DE19633826C1 - Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von Natriumhydroxid - Google Patents
Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von NatriumhydroxidInfo
- Publication number
- DE19633826C1 DE19633826C1 DE19633826A DE19633826A DE19633826C1 DE 19633826 C1 DE19633826 C1 DE 19633826C1 DE 19633826 A DE19633826 A DE 19633826A DE 19633826 A DE19633826 A DE 19633826A DE 19633826 C1 DE19633826 C1 DE 19633826C1
- Authority
- DE
- Germany
- Prior art keywords
- water
- sodium hydroxide
- solvent mixture
- cellulose ether
- mixture
- 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 - Fee Related
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 title claims abstract description 177
- 229920003086 cellulose ether Polymers 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 239000011877 solvent mixture Substances 0.000 claims abstract description 33
- 239000000725 suspension Substances 0.000 claims abstract description 25
- 238000004821 distillation Methods 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 238000006266 etherification reaction Methods 0.000 claims abstract description 11
- 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 claims abstract description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 3
- 239000000470 constituent Substances 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 23
- 238000000605 extraction Methods 0.000 claims description 18
- 239000000375 suspending agent Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 abstract description 15
- 239000001913 cellulose Substances 0.000 abstract description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 53
- 239000000243 solution Substances 0.000 description 40
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 28
- 239000012071 phase Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 19
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 19
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 19
- 239000003513 alkali Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 235000010980 cellulose Nutrition 0.000 description 14
- 150000002334 glycols Chemical class 0.000 description 14
- 238000006386 neutralization reaction Methods 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 229920002488 Hemicellulose Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000218657 Picea Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- -1 construction Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 238000004065 wastewater treatment 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
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/08—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with hydroxylated hydrocarbon radicals; Esters, ethers, or acetals thereof
-
- 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
- C08B11/20—Post-etherification treatments of chemical or physical type, e.g. mixed etherification in two steps, including purification
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19633826A DE19633826C1 (de) | 1996-08-22 | 1996-08-22 | Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von Natriumhydroxid |
| DE59706535T DE59706535D1 (de) | 1996-08-22 | 1997-08-01 | Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von Natriumhydroxid |
| EP97113275A EP0825199B1 (de) | 1996-08-22 | 1997-08-01 | Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von Natriumhydroxid |
| US08/911,946 US5840882A (en) | 1996-08-22 | 1997-08-20 | Process for preparing cellulose ethers with recovery of alkali |
| JP22519197A JP4192214B2 (ja) | 1996-08-22 | 1997-08-21 | 水酸化ナトリウムの回収を含む、水溶性セルロースエーテルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19633826A DE19633826C1 (de) | 1996-08-22 | 1996-08-22 | Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von Natriumhydroxid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19633826C1 true DE19633826C1 (de) | 1997-10-30 |
Family
ID=7803319
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19633826A Expired - Fee Related DE19633826C1 (de) | 1996-08-22 | 1996-08-22 | Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von Natriumhydroxid |
| DE59706535T Expired - Lifetime DE59706535D1 (de) | 1996-08-22 | 1997-08-01 | Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von Natriumhydroxid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59706535T Expired - Lifetime DE59706535D1 (de) | 1996-08-22 | 1997-08-01 | Verfahren zur Herstellung von wasserlöslichen Celluloseethern unter Rückgewinnung von Natriumhydroxid |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5840882A (enExample) |
| EP (1) | EP0825199B1 (enExample) |
| JP (1) | JP4192214B2 (enExample) |
| DE (2) | DE19633826C1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19849442A1 (de) * | 1998-10-27 | 2000-05-04 | Clariant Gmbh | Sulfoalkylgruppenhaltige hydrophob modifizierte Celluloseether, Verfahren zu deren Herstellung sowie deren Verwendung in Dispersionsfarben |
| DE19849441A1 (de) * | 1998-10-27 | 2000-05-04 | Clariant Gmbh | Sulfoalkylgruppenhaltige hydrophob modifizierte Celluloseether, Verfahren zu deren Herstellung sowie deren Verwndung als Schutzkolloide bei Polymerisationen |
| US6261218B1 (en) * | 1998-12-01 | 2001-07-17 | The Dow Chemical Company | Process and apparatus for making low molecular weight cellulose ethers |
| US6294008B1 (en) * | 1999-04-21 | 2001-09-25 | The Dow Chemical Company | Haze-free cellulose ether capsules and process for making |
| ITVA20020051A1 (it) * | 2002-10-14 | 2004-04-15 | Lamberti Spa | Modificatore di reologia per prodotti destinati all'edilizia. |
| KR100654421B1 (ko) * | 2004-12-07 | 2006-12-06 | 삼성정밀화학 주식회사 | 효소분해 저항성 향상된 히드록시알킬셀룰로오스 유도체의제조방법 |
| JP5030569B2 (ja) * | 2005-12-27 | 2012-09-19 | 信越化学工業株式会社 | セルロースエーテルの製造方法 |
| DE102008056086A1 (de) * | 2008-11-06 | 2010-05-12 | Gp Solar Gmbh | Additiv für alkalische Ätzlösungen, insbesondere für Texturätzlösungen sowie Verfahren zu dessen Herstellung |
| EP2998340B1 (en) * | 2014-09-22 | 2019-07-17 | Shin-Etsu Chemical Co., Ltd. | Method for continuously producing cellulose ether |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1177127B (de) * | 1960-04-13 | 1964-09-03 | Hercules Powder Co Ltd | Verfahren zur Herstellung wasserloeslicher Oxyalkylcelluloseaether |
| DE1668347A1 (de) * | 1967-12-20 | 1971-09-16 | Kalle Ag | Verfahren zum Reinigen roher Hydroxyaethylcellulose |
| DE3216786A1 (de) * | 1982-05-05 | 1983-11-10 | Wolff Walsrode Ag, 3030 Walsrode | Verfahren zur herstellung von hydroxyalkylmethylcellulosen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3167055B2 (ja) * | 1992-12-29 | 2001-05-14 | 住友精化株式会社 | ヒドロキシエチルセルロースの製造方法 |
-
1996
- 1996-08-22 DE DE19633826A patent/DE19633826C1/de not_active Expired - Fee Related
-
1997
- 1997-08-01 EP EP97113275A patent/EP0825199B1/de not_active Expired - Lifetime
- 1997-08-01 DE DE59706535T patent/DE59706535D1/de not_active Expired - Lifetime
- 1997-08-20 US US08/911,946 patent/US5840882A/en not_active Expired - Lifetime
- 1997-08-21 JP JP22519197A patent/JP4192214B2/ja not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1177127B (de) * | 1960-04-13 | 1964-09-03 | Hercules Powder Co Ltd | Verfahren zur Herstellung wasserloeslicher Oxyalkylcelluloseaether |
| DE1668347A1 (de) * | 1967-12-20 | 1971-09-16 | Kalle Ag | Verfahren zum Reinigen roher Hydroxyaethylcellulose |
| DE3216786A1 (de) * | 1982-05-05 | 1983-11-10 | Wolff Walsrode Ag, 3030 Walsrode | Verfahren zur herstellung von hydroxyalkylmethylcellulosen |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0825199B1 (de) | 2002-03-06 |
| JP4192214B2 (ja) | 2008-12-10 |
| EP0825199A2 (de) | 1998-02-25 |
| DE59706535D1 (de) | 2002-04-11 |
| US5840882A (en) | 1998-11-24 |
| EP0825199A3 (de) | 1998-09-16 |
| JPH10120701A (ja) | 1998-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |