SI9300692B - Postopek za pripravo 2-alkil-6-metil-N(1'-metoksi-2'-propil)-anilina in postopek za pripravo njegovih kloracetanilidov - Google Patents
Postopek za pripravo 2-alkil-6-metil-N(1'-metoksi-2'-propil)-anilina in postopek za pripravo njegovih kloracetanilidov Download PDFInfo
- Publication number
- SI9300692B SI9300692B SI9300692A SI9300692A SI9300692B SI 9300692 B SI9300692 B SI 9300692B SI 9300692 A SI9300692 A SI 9300692A SI 9300692 A SI9300692 A SI 9300692A SI 9300692 B SI9300692 B SI 9300692B
- Authority
- SI
- Slovenia
- Prior art keywords
- process according
- catalyst
- formula
- alkyl
- methyl
- Prior art date
Links
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)
Claims (28)
1 PATENTNI ZAHTEVKI 1. Postopek za pripravo 2-alkil-6-metil-N-(T-metoksi-2'-propil)-anilina s formulo I
kjer je R metil ali etil, s katalitskim redukcijskim alkiliranjem, pri čemer vsaj 1 mol ekvivalent metoksiacetona s formulo II CH3C(0)CH2-0-CH3 (II) reagira z 1 mol ekvivalentom 2-alkil-6-metil-anilina s formulo III NH2 (IH)
v tekočem mediju brez dodatnega topila, v prisotnosti katalizatorja platiniranega oglja in vodika ter v prisotnosti kislinskega sokatalizatorja, pod tlakom vodika med 2 χ 105 pa in 1 x 106 Pa pri temperaturi med 20 in 80 °C, označen s tem, da reakcijska zmes vsebuje od 5 do 50 mas. % vode, glede na metoksiaceton, od začetka reakcije, in po končanem hidrogeniranju dodamo bazo, reakcijsko zmes filtriramo, da ločimo katalizator, ki ga speremo z vodo in posušimo v toku tehničnega dušika, in spojino s formulo I rekuperiramo iz filtrata. 2
2. Postopek po zahtevku 1, označen s tem, daje R etil.
3. Postopek po zahtevku 1, označen s tem, da metoksiaceton s formulo II uporabimo direktno kot njegov azeotrop z vodo.
4. Postopek po zahtevku 1, označen s tem, da reakcija kondenzacije poteka v vodnem mediju, nakisanem s H3PO4 ali H2SO4 kot sokatalizatorjem.
5. Postopek po zahtevku 4, označen s tem, da žveplovo kislino uporabimo kot kislinski sokatalizator.
6. Postopek po zahtevku 4, označen s tem, da uporabimo 0,001 do 0,08 mol ekvivalentov kislinskega sokatalizatorja glede na količino prisotnega 2-alkil-6-metilanilina.
7. Postopek po zahtevku 1, označen s tem, da reakcijo med spojinama s formulama II in III izvedemo pri temperaturi med 35 in 60 °C.
8. Postopek po zahtevku 1, označen s tem, daje katalizator za hidrogeniranje platina na nosilcu aktivnem oglju.
9. Postopek po zahtevku 8, označen s tem, daje kovina platina prisotna v količini od 3 do 6 mas. % nosilca.
10. Postopek po zahtevku 1, označen s tem, daje baza KOH ali NaOH.
11. Postopek po zahtevku 1, označen s tem, da po hidrogeniranju avtoklav izperemo s plinom dušikom. 3
12. Postopek po zahtevku 1, označen s tem, da tlak dušika uporabimo v avtoklavu med filtracijo, da odstranimo katalizator.
13. Postopek po zahtevku 1, označen s tem, da rekuperirani katalizator recikliramo.
14. Postopek po zahtevku 13, označen s tem, da katalizator recikliramo do 100-krat.
15. Postopek za pripravo spojin s formulo IV O CH3
(IV) kjer je R metil ali etil, pri čemer a) v prvi stopnji izvedemo katalitsko redukcijsko alkiliranje, pri čemer vsaj 1 mol ekvivalent metoksiacetona s formulo II (II) CH3C(0)CH2-0-CH3 reagira z 1 mol ekvivalentom 2-alkil-6-metil-anilina s formulo III NH2
(III) 4 v tekočem mediju brez dodatnega topila, v prisotnosti katalizatorja platiniranega oglja in vodika ter v prisotnosti kislinskega sokatalizatorja, pod tlakom vodika med 2 χ 105 Pa in 1 x 106 Pa pri temperaturi med 20 in 80 °C, in b) v drugi stopnji izvedemo reakcijo spojine s formulo I s kloridom monoklorocetne kisline in izoliranje spojine s formulo IV, označen s tem, da v prvi reakcijski stopnji a) reakcijska zmes vsebuje od 5 do 50 mas.% vode, glede na metoksiaceton, od začetka reakcije in po končanem hidrogeniranju dodamo bazo in reakcijsko zmes filtriramo, da ločimo katalizator, ki ga speremo z vodo in posušimo v toku tehničnega dušika.
