DE2051320C3 - Process for the purification of aliphatic dicarboxylic acid mixtures - Google Patents
Process for the purification of aliphatic dicarboxylic acid mixturesInfo
- Publication number
- DE2051320C3 DE2051320C3 DE2051320A DE2051320A DE2051320C3 DE 2051320 C3 DE2051320 C3 DE 2051320C3 DE 2051320 A DE2051320 A DE 2051320A DE 2051320 A DE2051320 A DE 2051320A DE 2051320 C3 DE2051320 C3 DE 2051320C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- nitric acid
- copper
- mixture
- temperature
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/94—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the iron group metals or copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Description
350 kg einer rohen Dicarbonsäureschinelze, die man nach Abdesiillieren von Salpetersäure und Wasser aus einem Oxydationsgemisch erhält und die zu 31 Gewichtsprozent aus Adipinsäure, 20 Gewichtsprozent aus Bernsteinsäure und 47 Gewichtsprozent aus Glutarsäure besteht und noch 0,36 Gewichtsprozent Kupfer und 0,11 Gewichtsprozent Vanadium neben geringen Mengen an Verunreinigungen enthält, werden pro Stunde einem Sambay-Verdampfer mit einer Verdampferfläche von 2,4 m- über eine Pumpe zugeführt. Bei einer Temperatur von 182°C und einem Druck von 10 Torr destillieren 335 kg des Dicarbonsäuregemischs pro Stunde über, wobei sich die Zusammensetzung wie folgt einstellt: 31 Gewichtsprozent Adipinsäure. 21 Gewichtsprozent Bernsteinsäure und 48 Gewichtsprozent Glutarsäure. Dies entspricht einer Ausbeute von 95,5% an reinen Dicarbonsäuren, bezogen auf das Oxydaßonsgemisch vor Abtrennung von Salpetersäure und Wasser. Man erhält einen Rückstand, der die Gesamtmengen der Katalysatorsubstanz enthält und der sehr gut fließfähig ist.350 kg of a crude dicarboxylic acid shell, which is obtained after distilling off nitric acid and water an oxidation mixture obtained and 31 percent by weight of adipic acid, 20 percent by weight consists of succinic acid and 47 percent by weight of glutaric acid and another 0.36 percent by weight Contains copper and 0.11 percent by weight vanadium in addition to small amounts of impurities per hour a Sambay evaporator with an evaporator area of 2.4 m - fed via a pump. At a temperature of 182 ° C and a pressure of 10 torr distill over 335 kg of the dicarboxylic acid mixture per hour, with the composition adjusts as follows: 31 percent by weight adipic acid. 21 percent by weight succinic acid and 48 percent by weight Glutaric acid. This corresponds to a yield of 95.5% of pure dicarboxylic acids, based on on the oxydassons mixture before separation of nitric acid and water. A residue is obtained which contains the total amount of the catalyst substance and which is very fluid.
370 kg einer rohen Dicarbonsä ireschmelze, bestehend aus 29 Gewichtsprozent Adipinsäure,49 Gewichtsprozent Glutarsäure und 20 Gewichtsprozent Bernsteinsäure und daneben 0.41 Gewichtsprozent Kupfer und 0.12 Gewichtsprozent Vanadin neben geringen Mengen an Verunreinigungen, werden pro Stunde einem Sambay-Verdampfer über ε·"ε Pumpe zugeführt. Bei einer Temperatur von 184" C und einem Druck von 5 Torr destillieren 355 kg des Dicar^onsäuregemischs über, das entspricht einer Ausbeute von 96.1 Gewichtsprozent an reinen Dicarbonsäuren.370 kg of a crude dicarboxylic acid melt, consisting from 29 percent by weight adipic acid, 49 percent by weight glutaric acid and 20 percent by weight succinic acid and 0.41 percent by weight of copper and 0.12 percent by weight of vanadium as well as minor ones Amounts of impurities are fed to a Sambay vaporizer per hour via an ε · "ε pump. At a temperature of 184 "C and a pressure of 5 Torr distilled over 355 kg of the dicar ^ onic acid mixture, which corresponds to a yield of 96.1 percent by weight of pure dicarboxylic acids.
