GB1355220A - Tertiary amine esters acid addition salts and quaternary ammonium compounds thereof and their preparation - Google Patents
Tertiary amine esters acid addition salts and quaternary ammonium compounds thereof and their preparationInfo
- Publication number
- GB1355220A GB1355220A GB5136071A GB5136071A GB1355220A GB 1355220 A GB1355220 A GB 1355220A GB 5136071 A GB5136071 A GB 5136071A GB 5136071 A GB5136071 A GB 5136071A GB 1355220 A GB1355220 A GB 1355220A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tertiary amine
- alkyl
- acid addition
- preparation
- quaternary ammonium
- 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
- -1 Tertiary amine esters Chemical class 0.000 title abstract 3
- 239000002253 acid Substances 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 150000003512 tertiary amines Chemical group 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 abstract 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 abstract 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-M 4-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-M 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 229940070765 laurate Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F5/00—Obtaining drying-oils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1355220 Tertiary amine esters BRISTOLMYERS CO 4 Nov 1971 [4 Nov 1970 (2)] 51360/71 Heading C2C [Also in Division C3] Compounds of formula where B is or NR<SP>5</SP>, R<SP>1</SP>, R<SP>2</SP> are C 1-18 alkyl, or aralkyl, R<SP>5</SP> is (CH 2 ) 4 or (CH 2 ) 5 , optionally substituted with C 1-8 alkyl, R<SP>3</SP> is H or C 1-18 alkyl, R is H, C 1-18 alkyl, aryl or aralkyl, R<SP>4</SP> is a carboxy acid acyl radical with 2-27 C atoms, n has an average value of 5-50, A is an anion of valency y, and m and p are both 1, or m is 0 and p is 0 or 1, may be prepared in the tertiary amine form by acylating the corresponding tertiary amine alcohol, preferably with R<SP>4</SP>Cl, and may then be quaternized or converted into acid addition salt form. If the amine alcohols have been obtained in admixture with polyglycol ethers they may be purified before or preferably after acylation by forming an aqueous acid solution of the mixture, extracting with a water-immiscible organic solvent, e.g. diethyl ether or ethyl acetate, and recovering the amine alcohol or ester from the aqueous phase. In examples n is 7, R<SP>3</SP> is CH 3 , R<SP>1</SP> and R<SP>2</SP> are C 2 H 5 , and R<SP>4</SP> is acetate, laurate, stearate or p-nitrobenzoate, and the products are obtained in tertiary amine form, in quaternized form with CH 3 Cl, and in salt form with HCl. The nitrobenzoate is reduced to form the corresponding p-aminobenzoate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8696570A | 1970-11-04 | 1970-11-04 | |
| US8696770A | 1970-11-04 | 1970-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1355220A true GB1355220A (en) | 1974-06-05 |
Family
ID=26775361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5136071A Expired GB1355220A (en) | 1970-11-04 | 1971-11-04 | Tertiary amine esters acid addition salts and quaternary ammonium compounds thereof and their preparation |
Country Status (6)
| Country | Link |
|---|---|
| AU (1) | AU468971B2 (en) |
| BE (1) | BE774927A (en) |
| DE (1) | DE2154851A1 (en) |
| FR (1) | FR2113534A5 (en) |
| GB (1) | GB1355220A (en) |
| IT (1) | IT944777B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1588079A (en) * | 1977-09-12 | 1981-04-15 | Texaco Development Corp | Surface-active oxyalkylated amines |
| US5221771A (en) * | 1991-06-19 | 1993-06-22 | Xoma Corporation | Activated polymers and conjugates thereof |
-
1971
- 1971-11-02 AU AU35258/71A patent/AU468971B2/en not_active Expired
- 1971-11-03 IT IT5387371A patent/IT944777B/en active
- 1971-11-03 FR FR7139440A patent/FR2113534A5/fr not_active Expired
- 1971-11-04 GB GB5136071A patent/GB1355220A/en not_active Expired
- 1971-11-04 DE DE19712154851 patent/DE2154851A1/en not_active Withdrawn
- 1971-11-04 BE BE774927A patent/BE774927A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2154851A1 (en) | 1972-05-18 |
| FR2113534A5 (en) | 1972-06-23 |
| AU468971B2 (en) | 1976-01-29 |
| AU3525871A (en) | 1973-05-10 |
| IT944777B (en) | 1973-04-20 |
| BE774927A (en) | 1972-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |