DE318222C - - Google Patents
Info
- Publication number
- DE318222C DE318222C DENDAT318222D DE318222DA DE318222C DE 318222 C DE318222 C DE 318222C DE NDAT318222 D DENDAT318222 D DE NDAT318222D DE 318222D A DE318222D A DE 318222DA DE 318222 C DE318222 C DE 318222C
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- derivatives
- ester
- adipic acid
- 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.)
- Active
Links
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 7
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 description 5
- PJGSXYOJTGTZAV-UHFFFAOYSA-N Pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GCHCGDFZHOEXMP-UHFFFAOYSA-L Potassium adipate Chemical compound [K+].[K+].[O-]C(=O)CCCCC([O-])=O GCHCGDFZHOEXMP-UHFFFAOYSA-L 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000001608 potassium adipate Substances 0.000 description 2
- 235000011051 potassium adipate Nutrition 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-Dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- ISXPOEJSKALLKA-UHFFFAOYSA-N 1,2-diiodopropane Chemical compound CC(I)CI ISXPOEJSKALLKA-UHFFFAOYSA-N 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N Adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 210000002374 Sebum Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- -1 glycol Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MEBJLVMIIRFIJS-UHFFFAOYSA-N hexanedioic acid;propane-1,2-diol Chemical compound CC(O)CO.OC(=O)CCCCC(O)=O MEBJLVMIIRFIJS-UHFFFAOYSA-N 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical group [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Es wurde gefunden, daß die bisher noch nicht bekannten Ester von dihydroxylierten Kohlenwasserstoffen der Adipinsäure, oder ihrer Homologen und Derivate, technisch wertvolle Ersatzstoffe für Fette und Wachse dar-.stellen. Sie können dadurch erhalten werden, daß man die Adipinsäure oder ihre Derivate und Homologe mit dihydroxylierten Verbindungen, wie Glykol, oder ihren Derivaten ίο verestert.It has been found that the previously unknown esters of dihydroxylated Hydrocarbons of adipic acid, or its homologues and derivatives, technically valuable Represent substitutes for fats and waxes. They can be obtained by that adipic acid or its derivatives and homologues with dihydroxylated compounds, like glycol, or their derivatives ίο esterified.
Man löst 200 Gewichtsteile Adipinsäuredichlorid in dem dreifachen Volumen Pinacolin und fügt diese Mischung zu einer Lösung von 71 Gewichtsteilen Äthylenglykol und 250 Gewichtsteilen Pyridin, wasserfrei, in dem dreifachen Volumen Pinacolin. Unter starker Erwärmung und Abscheidung von salzsaurem Pyridin erfolgt Umsetzung. Der neutrale Ester löst sich in dem Pinacolin. Er hinterbleibt als tä^ähnliche Masse, wenn man nach dem Auswaschen des Pyridins mit verdünnter Salzsäure die über Chlorkalium getrocknete Pinacolinlösung im Vakuum bei siedendem Wasserbad von dem Lösungsmittel befreit.200 parts by weight of adipic acid dichloride are dissolved in three times the volume of pinacolin and adds this mixture to a solution of 71 parts by weight of ethylene glycol and 250 parts by weight Pyridine, anhydrous, in three times the volume of pinacolin. Under strong Heating and deposition of hydrochloric acid pyridine takes place. The neutral one Ester dissolves in the pinacolin. It remains behind as a daily similar mass if one goes after washing out the pyridine with dilute hydrochloric acid the dried over potassium chloride Pinacolin solution in vacuo at boiling Freed from the solvent in the water bath.
Derselbe Ester entsteht, wenn man 170 Gewichtsteile Äthylendibromid mit 200 Gewichtsteilen adipinsaurem Kalium im Autoklaven 5 Stunden auf 180 ° erhitzt. Das hierbei entstehende Bromkalium wird durch sorgfältiges Waschen mit heißem Wasser entfernt. Das zurückbleibende Öl erstarrt in der Kälte talgartig. Ebenso bildet sich der Ester nach der bekannten Schotten-Baumannsehen Veresterungsmethode.The same ester is formed if 170 parts by weight of ethylene dibromide are mixed with 200 parts by weight potassium adipate heated to 180 ° in an autoclave for 5 hours. That The resulting potassium bromide is removed by careful washing with hot water. The remaining oil solidifies in the cold like sebum. The ester is also formed according to the well-known Schotten-Baumannsehen Esterification method.
160 Gewichtsteile a - Methyladipinsäure löst man in der dreifachen Menge Aceton, versetzt mit 44 Gewichtsteilen Äthylenoxyd und erwärmt das Gemisch im Autoklaven 6 Stunden lang auf 6o°. Nach dem Abdestillieren des Lösungsmittels hinterbleibt der a-Methyladipinsäureglykolester als bräunliche Masse von wachsartiger Beschaffenheit.160 parts by weight of a - methyladipic acid is dissolved in three times the amount of acetone, mixed with 44 parts by weight of ethylene oxide and the mixture heated in an autoclave for 6 hours at 6o °. After the solvent has been distilled off, the a-methyl adipic acid glycol ester remains as a brownish mass of a waxy consistency.
296 Gewichtsteile Propylenjodid CH3 CH.,CH2,i erhitzt man mit 200 Gewichtsteilen adipinsaurem Kalium im Autoklaven 8 Stunden unter Rühren. Die weitere Aufarbeitung des Adipinsäurepropylenglykolesters erfolgt wie in Beispiel 1. Der Ester erstarrt in der Kälte butterartig.296 parts by weight of propylene iodide CH 3 CH., CH 2 , i are heated with 200 parts by weight of potassium adipate in an autoclave for 8 hours while stirring. The further work-up of the propylene glycol adipate is carried out as in Example 1. The ester solidifies like butter in the cold.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE318222C true DE318222C (en) |
Family
ID=570818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT318222D Active DE318222C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE318222C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567076A (en) * | 1947-11-06 | 1951-09-04 | Union Carbide & Carbon Corp | Production of polyoxyethylene glycol superesters |
| DE975309C (en) * | 1951-10-02 | 1961-11-02 | Johannes Dr-Ing Kleine | Process for the production of polyesters |
-
0
- DE DENDAT318222D patent/DE318222C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567076A (en) * | 1947-11-06 | 1951-09-04 | Union Carbide & Carbon Corp | Production of polyoxyethylene glycol superesters |
| DE975309C (en) * | 1951-10-02 | 1961-11-02 | Johannes Dr-Ing Kleine | Process for the production of polyesters |
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