16. Postopek po zahtevku 15, označen s tem, daje R etil.
17. Postopek po zahtevku 15, označen s tem, da metoksiaceton s formulo II uporabimo direktno kot njegov azeotrop z vodo.
18. Postopek po zahtevku 15, označen s tem, da reakcija kondenzacije poteka v vodnem mediju, nakisanem s H3P04 ali H2SO4 kot sokatalizatorjem.
19. Postopek po zahtevku 18, označen s tem, da žveplovo kislino uporabimo kot kislinski sokatalizator.
20. Postopek po zahtevku 18, označen s tem, da uporabimo 0,001 do 0,08 mol ekvivalentov kislinskega sokatalizatorja glede na količino prisotnega 2-alkil-6-metilanilina.
21. Postopek po zahtevku 15, označen s tem, da reakcijo med spojinama s formulama II in III izvedemo pri temperaturi med 35 in 60 °C.
22. Postopek po zahtevku 15, označen s tem, daje katalizator za hidrogeniranje platina na nosilcu aktivnem oglju. 5
23. Postopek po zahtevku 22, označen s tem, daje kovina platina prisotna v količini od 3 do 6 mas.% nosilca.
24. Postopek po zahtevku 15, označen s tem, daje baza KOH ali NaOH.
25. Postopek po zahtevku 15, označen s tem, da po hidrogeniranju avtoklav izperemo s plinom dušikom.
26. Postopek po zahtevku 15, označen s tem, da tlak dušika uporabimo v avtoklavu med filtracijo, da odstranimo katalizator.
27. Postopek po zahtevku 15, označen s tem, da rekuperirani katalizator recikliramo.
28. Postopek po zahtevku 27, označen s tem, da katalizator recikliramo do 100-krat.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99803092A | 1992-12-29 | 1992-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9300692A SI9300692A (en) | 1994-06-30 |
| SI9300692B true SI9300692B (sl) | 2002-02-28 |
Family
ID=25544671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9300692A SI9300692B (sl) | 1992-12-29 | 1993-12-29 | Postopek za pripravo 2-alkil-6-metil-N(1'-metoksi-2'-propil)-anilina in postopek za pripravo njegovih kloracetanilidov |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US5430188A (sl) |
| EP (1) | EP0605363B1 (sl) |
| JP (1) | JP3521285B2 (sl) |
| KR (1) | KR100271775B1 (sl) |
| CN (1) | CN1039994C (sl) |
| AT (1) | ATE139223T1 (sl) |
| AU (1) | AU667989B2 (sl) |
| BG (1) | BG61481B1 (sl) |
| BR (1) | BR9305272A (sl) |
| CA (1) | CA2112416C (sl) |
| CZ (1) | CZ286376B6 (sl) |
| DE (1) | DE69303155T2 (sl) |
| DK (1) | DK0605363T3 (sl) |
| EE (1) | EE03069B1 (sl) |
| FI (1) | FI113639B (sl) |
| GE (1) | GEP19991732B (sl) |
| GR (1) | GR3020221T3 (sl) |
| HR (1) | HRP931521B1 (sl) |
| HU (2) | HU216027B (sl) |
| IL (1) | IL108204A (sl) |
| LT (1) | LT3260B (sl) |
| LV (1) | LV10859B (sl) |
| MX (1) | MX9307814A (sl) |
| MY (1) | MY109091A (sl) |
| NO (2) | NO180536C (sl) |
| NZ (1) | NZ250549A (sl) |
| PH (1) | PH29918A (sl) |
| PL (1) | PL177669B1 (sl) |
| RO (2) | RO117018B1 (sl) |
| RU (1) | RU2127253C1 (sl) |
| SI (1) | SI9300692B (sl) |
| SK (1) | SK280155B6 (sl) |
| TR (1) | TR27179A (sl) |
| ZA (1) | ZA939720B (sl) |
Families Citing this family (17)
| 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 |
| CA2389561C (en) | 1999-12-17 | 2008-08-26 | Warner Lambert Research And Development Ireland Limited | A process for removing pyrophoric catalyst |
| US8076518B2 (en) | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
| CN101160283A (zh) * | 2005-03-28 | 2008-04-09 | 雅宝公司 | 二亚胺和仲二胺 |
| US7964695B2 (en) * | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| US20080315155A1 (en) * | 2005-12-30 | 2008-12-25 | Albemarle Corporation | Diamines Having Reduced Color |
