DE273706C - - Google Patents
Info
- Publication number
- DE273706C DE273706C DENDAT273706D DE273706DA DE273706C DE 273706 C DE273706 C DE 273706C DE NDAT273706 D DENDAT273706 D DE NDAT273706D DE 273706D A DE273706D A DE 273706DA DE 273706 C DE273706 C DE 273706C
- Authority
- DE
- Germany
- Prior art keywords
- insoluble
- acid
- acetic acid
- chloroform
- acetyl
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
- 229920002678 cellulose Polymers 0.000 claims description 16
- 235000010980 cellulose Nutrition 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 229960000583 Acetic Acid Drugs 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical compound OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 description 4
- 238000006640 acetylation reaction Methods 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- AOGYCOYQMAVAFD-UHFFFAOYSA-N Chloroformic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 229940081735 acetylcellulose Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-Tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- UIKHKLFBHLPAPO-UHFFFAOYSA-N 2,3-diacetyl-2,3-dihydroxybutanedioic acid Chemical class CC(=O)C(O)(C(O)=O)C(O)(C(C)=O)C(O)=O UIKHKLFBHLPAPO-UHFFFAOYSA-N 0.000 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N Nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000003945 chlorohydrins Chemical class 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- -1 etc. Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/22—Post-esterification treatments, including purification
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
.-Jn 273706-KLASSE 12 o. GRUPPE .-Jn 273706- CLASS 12 or GROUP
KNOLL & CO. in LUDWIGSHAFEN a. Rh.KNOLL & CO. in LUDWIGSHAFEN a. Rh.
Patentiert im Deutschen Reiche vom 29. April 1911 ab. Patented in the German Empire on April 29 , 1911.
Nach den bekannten Verfahren der Acetylierung von Cellulose und ihr nahestehenden Umwandlungsprodukten ohne oder in Gegenwart von Katalysatoren erhält man Acetylcellulosen, die in Essigsäure und in Chloroform löslich sind.According to the known process of acetylation of cellulose and related ones Conversion products without or in the presence of catalysts result in acetyl celluloses, which are soluble in acetic acid and in chloroform.
Es wurde nun gefunden, daß bei geeigneter Anwendung der verschiedensten Katalysatoren, wie Schwefelsäure, Neutralsalzen, Bisulfaten,It has now been found that with suitable use of the most varied of catalysts, such as sulfuric acid, neutral salts, bisulfates,
ίο organischen Sulfosäuren, Sulfinsäuren usw., bei Acetylierungsverfahren der Cellulosen die zunächst gebildeten, in Essigsäure und Chloroform löslichen Acetylcellulosen bei längerer Berührung mit diesen Katalysatoren je nach der Art des Katalysators und seiner Anwendungsweise nach Menge und Temperaturen mehr oder weniger rasch in neue Acetylcellulosen übergehen, die sich durch ihre Unlöslichkeit in Chloroform und in Essigsäure auszeichnen. Für diese Umwandlung ist es einerlei, ob die in Chloroform und in Essigsäure löslichen Acetycellulosen in Lösung oder im ungelösten Zustande vorliegen; in jedem Falle gehen sie bei geeigneter Berührung mit solchen Katalysatoren in die genannten unlöslichen Produkte über.ίο organic sulfonic acids, sulfinic acids, etc., with Acetylation process of the celluloses initially formed, in acetic acid and chloroform soluble acetyl celluloses after prolonged contact with these catalysts depending on Depending on the type of catalyst and its method of use, the amount and the temperature change more or less rapidly into new acetyl celluloses pass over, which are characterized by their insolubility in chloroform and in acetic acid. For this conversion it does not matter whether the acetycelluloses, which are soluble in chloroform and acetic acid, are in solution or are in the unsolved state; in any case they go along with appropriate contact such catalysts into the insoluble products mentioned.
Beispielsweise erhält man in Essigsäure und in Chloroform unlösliche Acetylcellulosen, wenn man gemäß den Verfahren der Patentschriften 159524, 180667, 203178 und anderen in Gegenwart, teils auch in Abwesenheit von Lösungsmitteln für Acetylcellulose die Acetylierung der Cellulose, wie bekannt, durchführt und dann z. B. bei Zimmertemperatur stehen läßt, bis entnommene Proben in Essigsäure und in Chloroform unlöslich geworden sind. Man erhält dieselben unlöslichen Acetylcellulosen auch, wenn man die fertigen, in Essigsäure und in Chloroform löslichen Acetylcellulosen in Lösungsmitteln oder ohne Lösungsmittel mit geeigneten Katalysatoren in Berührung bringt.For example, acetylcelluloses which are insoluble in acetic acid and in chloroform are obtained if one according to the procedures of patents 159524, 180667, 203178 and others in the presence, partly also in the absence of solvents for acetyl cellulose the acetylation the cellulose, as is known, carries out and then z. B. lets stand at room temperature, until samples taken have become insoluble in acetic acid and chloroform. You get the same insoluble acetyl celluloses, too, if the finished ones are dissolved in acetic acid and in Chloroform soluble acetyl celluloses in solvents or without solvents with suitable Bringing catalysts into contact.
Beispielsweise wird eine fertige Lösung von Acetylcellulose in Eisessig mit Schwefelsäure, Sulfoessigsäure, Chlorzink usw. versetzt, bis die entstandenen, anfangs gallertartig abgeschiedenen Produkte sich in feste, in Chloroform und in Essigsäure unlösliche Massen verwandelt haben.For example, a ready-made solution of acetyl cellulose in glacial acetic acid with sulfuric acid, Sulphoacetic acid, zinc chloride, etc. are added until the resulting, initially gelatinous deposited Products are transformed into solid masses that are insoluble in chloroform and acetic acid to have.
Ferner können fertige feste Acetylcellulosen in geeignet verteilter Form z. B. mit Benzol, wenig Sulfoessigsäure und einem Lösungsmittel für Sulfoessigsäure, z. B. Essigsäureanhydrid oder Essigsäure, Übergossen und so lange damit in Berührung gelassen werden, bis entnommene Proben die gewünschte Unlöslichkeit zeigen.Furthermore, ready-made solid acetyl celluloses can be used in a suitably distributed form, for. B. with benzene, little sulfoacetic acid and a solvent for sulfoacetic acid, e.g. B. acetic anhydride or acetic acid, poured over it and left in contact with it until removed Samples show the desired insolubility.
Diese neuen Acetylcellulosen sind in anderen Lösungsmitteln, wie Ameisensäure, Oxysäuren und deren Estern, sowie den Säurederivaten der Oxysäuren und deren Estern, wie Weinsäureester usw., Diacetylweinsäureester usw., in den Säurederivaten des Glycerins, ζ. B. in den Acetinen und Chlorhydrinen, in Nitromethan, Acetylentetrachlorid usw. löslich. Sie stellen technisch wertvolle Produkte dar, die für Kunstfäden, Films, Celluloid, Lacke usw. für sich und in Gemischen mit anderen Stoffen Verwendung finden können. Innige Gemische mit anderen Stoffen stellt man zweckmäßig durch ZumischungThese new acetyl celluloses are in other solvents such as formic acid, oxy acids and their esters, as well as the acid derivatives of oxy acids and their esters such as tartaric acid esters, etc., diacetyl tartaric acid esters etc., in the acid derivatives of glycerol, ζ. B. in the acetins and chlorohydrins, soluble in nitromethane, acetylene tetrachloride, etc. They make technically valuable products that can be used for synthetic threads, films, celluloid, lacquers, etc. for themselves and in mixtures with other substances. Intimate mixtures with other substances are expediently made by admixing them
solcher Stoffe bei der Bereitung dieser unlöslichen Acetylcellulosen aus ihren gelösten löslichen Vertretern dar, wobei sich die zugemischten Stoffe beim Unlöslichwerden der Acetylcellulosen mit diesen abscheiden.such substances in the preparation of these insoluble acetyl celluloses from their dissolved soluble ones Representatives, the mixed substances being deposited with the acetylcelluloses when they become insoluble.
Bei dem vorliegenden Verfahren findet keine Verseifung durch Wasser statt, wie bei der bekannten Überführung von Acetylcellulosen in acetonlösliche Produkte. Stärker verseifendIn the present process, there is no saponification by water, as in the known conversion of acetyl celluloses into acetone-soluble products. More saponifying
ίο wirkende Katalysatoren, wie Sulfoessigsäure und Schwefelsäure, können deshalb bei dem vorliegenden Verfahren nur bei Abwesenheit von Wasser angewendet werden.ίο acting catalysts, such as sulfoacetic acid and sulfuric acid, can therefore only be used in the present process in their absence applied by water.
Claims (2)
Publications (1)
Publication Number | Publication Date |
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DE273706C true DE273706C (en) |
Family
ID=530134
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT273706D Active DE273706C (en) |
Country Status (1)
Country | Link |
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DE (1) | DE273706C (en) |
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- DE DENDAT273706D patent/DE273706C/de active Active
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