GB452506A - Improvements in and relating to the production of cellulose ethers - Google Patents
Improvements in and relating to the production of cellulose ethersInfo
- Publication number
- GB452506A GB452506A GB3660534A GB3660534A GB452506A GB 452506 A GB452506 A GB 452506A GB 3660534 A GB3660534 A GB 3660534A GB 3660534 A GB3660534 A GB 3660534A GB 452506 A GB452506 A GB 452506A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cellulose
- sodium
- cupric
- solution
- sulphate
- 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
- 229920003086 cellulose ether Polymers 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 229920002678 cellulose Polymers 0.000 abstract 19
- 239000001913 cellulose Substances 0.000 abstract 19
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 10
- 239000011734 sodium Substances 0.000 abstract 10
- 229910052708 sodium Inorganic materials 0.000 abstract 10
- 239000000243 solution Substances 0.000 abstract 10
- 239000003513 alkali Substances 0.000 abstract 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 5
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 5
- 239000003518 caustics Substances 0.000 abstract 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 4
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052802 copper Inorganic materials 0.000 abstract 3
- 239000010949 copper Substances 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002168 alkylating agent Substances 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 abstract 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000001879 copper Chemical class 0.000 abstract 2
- 229960003280 cupric chloride Drugs 0.000 abstract 2
- 229920000609 methyl cellulose Polymers 0.000 abstract 2
- 239000001923 methylcellulose Substances 0.000 abstract 2
- 235000010981 methylcellulose Nutrition 0.000 abstract 2
- -1 nitro, acetyl Chemical group 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 abstract 1
- 239000005750 Copper hydroxide Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 229920001131 Pulp (paper) Polymers 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000007664 blowing Methods 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- 229910001956 copper hydroxide Inorganic materials 0.000 abstract 1
- 229960003750 ethyl chloride Drugs 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 229940050176 methyl chloride Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000012266 salt solution Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 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
- C08B1/06—Rendering cellulose suitable for etherification
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)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Cellulose ethers are prepared by acting on cellulose with a compound of copper in the presence of an alkali to form an alkali copper cellulose, and treating this with an alkylating or aralkylating agent in the presence of free alkali. The alkli copper cellulose, e.g. sodium cupric cellulose may be obtained by the action of caustic alkali and copper hydroxide on cellulose, by causing cellulose to absorb caustic alkali in excess and working up with finely powdered copper salt, or by impregnating cellulose with a copper salt solution and treating the mixture with caustic alkali. The product, with or without partial separation of the excess caustic alkali is treated with the alkylating agent, and the cellulose ether separated by treatment either with hydrochloric acid or a solution of alkali bisulphate. Separation of the ether in flakes may be assisted by using the hydrochloric acid or bisulphate solution hot, or by adding also salts such as magnesium or alkali sulphate. The cellulose ethers may be used for the manufacture of films, lacquers, filaments, glue-like liquids, or as starting materials for the manufacture of nitro, acetyl, and similar compounds. The following examples are given: (1) sulphite wood pulp is mixed with powdered cupric chloride and introduced into caustic soda solution. The sodium cupric cellulose formed is alkylated with methyl sulphate; (2) the cellulose is separated into fibres, treated with caustic soda solution and worked with cupric chloride. The sodium cupric cellulose is treated with methyl sulphate and the product separated by means of alcohol containing hydrochloric acid; (3) sodium cupric cellulose is treated with methyl sulphate in toluene and the product separated by means of dilute sulphuric acid or a solution of sodium bisulphate and magnesium sulphate; (4) sodium cupric cellulose is treated with methyl sulphate in small portions and the methyl cellulose separated by filtering and treating with methanol containing hydrochloric acid. The product may also be separated by treatment with a hot solution of magnesium sulphate containing sulphuric acid or sodium bisulphate, washing with a hot solution of magnesium sulphate and then with methanol; (5) sodium cupric cellulose is treated with methyl chloride and the product separated by treatment with a solution of magnesium sulphate and sodium bisulphate; (6) sodium cupric cellulose is suspended in sodium sulphate solution and treated with methyl sulphate; (7) sodium cupric cellulose is reacted with methyl sulphate, and sodium bisulphate added. The methyl cellulose is separated by adding magnesium sulphate solution and heating; (8) sodium cupric cellulose is etherified with ethyl chloride or bromide; (9) sodium cupric cellulose is treated with benzyl chloride, excess of which is removed by blowing in steam, and the benzyl cellulose separated by treatment with acid. By boiling with glacial acetic acid it is converted to an acetone-soluble acetyl benzyl cellulose.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3660534A GB452506A (en) | 1934-12-20 | 1934-12-20 | Improvements in and relating to the production of cellulose ethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3660534A GB452506A (en) | 1934-12-20 | 1934-12-20 | Improvements in and relating to the production of cellulose ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB452506A true GB452506A (en) | 1936-08-20 |
Family
ID=10389646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3660534A Expired GB452506A (en) | 1934-12-20 | 1934-12-20 | Improvements in and relating to the production of cellulose ethers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB452506A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117510654A (en) * | 2023-11-29 | 2024-02-06 | 哈尔滨工业大学(深圳)(哈尔滨工业大学深圳科技创新研究院) | A cation-assisted cellulose lithiation method |
-
1934
- 1934-12-20 GB GB3660534A patent/GB452506A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117510654A (en) * | 2023-11-29 | 2024-02-06 | 哈尔滨工业大学(深圳)(哈尔滨工业大学深圳科技创新研究院) | A cation-assisted cellulose lithiation method |
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