Der Sanibay-Rückstand, der 10.1% Kupfer und 2.9% Vanadin neben Spuren von Eisen und Kobalt enthält, wird in einer Verbrennungskammer mit Eirdgas bei 1200C verbrannt. Die Rauchgase werden auf 200 C abgekuhli und passieren anschließend einen Elektrofilter, an dem die Oxide abgeschieden werden. Auf diese Weise werden 95 Gewichtsprozent des Kupfers und Vanadins wiedergewonnen.The Sanibay residue, which is 10.1% copper and 2.9% Vanadium, along with traces of iron and cobalt, is added to a combustion chamber with natural gas Burned 1200C. The smoke gases are at 200 C cool and then pass through an electrostatic precipitator, on which the oxides are deposited. In this way, 95 percent by weight of the copper and Vanadins regained.
Die entscheidende Bedeutung der Verwendung eines Dünnschichtverdampfer^ bei der Durchführung des Verfahrens ergibt sich aus den folgenden Vergleiehslieispielen: The critical importance of using a thin film evaporator ^ when performing the Procedure results from the following comparison examples:
Vergleichsbeispid 1Comparison example 1
In dem gleichen Samb.i>VLrddinpLr wie in ücispicl 1. mit einer Verdampferfläche von 2,4 in-', werden bei 195 C unter Vakuum 335 kg/h Bernsteinsäure iiberdestilliert. Das Destillat enthält 217 kg Bernsteinsäure und 100 kg Bernsteinsäureanhydrid. Außerdem werden in einer Tiefkühlung 18 kg Wasser auskondensiert. Während der Destillation werden 32,5% der Bernsteinsäure in Bernsteinsäureanhydrid umgewandelt.In the same Samb.i> VLrddinpLr as in ücispicl 1. with an evaporator area of 2.4 in ', will be at 195 C under vacuum 335 kg / h succinic acid distilled over. The distillate contains 217 kg of succinic acid and 100 kg of succinic anhydride. In addition, in a deep freezing 18 kg of water condensed. During the distillation, 32.5% of the succinic acid becomes converted to succinic anhydride.
Vergleichsbeispiel 2Comparative example 2
In einem Rundkolben mit Claisenaufsatz werden 25 g geschmolzene Dicarbonsäure eingefüllt. Bei kontinuierlicher Zufuhr von 250 g Dicarbonsäuregemisch/h werden unter Ölbadheizung bei einer Temperatur von Ί84 C in Vakuum kontinuierlich 237 g Dcsüiiat über Kopf abgenommen und kontinuierlich 1 3 g/h Sumpfprodukt abgezogen. Die Destillation wird 4 Stunden kontinuierlich betrieben. Während dieser Zeit wird der Anfangsstand im Kolben gehallen, so daU die durchschnittliche Verweilzeil 6 min beträgt. Bu Verwendung eines Dicarbonsäuregemischs wie in Beispiel 1 erhielt man ein Destillat folgender Zusammensetzung:In a round bottom flask with a Claisen attachment, 25 g melted dicarboxylic acid filled. With a continuous supply of 250 g dicarboxylic acid mixture / h 237 g of Dcsüiiat are continuously over 237 g of Dcsüiiat under oil bath heating at a temperature of Ί84 C in vacuo The top is removed and 1 3 g / h of bottom product is continuously withdrawn. The distillation is 4 hours operated continuously. During this time, the initial level in the flask is kept, so that the average Dwell is 6 min. Bu using a dicarboxylic acid mixture as in Example 1 obtained a distillate of the following composition:
BernsteinsäureSuccinic acid
BernsteinsäureanhydridSuccinic anhydride
GlutarsäureGlutaric acid
GlutarsäurcanhydridGlutaric anhydride
AdipinsäureAdipic acid
J bJ b
32.V32.V
Aus den Beispielen und den Vergleichsbcispiclen ist ersichtlich, daß nur die Destillation des rohen nn.,ir(i(>n säuregemischs in einem Dünnschichtverdampfer /ti einem Destillat führt, das aus der unveränderten Dicarbonsäuren besieht. Destillation ein/eint.·, Komponenten (Bernsteinsäure) oder geringfügige V v-randerung des Destillaiionssystems führen zu Desiillaiin die nicht mehr aus den Gemischen der reinen Dicarbonsäuren bestehen.It can be seen from the examples and the comparative examples that only the distillation of the crude nn., Ir ( i ( > n acid mixture in a thin-film evaporator / ti leads to a distillate which consists of the unchanged dicarboxylic acids. Distillation incorporates., Components ( Succinic acid) or slight changes in the distillation system lead to desililins which no longer consist of mixtures of pure dicarboxylic acids.
