IL139346A - תהליך לחמצון סלקטיבי של אלכוהולים ראשוניים - Google Patents
תהליך לחמצון סלקטיבי של אלכוהולים ראשונייםInfo
- Publication number
- IL139346A IL139346A IL13934699A IL13934699A IL139346A IL 139346 A IL139346 A IL 139346A IL 13934699 A IL13934699 A IL 13934699A IL 13934699 A IL13934699 A IL 13934699A IL 139346 A IL139346 A IL 139346A
- Authority
- IL
- Israel
- Prior art keywords
- oxidation
- mmol
- acid
- process according
- primary alcohol
- Prior art date
Links
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 44
- 230000003647 oxidation Effects 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 23
- 150000003138 primary alcohols Chemical class 0.000 title claims abstract description 18
- 239000007800 oxidant agent Substances 0.000 claims abstract description 9
- 150000004820 halides Chemical class 0.000 claims abstract description 8
- 150000004965 peroxy acids Chemical group 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 239000002243 precursor Substances 0.000 claims abstract description 3
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 9
- 150000001720 carbohydrates Chemical class 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 150000001649 bromium compounds Chemical group 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 description 16
- 235000019698 starch Nutrition 0.000 description 16
- 239000008107 starch Substances 0.000 description 16
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000014633 carbohydrates Nutrition 0.000 description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- -1 hydroxvl groups Chemical group 0.000 description 6
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 6
- 229920002230 Pectic acid Polymers 0.000 description 5
- 239000010318 polygalacturonic acid Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- AIQDYKMWENWVQJ-QIUUJYRFSA-N 1-phospho-alpha-D-glucuronic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](OP(O)(O)=O)O[C@H](C(O)=O)[C@H]1O AIQDYKMWENWVQJ-QIUUJYRFSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- DCXJOVUZENRYSH-UHFFFAOYSA-N 4,4-dimethyloxazolidine-N-oxyl Chemical group CC1(C)COCN1[O] DCXJOVUZENRYSH-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- 229920000057 Mannan Polymers 0.000 description 1
- RPDUDBYMNGAHEM-UHFFFAOYSA-N PROXYL Chemical compound CC1(C)CCC(C)(C)N1[O] RPDUDBYMNGAHEM-UHFFFAOYSA-N 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HXXFSFRBOHSIMQ-VFUOTHLCSA-N alpha-D-glucose 1-phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O HXXFSFRBOHSIMQ-VFUOTHLCSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005571 anion exchange chromatography Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 1
- BRDYCNFHFWUBCZ-UHFFFAOYSA-N dodecaneperoxoic acid Chemical compound CCCCCCCCCCCC(=O)OO BRDYCNFHFWUBCZ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 description 1
- 229940029339 inulin Drugs 0.000 description 1
- LUEWUZLMQUOBSB-GFVSVBBRSA-N mannan Chemical class O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-GFVSVBBRSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- GUQPPNZGDSQJGT-UHFFFAOYSA-N octadecane-1,9-diol Chemical compound CCCCCCCCCC(O)CCCCCCCCO GUQPPNZGDSQJGT-UHFFFAOYSA-N 0.000 description 1
- GDUWKVCUIFEAGC-UHFFFAOYSA-N octane-1,6-diol Chemical compound CCC(O)CCCCCO GDUWKVCUIFEAGC-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- UBYZGUWQNIEQMH-SBBOJQDXSA-M potassium;(2s,3s,4s,5r)-2,3,4,5,6-pentahydroxy-6-oxohexanoate Chemical compound [K+].OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O UBYZGUWQNIEQMH-SBBOJQDXSA-M 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 0.000 description 1
- 150000003333 secondary alcohols Chemical group 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 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
