DE590235C - Process for the production of cellulose esters which contain halogen-substituted fatty acid groups - Google Patents
Process for the production of cellulose esters which contain halogen-substituted fatty acid groupsInfo
- Publication number
- DE590235C DE590235C DEE42526D DEE0042526D DE590235C DE 590235 C DE590235 C DE 590235C DE E42526 D DEE42526 D DE E42526D DE E0042526 D DEE0042526 D DE E0042526D DE 590235 C DE590235 C DE 590235C
- Authority
- DE
- Germany
- Prior art keywords
- fatty acid
- acid groups
- production
- cellulose esters
- cellulose
- 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
- 229920002678 cellulose Polymers 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 6
- 125000005313 fatty acid group Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000001913 cellulose Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920002301 cellulose acetate Polymers 0.000 description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 4
- KVNUTNMNBSFOAS-UHFFFAOYSA-N 2,2-dibromooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(Br)(Br)C(O)=O KVNUTNMNBSFOAS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940081735 acetylcellulose Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- IFWABNZFIRDYPW-UHFFFAOYSA-N 2,2,3,3-tetrachlorooctadecanoic acid Chemical compound ClC(C(C(=O)O)(Cl)Cl)(CCCCCCCCCCCCCCC)Cl IFWABNZFIRDYPW-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000003197 gene knockdown Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- SUEDKWOPFSSZJW-UHFFFAOYSA-L magnesium diperchlorate trihydrate Chemical compound O.O.O.[Mg++].[O-][Cl](=O)(=O)=O.[O-][Cl](=O)(=O)=O SUEDKWOPFSSZJW-UHFFFAOYSA-L 0.000 description 1
- CNCMVGXVKBJYNU-UHFFFAOYSA-N methyl oxane-4-carboxylate Chemical compound COC(=O)C1CCOCC1 CNCMVGXVKBJYNU-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005406 washing Methods 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
- C08B3/14—Preparation of cellulose esters of organic acids in which the organic acid residue contains substituents, e.g. NH2, Cl
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
Verfahren zur Herstellung von Celluloseestern, die halogensubstituierte Fettsäuregruppen enthalten Die Erfindung bezieht sich auf ein Verfahren zur Herstellung halogensubstituierte Fettsäuregruppen enthaltender Ester der Cellulose. Der Zweck der Erfindung ist, ein vereinfachtes und verhältnismäßig billig durchzuführendes Verfahren zur Herstellung solcher Estern durch eine einzige Reaktion zu schaffen.Process for the preparation of cellulose esters which are halogen-substituted Containing fatty acid groups The invention relates to a process for the preparation Esters of cellulose containing halogen-substituted fatty acid groups. The purpose of the invention is simplified and relatively inexpensive to implement To provide methods of making such esters by a single reaction.
Gemäß dem Hauptpatent wird Gellulose mit halogensubstituierten, mehr als 5 C-Atome enthaltenden Fettsäuren und halogensubstituierten Anhydriden organischer Säuren, gegeb:enenfalls unter Zusatz eines Katalysators, erhitzt.According to the main patent, gelulose with halogen-substituted ones becomes more than 5 carbon atoms containing fatty acids and halogen-substituted anhydrides of organic Acids, if necessary with the addition of a catalyst, heated.
Es hat sich ergeben, daß solche Ester dadurch hergestellt werden können, daß. als Ausgangsmaterial teilweise acetylierte Cellulose verwendet wird.It has been found that such esters can be made by that. partially acetylated cellulose is used as the starting material.
Als Ausgangsmaterial werden daher zweckmäßig in Aceton lösliche, von 34,5 bis 37,50/0 Aoetyl .enthaltende Celluloseacetate verwendet. Diese sind, wie ihre Fähigkeit, biegsame und durchscheinende Filme aus ihren Lösungen herzustellen, -ergibt, im wesentlichen unabgebaut. Es sind hydrolysierte Celluloseacetate, deren ursprünglicher Acetylprozentsatz oberhalb 43 lag, jedoch bei der Deacetylierung während der Hydrolyse herabgemindert wird. Selbstverständlich können deacetylierte Celluloseacetate mit außerhalb der obenerwähnten Grenze liegenden Acetylwerten benutzt werden, doch sind -die oben beschriebenen Aoetate wertvoll und ergeben zufriedenstellende Ergebnisse.As a starting material, therefore, appropriately soluble in acetone, of Cellulose acetates containing 34.5 to 37.50 / 0 aoetyl. These are how their ability to make flexible and translucent films from their solutions, - yields, essentially undegraded. There are hydrolyzed cellulose acetates, their original percentage of acetyl was above 43 but upon deacetylation is reduced during hydrolysis. Of course, deacetylated Cellulose acetates with acetyl values outside the above-mentioned limit are used but the aetates described above are valuable and give satisfactory results Results.
