GB1222169A - Process for the preparation of 3-aminopropanols - Google Patents
Process for the preparation of 3-aminopropanolsInfo
- Publication number
- GB1222169A GB1222169A GB61298/68A GB6129868A GB1222169A GB 1222169 A GB1222169 A GB 1222169A GB 61298/68 A GB61298/68 A GB 61298/68A GB 6129868 A GB6129868 A GB 6129868A GB 1222169 A GB1222169 A GB 1222169A
- Authority
- GB
- United Kingdom
- Prior art keywords
- contain
- oxetane
- general formula
- aminopropanols
- branched
- 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
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical class NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 abstract 1
- PBIHVCKVWPFHMN-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)CN(C)C PBIHVCKVWPFHMN-UHFFFAOYSA-N 0.000 abstract 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001347 alkyl bromides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000004694 iodide salts Chemical class 0.000 abstract 1
- 150000002921 oxetanes Chemical class 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Abstract
1,222,169. Preparation of 3-aminopropanols. FARBENFABRIKEN BAYER A.G. 24 Dec., 1968 [31 Jan., 1968], No. 61298/68. Heading C2C. [Also in Division C5] 3 - Aminopropanols of the general formula in which R<SP>1</SP> and R<SP>2</SP> each represent straightchain or branched-chain aliphatic radicals which may be substituted and which may contain a double bond, aryl or aralkyl radicals which may be substituted, or R<SP>1</SP> and R<SP>2</SP> together with the C atom to which they are attached form an optionally substituted carbocyclic 4- to 7- membered ring or an optionally substituted heterocyclic 4- to 7-membered ring which may be hydrogenated; and R<SP>3</SP> and R<SP>4</SP> each have the same meaning as R<SP>1</SP> and R<SP>2</SP> but do not contain primary or secondary amino groups or active halogen, and the active halogen of substituents R<SP>1</SP> and R<SP>2</SP> is replaced by the group -NR 3 R 4 , are prepared by reacting an oxetane of the general formula or a salt thereof, with at least an equimolar quantity of a secondary amine of the general formula R 3 R 4 NH in the presence of 0À01 to 1 acid equivalents of a weakly acid catalyst which has a pK value of 2À7 to 7À5, at 100-280‹ C. The salts of oxetane are defined as oxetanes which contain basic groups which have been quaternized by methyl chloride, dimethyl sulphate or diethyl sulphate or by branched or straight-chain alkyl bromides or iodides with up to 12 C atoms. The process is preferably performed in a polar solvent at elevated pressure at 150-250‹ C. in the presence of CO 2 as catalyst. Compounds of Formula I, wherein R 1 is -CH 2 OH and R<SP>2</SP> is not -CH 2 OH and does not contain a -NR 3 R 4 group, and their monoethers with monofunctional alcohols of up to 18 C atoms are said to be novel. Amongst the examples 2 - ethyl - 2 - dimethylaminomethyl- 1,3 - propanediol is prepared from 3 - ethyl - 3- hydroxymethyl - oxetane and dimethylamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681668900 DE1668900C3 (en) | 1968-01-31 | 1968-01-31 | Process for the preparation of 3-aminopropanols and some 2-ethyl-2- (dialkylaminomethyl) -propanediols- (1,3) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1222169A true GB1222169A (en) | 1971-02-10 |
Family
ID=5686151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB61298/68A Expired GB1222169A (en) | 1968-01-31 | 1968-12-24 | Process for the preparation of 3-aminopropanols |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4945381B1 (en) |
| AT (1) | AT286252B (en) |
| BE (1) | BE727655A (en) |
| CH (1) | CH508583A (en) |
| FR (1) | FR2001067A1 (en) |
| GB (1) | GB1222169A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156693A (en) * | 1975-04-23 | 1979-05-29 | Merck & Co., Inc. | Process for preparing 3-[N'-(3-halopropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium halide |
| WO2007121205A2 (en) * | 2006-04-12 | 2007-10-25 | The Lubrizol Corporation | Hydroxy-containing tertiary amines as friction modifiers for automatic transmission fluids |
| US7439213B2 (en) | 2004-10-19 | 2008-10-21 | The Lubrizol Corporation | Secondary and tertiary amines as friction modifiers for automatic transmission fluids |
| CN103992457A (en) * | 2014-05-26 | 2014-08-20 | 合肥市科天化工有限公司 | Cationic hydrophilic chain extender and application thereof in synthesizing cationic aqueous polyurethane dispersion |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793131A (en) * | 1971-12-22 | 1973-06-21 | Bayer Ag | 2-ALCOYL-2-MECAPTOMETHYLPROPANE DIOLS-1,3 AND PREPARATION PROCESS |
| JPH04126977U (en) * | 1991-05-13 | 1992-11-19 | 石野 香麻理 | drainage trap |
-
1968
- 1968-12-19 CH CH1897768A patent/CH508583A/en not_active IP Right Cessation
- 1968-12-24 GB GB61298/68A patent/GB1222169A/en not_active Expired
-
1969
- 1969-01-30 BE BE727655D patent/BE727655A/xx not_active IP Right Cessation
- 1969-01-30 JP JP44006398A patent/JPS4945381B1/ja active Pending
- 1969-01-31 FR FR6902141A patent/FR2001067A1/fr not_active Withdrawn
- 1969-01-31 AT AT98469A patent/AT286252B/en not_active IP Right Cessation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156693A (en) * | 1975-04-23 | 1979-05-29 | Merck & Co., Inc. | Process for preparing 3-[N'-(3-halopropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium halide |
| US7439213B2 (en) | 2004-10-19 | 2008-10-21 | The Lubrizol Corporation | Secondary and tertiary amines as friction modifiers for automatic transmission fluids |
| US7618929B2 (en) | 2004-10-19 | 2009-11-17 | The Lubrizol Corporation | Secondary and tertiary amines as friction modifiers for automatic transmission fluids |
| WO2007121205A2 (en) * | 2006-04-12 | 2007-10-25 | The Lubrizol Corporation | Hydroxy-containing tertiary amines as friction modifiers for automatic transmission fluids |
| WO2007121205A3 (en) * | 2006-04-12 | 2007-12-21 | Lubrizol Corp | Hydroxy-containing tertiary amines as friction modifiers for automatic transmission fluids |
| CN101421380B (en) * | 2006-04-12 | 2012-05-02 | 卢布里佐尔公司 | Hydroxyl-containing tertiary amines as friction modifiers for automatic transmission fluids |
| CN103992457A (en) * | 2014-05-26 | 2014-08-20 | 合肥市科天化工有限公司 | Cationic hydrophilic chain extender and application thereof in synthesizing cationic aqueous polyurethane dispersion |
Also Published As
| Publication number | Publication date |
|---|---|
| CH508583A (en) | 1971-06-15 |
| FR2001067A1 (en) | 1969-09-19 |
| AT286252B (en) | 1970-12-10 |
| JPS4945381B1 (en) | 1974-12-04 |
| BE727655A (en) | 1969-07-01 |
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