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/033—Uronic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/18—Oxidised starch
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98201495 | 1998-05-07 | ||
| PCT/NL1999/000272 WO1999057158A1 (en) | 1998-05-07 | 1999-05-04 | Process for selective oxidation of primary alcohols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL139346A0 IL139346A0 (en) | 2001-11-25 |
| IL139346A true IL139346A (he) | 2004-06-20 |
Family
ID=8233692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13934699A IL139346A (he) | 1998-05-07 | 1999-05-04 | תהליך לחמצון סלקטיבי של אלכוהולים ראשוניים |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6518419B1 (he) |
| EP (1) | EP1093467B1 (he) |
| JP (1) | JP2002513809A (he) |
| KR (1) | KR20010071212A (he) |
| CN (1) | CN1141322C (he) |
| AT (1) | ATE215097T1 (he) |
| AU (1) | AU746462B2 (he) |
| BR (1) | BR9910274A (he) |
| CA (1) | CA2331701C (he) |
| DE (1) | DE69901117T2 (he) |
| DK (1) | DK1093467T3 (he) |
| ES (1) | ES2174605T3 (he) |
| HU (1) | HUP0101777A3 (he) |
| IL (1) | IL139346A (he) |
| NZ (1) | NZ507873A (he) |
| PL (1) | PL188781B1 (he) |
| WO (1) | WO1999057158A1 (he) |
| ZA (1) | ZA200006305B (he) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997036052A2 (en) | 1996-03-28 | 1997-10-02 | The Procter & Gamble Company | Paper products having wet strength from aldehyde-functionalized cellulosic fibers and polymers |
| US6524348B1 (en) | 1999-03-19 | 2003-02-25 | Weyerhaeuser Company | Method of making carboxylated cellulose fibers and products of the method |
| WO2002048197A1 (en) * | 2000-12-13 | 2002-06-20 | Sca Hygiene Products Zeist B.V. | Process for oxidising primary alcohols |
| US20030051834A1 (en) * | 2001-06-06 | 2003-03-20 | Weerawarna S. Ananda | Method for preparation of stabilized carboxylated cellulose |
| US6919447B2 (en) | 2001-06-06 | 2005-07-19 | Weyerhaeuser Company | Hypochlorite free method for preparation of stable carboxylated carbohydrate products |
| US6916466B2 (en) | 2001-07-11 | 2005-07-12 | Sca Hygiene Products Ab | Coupling of modified cyclodextrins to fibers |
| EP1329498A1 (en) * | 2002-01-18 | 2003-07-23 | Nederlandse Organisatie voor Toegepast-Natuuurwetenschappelijk Onderzoek TNO | Process for cleaning filters |
| US6789744B2 (en) * | 2002-01-29 | 2004-09-14 | Valeo Electrical Systems, Inc. | Fluid heater with a variable mass flow path |
| JP4820284B2 (ja) * | 2003-01-30 | 2011-11-24 | ニュートラスウィート プロパティ ホールディングス，インコーポレイテッド | 酸化剤としてＮａＯＣｌを用いて第１級及び第２級アルコールを酸化する無臭素ＴＥＭＰＯ系触媒システム |
| US7001483B2 (en) | 2003-08-05 | 2006-02-21 | Weyerhaeuser Company | Apparatus for making carboxylated pulp fibers |
| US7125469B2 (en) * | 2003-10-16 | 2006-10-24 | The Procter & Gamble Company | Temporary wet strength resins |
| DE10354259A1 (de) | 2003-11-20 | 2005-06-09 | Wacker-Chemie Gmbh | Verfahren zur Herstellung von Carbonylreste-aufweisenden Organosiliciumverbindungen |
| EP1689787A2 (en) | 2003-11-28 | 2006-08-16 | Eastman Chemical Company | Cellulose interpolymers and method of oxidation |
| US6825384B1 (en) * | 2004-01-29 | 2004-11-30 | The Nutrasweet Company | Bromine free TEMPO based catalyst system for oxidation of primary and secondary alcohols using NaOCl as an oxidant |
| EP1580228A1 (en) * | 2004-03-24 | 2005-09-28 | Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO | Process for gelatinising starch using a biodegradable polymer material bearing aldehyde groups |
| US7833676B2 (en) * | 2004-07-09 | 2010-11-16 | Nissan Motor Co., Ltd. | Fuel cell system and solid polymer electrolyte film |
| US7799485B2 (en) * | 2004-07-09 | 2010-09-21 | Nissan Motor Co., Ltd. | Fuel cell system and composition for electrode |
