US999236A - Process of preparing cellulose esters in definite forms. - Google Patents
Process of preparing cellulose esters in definite forms. Download PDFInfo
- Publication number
- US999236A US999236A US34577606A US1906345776A US999236A US 999236 A US999236 A US 999236A US 34577606 A US34577606 A US 34577606A US 1906345776 A US1906345776 A US 1906345776A US 999236 A US999236 A US 999236A
- Authority
- US
- United States
- Prior art keywords
- cellulose esters
- cellulose
- preparing cellulose
- definite forms
- esters
- 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 - Lifetime
Links
- 229920002678 cellulose Polymers 0.000 title description 11
- 238000000034 method Methods 0.000 title description 8
- 239000001913 cellulose Substances 0.000 description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000005406 washing Methods 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
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- -1 fatty acid esters Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 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
- C08B1/00—Preparatory treatment of cellulose for making derivatives thereof, e.g. pre-treatment, pre-soaking, activation
- C08B1/02—Rendering cellulose suitable for esterification
Definitions
- PROCESS FOR PREPARING CELLULOSE ESTERS IN DEFINITE FORMS PROCESS FOR PREPARING CELLULOSE ESTERS IN DEFINITE FORMS.
- esterifying cellulose by means of or ganic acid chlorids or anhydrids a fluid mass is generally obtained as the product of the reactions, from which the cellulose-esters must then be separated. This can be avoided and the esters obtained immediately in a solid form, if the acidifying process is car ried out in the presence of a substance which does not dissolve acidified cellulose.
- the hydrolyzation requires from 12 to 24 hours, and an equal space of time is occupied by the acetylization; at a higher temperature less time is required for both processes.
- the cellulose acetate which has the structure of the starting material, is separated from the fluid mass by pressing or by centrifugalforce and freed from acid in the usual way by washing with alcohol or water.
- yarn, fabrics and other objects consisting of pure cellulose or mixed with other fibrous mate rials may be acetylized.
- the products obtained as described are sparingly and incompletely soluble in chloroform, but easily soluble in chloroform containing alcohol. If filaments treated by the new process are woven together with other textile fibers, and the woven fabric thus produced is dyed, special color effects may be produced, because the products olr tained according to the present application will not readily absorb coloring matter.
- the process may be conducted in such a manner, that acetylization takes place throughout the thickness of the raw material, or so as to leave a core of untreated cotton fiber.
- fatty acid esters such as the esters of propionic or butyric acid
- corresponding quantities ofthe necessary acid anhydrids say 4%- parts by weight of propionic anhydrid or 5.6 parts of butyric anhydrid, are employed instead of acetic anhydrid, and in other respects the process 'iscarried out as described above.
- WVhat I claim is The process for obtaining cellulose esters in the same physical form as the raw material employed, which consists in first hydrolyzing cellulose by treating it with a hydrolyzing agent, esterifying the hydrocellulose thus produced by causing the anhydrid of the acid employed to act .on the same in the presence of carbon tetrachlorid, mechani ca-lly separating the product from the accompanying liquid and then Washing 1t, substantially as described.
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
LEONHARD LEDERER, OF SULZBAGH, GERMANY.
PROCESS FOR PREPARING CELLULOSE ESTERS IN DEFINITE FORMS.
aeaaae.
No Drawing.
. Specification of Letters Patent.
T 0 all whom it may concern:
Be it known that I, LEONHARD LEDERER, a subject of the Emperor of Germany, residing at Sulzbach', Germany, have invented a certain new and useful Process for Preparing Cellulose Esters in Definite Forms, of which the following is a specification.
In esterifying cellulose by means of or ganic acid chlorids or anhydrids a fluid mass is generally obtained as the product of the reactions, from which the cellulose-esters must then be separated. This can be avoided and the esters obtained immediately in a solid form, if the acidifying process is car ried out in the presence of a substance which does not dissolve acidified cellulose. F or this purpose carbon tetrachlorid has been found exceedingly well adapted, being not only cheap but also possessing the highly estimable advantage above the diluent used for similar purposes French patent specification 347,906) of not being combustible and at the same time having a boiling point sufficiently different from that of the fatty acids and their anhydrids to enable a separation and recovery of the various fluid substances to be effected without difficulty. The use of carbon tetrachlorid was however not immediately to be expected. As is well-known, cellulose acetates dissolve in acetic acid, chloroform and tetrachlorethane. Owing to the close relationship of the two last-named substances to carbon tetrachlorid the assumption was justified that carbon tetrachlorid would also take up cellulose. In reality however this promising assumption does not hold good. i
Example: In order to obtain say cellulose acetate in the form of cotton, one proceeds for instance, in such a manner that the cotton is first hydrolyzed with an equal weight of glacial acetic acid containing 2-} per cent. of sulfuric acid, then three times the weight of carbon tetrachlorid is added and the cellulose acet-ylized with 31} times the weight of acetic anhydrid, which has been diluted with an equal weight of carbon tetrachlorid. At ordinary temperature the hydrolyzation requires from 12 to 24 hours, and an equal space of time is occupied by the acetylization; at a higher temperature less time is required for both processes. After the reaction is completed, the cellulose acetate, which has the structure of the starting material, is separated from the fluid mass by pressing or by centrifugalforce and freed from acid in the usual way by washing with alcohol or water. In a similar manner, yarn, fabrics and other objects consisting of pure cellulose or mixed with other fibrous mate rials may be acetylized.
The products obtained as described are sparingly and incompletely soluble in chloroform, but easily soluble in chloroform containing alcohol. If filaments treated by the new process are woven together with other textile fibers, and the woven fabric thus produced is dyed, special color effects may be produced, because the products olr tained according to the present application will not readily absorb coloring matter.
In treating cotton by my present process, the process may be conducted in such a manner, that acetylization takes place throughout the thickness of the raw material, or so as to leave a core of untreated cotton fiber.
For producing other fatty acid esters, such as the esters of propionic or butyric acid, corresponding quantities ofthe necessary acid anhydrids, say 4%- parts by weight of propionic anhydrid or 5.6 parts of butyric anhydrid, are employed instead of acetic anhydrid, and in other respects the process 'iscarried out as described above.
WVhat I claim is The process for obtaining cellulose esters in the same physical form as the raw material employed, which consists in first hydrolyzing cellulose by treating it with a hydrolyzing agent, esterifying the hydrocellulose thus produced by causing the anhydrid of the acid employed to act .on the same in the presence of carbon tetrachlorid, mechani ca-lly separating the product from the accompanying liquid and then Washing 1t, substantially as described.
In witness whereof I have hereunto set my hand in the presence of two witnesses.
Witnesses I PAUL CUBAsoH,
J OHANN STRoBEL.
Patented Aug. 1, 1911.
Application filed November 30, 1906. Serial No. 345,776. (Specimens)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34577606A US999236A (en) | 1906-11-30 | 1906-11-30 | Process of preparing cellulose esters in definite forms. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34577606A US999236A (en) | 1906-11-30 | 1906-11-30 | Process of preparing cellulose esters in definite forms. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US999236A true US999236A (en) | 1911-08-01 |
Family
ID=3067564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US34577606A Expired - Lifetime US999236A (en) | 1906-11-30 | 1906-11-30 | Process of preparing cellulose esters in definite forms. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US999236A (en) |
-
1906
- 1906-11-30 US US34577606A patent/US999236A/en not_active Expired - Lifetime
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