LV10859B - Process for the preparation of 2-alkyl-6-methyl-n-(1'-methoxy-2'-propyl)-aniline and a process for the preparation of their chloracetanilides - Google Patents
Process for the preparation of 2-alkyl-6-methyl-n-(1'-methoxy-2'-propyl)-aniline and a process for the preparation of their chloracetanilides Download PDFInfo
- Publication number
- LV10859B LV10859B LVP-93-1381A LV931381A LV10859B LV 10859 B LV10859 B LV 10859B LV 931381 A LV931381 A LV 931381A LV 10859 B LV10859 B LV 10859B
- Authority
- LV
- Latvia
- Prior art keywords
- catalyst
- process according
- formula
- reaction
- hydrogenation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 96
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 239000011541 reaction mixture Substances 0.000 claims abstract description 29
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 claims abstract description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000005932 reductive alkylation reaction Methods 0.000 claims abstract description 11
- 230000003197 catalytic effect Effects 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052697 platinum Inorganic materials 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 1
- 230000037213 diet Effects 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 11
- 239000007788 liquid Substances 0.000 abstract description 6
- 239000000706 filtrate Substances 0.000 abstract description 4
- 239000004009 herbicide Substances 0.000 abstract description 3
- -1 N-substituted chloracetanilide Chemical class 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- YXWIRQHVEQIJOV-UHFFFAOYSA-N 2-ethyl-n-(1-methoxypropan-2-yl)-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1NC(C)COC YXWIRQHVEQIJOV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PPHQUIPUBYPZLD-UHFFFAOYSA-N n-ethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99803092A | 1992-12-29 | 1992-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV10859A LV10859A (lv) | 1995-10-20 |
| LV10859B true LV10859B (en) | 1996-06-20 |
Family
ID=25544671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-93-1381A LV10859B (en) | 1992-12-29 | 1993-12-28 | Process for the preparation of 2-alkyl-6-methyl-n-(1'-methoxy-2'-propyl)-aniline and a process for the preparation of their chloracetanilides |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US5430188A (cs) |
| EP (1) | EP0605363B1 (cs) |
| JP (1) | JP3521285B2 (cs) |
| KR (1) | KR100271775B1 (cs) |
| CN (1) | CN1039994C (cs) |
| AT (1) | ATE139223T1 (cs) |
| AU (1) | AU667989B2 (cs) |
| BG (1) | BG61481B1 (cs) |
| BR (1) | BR9305272A (cs) |
| CA (1) | CA2112416C (cs) |
| CZ (1) | CZ286376B6 (cs) |
| DE (1) | DE69303155T2 (cs) |
| DK (1) | DK0605363T3 (cs) |
| EE (1) | EE03069B1 (cs) |
| FI (1) | FI113639B (cs) |
| GE (1) | GEP19991732B (cs) |
| GR (1) | GR3020221T3 (cs) |
| HR (1) | HRP931521B1 (cs) |
| HU (2) | HU216027B (cs) |
| IL (1) | IL108204A (cs) |
| LT (1) | LT3260B (cs) |
| LV (1) | LV10859B (cs) |
| MX (1) | MX9307814A (cs) |
| MY (1) | MY109091A (cs) |
| NO (2) | NO180536C (cs) |
| NZ (1) | NZ250549A (cs) |
| PH (1) | PH29918A (cs) |
| PL (1) | PL177669B1 (cs) |
| RO (2) | RO117320B1 (cs) |
| RU (1) | RU2127253C1 (cs) |
| SI (1) | SI9300692B (cs) |
| SK (1) | SK280155B6 (cs) |
| TR (1) | TR27179A (cs) |
| ZA (1) | ZA939720B (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP960295A2 (en) * | 1995-07-06 | 1997-08-31 | Ciba Geigy Ag | Process for the hydrogenation of imines in the presence of immobilized iridium-diphosphine catalysts |
| HRP960302A2 (en) * | 1995-07-26 | 1998-04-30 | Ciba Geigy Ag | Process for the hydrogenation of imines |
| US6140538A (en) * | 1998-05-18 | 2000-10-31 | Flexsys America L.P. | Process for preparing 4-aminodiphenylamines |
| WO2001043864A1 (en) * | 1999-12-17 | 2001-06-21 | Warner Lambert Research And Development Ireland Limited | An apparatus for removing pyrophoric catalyst |
| US7964695B2 (en) * | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| EP2143707B1 (en) * | 2005-03-28 | 2018-04-11 | Line-X LLC | Secondary diamine |
| US8076518B2 (en) | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
| JP2009522307A (ja) * | 2005-12-30 | 2009-06-11 | アルベマール・コーポレーシヨン | 低減された色を有するジアミン |
