JPS6218561B2 - - Google Patents
Info
- Publication number
- JPS6218561B2 JPS6218561B2 JP57029060A JP2906082A JPS6218561B2 JP S6218561 B2 JPS6218561 B2 JP S6218561B2 JP 57029060 A JP57029060 A JP 57029060A JP 2906082 A JP2906082 A JP 2906082A JP S6218561 B2 JPS6218561 B2 JP S6218561B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- cmec
- cmc
- degree
- group substitution
- 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 43
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 43
- 238000006467 substitution reaction Methods 0.000 claims description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- -1 ethyl halide Chemical class 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 30
- 239000003513 alkali Substances 0.000 claims description 13
- 150000003839 salts Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229920002678 cellulose Polymers 0.000 claims description 7
- 239000001913 cellulose Substances 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000003518 caustics Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229910052698 phosphorus Chemical group 0.000 claims description 5
- 239000011574 phosphorus Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000012530 fluid Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006266 etherification reaction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000002002 slurry Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 9
- 229960003750 ethyl chloride Drugs 0.000 description 9
- 230000000968 intestinal effect Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000002496 gastric effect Effects 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 210000004051 gastric juice Anatomy 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000006200 ethylation reaction Methods 0.000 description 4
- 238000005517 mercerization Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000011253 protective coating Substances 0.000 description 4
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920003086 cellulose ether Polymers 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000009827 uniform distribution Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000006355 external stress Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000012021 ethylating agents Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 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 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000009828 non-uniform distribution Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FBOJNMRAZJRCNS-UHFFFAOYSA-M tetraethylphosphanium;chloride Chemical compound [Cl-].CC[P+](CC)(CC)CC FBOJNMRAZJRCNS-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2906082A JPS58147402A (ja) | 1982-02-26 | 1982-02-26 | カルボキシメチルエチルセルロ−スの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2906082A JPS58147402A (ja) | 1982-02-26 | 1982-02-26 | カルボキシメチルエチルセルロ−スの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58147402A JPS58147402A (ja) | 1983-09-02 |
| JPS6218561B2 true JPS6218561B2 (fr) | 1987-04-23 |
Family
ID=12265816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2906082A Granted JPS58147402A (ja) | 1982-02-26 | 1982-02-26 | カルボキシメチルエチルセルロ−スの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58147402A (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3478445D1 (en) * | 1983-10-06 | 1989-07-06 | Kohjin Co | Process for preparing carboxymethyl ethyl cellulose suitable for enteric coating |
| JPS60130576A (ja) * | 1983-12-20 | 1985-07-12 | Mitsui Toatsu Chem Inc | グリシジルエ−テル類の製造法 |
| JP2010031165A (ja) * | 2008-07-30 | 2010-02-12 | Sanyo Chem Ind Ltd | アルキルエーテル化カルボキシアルキルセルロース |
| JP5362483B2 (ja) * | 2008-08-27 | 2013-12-11 | 三洋化成工業株式会社 | アルキルエーテル化カルボキシアルキルセルロースの製造方法 |
| JP5723537B2 (ja) * | 2009-03-23 | 2015-05-27 | 三洋化成工業株式会社 | アルキルエーテル化セルロースおよびその誘導体の製造方法 |
| JP6886328B2 (ja) * | 2017-03-30 | 2021-06-16 | 三洋化成工業株式会社 | カルボキシメチルエチルセルロース又はその塩の製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55118901A (en) * | 1979-03-06 | 1980-09-12 | Daicel Chem Ind Ltd | Preparation of ethylcarboxymethylcellulose |
| JPS55118902A (en) * | 1979-03-06 | 1980-09-12 | Daicel Chem Ind Ltd | Preparation of ethylcarboxymethylcellulose |
-
1982
- 1982-02-26 JP JP2906082A patent/JPS58147402A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55118901A (en) * | 1979-03-06 | 1980-09-12 | Daicel Chem Ind Ltd | Preparation of ethylcarboxymethylcellulose |
| JPS55118902A (en) * | 1979-03-06 | 1980-09-12 | Daicel Chem Ind Ltd | Preparation of ethylcarboxymethylcellulose |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58147402A (ja) | 1983-09-02 |
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