CA2127292A1 - Process for producing hydroxyalkane carboxylic acid amides - Google Patents
Process for producing hydroxyalkane carboxylic acid amidesInfo
- Publication number
- CA2127292A1 CA2127292A1 CA002127292A CA2127292A CA2127292A1 CA 2127292 A1 CA2127292 A1 CA 2127292A1 CA 002127292 A CA002127292 A CA 002127292A CA 2127292 A CA2127292 A CA 2127292A CA 2127292 A1 CA2127292 A1 CA 2127292A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- general formula
- carbon atoms
- mol
- taken place
- 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.)
- Abandoned
Links
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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Abstract A process is described for the production of hydroxyalkane carboxylic acid amides of general formula I
(I), in which n represents a whole number from 1 to 20 and R1 and R2 each mean alkyl groups with a maximum of 8 carbon atoms or together mean an alkylene group with 4 to 8 carbon atoms optionally interrupted by an oxygen atom or a nitrogen atom, from hydroxyalkane carboxylic acids of general formula II
HO-CnH2n-COOH (II), in which n has the above-mentioned meaning and amines of general formula III
(III), in which R1 and R2 have the above-mentioned meanings that is characterized in that the hydroxyalkane carboxylic acid is refluxed in a one-pot reaction with 10 to 30 mol of acetyl chloride per mol of acid each, the excess acetyl chloride is distilled off after acetylation has taken place, the residue is refluxed with 1.5 to 5 mol of thionyl chloride per mol of acid, the thionyl chloride is removed by distillation after acid chloride formation has taken place, the residue is dissolved in a dialkyl ether with 4 to 8 carbon atoms, the solution obtained is placed proportionately in an aqueous solution of the amine cooled to 0°C
to 10°C and the acetate group is cleaved off after amide formation has taken place by treatment with aqueous sodium hydroxide solution at a reaction temperature of 10°C to 30°C.
(I), in which n represents a whole number from 1 to 20 and R1 and R2 each mean alkyl groups with a maximum of 8 carbon atoms or together mean an alkylene group with 4 to 8 carbon atoms optionally interrupted by an oxygen atom or a nitrogen atom, from hydroxyalkane carboxylic acids of general formula II
HO-CnH2n-COOH (II), in which n has the above-mentioned meaning and amines of general formula III
(III), in which R1 and R2 have the above-mentioned meanings that is characterized in that the hydroxyalkane carboxylic acid is refluxed in a one-pot reaction with 10 to 30 mol of acetyl chloride per mol of acid each, the excess acetyl chloride is distilled off after acetylation has taken place, the residue is refluxed with 1.5 to 5 mol of thionyl chloride per mol of acid, the thionyl chloride is removed by distillation after acid chloride formation has taken place, the residue is dissolved in a dialkyl ether with 4 to 8 carbon atoms, the solution obtained is placed proportionately in an aqueous solution of the amine cooled to 0°C
to 10°C and the acetate group is cleaved off after amide formation has taken place by treatment with aqueous sodium hydroxide solution at a reaction temperature of 10°C to 30°C.
Description
2 1 2 7 ~
Pro¢esq for the production of ; ~
" . .
hydroxyalkane carboxylic aci~ ami~es ,~
. . . ~ -, - . .
~he invention relates to a process for the production of ~: :
hydroxyalkane carboxylic acid amides of general formula I ; -~ R
EIO-C~ ,-CO~
~R~
in which n represents a whole number from 1 to 20 and R1 and F~ each mean alkyl groups with a maximum of 8 carbon atoms or together mean an alkylene group with 4 to 8 carbon atoms ;~
optionally interrupted by an oxygen atom or a nitrogen atom, from .
hydroxyalkane carboxylic acids of general formula II
HO-C~H2n-COOH (II), ' ~
in which : ~:
n has the above-mentioned meaning and amines of general formula III .
/~1 HN
R~
~:
. ~
21~72~2 in which R1 and F7 have the above-mentioned meanings that is characterized in that the hydroxyalkane carboxylic acid is refluxed in a one-pot reaction with 10 to 30 mol of acetyl chloride per mol of acid, the excess acetyl chloride is distilled off after acetylation has taken place, the residue is refluxed with 1.5 to 5 mol of thionyl chloride per mol of acid, the thionyl chloride is removed by distillation after acid chloride formation has taken place, the residue is dissolved in a dialkyl ether with 4 to 8 carbon atoms, the solution obtained is placed proportionally in an aqueous solution of amine cooled to oC to 10C and the acetate qroup is cleaved off after amide formation has taken place by treatment with aqueous sodium hydroxide solution at a reaction temperature of 10C to 30C.
The invention especially relates to the production of hydroxyalkane carboxylic acid amides of general formula I in which the group ~ . '~'''"
means a dialkylamino group with 1 to 4 carbon atoms each in the alkyl radicals or the grouping ~3 ~;
~4 ;:
'.. ' ~:''' ; :~
2127~9 in which R5 and R4 independently of one another represent a hydrogen atom or a methyl group and X means a methylene group, an .
oxygen atom or a N-CH3.group.
As is generally known, the hydroxyalkane carboxyiic acid amides of general formula I are valuable intermediate products . and/or pharmacologically effective substances.
Thus, for example, hydroxyalkane carboxylic acid amides of general formula Ia /~1 Rs-CH-CON (~a)J
~H \ R2 ~:
in which R~ represents a hydrogen atom or an alkyl group, are valuable intermediate products for the production of herbicides ~ -(DE-A 30 38 598).
Hydroxyalkane carboxylic acid amides of general formula Ib ~ Rl ;.
HO-(C~m-CO~ \ (Ib), in which m means the numbers 7 to 18 are especially suitable for the production of pharmaceutical agents for the local treatment of :
diseases of the skin or mucous membrane (WO 90/09373) or can be 2127~
used as intermediate products for the production of detergents (US-A 2,936,325). However, the synthesis of these hydroxyalkane carboxylic acid amides is quite expensive as a rule and the yield and purity of the obtained products is often unsatisfactory. In contrast, the one~pot reaction according to the invention offers both ecological and economic advantages. It iæ relatively simple to perform in comparison with the previously known processes and provides the products of the process in surprisingly high yield and purity.
The process accordinq to the invention is performed in such a way that the hydroxyalkane carboxylic acid is dissolved or suspended in 10 to 30 mol of acetyl chloride per mol of acid and the reaction mixture is refluxed. After acetylation has taken place (recognizable by thin-layer chromatographic analysis, or in that no more hydrogenchloride generation takes place) the excess acetyl chloride is distilled off, and by application of a vacuum care i8 taken to achieve as complete as possible removal of the acetyl chloride. ~ ;
:. ;.
The residue obtained is then mixed with 1.5 to 5 mol of thionyl chloride per mol of acid used and the mixture obtained is refluxed. After the acid chloride formation has taken place, the thionyl chloride is removed as completely as possible in the same ~ ;-way as previously the acetyl chloride and the residue obtained is dissolved in a dialkyl ether with 4 to 8 carbon atoms. As dialkyl ether, for example, diethyl ether, diisopropyl ether, dibutyl ether or especially methyl-tert.-butyl ether are suitable. ;~
.:,', :~ ' ' .
~ ~ ~ o 2~27~
The ethereal solution of the acid chloride is then introduced proportionately in an aqueous solution, preferably stirred and optionally mixed with the same ether, cooled to 0C
to 10C, of preferably 2 to 5 mol of amine per mol of acid used, so that the reaction temperature does not exceed 10C. Then the reaction mixture i8 allowed to stand for 20-60 minutes at room -~
temperature for completion of the reaction and it is mixed with - -;~
an excess of aqueous or aqueous/alcoholic sodium hydroxide solution and stirred for 20-60 minutes at room temperature.
The working up of the reaction mixture takes place in the usual way, by, for example, the organic phase being separated, washed, concentrated by evaporation and the residue being purified by recrystallization.
The following embodiments serve to further explain the process according to the invention.
:
~,3~
2127~
General instructions for the production of ~-hydroxyalkane carboxylic acid amides of aeneral formula I
a g of ~-hydroxyalkanoic acid is suspended in b ml of acetyl chloride and refluxed and stirred for 30 minutes. Then the acetyl chloride is distilled off in a vacuum, the residue is mixed with c ml of thionyl chloride and the mixture is heated for one hour at 60C. Then the thionyl chloride is distilled off in a vacuum and the residue is dissolved in d ml of methyl-tert.-butyl ether.
e ml of 40% aqueous dimethylamine solution is mixed with f ml of methyl-tert.-butyl ether and cooled with stirring to 0C.
Then the ethereal acid chloride solution is instilled in this mixture so that the reaction temperature does not exceed 10C, it is stirred for 30 minutes more at room temperature, a solution of h g of sodium hydroxide in a mixture of i ml of methanol and k ml of water is added to the reaction mixture and stirred for another 30 minutes at room temperature.
Then the mixture is diluted with water and methyl-tert.-~;
butyl ether, the organic phase is separated, washed and concentrated by evaporation in a vacuum. The residue is recrystallized from ethyl acetate/hexane and 1 g of ~-hydroxyalkanoic acid dimethylamide of a melting point mC (= p %
of theory) is obtained. ; ~ -, ,=...
21272~i~f Fxample 1 ~-13-Hydroxytridecanoic acid-dimethylamide from 13-hydroxytridecanoic acid ` -Cl5H31N02(257-42) Cld. C 69.99 H 12.14 N 5.44 Fnd. C 70.38 H 11.98 N 5.43 ~mplo 2 ll-Hydroxyundecanoic acid-dimethylamide from 11-hydroxyundecanoic acid C~6H33N02(227l-44) Cld. C 68.08 H 11.87 N 6.11 Fnd. C 68.45 H 11.76 N 6.13 Ex~mple 3 14-Hydroxytetradecanoic acid-dimethylamide from 14-hydroxytetradecanoic acid C13H2jN02(229.36) Cld. C 70.80 H 12.25 N 5.16 ;
Fnd. C 71.16 H 12.27 N 5.20 !~
Ex~ple 15-Hydroxypentadecanoic acid-dimethylamide from 15-hydroxypentadecanoic acid C1~H3sNo2(285-47) Cld. C 71.53 H 12.36 N 4.91 Fnd. C 71.6S H 12.19 N 4.93 2127?.92 Example 5 4-(13-Hydroxy-1-oxotridecyl)morpholine from 13-hydroxytridecanoic acid Cl7H33N03(299.45)Cld. C 68.19 H 11.11 N 4.68 Fnd. C 68.16 H 11.03 N 4.74 Fx. ~ b c d e f h i k 1 m ~
128.0 252 24.673 40 73 22.4 1906726.9 69-71 86.0 219.5 200 19.558 32 58 17.7 1515317.7 57-58 80.0 315.5 131 12.838 21 38 11.7 9935 14.3 70-71 83.1 411.4 91 8.9 26 15 26 8.1 6924 10.7 73-74 82.6 53.5 31 3.1 9 8 9 2.8 24 8 2.8 75-76 62.1 ''-'".: . '.
: ' ~' '.''' ''';; '-..'.~''
Pro¢esq for the production of ; ~
" . .
hydroxyalkane carboxylic aci~ ami~es ,~
. . . ~ -, - . .
~he invention relates to a process for the production of ~: :
hydroxyalkane carboxylic acid amides of general formula I ; -~ R
EIO-C~ ,-CO~
~R~
in which n represents a whole number from 1 to 20 and R1 and F~ each mean alkyl groups with a maximum of 8 carbon atoms or together mean an alkylene group with 4 to 8 carbon atoms ;~
optionally interrupted by an oxygen atom or a nitrogen atom, from .
hydroxyalkane carboxylic acids of general formula II
HO-C~H2n-COOH (II), ' ~
in which : ~:
n has the above-mentioned meaning and amines of general formula III .
/~1 HN
R~
~:
. ~
21~72~2 in which R1 and F7 have the above-mentioned meanings that is characterized in that the hydroxyalkane carboxylic acid is refluxed in a one-pot reaction with 10 to 30 mol of acetyl chloride per mol of acid, the excess acetyl chloride is distilled off after acetylation has taken place, the residue is refluxed with 1.5 to 5 mol of thionyl chloride per mol of acid, the thionyl chloride is removed by distillation after acid chloride formation has taken place, the residue is dissolved in a dialkyl ether with 4 to 8 carbon atoms, the solution obtained is placed proportionally in an aqueous solution of amine cooled to oC to 10C and the acetate qroup is cleaved off after amide formation has taken place by treatment with aqueous sodium hydroxide solution at a reaction temperature of 10C to 30C.
The invention especially relates to the production of hydroxyalkane carboxylic acid amides of general formula I in which the group ~ . '~'''"
means a dialkylamino group with 1 to 4 carbon atoms each in the alkyl radicals or the grouping ~3 ~;
~4 ;:
'.. ' ~:''' ; :~
2127~9 in which R5 and R4 independently of one another represent a hydrogen atom or a methyl group and X means a methylene group, an .
oxygen atom or a N-CH3.group.
As is generally known, the hydroxyalkane carboxyiic acid amides of general formula I are valuable intermediate products . and/or pharmacologically effective substances.
Thus, for example, hydroxyalkane carboxylic acid amides of general formula Ia /~1 Rs-CH-CON (~a)J
~H \ R2 ~:
in which R~ represents a hydrogen atom or an alkyl group, are valuable intermediate products for the production of herbicides ~ -(DE-A 30 38 598).
Hydroxyalkane carboxylic acid amides of general formula Ib ~ Rl ;.
HO-(C~m-CO~ \ (Ib), in which m means the numbers 7 to 18 are especially suitable for the production of pharmaceutical agents for the local treatment of :
diseases of the skin or mucous membrane (WO 90/09373) or can be 2127~
used as intermediate products for the production of detergents (US-A 2,936,325). However, the synthesis of these hydroxyalkane carboxylic acid amides is quite expensive as a rule and the yield and purity of the obtained products is often unsatisfactory. In contrast, the one~pot reaction according to the invention offers both ecological and economic advantages. It iæ relatively simple to perform in comparison with the previously known processes and provides the products of the process in surprisingly high yield and purity.
The process accordinq to the invention is performed in such a way that the hydroxyalkane carboxylic acid is dissolved or suspended in 10 to 30 mol of acetyl chloride per mol of acid and the reaction mixture is refluxed. After acetylation has taken place (recognizable by thin-layer chromatographic analysis, or in that no more hydrogenchloride generation takes place) the excess acetyl chloride is distilled off, and by application of a vacuum care i8 taken to achieve as complete as possible removal of the acetyl chloride. ~ ;
:. ;.
The residue obtained is then mixed with 1.5 to 5 mol of thionyl chloride per mol of acid used and the mixture obtained is refluxed. After the acid chloride formation has taken place, the thionyl chloride is removed as completely as possible in the same ~ ;-way as previously the acetyl chloride and the residue obtained is dissolved in a dialkyl ether with 4 to 8 carbon atoms. As dialkyl ether, for example, diethyl ether, diisopropyl ether, dibutyl ether or especially methyl-tert.-butyl ether are suitable. ;~
.:,', :~ ' ' .
~ ~ ~ o 2~27~
The ethereal solution of the acid chloride is then introduced proportionately in an aqueous solution, preferably stirred and optionally mixed with the same ether, cooled to 0C
to 10C, of preferably 2 to 5 mol of amine per mol of acid used, so that the reaction temperature does not exceed 10C. Then the reaction mixture i8 allowed to stand for 20-60 minutes at room -~
temperature for completion of the reaction and it is mixed with - -;~
an excess of aqueous or aqueous/alcoholic sodium hydroxide solution and stirred for 20-60 minutes at room temperature.
The working up of the reaction mixture takes place in the usual way, by, for example, the organic phase being separated, washed, concentrated by evaporation and the residue being purified by recrystallization.
The following embodiments serve to further explain the process according to the invention.
:
~,3~
2127~
General instructions for the production of ~-hydroxyalkane carboxylic acid amides of aeneral formula I
a g of ~-hydroxyalkanoic acid is suspended in b ml of acetyl chloride and refluxed and stirred for 30 minutes. Then the acetyl chloride is distilled off in a vacuum, the residue is mixed with c ml of thionyl chloride and the mixture is heated for one hour at 60C. Then the thionyl chloride is distilled off in a vacuum and the residue is dissolved in d ml of methyl-tert.-butyl ether.
e ml of 40% aqueous dimethylamine solution is mixed with f ml of methyl-tert.-butyl ether and cooled with stirring to 0C.
Then the ethereal acid chloride solution is instilled in this mixture so that the reaction temperature does not exceed 10C, it is stirred for 30 minutes more at room temperature, a solution of h g of sodium hydroxide in a mixture of i ml of methanol and k ml of water is added to the reaction mixture and stirred for another 30 minutes at room temperature.
Then the mixture is diluted with water and methyl-tert.-~;
butyl ether, the organic phase is separated, washed and concentrated by evaporation in a vacuum. The residue is recrystallized from ethyl acetate/hexane and 1 g of ~-hydroxyalkanoic acid dimethylamide of a melting point mC (= p %
of theory) is obtained. ; ~ -, ,=...
21272~i~f Fxample 1 ~-13-Hydroxytridecanoic acid-dimethylamide from 13-hydroxytridecanoic acid ` -Cl5H31N02(257-42) Cld. C 69.99 H 12.14 N 5.44 Fnd. C 70.38 H 11.98 N 5.43 ~mplo 2 ll-Hydroxyundecanoic acid-dimethylamide from 11-hydroxyundecanoic acid C~6H33N02(227l-44) Cld. C 68.08 H 11.87 N 6.11 Fnd. C 68.45 H 11.76 N 6.13 Ex~mple 3 14-Hydroxytetradecanoic acid-dimethylamide from 14-hydroxytetradecanoic acid C13H2jN02(229.36) Cld. C 70.80 H 12.25 N 5.16 ;
Fnd. C 71.16 H 12.27 N 5.20 !~
Ex~ple 15-Hydroxypentadecanoic acid-dimethylamide from 15-hydroxypentadecanoic acid C1~H3sNo2(285-47) Cld. C 71.53 H 12.36 N 4.91 Fnd. C 71.6S H 12.19 N 4.93 2127?.92 Example 5 4-(13-Hydroxy-1-oxotridecyl)morpholine from 13-hydroxytridecanoic acid Cl7H33N03(299.45)Cld. C 68.19 H 11.11 N 4.68 Fnd. C 68.16 H 11.03 N 4.74 Fx. ~ b c d e f h i k 1 m ~
128.0 252 24.673 40 73 22.4 1906726.9 69-71 86.0 219.5 200 19.558 32 58 17.7 1515317.7 57-58 80.0 315.5 131 12.838 21 38 11.7 9935 14.3 70-71 83.1 411.4 91 8.9 26 15 26 8.1 6924 10.7 73-74 82.6 53.5 31 3.1 9 8 9 2.8 24 8 2.8 75-76 62.1 ''-'".: . '.
: ' ~' '.''' ''';; '-..'.~''
Claims
Claims Process for the production of hydroxyalkane carboxylic acid amides of general formula I
(I), in which n represents a whole number from 1 to 20 and R1 and R2 each mean alkyl groups with a maximum of 8 carbon atoms or together mean an alkylene group with 4 to 8 carbon atoms optionally interrupted by an oxygen atom or a nitrogen atom, from hydroxyalkane carboxylic acids of general formula II
HO-CnH2n-COOH (II), in which n has the above-mentioned meaning and amines of general formula III
(III), in which R1 and R2 have the above-mentioned meanings characterized in that the hydroxyalkane carboxylic acid is refluxed in a one-pot reaction with 10 to 30 mol of acetyl chloride per mol of acid each, the excess acetyl chloride is distilled off after acetylation has taken place, the residue is refluxed with 1.5 to 5 mol of thionyl chloride per mol of acid, the thionyl chloride is removed by distillation after acid chloride formation has taken place, the residue is dissolved in a dialkyl ether with 4 to 8 carbon atoms, the solution obtained is placed proportionately in an aqueous solution of the amine cooled to 0°C
to 10°C and the acetate group is cleaved off after amide formation has taken place by treatment with aqueous sodium hydroxide solution at a reaction temperature of 10°C to 30°C.
(I), in which n represents a whole number from 1 to 20 and R1 and R2 each mean alkyl groups with a maximum of 8 carbon atoms or together mean an alkylene group with 4 to 8 carbon atoms optionally interrupted by an oxygen atom or a nitrogen atom, from hydroxyalkane carboxylic acids of general formula II
HO-CnH2n-COOH (II), in which n has the above-mentioned meaning and amines of general formula III
(III), in which R1 and R2 have the above-mentioned meanings characterized in that the hydroxyalkane carboxylic acid is refluxed in a one-pot reaction with 10 to 30 mol of acetyl chloride per mol of acid each, the excess acetyl chloride is distilled off after acetylation has taken place, the residue is refluxed with 1.5 to 5 mol of thionyl chloride per mol of acid, the thionyl chloride is removed by distillation after acid chloride formation has taken place, the residue is dissolved in a dialkyl ether with 4 to 8 carbon atoms, the solution obtained is placed proportionately in an aqueous solution of the amine cooled to 0°C
to 10°C and the acetate group is cleaved off after amide formation has taken place by treatment with aqueous sodium hydroxide solution at a reaction temperature of 10°C to 30°C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19924214895 DE4214895A1 (en) | 1992-05-07 | 1992-05-07 | Process for the preparation of hydroxyalkane carboxamides |
| DEP4214895.2 | 1992-05-07 | ||
| PCT/DE1993/000413 WO1993022278A1 (en) | 1992-05-07 | 1993-05-05 | Process for producing hydroxyalkane carboxylic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2127292A1 true CA2127292A1 (en) | 1993-11-11 |
Family
ID=6458253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002127292A Abandoned CA2127292A1 (en) | 1992-05-07 | 1993-05-05 | Process for producing hydroxyalkane carboxylic acid amides |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0639177A1 (en) |
| JP (1) | JPH07506819A (en) |
| AU (1) | AU4259493A (en) |
| CA (1) | CA2127292A1 (en) |
| DE (1) | DE4214895A1 (en) |
| FI (1) | FI945181A0 (en) |
| HU (1) | HUT68198A (en) |
| NO (1) | NO944238D0 (en) |
| WO (1) | WO1993022278A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4420736C1 (en) * | 1994-06-15 | 1995-08-10 | Henkel Kgaa | New pseudo-ceramide cpds. |
| DE4427837A1 (en) * | 1994-08-05 | 1996-02-08 | Hoechst Ag | Process for the preparation of O-acylglycolic acid anilides |
| DE19525098A1 (en) * | 1995-07-10 | 1997-01-16 | Hoechst Ag | Process for the preparation of hydroxycarboxylic acid anilides |
| US7541489B2 (en) | 2004-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method of making halophthalic acids and halophthalic anhydrides |
| DE102008017213B4 (en) * | 2008-04-04 | 2012-08-09 | Clariant International Limited | Continuous process for the preparation of amides of aliphatic hydroxycarboxylic acids |
| WO2010108817A1 (en) | 2009-03-26 | 2010-09-30 | Basf Se | Method for producing n,n`-lactic acid dialkylamide using ionic liquids |
| WO2010108814A1 (en) | 2009-03-26 | 2010-09-30 | Basf Se | Method for producing n,n`-lactic acid dialkylamide under pressure |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB868556A (en) * | 1957-05-02 | 1961-05-17 | Hoechst Ag | Analeptically active ª--hydroxy-and ª--acyloxy-butyric acid alkyl-amides and a process for their manufacture |
| DE3905325A1 (en) * | 1989-02-17 | 1990-09-06 | Schering Ag | HYDROXYALKANCARBONE ACID DERIVATIVES, THEIR PREPARATION AND USE |
-
1992
- 1992-05-07 DE DE19924214895 patent/DE4214895A1/en not_active Withdrawn
-
1993
- 1993-05-05 CA CA002127292A patent/CA2127292A1/en not_active Abandoned
- 1993-05-05 HU HU9401335A patent/HUT68198A/en unknown
- 1993-05-05 JP JP5518842A patent/JPH07506819A/en active Pending
- 1993-05-05 EP EP93911742A patent/EP0639177A1/en not_active Withdrawn
- 1993-05-05 WO PCT/DE1993/000413 patent/WO1993022278A1/en not_active Application Discontinuation
- 1993-05-05 AU AU42594/93A patent/AU4259493A/en not_active Abandoned
-
1994
- 1994-11-03 FI FI945181A patent/FI945181A0/en not_active Application Discontinuation
- 1994-11-07 NO NO944238A patent/NO944238D0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU9401335D0 (en) | 1994-08-29 |
| EP0639177A1 (en) | 1995-02-22 |
| NO944238L (en) | 1994-11-07 |
| FI945181A (en) | 1994-11-03 |
| FI945181A0 (en) | 1994-11-03 |
| DE4214895A1 (en) | 1993-11-11 |
| NO944238D0 (en) | 1994-11-07 |
| WO1993022278A1 (en) | 1993-11-11 |
| HUT68198A (en) | 1995-05-29 |
| AU4259493A (en) | 1993-11-29 |
| JPH07506819A (en) | 1995-07-27 |
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