DE1231435B - Process for the production of copolymers of acrylonitrile and acrolein - Google Patents
Process for the production of copolymers of acrylonitrile and acroleinInfo
- Publication number
- DE1231435B DE1231435B DED45662A DED0045662A DE1231435B DE 1231435 B DE1231435 B DE 1231435B DE D45662 A DED45662 A DE D45662A DE D0045662 A DED0045662 A DE D0045662A DE 1231435 B DE1231435 B DE 1231435B
- Authority
- DE
- Germany
- Prior art keywords
- acrolein
- acrylonitrile
- copolymers
- production
- hydroperoxide
- 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
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 7
- 229920001577 copolymer Polymers 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 239000004296 sodium metabisulphite Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- RRCMEPHKTHMOKV-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical compound OO.OO.CC(C)C1=CC=CC=C1 RRCMEPHKTHMOKV-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 238000003756 stirring Methods 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/44—Acrylonitrile
-
- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
-
- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/26—Copolymerisation of aldehydes or ketones with compounds containing carbon-to-carbon unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerization Catalysts (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. Ο.:Int. Ο .:
C08fC08f
Deutsche Kl.: 39 c-25/01 German class: 39 c -25/01
Nummer: 1231435Number: 1231435
Aktenzeichen: D 45662IV d/39 cFile number: D 45662IV d / 39 c
Anmeldetag: 6. September 1961Filing date: September 6, 1961
Auslegetag: 29. Dezember 1966Opening day: December 29, 1966
Gegenstand des Patents 1 201556 ist ein Verfahren zur Herstellung von Mischpolymerisaten des Acroleins und Acrylnitrils durch Polymerisation von Acrolein und Acrylnitril im Überschuß in wäßriger Lösung in Gegenwart eines ein Hydroperoxyd enthaltenden Redoxsystems, wobei als Redoxsystem die Kombination aus tert.-Butylperoxyd und Natriummetabisulfit eingesetzt wird und die Monomeren entsprechend der Polymerisationsgeschwindigkeit allmählich zugesetzt werden.The subject of patent 1 201556 is a process for the production of copolymers of acrolein and acrylonitrile by polymerization of acrolein and acrylonitrile in excess in aqueous solution in the presence of a hydroperoxide containing redox system, the combination of tert-butyl peroxide and sodium metabisulfite as the redox system is used and the monomers gradually according to the rate of polymerization can be added.
Es wurde nun gefunden, daß mit Erfolg als Hydroperoxyd Cumolhydroperoxyd eingesetzt werden kann.It has now been found that with success as a hydroperoxide Cumene hydroperoxide can be used.
Zu einem Gemisch aus 680 Teilen Wasser, 2,2 Teilen Acrolein, 3,1 Teilen Acrylnitril und 0,61 Teilen Cumolhydroperoxyd läßt man bei 40° C unter Rühren und Durchleiten von Stickstoff eine Lösung von 1,14 Teilen Natriummetabisulfit in 60 Teilen Wasser ao innerhalb von 5 Stunden langsam zutropfen. Nach einer Reaktionsdauer von 4 Stunden werden 0,3 Teile Cumolhydroperoxyd nachgesetzt. Der Ansatz wird nach erfolgter Zugabe von 2lk Stunden bei 40° C gerührt und anschließend mit 740 Teilen einer 40%igen Aluminiumsulfatlösung versetzt. Das Polymerisat wird abgesaugt, mit Wasser gewaschen und im Vakuum bei Raumtemperatur über Schwefelsäure getrocknet.A solution of 1.14 parts of sodium metabisulphite in 60 parts of water is added to a mixture of 680 parts of water, 2.2 parts of acrolein, 3.1 parts of acrylonitrile and 0.61 part of cumene hydroperoxide at 40 ° C. while stirring and passing nitrogen through slowly add dropwise within 5 hours. After a reaction time of 4 hours, 0.3 parts of cumene hydroperoxide are added. After the addition has taken place, the batch is stirred at 40 ° C. for 2 1 k hours and then 740 parts of a 40% strength aluminum sulfate solution are added. The polymer is filtered off with suction, washed with water and dried over sulfuric acid in vacuo at room temperature.
Ausbeute: 52 Teile=96% der Theorie; η rel: 1,43; Stickstoffgehalt (nach Kjeldahl bestimmt): 15,3%.Yield: 52 parts = 96% of theory; η rel: 1.43; Nitrogen content (determined according to Kjeldahl): 15.3%.
Die nach dem Verfahren der Erfindung erhaltenen Mischpolymerisate können zur Herstellung von Filmen und Fäden verwendet werden.Those obtained by the process of the invention Copolymers can be used to make films and threads.
Verfahren zur Herstellung von Copolymerisaten
des Acrylnitrils und AcroleinsProcess for the production of copolymers
of acrylonitrile and acrolein
Anmelder:Applicant:
Deutsche Gold- und Silber-ScheideanstaltGerman gold and silver refinery
vormals Roessler, Frankfurt/M., Weißfrauenstr. 9formerly Roessler, Frankfurt / M., Weißfrauenstr. 9
Als Erfinder benannt:Named as inventor:
Dr. Wolfgang Göltner, Kriftel;Dr. Wolfgang Göltner, Kriftel;
Dr. Paul Schlack, Sterten (Filder)Dr. Paul Schlack, Sterten (Filder)
Claims (1)
Deutsches Patent Nr. 1201556.Legacy Patents Considered:
German Patent No. 1201556.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED45662A DE1231435B (en) | 1961-09-06 | 1961-09-06 | Process for the production of copolymers of acrylonitrile and acrolein |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED45662A DE1231435B (en) | 1961-09-06 | 1961-09-06 | Process for the production of copolymers of acrylonitrile and acrolein |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1231435B true DE1231435B (en) | 1966-12-29 |
Family
ID=7049163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED45662A Pending DE1231435B (en) | 1961-09-06 | 1961-09-06 | Process for the production of copolymers of acrylonitrile and acrolein |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1231435B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201556B (en) | 1959-09-09 | 1965-09-23 | Degussa | Process for the production of mixed polymers of acrylonitrile and acrolein |
-
1961
- 1961-09-06 DE DED45662A patent/DE1231435B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201556B (en) | 1959-09-09 | 1965-09-23 | Degussa | Process for the production of mixed polymers of acrylonitrile and acrolein |
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