1N=NC1=CC=C(Cl)C=C1Cl BATIQQWMBZSQEP-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752553566 DE2553566B1 (de) | 1975-11-28 | 1975-11-28 | Verfahren zur herstellung von n-phenyl-5-chlor-2-nitranilin |
| DE2648944A DE2648944C3 (de) | 1976-10-28 | 1976-10-28 | Verfahren zur Herstellung von N-Phenyl-5-chlor-2-nitranilin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE44134L IE44134L (en) | 1977-05-28 |
| IE44134B1 true IE44134B1 (en) | 1981-10-26 |
Family
ID=25769665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2605/76A IE44134B1 (en) | 1975-11-28 | 1976-11-26 | Process for the preparation of n-phenyl-5-chloro-2-nitroaniline |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3924092C1 (enrdf_load_stackoverflow) * | 1989-07-20 | 1990-11-29 | Hoechst Ag, 6230 Frankfurt, De |
-
1976
- 1976-11-23 NL NL7613043A patent/NL7613043A/xx not_active Application Discontinuation
- 1976-11-23 ES ES453556A patent/ES453556A1/es not_active Expired
- 1976-11-24 CH CH1479076A patent/CH599109A5/xx not_active IP Right Cessation
- 1976-11-26 JP JP14280776A patent/JPS5287125A/ja active Pending
- 1976-11-26 DK DK534276A patent/DK534276A/da unknown
- 1976-11-26 LU LU76271A patent/LU76271A1/xx unknown
- 1976-11-26 GB GB49432/76A patent/GB1554578A/en not_active Expired
- 1976-11-26 IE IE2605/76A patent/IE44134B1/en unknown
- 1976-11-26 AT AT877976A patent/AT345782B/de active
- 1976-11-26 IT IT29866/76A patent/IT1070439B/it active
- 1976-11-29 FR FR7635933A patent/FR2332973A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1070439B (it) | 1985-03-29 |
| NL7613043A (nl) | 1977-06-01 |
| DK534276A (da) | 1977-05-29 |
| ATA877976A (de) | 1978-02-15 |
| GB1554578A (en) | 1979-10-24 |
| CH599109A5 (enrdf_load_stackoverflow) | 1978-05-12 |
| FR2332973B1 (enrdf_load_stackoverflow) | 1980-08-01 |
| AT345782B (de) | 1978-10-10 |
| IE44134L (en) | 1977-05-28 |
| ES453556A1 (es) | 1977-11-16 |
| JPS5287125A (en) | 1977-07-20 |
| LU76271A1 (enrdf_load_stackoverflow) | 1977-06-07 |
| FR2332973A1 (fr) | 1977-06-24 |
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