DE2651984C2 - Verfahren zur Herstellung von N,N-Dimethylpiperidiniumchlorid oder N,N-Dimethylmorpholiniumchlorid - Google Patents
Verfahren zur Herstellung von N,N-Dimethylpiperidiniumchlorid oder N,N-DimethylmorpholiniumchloridInfo
- Publication number
- DE2651984C2 DE2651984C2 DE2651984A DE2651984A DE2651984C2 DE 2651984 C2 DE2651984 C2 DE 2651984C2 DE 2651984 A DE2651984 A DE 2651984A DE 2651984 A DE2651984 A DE 2651984A DE 2651984 C2 DE2651984 C2 DE 2651984C2
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- reaction
- methyl chloride
- dimethylmorpholinium
- pressure
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 12
- RBIPMCDRANHGQI-UHFFFAOYSA-M 4,4-dimethylmorpholin-4-ium;chloride Chemical compound [Cl-].C[N+]1(C)CCOCC1 RBIPMCDRANHGQI-UHFFFAOYSA-M 0.000 title 1
- VHOVSQVSAAQANU-UHFFFAOYSA-M mepiquat chloride Chemical compound [Cl-].C[N+]1(C)CCCCC1 VHOVSQVSAAQANU-UHFFFAOYSA-M 0.000 title 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 34
- 229940050176 methyl chloride Drugs 0.000 claims description 17
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 14
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 5
- -1 monomethyl compound Chemical class 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QDUXDCXILAPLAG-UHFFFAOYSA-N hydron;1-methylpiperidine;chloride Chemical compound Cl.CN1CCCCC1 QDUXDCXILAPLAG-UHFFFAOYSA-N 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2651984A DE2651984C2 (de) | 1976-11-15 | 1976-11-15 | Verfahren zur Herstellung von N,N-Dimethylpiperidiniumchlorid oder N,N-Dimethylmorpholiniumchlorid |
| IL53112A IL53112A (en) | 1976-11-15 | 1977-10-12 | Preparation of n,n-dimethylpiperidinium chloride and n,n-dimethylmorpholinium chloride |
| CA288,706A CA1072561A (en) | 1976-11-15 | 1977-10-13 | Preparation of n,n-dimethylpiperidinium chloride and n,n-dimethylmorpholinium chloride |
| JP13260077A JPS5363384A (en) | 1976-11-15 | 1977-11-07 | Method of producing n*nndimethylpiperidiniumm chloride and n*nndimethylmorphoriniumchloride |
| NLAANVRAGE7712395,A NL189131C (nl) | 1976-11-15 | 1977-11-10 | Werkwijze voor de bereiding van n.n-dimethylpiperidiniumchloride respectievelijk n.n-dimethylmorfoliniumchloride. |
| FR7733898A FR2370740A1 (fr) | 1976-11-15 | 1977-11-10 | Procede de preparation de chlorure de n,n-dimethyl-piperidinium ou de chlorure de n,n-dimethylmorpholinium |
| IT51785/77A IT1091782B (it) | 1976-11-15 | 1977-11-11 | Procedimento per la produzione di cloruro di n,n-dimetilpiperidinio o rispettivamente di cloruro di n,n dimetilmorfolino |
| DD7700202046A DD132342A5 (de) | 1976-11-15 | 1977-11-11 | Verfahren zur herstellung von n,n-dimethylpiperidiniumchlorid bzw.n,n-dimethylmorpholiniumchlorid |
| SE7712787A SE7712787L (sv) | 1976-11-15 | 1977-11-11 | Forfarande for framstellning av n,n-dimetylpiperidinium- eller n,n-dimetylmorfoliniumklorid |
| CH1387677A CH630913A5 (en) | 1976-11-15 | 1977-11-14 | Process for the preparation of N-N-dimethylpiperidinium chloride and N,N-dimethylmorpholinium chloride |
| SU772541700A SU671730A3 (ru) | 1976-11-15 | 1977-11-14 | Способ получени -диметилпиперидиний хлорида или -диметилморфолиний хлорида |
| GB47238/77A GB1587925A (en) | 1976-11-15 | 1977-11-14 | Manufacture of n,n-dimethylpiperidinium chloride and n,n-dimethylmorpholinium chloride |
| BE182589A BE860788A (fr) | 1976-11-15 | 1977-11-14 | Procede de preparation de chlorure de n,n-dimethyl-piperidinium et du chlorure de n,n-dimethyl-morpholinium |
