GB659506A - Improved method of making methyl carboxyalkyl ethers of cellulose - Google Patents
Improved method of making methyl carboxyalkyl ethers of celluloseInfo
- Publication number
- GB659506A GB659506A GB841749A GB841749A GB659506A GB 659506 A GB659506 A GB 659506A GB 841749 A GB841749 A GB 841749A GB 841749 A GB841749 A GB 841749A GB 659506 A GB659506 A GB 659506A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cellulose
- per
- per cent
- groups
- pressed
- 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
- 239000001913 cellulose Substances 0.000 title abstract 4
- 229920002678 cellulose Polymers 0.000 title abstract 4
- -1 methyl carboxyalkyl ethers Chemical class 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 abstract 3
- 229940050176 methyl chloride Drugs 0.000 abstract 3
- 230000011987 methylation Effects 0.000 abstract 3
- 238000007069 methylation reaction Methods 0.000 abstract 3
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229940100198 alkylating agent Drugs 0.000 abstract 2
- 239000002168 alkylating agent Substances 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical class CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 abstract 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 229910000831 Steel Inorganic materials 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000001768 carboxy methyl cellulose Substances 0.000 abstract 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000012153 distilled water Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 229920000609 methyl cellulose Polymers 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000001923 methylcellulose Substances 0.000 abstract 1
- 235000010981 methylcellulose Nutrition 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 230000000717 retained effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000010959 steel Substances 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
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/10—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals
- C08B11/12—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals substituted with carboxylic radicals, e.g. carboxymethylcellulose [CMC]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/193—Mixed ethers, i.e. ethers with two or more different etherifying groups
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 fibres are immersed in a 5 to 27.5 per cent aqueous solution of a carboxy alkylating agent, pressed to bring the amount of retained carboxy-alkylating agent within 0.05 to 0.22 parts by weight per weight of cellulose, immersed in a 40 to 55 per cent aqueous sodium hydroxide at a temperature not exceeding 60 DEG C., pressed to bring the alkali-cellulose ratio within 0.7 to 1.3, then methylated with 1.2 to 1.4 parts by weight of methyl chloride per part of cellulose under pressure below 80 DEG C., the methylation being stopped before the methylation exceeds 2.1 methoxyl groups per anhydro-glycose unit, the so-formed mixed ether being recovered by treatment with acidified water. Ethers containing 0.02 to 0.3 carboxyalkyl groups and 0.7 to 2.1 methyl groups per anhydro-glucose unit are so obtained. The products behave like carboxymethyl cellulose in media having a pH above 6 (i.e. they remain in solution at temperatures up to 90 DEG C. or higher), and like methyl cellulose when in acid aqueous media of pH 4-2 (i.e. gell at temperatures above about 55 DEG C.). Specified carboxyalkylating agents are choroacetic, chloropropionic and chlorobutyric acids and their salts. In an example a sheet of cotton linters is saturated with a 25 per cent aqueous solution of sodium chloroacetate at room temperature, and pressed to remove excess. It is then dipped into 50 per cent aqueous sodium hydroxide at 25 DEG C. and again pressed. After shredding the treated sheet into a pressure vessel, 1-33 times its own weight of methyl chloride is added and the methylation carried out for 10 hours at 60-80 DEG C. Excess methyl chloride is driven off, 300 g. of the reaction mixture are stirred into 1700 c.c. of water containing 50 c.c. of concentrated hydrochloric acid at 90 DEG C. Filtration is carried out in a basket centrifuge and the solids washed with hot distilled water at 75 DEG C. After drying, the acid product is spread in a thin layer on a steel pan and sprayed with just enough 25 per cent caustic soda to neutralize the carboxyl groups present. The product contained 1.45 methoxyl groups and 0.14 carboxymethyl groups per anhydroglucose unit. Example 3 describes the production of an ether containing 1.83 methoxyl and 0.10 carboxyethyl groups per anhydroglucose unit.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB841749A GB659506A (en) | 1949-03-28 | 1949-03-28 | Improved method of making methyl carboxyalkyl ethers of cellulose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB841749A GB659506A (en) | 1949-03-28 | 1949-03-28 | Improved method of making methyl carboxyalkyl ethers of cellulose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB659506A true GB659506A (en) | 1951-10-24 |
Family
ID=9852124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB841749A Expired GB659506A (en) | 1949-03-28 | 1949-03-28 | Improved method of making methyl carboxyalkyl ethers of cellulose |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB659506A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4048433A (en) | 1976-02-02 | 1977-09-13 | The Procter & Gamble Company | Cellulose ethers having a low molecular weight and a high degree of methyl substitution |
| EP0319865A3 (en) * | 1987-12-11 | 1990-07-25 | Wolff Walsrode Aktiengesellschaft | Carboxymethyl sulfoethyl cellulose and process for its preparation |
-
1949
- 1949-03-28 GB GB841749A patent/GB659506A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4048433A (en) | 1976-02-02 | 1977-09-13 | The Procter & Gamble Company | Cellulose ethers having a low molecular weight and a high degree of methyl substitution |
| EP0319865A3 (en) * | 1987-12-11 | 1990-07-25 | Wolff Walsrode Aktiengesellschaft | Carboxymethyl sulfoethyl cellulose and process for its preparation |
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