CA1072561A - Preparation of n,n-dimethylpiperidinium chloride and n,n-dimethylmorpholinium chloride - Google Patents
Preparation of n,n-dimethylpiperidinium chloride and n,n-dimethylmorpholinium chlorideInfo
- Publication number
- CA1072561A CA1072561A CA288,706A CA288706A CA1072561A CA 1072561 A CA1072561 A CA 1072561A CA 288706 A CA288706 A CA 288706A CA 1072561 A CA1072561 A CA 1072561A
- Authority
- CA
- Canada
- Prior art keywords
- chloride
- reaction
- dimethylpiperidinium
- dimethylmorpholinium
- methyl
- 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
- VHOVSQVSAAQANU-UHFFFAOYSA-M mepiquat chloride Chemical compound [Cl-].C[N+]1(C)CCCCC1 VHOVSQVSAAQANU-UHFFFAOYSA-M 0.000 title claims abstract description 9
- RBIPMCDRANHGQI-UHFFFAOYSA-M 4,4-dimethylmorpholin-4-ium;chloride Chemical compound [Cl-].C[N+]1(C)CCOCC1 RBIPMCDRANHGQI-UHFFFAOYSA-M 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title abstract description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229940050176 methyl chloride Drugs 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 13
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000000243 solution Substances 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- -1 sodiu~ hydroxide Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HSQOPVUSHBNOOL-UHFFFAOYSA-M 1,1-dimethylpiperidin-1-ium;iodide Chemical compound [I-].C[N+]1(C)CCCCC1 HSQOPVUSHBNOOL-UHFFFAOYSA-M 0.000 description 1
- YGNXNQMVWHPUET-UHFFFAOYSA-M 4,4-dimethylmorpholin-4-ium;iodide Chemical compound [I-].C[N+]1(C)CCOCC1 YGNXNQMVWHPUET-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- QDUXDCXILAPLAG-UHFFFAOYSA-N hydron;1-methylpiperidine;chloride Chemical compound Cl.CN1CCCCC1 QDUXDCXILAPLAG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000000126 substance Substances 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1072561A true CA1072561A (en) | 1980-02-26 |
Family
ID=5993174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA288,706A Expired CA1072561A (en) | 1976-11-15 | 1977-10-13 | Preparation of n,n-dimethylpiperidinium chloride and n,n-dimethylmorpholinium chloride |
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 |
| DE2651984C2 (de) | 1983-01-27 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6613908B2 (en) | Method for carbamoylating alcohols | |
| US3752841A (en) | Process for the preparation of carbamates of alkylthiolhydroxamates and intermediates | |
| CA1072561A (en) | Preparation of n,n-dimethylpiperidinium chloride and n,n-dimethylmorpholinium chloride | |
| US3836524A (en) | Preparation of esters of thiocarbamic acids | |
| CA1145360A (en) | Preparation of cyanoacetamide and 2,2 -dibromo-3-nitrilopropionamide compositions | |
| NO176136B (no) | Fremgangsmåte ved fremstilling av cyanamid | |
| US4740623A (en) | Method for preparation of benzyl mercaptan | |
| US4247479A (en) | Process for the manufacture of aromatic amines from α, β-unsaturated cycloaliphatic ketoximes | |
| US2411875A (en) | Beta-halo acyl halides | |
| DE69006994T2 (de) | Verfahren zur herstellung von antimikrobiellen zubereitungen von 2-(alkylthioäthanamin)hydrohaliden. | |
| US2805257A (en) | 1-ethynyl-cyclohexylthiols | |
| US4084055A (en) | Preparation of chlorinated indazoles | |
| EP0131472B1 (en) | 5-mercapto-1,2,3-thiadiazoles composition and process for preparing the same | |
| KR920004603B1 (ko) | 2,2-디메톡시-2-페닐아세토페논의 제조방법 | |
| US4770820A (en) | Process for the preparation of carbamoyl chlorides derived from secondary amines | |
| US4877874A (en) | Process for producing N-aminohexamethyleneimine | |
| EP0015577B1 (en) | Process for producing 1,1,3,3-tetrafluoro-1,3-dihydro-isobenzofuran | |
| JPH01160952A (ja) | モノーまたはビス−ジチオカルバミン酸ないしは該酸の塩の製造法 | |
| US4992583A (en) | Process for synthesizing N-chlorothio-sulfonamides | |
| JPS62249946A (ja) | ジアミノジフエニルメタン系化合物の製法 | |
| US3249606A (en) | Process of preparing beta-amino-arylethylketone picrates | |
| IE42100B1 (en) | Process for the preparation of 2,2,2-trichloroethyl chloroformate | |
| US4013674A (en) | N-(1,2,2,2-tetrachloroethyl)-formimide-chloride for synthesizing trichlorothiazole | |
| US5436373A (en) | Process for the preparation of N-benzyl-N-organoaminoalkanol | |
| JPS6013022B2 (ja) | ジアルキルアルカノ−ルアミンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |