DE1071711B - Process for the purification of saturated aliphatic diamines by distillation - Google Patents
Process for the purification of saturated aliphatic diamines by distillationInfo
- Publication number
- DE1071711B DE1071711B DENDAT1071711D DE1071711DA DE1071711B DE 1071711 B DE1071711 B DE 1071711B DE NDAT1071711 D DENDAT1071711 D DE NDAT1071711D DE 1071711D A DE1071711D A DE 1071711DA DE 1071711 B DE1071711 B DE 1071711B
- Authority
- DE
- Germany
- Prior art keywords
- distillation
- purification
- saturated aliphatic
- aliphatic diamines
- diamines
- 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.)
- Pending
Links
- 238000004821 distillation Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 238000000746 purification Methods 0.000 title claims description 3
- -1 saturated aliphatic diamines Chemical class 0.000 title claims description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- 102220586119 Tubulin polymerization-promoting protein_S45E_mutation Human genes 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
DEUTSCHESGERMAN
KL 12q 4KL 12q 4
INTERNAT. KL. C 07 CINTERNAT. KL. C 07 C
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFT 1071711EDITORIAL NOTICE 1071711
V 13844 IVb/12 qV 13844 IVb / 12 q
ANMELDETAG: 13. F E B R U AR 1958REGISTRATION DATE: 13th F E B R U AR 1958
BEKANNTMACHUNG
DER ANMELDUNG
UND AUSGABE DER
AUSLEGESCHRIFT:NOTICE
THE REGISTRATION
AND ISSUE OF THE
EDITORIAL:
24. DEZEMBER 1959DECEMBER 24, 1959
Es ist bekannt, daß zur Herstellung von Polyamiden aus Diaminen und Dicarbonsäuren an die Ausgangsprodukte hohe Anforderungen hinsichtlich des Reinheitsgrades, gestellt werden. Man hat versucht, die Diamine durch mehrfache Destillation zu reinigen, doch gelingt es auf diesem Wege nicht, rein weiße Produkte zu gewinnen.It is known that the starting materials are used to produce polyamides from diamines and dicarboxylic acids high requirements in terms of the degree of purity are made. One tried that To purify diamines by multiple distillations, it is not possible to obtain pure white ones in this way Products to win.
Weiterhin ist vorgeschlagen worden, die Destillation in Gegenwart geringer Mengen alkalisch oder sauer wirkender Zusätze durchzuführen. Beispielsweise kann man Alkalihydroxide. Alkalicarbonate. Akaliacetate. Lrdalkalioxyde und -hydroxyde, Phosphor-, Bor-, Essig-, Oxal-, Adipinsäure oder Xatriumphosphatc. Kaliumbisulfat oder Weinstein als Zusatzmittel verwenden. — Durch diese Arbeitsweise kommt man /.war zu reinen Diaminen, jedoch ist eine mehrfache Destillation notwendig.It has also been proposed that distillation to be carried out in the presence of small amounts of alkaline or acidic additives. For example, can one alkali hydroxides. Alkali carbonates. Akaliacetate. Alkaline earth oxides and hydroxides, phosphoric, boric, acetic, oxalic, adipic acid or sodium phosphate c. Use potassium bisulfate or tartar as an additive. - You get through this way of working /. was too pure diamines, but multiple distillation is necessary.
Ms wurde nun gefunden, daß man bereits bei einmaliger Destillation zu einem sehr reinen Produkt kommt, wenn man die gesättigten aliphatischen Oiamine mit geringen Mengen von Bleicherde destilliert. Im allgemeinen genügt der Zusatz von 2 0Ai Bleicherde, doch erweist es sich in manchen Fällen — wenn beispielsweise aus Polyamidabfällen zurückgewonnenes Hexamethylendiamin gereinigt werden soll — als /.weckmäßig, bis zu 6°/» anzuwenden.It has now been found that a very pure product is obtained even with a single distillation if the saturated aliphatic oiamines are distilled with small amounts of fuller's earth. In general, the addition of sufficient bleaching earth 2 0 Ai, but it turns out, in some cases - if you want to, for example purified from polyamide waste recovered hexamethylenediamine - as /.weckmäßig, up to 6 apply ° / ».
KX)O Teile Hexamethylendiamin, welches man z. 13. durch Hydrieren von Adipinsäuredinitril gewonnen hat. werden nach der Zugabe von 20 Teilen Bleicherde unter vermindertem Druck fraktioniert über eine Kolonne destilliert.KX) O parts of hexamethylenediamine, which one z. 13. Obtained by hydrogenating adipic dinitrile Has. are after the addition of 20 parts of fuller's earth fractionated under reduced pressure over a Distilled column.
Das erhaltene rein weiße Destillat fällt praktisch fast ohne einen Ausbeuteverlust an. Es entspricht ganz ausgezeichnet den Bedingungen, die an ein für·die Polykondensation mit Dicarbonsäuren zu verwendendes Diamin gestellt werden. Es ist unverdünnt und in wäBriger Lösung monatelang ohne Verfärbung haltbar, und seine wäl.irigen Lösungen können nach der .Veutralisation mit reiner Adipinsäure 24 Stunden auf dem Dampfbad erhitzt werden, ohne sich dabei zu 'erfärbeuThe pure white distillate obtained is obtained with practically no loss in yield. It is quite the same excellent the conditions given to one for · the Polycondensation with dicarboxylic acids to be used diamine. It's undiluted and in aqueous solution can be kept for months without discoloration, and its vicious solutions can after the .Neutralization with pure adipic acid for 24 hours the steam room can be heated without becoming too 'discolored
Der besondere Vorteil, den das eiTindungsgcmäße Verfahren gegenüber der eingangs erwähnten Arbeitsweise bringt, lädt sich eindeutig aus den nachfolgenden Tabellen ablesen.The particular advantage that the induction capacity Process compared to the method of operation mentioned at the beginning brings, loads can be clearly read from the following tables.
Wenn man die Destillation von Hexamethylendiamin unter Zusatz von 3 % Natriumhydroxyd durchführt, so erhält man folgende Werte:If you consider the distillation of hexamethylenediamine with the addition of 3% sodium hydroxide the following values are obtained:
Verfahren zur destillativen Reinigung
gesättigter aliphatischer DiamineProcess for purification by distillation
saturated aliphatic diamines
Anmelder:Applicant:
Vereinigte Glanzstoff-Fabriken A. G,,
Wuppertal-ElberfeldUnited Glossstoff-Fabriken A. G ,,
Wuppertal-Elberfeld
Dr. Gerhard Meyer und Dr. Horst Taul,Dr. Gerhard Meyer and Dr. Horst Taul,
Obernburg (UFr.),
sind als Erfinder genannt wordenObernburg (UFr.),
have been named as inventors
Im Vergleich hierzu ergeben sich folgende Werte bei einer Destillation mit 6°'e Bleicherde (Terrana A Superior; Handelsname):In comparison, the following values result from a distillation with 6 ° 'e fuller's earth (Terrana A. Superior; Trade name):
4545
Die Gilbungsmessung wurde durchgeführt mit einem Hexamethylendiamin, welches mit reinster Adipinsäure in wäßriger Lösung neutralisiert wurde (ρ,,-Wert 7,9 bis 8,0). Die Gilbung wurde durch [•"xtinktiorismessung mittels eines Elko-Photometers von Zeiss durchgeführt, und zwar mit einer 5-cm-Cinette mit einem Euter »S45E« (450 mu).The yellowing measurement was carried out with a hexamethylenediamine which was neutralized with the purest adipic acid in aqueous solution (ρ 1, value 7.9 to 8.0). The yellowing was carried out by means of an electrolytic photometer from Zeiss using a 5 cm Cinette with an udder "S45E" (450 mu).
Claims (1)
Deutsche Patentschrift Nr. 848 194.Considered publications:
German patent specification No. 848 194.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1071711B true DE1071711B (en) | 1959-12-24 |
Family
ID=596339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1071711D Pending DE1071711B (en) | Process for the purification of saturated aliphatic diamines by distillation |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1071711B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4570019A (en) * | 1981-02-25 | 1986-02-11 | Union Carbide Corporation | Method of preparing polyethylene polyamines having improved color |
-
0
- DE DENDAT1071711D patent/DE1071711B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4570019A (en) * | 1981-02-25 | 1986-02-11 | Union Carbide Corporation | Method of preparing polyethylene polyamines having improved color |
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