| JP2010515811A (ja) * | 2007-01-10 | 2010-05-13 | アルベマール・コーポレーシヨン | 反応射出成形および噴霧システムのための組成物 |
| AU2009245307B2 (en) * | 2008-04-17 | 2014-01-30 | Upl Limited | Hydrogenation of imines |
| 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 |
| CN115784909A (zh) * | 2022-11-30 | 2023-03-14 | 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3937730A (en) | 1972-06-06 | 1976-02-10 | Ciba-Geigy Corporation | Plant growth regulating agent |
| US4200451A (en) * | 1972-06-06 | 1980-04-29 | 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 (en) | 1989-01-20 | 1990-07-12 | Beska Emanuel | Method of 2-ethyl-6-methyl-n-/1 -methoxy-2-propyl/aniline preparation |
-
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 AT AT93810895T patent/ATE139223T1/de not_active IP Right Cessation
- 1993-12-21 DE DE69303155T patent/DE69303155T2/de not_active Expired - Lifetime
- 1993-12-21 EP EP93810895A patent/EP0605363B1/en 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 CA CA002112416A patent/CA2112416C/en not_active Expired - Lifetime
- 1993-12-24 AU AU52681/93A patent/AU667989B2/en not_active Expired
- 1993-12-24 KR KR1019930030083A patent/KR100271775B1/ko not_active IP Right Cessation
- 1993-12-27 FI FI935886A patent/FI113639B/fi not_active IP Right Cessation
- 1993-12-27 PL PL93301650A patent/PL177669B1/pl unknown
- 1993-12-27 CZ CZ19932902A patent/CZ286376B6/cs not_active IP Right Cessation
- 1993-12-27 RO RO93-01795A patent/RO117018B1/ro 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 CN CN93121226A patent/CN1039994C/zh not_active Expired - Lifetime
- 1993-12-28 BG BG98337A patent/BG61481B1/bg 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 LV LVP-93-1381A patent/LV10859B/en unknown
- 1993-12-28 NO NO934861A patent/NO180536C/no not_active IP Right Cessation
- 1993-12-28 ZA ZA939720A patent/ZA939720B/xx unknown
- 1993-12-28 PH PH47562A patent/PH29918A/en unknown
- 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 JP JP35319893A patent/JP3521285B2/ja not_active Expired - Fee Related
- 1993-12-28 HU HU9303775A patent/HU213259B/hu unknown
- 1993-12-28 BR BR9305272A patent/BR9305272A/pt not_active IP Right Cessation
- 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
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SI9300692B (sl) | Postopek za pripravo 2-alkil-6-metil-N(1'-metoksi-2'-propil)-anilina in postopek za pripravo njegovih kloracetanilidov | |
| US4356124A (en) | Process for the production of pyrrolidones | |
| JPS5848540B2 (ja) | 塩素でメタ置換されたアニリンの製造方法 | |
| NL8403609A (nl) | Werkwijze ter bereiding van 4-alkoxyanilinen. | |
| EP0013554B1 (en) | Process for production of 1,17-diamino-9-azaheptadecane | |
| US5288906A (en) | Preparation of p-aminophenols | |
| US5998669A (en) | Process for production of 2-amino-1,3-propanediol | |
| AU763072B2 (en) | Phosphoric acid salt of an aromatic diamine | |
| CN112608247B (zh) | 辣椒素的制备方法及利用该方法制备得到的辣椒素 | |
| GB1575860A (en) | Process for the manufacture of m-aminophenols | |
| JPS62292747A (ja) | Ｎ，ｎ−ジアルキル置換アミノフエノ−ル類の製造方法 | |
| JPH07330711A (ja) | 高純度４，４’−チオビス（ジフェニルチオウレア）の製造法 | |
| JPH01135779A (ja) | Ｎ−エチルピペラジンの製造方法 | |
| JPH03287546A (ja) | 芳香族アミノ化合物の製造法 | |
| MXPA01006142A (en) | Method for preparing polyhalogenated paratrifluoromethylanilines | |
| JPH01221356A (ja) | ３‐アミノ‐４‐トリフルオロメチル安息香酸およびその製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF | Valid on the event date |