Nachstehendes Beispiel erläutert das Verfahren nach der Erfindung, und in diesem Beispiel sind die einzelnen Teile nach Gewicht angegeben.The following example explains the method according to the invention, and in this example the individual parts are given by weight.
5 Teile eines teilweise deacetylierten Celluloseacetates mit 37,5% Acetyl werden einer Mischung aus 2o Teilen Chloressigsäureanhydrid und 4o Teilen Chloressigsäure zugesetzt. Sobald alle Bestandteile gelöst worden sind, werden der Mischung 2o Gewichtsteile einer 9 : i o Dibrom-Stearin-Säure und 0,05 Teile Magnesium-Perchlorat-Trihydrat zugesetzt. Die Mischung wird für etwa Stunden auf 6o bis 65° gehalten. Das Niederschlagen und Waschen wird mit Methylalkohol _ durchgeführt. _ Das so erzielte Cellulose-ACet0-1)ibrom-Steara;t enthält 15,7 % Brom, ist in Aceton löslich und kann zu biegsamen durchsichtigen Filmen außerordentlich geringer Entzündbarkeit verarbeitet werden. Der Prozentsatz des Broms in dem Produln kann auf i 9, 5 % dadurch erhöht werden, daß mit einer Acetylcellulose begonnen wird, die 34,5% Acetyl enthält.5 parts of a partially deacetylated cellulose acetate with 37.5% Acetyl is a mixture of 20 parts of chloroacetic anhydride and 40 parts Chloroacetic acid added. Once all of the ingredients have been dissolved, the Mixture of 20 parts by weight of a 9: 10 dibromostearic acid and 0.05 part of magnesium perchlorate trihydrate added. The mixture is held at 60 ° to 65 ° for about hours. That Knock down and washing is carried out with methyl alcohol _. _ The cellulose ACet0-1) ibrom-steara obtained in this way contains 15.7% bromine, is soluble in acetone and can become pliable clear Films of extremely low flammability can be processed. The percentage of the bromine in the product can be increased to 9.5% by using a Acetyl cellulose is started, which contains 34.5% acetyl.
Wenn bei diesem Ausführungsbeispiel 9 : 1o Dichlor-Stearin-Säure an Stelle der Dibrom-Stearin-Säure benutzt wird, werden entsprechende Cellulose;Aeeto-Dichlor-Stearate erzielt, welche abhängig von dem jeweils Verwendung findenden hydrolysierten Celluloseacetat von 7,3 bis 9,6% Chlor enthalten. Wenn an Stelle der Dibrom-Stearin-Säure bei diesem Beispiel Tetrachlor-Stearin-Säure verwendet wird, werden Cellulose-Aoeto-Tetrachlor-Stearate erzielt, die von 2o bis 30% Chlor enthalten. Diese sind in Aceton löslich und liefern biegsame Filme.If in this embodiment example 9: 1o dichlorostearic acid on Instead of dibromostearic acid, the corresponding cellulose is used; aeeto-dichlorostearate achieved, which depends on the particular use of hydrolyzed cellulose acetate contain from 7.3 to 9.6% chlorine. If in place of the dibromostearic acid with this one Example tetrachlorostearic acid is used, cellulose aoeto-tetrachlorostearate obtained, which contain from 2o to 30% chlorine. These are soluble in acetone and deliver flexible films.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US590235XA | 1928-01-18 | 1928-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE590235C true DE590235C (en) | 1934-01-04 |
Family
ID=22020319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEE42526D Expired DE590235C (en) | 1928-01-18 | 1929-01-17 | Process for the production of cellulose esters which contain halogen-substituted fatty acid groups |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE590235C (en) |
-
1929
- 1929-01-17 DE DEE42526D patent/DE590235C/en not_active Expired
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