Claims (1)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2051320A DE2051320C3 (en) | 1970-10-20 | 1970-10-20 | Process for the purification of aliphatic dicarboxylic acid mixtures |
FR7135822A FR2111003A5 (en) | 1970-10-20 | 1971-10-05 | |
BE773890A BE773890A (en) | 1970-10-20 | 1971-10-13 | PROCESS FOR PURIFYING MIXTURES OF DICARBOXYLIC ACIDS ALIPHATIC |
NL7114294A NL7114294A (en) | 1970-10-20 | 1971-10-18 | |
GB4851171A GB1356620A (en) | 1970-10-20 | 1971-10-19 | Purifying mixtures of aliphatic dicarboxylic acids |
IT53569/71A IT944759B (en) | 1970-10-20 | 1971-10-19 | PROCEDURE FOR THE PURIFICATION OF ALIPHATIC DICARBOXYLIC ACIDS |
JP8255671A JPS5619336B1 (en) | 1970-10-20 | 1971-10-20 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2051320A DE2051320C3 (en) | 1970-10-20 | 1970-10-20 | Process for the purification of aliphatic dicarboxylic acid mixtures |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2051320A1 DE2051320A1 (en) | 1972-04-27 |
DE2051320B2 DE2051320B2 (en) | 1975-09-25 |
DE2051320C3 true DE2051320C3 (en) | 1982-04-29 |
Family
ID=5785588
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2051320A Expired DE2051320C3 (en) | 1970-10-20 | 1970-10-20 | Process for the purification of aliphatic dicarboxylic acid mixtures |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS5619336B1 (en) |
BE (1) | BE773890A (en) |
DE (1) | DE2051320C3 (en) |
FR (1) | FR2111003A5 (en) |
GB (1) | GB1356620A (en) |
IT (1) | IT944759B (en) |
NL (1) | NL7114294A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1208239A (en) * | 1983-06-07 | 1986-07-22 | Christian Leboeuf | Semi-refined mixed dicarboxylic acids |
-
1970
- 1970-10-20 DE DE2051320A patent/DE2051320C3/en not_active Expired
-
1971
- 1971-10-05 FR FR7135822A patent/FR2111003A5/fr not_active Expired
- 1971-10-13 BE BE773890A patent/BE773890A/en not_active IP Right Cessation
- 1971-10-18 NL NL7114294A patent/NL7114294A/xx unknown
- 1971-10-19 IT IT53569/71A patent/IT944759B/en active
- 1971-10-19 GB GB4851171A patent/GB1356620A/en not_active Expired
- 1971-10-20 JP JP8255671A patent/JPS5619336B1/ja active Pending
Non-Patent Citations (1)
Title |
---|
NICHTS-ERMITTELT |
Also Published As
Publication number | Publication date |
---|---|
GB1356620A (en) | 1974-06-12 |
DE2051320A1 (en) | 1972-04-27 |
IT944759B (en) | 1973-04-20 |
JPS5619336B1 (en) | 1981-05-07 |
NL7114294A (en) | 1972-04-24 |
FR2111003A5 (en) | 1972-06-02 |
BE773890A (en) | 1972-04-13 |
DE2051320B2 (en) | 1975-09-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C3 | Grant after two publication steps (3rd publication) | ||
8330 | Complete disclaimer |