DE2415155C2 - Verfahren zur Herstellung von 2,3-Dihydroxypropylcellulose - Google Patents
Verfahren zur Herstellung von 2,3-DihydroxypropylcelluloseInfo
- Publication number
- DE2415155C2 DE2415155C2 DE2415155A DE2415155A DE2415155C2 DE 2415155 C2 DE2415155 C2 DE 2415155C2 DE 2415155 A DE2415155 A DE 2415155A DE 2415155 A DE2415155 A DE 2415155A DE 2415155 C2 DE2415155 C2 DE 2415155C2
- Authority
- DE
- Germany
- Prior art keywords
- cellulose
- boric acid
- reaction
- water
- alkali
- 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
- 229920002678 cellulose Polymers 0.000 title claims description 33
- 239000001913 cellulose Substances 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 16
- -1 2,3-dihydroxypropyl Chemical group 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000004327 boric acid Substances 0.000 claims description 18
- 239000003513 alkali Substances 0.000 claims description 17
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 12
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 5
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 235000010980 cellulose Nutrition 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000243 solution Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000006266 etherification reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229920003086 cellulose ether Polymers 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241000294754 Macroptilium atropurpureum Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- URWVQQSVEPXYET-UHFFFAOYSA-N 1-chloropropane-1,2,3-triol Chemical compound OCC(O)C(O)Cl URWVQQSVEPXYET-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure 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
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 |
|---|---|---|---|
| DE2415155A DE2415155C2 (de) | 1974-03-29 | 1974-03-29 | Verfahren zur Herstellung von 2,3-Dihydroxypropylcellulose |
| US05/558,632 US4001210A (en) | 1974-03-29 | 1975-03-17 | Process for manufacturing cellulose containing 2,3-dihydroxypropyl ether groups |
| IT21576/75A IT1034585B (it) | 1974-03-29 | 1975-03-24 | Procedimento per la produzione di 2.3 diidrossipropilcellulosa |
| FR7509831A FR2265760B1 (enExample) | 1974-03-29 | 1975-03-28 | |
| JP50037018A JPS5925801B2 (ja) | 1974-03-29 | 1975-03-28 | ２，３−ジヒドロキシプロピルセルロ−ズの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2415155A DE2415155C2 (de) | 1974-03-29 | 1974-03-29 | Verfahren zur Herstellung von 2,3-Dihydroxypropylcellulose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2415155A1 DE2415155A1 (de) | 1975-10-16 |
| DE2415155C2 true DE2415155C2 (de) | 1985-05-23 |
Family
ID=5911515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2415155A Expired DE2415155C2 (de) | 1974-03-29 | 1974-03-29 | Verfahren zur Herstellung von 2,3-Dihydroxypropylcellulose |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4001210A (enExample) |
| JP (1) | JPS5925801B2 (enExample) |
| DE (1) | DE2415155C2 (enExample) |
| FR (1) | FR2265760B1 (enExample) |
| IT (1) | IT1034585B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4096326A (en) * | 1976-10-13 | 1978-06-20 | Hercules Incorporated | Dihydroxypropyl cellulose |
| US4298728A (en) * | 1980-06-03 | 1981-11-03 | Hercules Incorporated | Method of preparing hydroxyethyl ethers of cellulose |
| US4306061A (en) * | 1980-12-29 | 1981-12-15 | Hercules Incorporated | Preparation of CMC with improved substituent uniformity using borax |
| DE3112946A1 (de) * | 1981-03-31 | 1982-10-07 | Hoechst Ag, 6000 Frankfurt | Gelbildende zusammensetzung auf der basis eines celluloseethers, ein verfahren zur herstellung eines gels, ein verfahren zur reversiblen aufhebung des gels und ihre verwendung bei der sekundaerfoerderung von erdoel |
| DE3335323A1 (de) | 1983-09-27 | 1985-04-04 | Schering AG, 1000 Berlin und 4709 Bergkamen | Substituierte ss-carboline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4523010A (en) * | 1984-06-15 | 1985-06-11 | Hercules Incorporated | Dihydroxypropyl mixed ether derivatives of cellulose |
| US4579942A (en) * | 1984-09-26 | 1986-04-01 | Union Carbide Corporation | Polysaccharides, methods for preparing such polysaccharides and fluids utilizing such polysaccharides |
| US5030340A (en) * | 1990-06-08 | 1991-07-09 | American Cyanamid Company | Method for the depressing of hydrous silicates and iron sulfides with dihydroxyalkyl polysaccharides |
| JP4914722B2 (ja) * | 2004-09-29 | 2012-04-11 | 興和株式会社 | セルロース誘導体リン酸エステル及びそれを用いた金属吸着材 |
| US8252266B2 (en) | 2010-08-09 | 2012-08-28 | Nalco Company | Recovery of alumina trihydrate during the bayer process using scleroglucan |
| US10427950B2 (en) | 2015-12-04 | 2019-10-01 | Ecolab Usa Inc. | Recovery of mining processing product using boronic acid-containing polymers |
| CN116802152A (zh) | 2021-02-12 | 2023-09-22 | 埃科莱布美国股份有限公司 | 使用硼酸官能化化合物纯化铝土矿矿石 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2135128A (en) * | 1935-09-23 | 1938-11-01 | Celanese Corp | Manufacture of derivatives of cellulose and other polymeric hydroxy compounds |
| US2388764A (en) * | 1938-10-20 | 1945-11-13 | Sylvania Ind Corp | Cellulose ethers and process for producing the same |
| US2687411A (en) * | 1952-03-15 | 1954-08-24 | American Viscose Corp | Production of water soluble cellulose ethers |
| US2854447A (en) * | 1953-06-04 | 1958-09-30 | Petrolite Corp | Process for preparing oxyalkylated derivatives |
| US2834777A (en) * | 1957-04-30 | 1958-05-13 | Mo Och Domsjoe Ab | Methods of treating cellulose ethers |
| US3356519A (en) * | 1964-02-28 | 1967-12-05 | Dow Chemical Co | Cellulose ether composition |
| CH1767565D (enExample) * | 1965-02-17 | |||
| US3903075A (en) * | 1967-12-22 | 1975-09-02 | Hoechst Ag | Process for the preparation of water-insoluble hydroxybutyl cellulose |
| US3652539A (en) * | 1970-03-09 | 1972-03-28 | Nippon Soda Co | Process for the production of hydroxypropyl cellulose |
-
1974
- 1974-03-29 DE DE2415155A patent/DE2415155C2/de not_active Expired
-
1975
- 1975-03-17 US US05/558,632 patent/US4001210A/en not_active Expired - Lifetime
- 1975-03-24 IT IT21576/75A patent/IT1034585B/it active
- 1975-03-28 JP JP50037018A patent/JPS5925801B2/ja not_active Expired
- 1975-03-28 FR FR7509831A patent/FR2265760B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1034585B (it) | 1979-10-10 |
| FR2265760A1 (enExample) | 1975-10-24 |
| JPS50130884A (enExample) | 1975-10-16 |
| JPS5925801B2 (ja) | 1984-06-21 |
| DE2415155A1 (de) | 1975-10-16 |
| FR2265760B1 (enExample) | 1979-06-08 |
| US4001210A (en) | 1977-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |