CA2808258A1 - Process for the selective meta-chlorination of alkylanilines - Google Patents
Process for the selective meta-chlorination of alkylanilines Download PDFInfo
- Publication number
- CA2808258A1 CA2808258A1 CA2808258A CA2808258A CA2808258A1 CA 2808258 A1 CA2808258 A1 CA 2808258A1 CA 2808258 A CA2808258 A CA 2808258A CA 2808258 A CA2808258 A CA 2808258A CA 2808258 A1 CA2808258 A1 CA 2808258A1
- Authority
- CA
- Canada
- Prior art keywords
- sulfuric acid
- reaction
- diethylaniline
- chlorination
- alkylaniline
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000005660 chlorination reaction Methods 0.000 title abstract description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 98
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 239000000460 chlorine Substances 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 33
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 23
- 235000011149 sulphuric acid Nutrition 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical group [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 23
- 238000004817 gas chromatography Methods 0.000 description 20
- VDJBIPLKIGSVRG-UHFFFAOYSA-N 3-chloro-2,6-diethylaniline Chemical compound CCC1=CC=C(Cl)C(CC)=C1N VDJBIPLKIGSVRG-UHFFFAOYSA-N 0.000 description 17
- 239000012043 crude product Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229960005419 nitrogen Drugs 0.000 description 12
- 239000007858 starting material Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 238000005191 phase separation Methods 0.000 description 8
- QMOUFSYFOJSMLI-UHFFFAOYSA-N 3,5-dichloro-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=C(Cl)C=C1Cl QMOUFSYFOJSMLI-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- -1 anilinium sulfates Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- RLPKDPGRZGVHFM-UHFFFAOYSA-N 4-chloro-2,6-diethylaniline Chemical compound CCC1=CC(Cl)=CC(CC)=C1N RLPKDPGRZGVHFM-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ZNHBPIGKELNUBO-UHFFFAOYSA-N hydrogen sulfate phenylazanium Chemical compound OS([O-])(=O)=O.OS([O-])(=O)=O.[NH3+]c1ccccc1.[NH3+]c1ccccc1 ZNHBPIGKELNUBO-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- FUKMEFZGEMVGLD-UHFFFAOYSA-N phenylazanium;sulfate Chemical compound OS(O)(=O)=O.NC1=CC=CC=C1.NC1=CC=CC=C1 FUKMEFZGEMVGLD-UHFFFAOYSA-N 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DDTKYVBFPULMGN-UHFFFAOYSA-N 2-methyl-6-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(C)=C1N DDTKYVBFPULMGN-UHFFFAOYSA-N 0.000 description 2
- VJMLNTUETPAFBL-UHFFFAOYSA-N 3-chloro-2-methyl-6-propan-2-ylaniline Chemical compound CC(C)C1=CC=C(Cl)C(C)=C1N VJMLNTUETPAFBL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- QGGQOOKAYLQQGX-UHFFFAOYSA-N 3,5-dichloro-5,6-diethylcyclohexa-1,3-dien-1-amine Chemical compound CCC1C(N)=CC(Cl)=CC1(Cl)CC QGGQOOKAYLQQGX-UHFFFAOYSA-N 0.000 description 1
- BNFNLVZYBUWZCJ-UHFFFAOYSA-N 3-chloro-6-methyl-2-propan-2-ylaniline Chemical compound CC(C)C1=C(Cl)C=CC(C)=C1N BNFNLVZYBUWZCJ-UHFFFAOYSA-N 0.000 description 1
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- OGVXWEOZQMAAIM-UHFFFAOYSA-N hydron;2-methylaniline;chloride Chemical compound Cl.CC1=CC=CC=C1N OGVXWEOZQMAAIM-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QNVKMXGRFVLMBM-UHFFFAOYSA-N n-chloro-n-phenylacetamide Chemical class CC(=O)N(Cl)C1=CC=CC=C1 QNVKMXGRFVLMBM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/64—Quaternary ammonium compounds having quaternised nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10173496 | 2010-08-20 | ||