| AU2008204847A1 (en) * | 2007-01-10 | 2008-07-17 | Albemarle Corporation | Formulations for reaction injection molding and for spray systems |
| CN102006930B (zh) * | 2008-04-17 | 2013-09-25 | 联合磷业有限公司 | 亚胺的氢化 |
| US9199930B2 (en) | 2012-09-06 | 2015-12-01 | Council Of Scientific And Industrial Research | Process for the preparation of (S)-2-ethyl-N-(1-methoxypropan-2-yl)-6-methyl aniline |
| CN102887832B (zh) * | 2012-09-29 | 2014-07-16 | 西安近代化学研究所 | 一种水相反应合成大位阻氯乙酰胺化合物的方法 |
| CN104445068B (zh) * | 2014-11-21 | 2016-09-28 | 山东侨昌化学有限公司 | 一种异丙甲草胺生产过程中副产氢气的回收方法 |
| CN104803875A (zh) * | 2015-03-27 | 2015-07-29 | 江苏长青农化南通有限公司 | 一种s-异丙甲草胺的合成方法 |
| CN105461580B (zh) * | 2015-11-12 | 2018-04-20 | 上虞颖泰精细化工有限公司 | 一种异丙甲草胺的合成方法 |
| CN109280012A (zh) * | 2017-07-19 | 2019-01-29 | 山东侨昌化学有限公司 | 一种无溶剂合成异丙甲草胺中间体2-乙基-6-甲基-n-（1’-甲氧基-2’-丙基）苯胺的方法 |
| CN115784909B (zh) * | 2022-11-30 | 2025-05-27 | 浙江工业大学 | 一种合成2-乙基-n-（2-甲氧基-1-甲基乙基）-6-甲基苯胺的方法 |
| CN116851035A (zh) * | 2023-06-27 | 2023-10-10 | 浙江工业大学 | 一种磺酸树脂负载铂催化剂的制备及催化合成异丙甲草胺中间体的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200451A (en) * | 1972-06-06 | 1980-04-29 | Ciba-Geigy Corporation | Plant growth regulating agent |
| US3937730A (en) | 1972-06-06 | 1976-02-10 | Ciba-Geigy Corporation | Plant growth regulating agent |
| US3929855A (en) * | 1974-10-10 | 1975-12-30 | Monsanto Co | N-1,3-Dimethylbutyl-N{40 -1,4-dimethylpentyl-p-phenylenediamine antiozonants |
| US4463191A (en) * | 1983-09-26 | 1984-07-31 | The Goodyear Tire & Rubber Company | Process for the reductive alkylation of aromatic nitro-containing compounds with ketones or aldehydes |
| CS270548B1 (sk) | 1989-01-20 | 1990-07-12 | Beska Emanuel | Sposob pripravy 2-atyl-6-metyl-N-/l'- -metoxy-2'-propyl/ anilinu |
-
1993
- 1993-12-02 MY MYPI93002557A patent/MY109091A/en unknown
- 1993-12-10 LT LTIP1586A patent/LT3260B/lt not_active IP Right Cessation
- 1993-12-10 MX MX9307814A patent/MX9307814A/es unknown
- 1993-12-15 US US08/168,034 patent/US5430188A/en not_active Expired - Lifetime
- 1993-12-17 GE GEAP19931688D patent/GEP19991732B/en unknown
- 1993-12-21 DK DK93810895.8T patent/DK0605363T3/da active
- 1993-12-21 EP EP93810895A patent/EP0605363B1/en not_active Expired - Lifetime
- 1993-12-21 AT AT93810895T patent/ATE139223T1/de not_active IP Right Cessation
- 1993-12-21 DE DE69303155T patent/DE69303155T2/de not_active Expired - Lifetime
- 1993-12-22 NZ NZ250549A patent/NZ250549A/en not_active IP Right Cessation
- 1993-12-23 RU RU93056851A patent/RU2127253C1/ru active
- 1993-12-24 AU AU52681/93A patent/AU667989B2/en not_active Expired
- 1993-12-24 CA CA002112416A patent/CA2112416C/en not_active Expired - Lifetime
- 1993-12-24 KR KR1019930030083A patent/KR100271775B1/ko not_active Expired - Lifetime
- 1993-12-27 PL PL93301650A patent/PL177669B1/pl unknown
- 1993-12-27 RO ROA200100609A patent/RO117320B1/ro unknown
- 1993-12-27 SK SK1488-93A patent/SK280155B6/sk not_active IP Right Cessation
- 1993-12-27 FI FI935886A patent/FI113639B/fi not_active IP Right Cessation
- 1993-12-27 CZ CZ19932902A patent/CZ286376B6/cs not_active IP Right Cessation
- 1993-12-27 CN CN93121226A patent/CN1039994C/zh not_active Expired - Lifetime
- 1993-12-27 RO RO93-01795A patent/RO117018B1/ro unknown
- 1993-12-28 ZA ZA939720A patent/ZA939720B/xx unknown
- 1993-12-28 HR HR07/998,030A patent/HRP931521B1/xx not_active IP Right Cessation
- 1993-12-28 HU HUP9603419A patent/HU216027B/hu unknown
- 1993-12-28 NO NO934861A patent/NO180536C/no not_active IP Right Cessation
- 1993-12-28 TR TR01225/93A patent/TR27179A/xx unknown
- 1993-12-28 IL IL108204A patent/IL108204A/xx not_active IP Right Cessation
- 1993-12-28 HU HU9303775A patent/HU213259B/hu unknown
- 1993-12-28 LV LVP-93-1381A patent/LV10859B/en unknown
- 1993-12-28 BR BR9305272A patent/BR9305272A/pt not_active IP Right Cessation
- 1993-12-28 JP JP35319893A patent/JP3521285B2/ja not_active Expired - Fee Related
- 1993-12-28 PH PH47562A patent/PH29918A/en unknown
- 1993-12-28 BG BG98337A patent/BG61481B1/bg unknown
- 1993-12-29 SI SI9300692A patent/SI9300692B/sl unknown
-
1994
- 1994-11-17 EE EE9400329A patent/EE03069B1/xx unknown
-
1996
- 1996-06-13 GR GR960401462T patent/GR3020221T3/el unknown
- 1996-07-15 NO NO962959A patent/NO301418B1/no not_active IP Right Cessation
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