DE1443724A1 - Process for the oxidation of aldehydes - Google Patents

Process for the oxidation of aldehydes

Info

Publication number
DE1443724A1
DE1443724A1 DE19641443724 DE1443724A DE1443724A1 DE 1443724 A1 DE1443724 A1 DE 1443724A1 DE 19641443724 DE19641443724 DE 19641443724 DE 1443724 A DE1443724 A DE 1443724A DE 1443724 A1 DE1443724 A1 DE 1443724A1
Authority
DE
Germany
Prior art keywords
oxygen
aldehydes
oxidation
silver
bicarbonates
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
Application number
DE19641443724
Other languages
German (de)
Inventor
Bier Dr Gerhard
Hartel Dr Heinz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dynamit Nobel AG
Original Assignee
Dynamit Nobel AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dynamit Nobel AG filed Critical Dynamit Nobel AG
Publication of DE1443724A1 publication Critical patent/DE1443724A1/en
Pending legal-status Critical Current

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
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D5/00—Rigid or semi-rigid containers of polygonal cross-section, e.g. boxes, cartons or trays, formed by folding or erecting one or more blanks made of paper
    • B65D5/02—Rigid or semi-rigid containers of polygonal cross-section, e.g. boxes, cartons or trays, formed by folding or erecting one or more blanks made of paper by folding or erecting a single blank to form a tubular body with or without subsequent folding operations, or the addition of separate elements, to close the ends of the body
    • B65D5/16—Rigid or semi-rigid containers of polygonal cross-section, e.g. boxes, cartons or trays, formed by folding or erecting one or more blanks made of paper by folding or erecting a single blank to form a tubular body with or without subsequent folding operations, or the addition of separate elements, to close the ends of the body the tubular body being formed with an aperture or removable portion arranged to allow removal or insertion of contents through one or more sides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D5/00—Rigid or semi-rigid containers of polygonal cross-section, e.g. boxes, cartons or trays, formed by folding or erecting one or more blanks made of paper
    • B65D5/42—Details of containers or of foldable or erectable container blanks
    • B65D5/54—Lines of weakness to facilitate opening of container or dividing it into separate parts by cutting or tearing
    • B65D5/5405—Lines of weakness to facilitate opening of container or dividing it into separate parts by cutting or tearing for opening containers formed by erecting a blank in tubular form
    • B65D5/542—Lines of weakness to facilitate opening of container or dividing it into separate parts by cutting or tearing for opening containers formed by erecting a blank in tubular form the lines of weakness being provided in the container body
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids

Description

TroledVrf, den SoΓ\'. 1964TroledVrf, the SoΓ \ '. 1964

DTIlMIT SOBBI. ArTIE»QE3ELL3CHAn Troisdorf / Be*. KölnDTIlMIT SOBBI. ArTIE »QE3ELL3CHAn Troisdorf / Be *. Cologne

Verfahren iur Oxydation τοη AldehydenProcess iur oxidation τοη aldehydes

Sm tat bekannt, Aldehyde »it Gemischen au· Kupfer-(ll)-oxyd and geringen Mengen Silberoxyd in Gegenwart τοη Alkalihydroxyden, wie sun Beispiel Natrium- oder Kaliumhydroxyd, la wässerigen Medina >u Salsen der entsprechenden Carbonsäuren se oxydieren· Der 3auerstoffüberträger wurde dabei gesondert hergestellt. Später wurde dann vorgeschlagen, dieees Verfahren in rersohledener iiiohtung zu verbessern. So wurde das Oxydationsmittel in Gegenwart des au oxydierenden Aldehyds auegefallt, und eine Regenerierung des Oxydationsmittels erfolgte duroh Behandlung einer Suspension desselben in rerdünnter Matron- oder Kalilauge duroh Behandlung mit Sauerstoff oder Sauerstoff enthaltenden Oasen, wie Luft, bei Temperaturen Bwisehea etwa 60 bis etwa 10O0O. Auf diese Weise konnte, der ProseB kontinuierlich gestaltet werden. Weiterhin wurde vorgesohlagea, anstatt τοη Kupfer-(ll)-oxyd-8ilberexyd-Gemisohen, ein Kupfer-(il)-oxyd eimusotsen, das gerinne Mengen metalllsohes Silber eathielt, wobei nuoh dieses Oxydationsmittel in der oben angegebenen Weise regeneriert werden konnte« Allerdings auSte »an bei allen diesen Verfahren unter relativ milden Bedingungen, >·3· bei groSer Verdünnung, arbeiten, um Ganniiaro-Beak,tlonen *u vermeiden, It was known that aldehydes were oxidized with mixtures of copper (II) oxide and small amounts of silver oxide in the presence of alkali hydroxides, such as sodium or potassium hydroxide, for example, aqueous medina and salsa of the corresponding carboxylic acids manufactured separately. It was later proposed to improve this process in terms of processing. Thus, the oxidizing agent was precipitated in the presence of the oxidizing aldehyde, and the oxidizing agent was regenerated by treating a suspension of the same in dilute Matron or potassium hydroxide solution by treating with oxygen or oxygen-containing oases, such as air, at temperatures Bwisehea about 60 to about 10O 0 O. In this way, the ProseB could be designed continuously. Furthermore, instead of τοη copper (II) oxide-silver oxide mixture, a copper (II) oxide was used, which contained coagulated amounts of metal-free silver, whereby this oxidizing agent could only be regenerated in the above-mentioned manner »Work on all of these processes under relatively mild conditions,> · 3 · at great dilution, in order to avoid Ganniiaro-Beak, cloning,

B* wurde nun gefunden, daß man die erwähnten Nachteile Termeidee kann, weaa aaa bei der Oxydation τοη Aldehyden mittels Ou-(II)-Verbindungen in Gegenwart τοη Silber oder Silberverbindungen in alkalisohem, wässerigem Medium la der Weise arbeitet, daB aan anateile der bisher verwendeten Alkal!hydroxyde die eatspreoheaaen Carboaate oder Bloarbonate einsetst, d.h.».B, Matriumoarbonat, Vatriuabloarbonat, Kaliumoarbonat oder Xeliuabioarbonat« Das verbrauchte Oxydationsmittel kann dabei •Wafolls la Gegenwart der genannten Carbonate bzw. Bicarbonate iarek lenaadlmag alt Sauerstoff oder Sauerstoff enthaltenden Oasen la wässerig·» tuspension bei Temperaturen τοη etwaB * it has now been found that the mentioned disadvantages term idea can, weaa aaa in the oxidation τοη aldehydes by means of Ou- (II) compounds in the presence of τοη silver or silver compounds in an alkaline, aqueous medium la works in such a way that aanate parts of the previously used alkali hydroxides die eatspreoheaaen Using carboaate or bloarbonate, i.e. ». B, Matrium carbonate, vatriu carbonate, potassium carbonate or Xeliuabioarbonat «The used oxidizing agent can • Wafolls la presence of the carbonates or bicarbonates mentioned iarek lenaadlmag alt oxygen or containing oxygen Oases la watery suspension at temperatures τοη about

809902/0886 BAD ORIGINAL809902/0886 ORIGINAL BATHROOM

60 bis etwa 10O0G regeneriert werden« >o daß auoh in diesem falle ein kontinuierliches Arbeiten gewährleistet ist· ..-·-, -60 to about 10O 0 G can be regenerated «> o that also in this case continuous work is guaranteed · ..- · -, -

Beispiel 1tExample 1t

In 2^0 ml einer vorgelegten 20 #igen wäaeerigen Sodalösung wurden innerhalb τοη wenigen Minuten gleichzeitig Lösungen von 73 g Cu (MO-)2 , 3H2O und 12 g AgIO, in 250 ml Wasser und 5,6 g Akrolein, stabilisiert mit 1 fo Hydrochinon besogen auf das Al dehydgewicht, in 100 ml Wasser eingetropft. Die Heaktionutemperatur lag bei etwa 25°C. Anschließend wurde aufgeheist und letzte Spuren noch nicht umgesetsten Akroleins mittels Durchblasen von Stickstoff entfernt. Der dunkelbraun gefärbte Festkörper wurde isoliert und der Sehalt der Lösung an akrylsaurem Natrium titrimetrisoh au Q?,8 96 der Theorie bestimmt.In 2 ^ 0 ml of a 20 # aqueous soda solution submitted, solutions of 73 g Cu (MO-) 2 , 3H 2 O and 12 g AgIO, in 250 ml water and 5.6 g acrolein, were stabilized with within a few minutes 1 fo hydroquinone sucked on the aldehyde weight, added dropwise to 100 ml of water. The reaction temperature was around 25 ° C. It was then heated up and the last traces of unreacted acroleins were removed by purging with nitrogen. The dark brown colored solid was isolated and the content of the solution in acrylic acid sodium titrimetrisoh au Q?, 8 96 of theory was determined.

D*r Festkörper wurde nun in siedender 20 $iger wässeriger W&tri-djakarbonatlüBung alt Sauerstoff oder Luft behandelt und naoh kuraaeitigem Durohleiten von Stickstoff (sur Vermeidung explosiver Gemische von Akrolein mit reetliohem Sauerstoff) erneut mit 5»6 g Akrolein in 100 ml Yasser versetat. Mach der aufarbeitung, wie oben beschrieben, lag der titrimetrieoh bestimmte Gehalt der Lösung an akrylsaurem Natrium bei 85,2 # der Theorie.The solid became more watery in boiling 20% W & tri-djakarbonatlüBung old treated with oxygen or air and after thermosetting nitrogen on the Kura side (to avoid explosive mixtures of acrolein with reetliohem Oxygen) again mixed with 5 »6 g of acrolein in 100 ml of water. After the work-up, as described above, the titrimetrically determined content of the solution was acrylic acid Sodium at 85.2 # of theory.

Beispiel 2iExample 2i

96,5 g Gu (MO3)2 , 3 H2O, 53 β Ha2CO3 und 11,2 g Akrolein wurden nacheinander in soviel Wasser eingetragen, daß eine 5 gew.-^ige wässerige Lösung des Aldehyds resultierte, der zusätalioh mit 1 i» Hydrochinon, bezogen auf das Aldehydgewicht, stabilisiert wurde. Sann wurde innerhalb einer Tiertelstunde aufgeheist, letate Spuren Akrolein wurden durch eingeblasenen Stickstoff entfernt und in der anschließend isolierten Lösung wurde der Gehalt an akrylsnurem Natrium bu 76,1 $> der Theorie bestimmt. Allylalkohol konnte nicht nachgewiesen werden.96.5 g of Gu (MO 3 ) 2 , 3 H 2 O, 53 β Ha 2 CO 3 and 11.2 g of acrolein were added one after the other to so much water that a 5% strength by weight aqueous solution of the aldehyde resulted was additionally stabilized with 1 » hydroquinone, based on the aldehyde weight. Mused was Heist within a Tiertelstunde, letate traces of acrolein were removed by the injected nitrogen, and then isolated in the solution, the content of sodium was akrylsnurem bu $ 76.1> determined theory. Allyl alcohol could not be detected.

Daneben wurden 96,5 g Cu (N0,)2 , 3 H2O, 40 g NaOH und 11,2 g Akrolein nacheinander in soviel tfaseer eingetragen, daß eine 5 gew.-jiige wässerige Lösung des Aldehyde resultierte, der.ausätslioh mit 1 i» Hydrochinon, beaogen auf das AldehydgewiohtIn addition, 96.5 g of Cu (NO,) 2 , 3 H 2 O, 40 g of NaOH and 11.2 g of acrolein were added one after the other to so much tfaseer that a 5% strength by weight aqueous solution of the aldehyde resulted, which was also contained 1 i » Hydroquinone, weighted on the aldehyde

BAD ORIGINAL 809902/0886BATH ORIGINAL 809902/0886

Wtkbilieltort wurde. Haoh der Aufarbeitung geaäß Abschnitt Γ dieses Beispiels wurde der Gehalt der Lösung an akrylsaurea Vatriux su 65*0 i» der Theorie und der Gehalt an Allylalkohol sn 12,6 i» der Theorie ermittelt.Wtkbilieltort was. Haoh workup geaäß section Γ of this example was the content of the solution akrylsaurea Vatriux below 65 * 0 i "theory and the content of allyl alcohol sn 12.6 i" determines the theory.