| EP10173496.0 | 2010-08-20 | ||
| PCT/EP2011/004099 WO2012022460A1 (en) | 2010-08-20 | 2011-08-16 | Process for the selective meta-chlorination of alkylanilines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2808258A1 true CA2808258A1 (en) | 2012-02-23 |
Family
ID=43430640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2808258A Abandoned CA2808258A1 (en) | 2010-08-20 | 2011-08-16 | Process for the selective meta-chlorination of alkylanilines |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9193667B2 (enExample) |
| EP (1) | EP2606028A1 (enExample) |
| JP (1) | JP5917514B2 (enExample) |
| KR (1) | KR20130099929A (enExample) |
| CN (1) | CN103068789B (enExample) |
| BR (1) | BR112013003937A2 (enExample) |
| CA (1) | CA2808258A1 (enExample) |
| WO (1) | WO2012022460A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012048845A1 (en) * | 2010-10-14 | 2012-04-19 | Lonza Ltd | Halogenated diethyltoluenediamines |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE499591C (de) * | 1926-10-07 | 1930-06-10 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Chlorsubstitutionsprodukten des 1-Amino-2, 4-dimethylbenzols |
| JPS4910938B1 (enExample) * | 1970-02-05 | 1974-03-13 | ||
| DE2319645C3 (de) * | 1973-04-18 | 1978-12-07 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 5-Chlor-2-toluidin |
| US3890388A (en) * | 1974-03-04 | 1975-06-17 | Du Pont | Ring chlorination of ortho-toluidine |
| DE2449285A1 (de) * | 1974-10-16 | 1976-04-22 | Hoechst Ag | Verfahren zur herstellung von chlorierten aromatischen aminen |
| FR2487823A1 (fr) * | 1980-08-01 | 1982-02-05 | Rhone Poulenc Agrochimie | Procede de preparation selective d'anilines metachlorees |
| DE3042242A1 (de) * | 1980-11-08 | 1982-06-09 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von m-halogensubstituierten anilinen |
| DE3043206A1 (de) * | 1980-11-15 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 4-chlor-2,6-dialkylanilinen |
| FR2532305A1 (fr) * | 1982-08-24 | 1984-03-02 | Rhone Poulenc Agrochimie | Procede de preparation d'anilines metachlorees |
| JPS62178548A (ja) * | 1986-01-31 | 1987-08-05 | Mitsui Toatsu Chem Inc | ３−クロロ−４−イソプロピルアニリンの製造方法 |
-
2011
- 2011-08-16 EP EP11746178.0A patent/EP2606028A1/en not_active Withdrawn
- 2011-08-16 BR BR112013003937A patent/BR112013003937A2/pt not_active IP Right Cessation
- 2011-08-16 KR KR1020137005651A patent/KR20130099929A/ko not_active Ceased
- 2011-08-16 JP JP2013525168A patent/JP5917514B2/ja not_active Expired - Fee Related
- 2011-08-16 WO PCT/EP2011/004099 patent/WO2012022460A1/en not_active Ceased
- 2011-08-16 CN CN201180040323.8A patent/CN103068789B/zh not_active Expired - Fee Related
- 2011-08-16 US US13/817,972 patent/US9193667B2/en not_active Expired - Fee Related
- 2011-08-16 CA CA2808258A patent/CA2808258A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2606028A1 (en) | 2013-06-26 |
| WO2012022460A1 (en) | 2012-02-23 |
| JP5917514B2 (ja) | 2016-05-18 |
| CN103068789A (zh) | 2013-04-24 |
| BR112013003937A2 (pt) | 2016-07-12 |
| US9193667B2 (en) | 2015-11-24 |
| US20130338400A1 (en) | 2013-12-19 |
| JP2013538201A (ja) | 2013-10-10 |
| KR20130099929A (ko) | 2013-09-06 |
| CN103068789B (zh) | 2015-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160429 |
|
| FZDE | Discontinued |
Effective date: 20180816 |