| DK503177A DK159682C (da) | 1976-11-15 | 1977-11-14 | Fremgangsmaade til fremstilling af n,n-dimethylpiperidiniumchlorid eller n,n-dimethylmorpholiniumchlorid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2651984A DE2651984C2 (de) | 1976-11-15 | 1976-11-15 | Verfahren zur Herstellung von N,N-Dimethylpiperidiniumchlorid oder N,N-Dimethylmorpholiniumchlorid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2651984A1 DE2651984A1 (de) | 1978-05-18 |
| DE2651984C2 true DE2651984C2 (de) | 1983-01-27 |
Family
ID=5993174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2651984A Expired DE2651984C2 (de) | 1976-11-15 | 1976-11-15 | Verfahren zur Herstellung von N,N-Dimethylpiperidiniumchlorid oder N,N-Dimethylmorpholiniumchlorid |
Country Status (14)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EG20423A (en) * | 1992-06-04 | 1999-04-29 | Micro Flo Co | Mepiquat chloride |
| EP3039007A1 (en) * | 2013-08-28 | 2016-07-06 | Johnson Matthey PLC | Method of making a templating agent |
| CN113024413B (zh) * | 2019-12-25 | 2022-12-06 | 北京颖泰嘉和生物科技股份有限公司 | 水杨腈联产植物生长调节剂的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE756185C (de) * | 1939-08-27 | 1952-05-19 | Onderzoekings Inst Res | Verfahren zur Herstellung quartaerer aliphatischer Ammoniumchloride |
| US3928423A (en) * | 1972-07-17 | 1975-12-23 | Kendall & Co | Monomeric emulsion stabilizers |
| DE2247501A1 (de) * | 1971-10-02 | 1973-04-05 | Inst Przemyslu Organiczego | Verfahren zur herstellung von quartaeren ammoniumsalzen |
| BE795534A (fr) * | 1972-02-18 | 1973-08-16 | Basf Ag | Agents pour la regulation de la croissance des plantes, contenant comme principe actif un sel azote |
-
1976
- 1976-11-15 DE DE2651984A patent/DE2651984C2/de not_active Expired
-
1977
- 1977-10-12 IL IL53112A patent/IL53112A/xx unknown
- 1977-10-13 CA CA288,706A patent/CA1072561A/en not_active Expired
- 1977-11-07 JP JP13260077A patent/JPS5363384A/ja active Granted
- 1977-11-10 FR FR7733898A patent/FR2370740A1/fr active Granted
- 1977-11-10 NL NLAANVRAGE7712395,A patent/NL189131C/xx not_active IP Right Cessation
- 1977-11-11 IT IT51785/77A patent/IT1091782B/it active
- 1977-11-11 DD DD7700202046A patent/DD132342A5/xx unknown
- 1977-11-11 SE SE7712787A patent/SE7712787L/xx not_active Application Discontinuation
- 1977-11-14 DK DK503177A patent/DK159682C/da active
- 1977-11-14 BE BE182589A patent/BE860788A/xx not_active IP Right Cessation
- 1977-11-14 CH CH1387677A patent/CH630913A5/de not_active IP Right Cessation
- 1977-11-14 GB GB47238/77A patent/GB1587925A/en not_active Expired
- 1977-11-14 SU SU772541700A patent/SU671730A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6225144B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-06-01 |
| IT1091782B (it) | 1985-07-06 |
| NL7712395A (nl) | 1978-05-17 |
| CA1072561A (en) | 1980-02-26 |
| SE7712787L (sv) | 1978-05-16 |
| DE2651984A1 (de) | 1978-05-18 |
| IL53112A (en) | 1981-03-31 |
| GB1587925A (en) | 1981-04-15 |
| FR2370740A1 (fr) | 1978-06-09 |
| CH630913A5 (en) | 1982-07-15 |
| JPS5363384A (en) | 1978-06-06 |
| BE860788A (fr) | 1978-05-16 |
| NL189131C (nl) | 1993-01-18 |
| FR2370740B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-06-19 |
| DK159682C (da) | 1991-04-15 |
| DD132342A5 (de) | 1978-09-20 |
| SU671730A3 (ru) | 1979-06-30 |
| DK503177A (da) | 1978-05-16 |
| DK159682B (da) | 1990-11-19 |
| IL53112A0 (en) | 1977-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |