CH398542A - Process for the preparation of a succinamide - Google Patents
Process for the preparation of a succinamideInfo
- Publication number
- CH398542A CH398542A CH449362A CH449362A CH398542A CH 398542 A CH398542 A CH 398542A CH 449362 A CH449362 A CH 449362A CH 449362 A CH449362 A CH 449362A CH 398542 A CH398542 A CH 398542A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- preparation
- succinamide
- parts
- weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 title description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
- 239000001384 succinic acid Substances 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- PBZAGXRVDLNBCJ-UHFFFAOYSA-N diheptyl butanedioate Chemical compound CCCCCCCOC(=O)CCC(=O)OCCCCCCC PBZAGXRVDLNBCJ-UHFFFAOYSA-N 0.000 description 1
- 229940024497 diheptyl succinate Drugs 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé pour la préparation d'une succinamide
La présente invention a pour objet un procédé pour la préparation de la diamide de l'acide succinique et de la N-méthyl-ss-hydroxy-éthylamine de formule:
EMI1.1
Cette diamide est, à l'état pur, un produit cristallin blanc très soluble dans l'eau (29,5 o/o à 200 C), peu soluble dans l'huile d'olive, de point de fusion instantané au bloc Maquenne: 121-1220 C et dont le spectre d'absorption dans l'infrarouge présente en particulier une seule bande entre 6,1 et 6,2 w1 et une bande à 2,8 Il. Le procédé de préparation conforme à l'invention est caractérisé par la réaction d'un ester de l'acide succinique avec la N-méthyl-ss-hydroxy- éthylamine. La réaction peut être conduite à chaud sans catalyseur.
On utilise, de préférence, un excès de N-méthyl-p-hydroxyéthylamme.
La diamide de formule ci-dessus peut être utilisée en tant que matière première pour la fabrication de résines synthétiques, de matières plastiques, de produits auxiliaires pour l'industrie textile, en particulier pour la fabrication de polyesters-polyamides elle possède en outre des propriétés antiphlogistiques
et anti-inflammatoires et peut être utilisée comme
médicament antirhumatismal.
Les exemples suivants illustrent l'invention sans
la limiter.
Exemple 1
On introduit dans un appareil de réaction muni
d'un réfrigérant ascendant, 570 parties en poids de
succinate diéthylique et 1000 parties en poids de N
méthyl-ss-hydroxyéthylamine et chauffe à reflux pen
dant 2 heures. On remplace ensuite le réfrigérant
ascendant par une colonne reliée à un réfrigérant des
cendant et distille lentement l'alcool éthylique formé
au cours de la réaction. Par refroidissement le mé
lange réactionnel cristallise; on filtre et essore à fond.
On obtient environ 1154 parties en poids de produit
technique fondant au bloc Maquenne vers 1150 C.
On purifie le produit par dissolution dans environ son poids d'alcool méthylique, chauffage à reflux
pendant 20 minutes en présence de 20 parties en
poids de charbon actif, filtration à chaud, refroidis
sement lent et filtration après cristallisation. On ob
tient environ 630 parties en poids de produit pur
présentant les caractéristiques susindiquées.
Exemple 2
On opère comme à l'exemple 1 mais en rempla
çant le succinate diéthylique par le succinate dimé
thylique. On obtient la succinamide avec un rende
ment égal à 75-80 o/o de la théorie.
Exemple 3
On mélange 21,44 parties de succinate diheptylique avec 15 parties de N-méthyl-ss-hydroxyéthyl- amine. On chauffe une heure à 1300 C et laisse refroidir. On chauffe ensuite sous vide à une pression comprise entre 20 et 50 mm/Hg pour éliminer l'excès de N-méthyl-ss-hydroxyéthylamine et l'alcool heptylique formé. Le résidu huileux obtenu cristallise. Recristallisé à partir du méthanol, il présente un point de fusion de 121-1220 C. Rendement 80 /e.
Process for the preparation of a succinamide
The present invention relates to a process for the preparation of the diamide of succinic acid and of N-methyl-ss-hydroxy-ethylamine of formula:
EMI1.1
This diamide is, in its pure state, a white crystalline product very soluble in water (29.5 o / o at 200 C), sparingly soluble in olive oil, with an instantaneous melting point at the Maquenne block. : 121-1220 C and whose absorption spectrum in the infrared presents in particular a single band between 6.1 and 6.2 w1 and a band at 2.8 Il. The preparation process according to the invention is characterized by the reaction of an ester of succinic acid with N-methyl-ss-hydroxy-ethylamine. The reaction can be carried out hot without a catalyst.
Preferably, an excess of N-methyl-p-hydroxyethylamme is used.
The diamide of the above formula can be used as a raw material for the manufacture of synthetic resins, plastics, auxiliary products for the textile industry, in particular for the manufacture of polyesters-polyamides, it also has properties. antiphlogistic
and anti-inflammatory drugs and can be used as
anti-rheumatic drug.
The following examples illustrate the invention without
limit it.
Example 1
It is introduced into a reaction apparatus equipped
of an ascending refrigerant, 570 parts by weight of
diethyl succinate and 1000 parts by weight of N
methyl-ss-hydroxyethylamine and reflux heater pen
within 2 hours. The refrigerant is then replaced
ascending by a column connected to a refrigerant of
ash and slowly distils the ethyl alcohol formed
during the reaction. By cooling the m
reaction mixture crystallizes; filter and wring thoroughly.
Approximately 1154 parts by weight of product are obtained
melting technique at the Maquenne block around 1150 C.
The product is purified by dissolving in approximately its weight of methyl alcohol, heating at reflux
for 20 minutes in the presence of 20 parties in
activated carbon weight, hot filtration, cooled
Slow formation and filtration after crystallization. We ob
holds about 630 parts by weight of pure product
having the above-mentioned characteristics.
Example 2
We operate as in Example 1 but replace
eant diethyl succinate by dimé succinate
thylic. We obtain succinamide with a rendering
ment equal to 75-80 o / o of theory.
Example 3
21.44 parts of diheptyl succinate are mixed with 15 parts of N-methyl-ss-hydroxyethylamine. Heated for one hour at 1300 C and allowed to cool. Then heated under vacuum at a pressure between 20 and 50 mm / Hg to remove excess N-methyl-ss-hydroxyethylamine and heptyl alcohol formed. The oily residue obtained crystallizes. Recrystallized from methanol, it has a melting point of 121-1220 C. Yield 80 / e.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH449362A CH398542A (en) | 1962-04-12 | 1962-04-12 | Process for the preparation of a succinamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH449362A CH398542A (en) | 1962-04-12 | 1962-04-12 | Process for the preparation of a succinamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH398542A true CH398542A (en) | 1966-03-15 |
Family
ID=4277124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH449362A CH398542A (en) | 1962-04-12 | 1962-04-12 | Process for the preparation of a succinamide |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH398542A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0473380A1 (en) * | 1990-08-27 | 1992-03-04 | Rohm And Haas Company | Process for the preparation of hydroxyamides |
-
1962
- 1962-04-12 CH CH449362A patent/CH398542A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0473380A1 (en) * | 1990-08-27 | 1992-03-04 | Rohm And Haas Company | Process for the preparation of hydroxyamides |
| TR27054A (en) * | 1990-08-27 | 1994-10-11 | Rohm & Haas Comp | Process for the preparation of hydroxyamides. |
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