1*01 * 0

BAD 902/088 6BATH 902/088 6

Claims (1)

Verfahren zur Oxydation von Aldehyden mittel· Cu-(Xl)«Verbindungen in Gegenwart von Silber oder Silberverbindungen in alkalische*» wässerigem Medium» dadurch gekennzeichnett daß man anstelle der bisher verwendeten Alkalihydroxide die entsprechenden Carbonate oder Bicarbonate eineetat«,A process for the oxidation of aldehydes in t medium · Cu (Xl) 'compounds in the presence of silver or silver compounds in alkaline * "aqueous medium" in the fact that a budget instead of the previously used alkali metal hydroxides, the corresponding carbonates or bicarbonates, " Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die verwendeten Sauerstoffüberträger in wässeriger Suspension in Gegenwart von Alkalioarbonaten oder -bicarbonaten durch Behandlung mit Sauerstoff oder Sauerstoff enthaltenden Gasen bei Temperaturen von etwa 60 bis etwa 1000O regeneriert·Process according to claim 1, characterized in that the oxygen carriers used are regenerated in aqueous suspension in the presence of alkali carbonates or bicarbonates by treatment with oxygen or oxygen-containing gases at temperatures of about 60 to about 100 0 O · Dr.Mi/Hä.Dr Mi / Hä. BAD ORIGJNALBAD ORIGJNAL 809 902/0886809 902/0886
DE19641443724 1964-01-17 1964-02-13 Process for the oxidation of aldehydes Pending DE1443724A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DED43372A DE1195754B (en) 1964-01-17 1964-01-17 Process for the preparation of alkali salts of carboxylic acids by oxidation of aldehydes
DED0043617 1964-02-13
DED0043627 1964-02-14
DE1964D0043788 DE1443726A1 (en) 1964-01-17 1964-04-03 Process for the production of alkali salts of carboxylic acids by oxidation of aldehydes

Publications (1)

Publication Number Publication Date
DE1443724A1 true DE1443724A1 (en) 1969-01-09

Family

ID=27436776

Family Applications (4)

Application Number Title Priority Date Filing Date
DED43372A Pending DE1195754B (en) 1964-01-17 1964-01-17 Process for the preparation of alkali salts of carboxylic acids by oxidation of aldehydes
DE19641443724 Pending DE1443724A1 (en) 1964-01-17 1964-02-13 Process for the oxidation of aldehydes
DE19641486300 Withdrawn DE1486300A1 (en) 1964-01-17 1964-02-14 Lidless packaging
DE1964D0043788 Pending DE1443726A1 (en) 1964-01-17 1964-04-03 Process for the production of alkali salts of carboxylic acids by oxidation of aldehydes

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DED43372A Pending DE1195754B (en) 1964-01-17 1964-01-17 Process for the preparation of alkali salts of carboxylic acids by oxidation of aldehydes

Family Applications After (2)

Application Number Title Priority Date Filing Date
DE19641486300 Withdrawn DE1486300A1 (en) 1964-01-17 1964-02-14 Lidless packaging
DE1964D0043788 Pending DE1443726A1 (en) 1964-01-17 1964-04-03 Process for the production of alkali salts of carboxylic acids by oxidation of aldehydes

Country Status (11)

Country Link
US (1) US3315875A (en)
BE (2) BE658222A (en)
CH (1) CH417466A (en)
DE (4) DE1195754B (en)
FR (1) FR1420965A (en)
GB (2) GB1023728A (en)
IL (1) IL22854A (en)
LU (1) LU47803A1 (en)
NL (2) NL6500505A (en)
NO (1) NO117730B (en)
SE (1) SE311275B (en)

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Also Published As

Publication number Publication date
GB1023728A (en) 1966-03-23
BE658222A (en) 1965-04-30
LU47803A1 (en) 1965-03-15
IL22854A (en) 1969-04-30
DE1443726A1 (en) 1969-03-20
SE311275B (en) 1969-06-02
CH417466A (en) 1966-07-15
GB1054234A (en)
NO117730B (en) 1969-09-15
BE659584A (en) 1965-05-28
DE1195754B (en) 1965-07-01
US3315875A (en) 1967-04-25
DE1486300A1 (en) 1969-01-09
NL6500505A (en) 1965-07-19
NL6501765A (en) 1965-08-16
FR1420965A (en) 1965-12-10

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