| JP2006182764A (ja) * | 2004-12-03 | 2006-07-13 | Daiso Co Ltd | 第１級または第２級アルコールの新規酸化方法 |
| EP1666441A1 (en) * | 2004-12-03 | 2006-06-07 | Daiso Co., Ltd. | Oxidation method for primary or secondary alcohols |
| US7923231B2 (en) * | 2004-12-17 | 2011-04-12 | Cargill, Incorporated | Production of glucuronic acid using myo-inositol oxygenase from cryptococcus neoformans |
| US7259218B2 (en) * | 2005-02-17 | 2007-08-21 | The Procter + Gamble Company | Processes for making temporary wet strength additives |
| JP5205694B2 (ja) * | 2005-12-15 | 2013-06-05 | 日産自動車株式会社 | 燃料、燃料電池システム及び燃料電池車輌 |
| CN101069495B (zh) * | 2006-05-11 | 2011-12-07 | 广州神阳高新技术有限公司 | 过滤盒 |
| CN100463914C (zh) * | 2006-06-26 | 2009-02-25 | 重庆华邦制药股份有限公司 | 一种单糖苷酸纯化方法 |
| EP2108676B1 (en) * | 2008-04-03 | 2017-12-27 | OrganoClick AB | Crosslinked paper based material |
| US9512237B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Method for inhibiting the growth of microbes with a modified cellulose fiber |
| US9512563B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Surface treated modified cellulose from chemical kraft fiber and methods of making and using same |
| BRPI1012052A2 (pt) | 2009-05-28 | 2017-12-26 | Gp Cellulose Gmbh | fibras kraft hidrolisadas e quimicamente modificadas e métodos de produção e de branqueamento de fibras kraft |
| US9511167B2 (en) | 2009-05-28 | 2016-12-06 | Gp Cellulose Gmbh | Modified cellulose from chemical kraft fiber and methods of making and using the same |
| EP2309059A1 (en) | 2009-10-02 | 2011-04-13 | Organoclick Aktiebolag | Method of improving properties of cellulose-based fibrous sheet-formed materials |
| GB0918616D0 (en) * | 2009-10-23 | 2009-12-09 | 3M Innovative Properties Co | Method of preparing highly fluorinated carboxylic acids and their salts |
| CZ302504B6 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
| CZ302503B6 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
| CA2836895C (en) | 2011-05-23 | 2020-03-31 | Arthur J. Nonni | Softwood kraft fiber having improved whiteness and brightness and methods of making and using the same |
| MX366988B (es) | 2012-01-12 | 2019-08-01 | Gp Cellulose Gmbh | Fibra kraft de baja viscosidad que tiene propiedades de amarillez reducida, y metodos para prepararla y usarla. |
| CZ2012136A3 (cs) | 2012-02-28 | 2013-06-05 | Contipro Biotech S.R.O. | Deriváty na bázi kyseliny hyaluronové schopné tvorit hydrogely, zpusob jejich prípravy, hydrogely na bázi techto derivátu, zpusob jejich prípravy a pouzití |
| US9079844B2 (en) | 2012-04-04 | 2015-07-14 | Stichting Dienst Landbouwkundig Onderzoek | Catalytic oxidation of uronic acids to aldaric acids |
| MX364847B (es) | 2012-04-18 | 2019-05-08 | Gp Cellulose Gmbh | El uso de surfactante para tratar pulpa y mejorar la incorporacion de pulpa kraft en fibra para la produccion de viscosa y otros productos de fibra secundarios. |
| CZ304512B6 (cs) * | 2012-08-08 | 2014-06-11 | Contipro Biotech S.R.O. | Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití |
| CZ304654B6 (cs) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
| PL3363806T3 (pl) | 2012-12-20 | 2022-12-19 | Pfizer Inc. | Sposób glikokoniugacji |
| KR101475136B1 (ko) * | 2013-02-07 | 2014-12-22 | 한양대학교 에리카산학협력단 | 수용액 상에서의 2-(4-포르밀페닐)프로피온산의 친환경적인 제조방법 |
| KR102180512B1 (ko) | 2013-02-08 | 2020-11-19 | 게페 첼루로제 게엠베하 | 개선된 알파 셀룰로스 함량을 갖는 연재 크래프트 섬유 및 화학적 셀룰로스 제품의 생산에서의 그의 용도 |
| WO2014140852A2 (en) | 2013-03-14 | 2014-09-18 | Gp Cellulose Gmbh | A method of making highly functional, low viscosity kraft fiber using an acidic bleaching sequence and a fiber made by the process |
| CN105143547B (zh) | 2013-03-15 | 2018-05-01 | Gp 纤维素股份有限公司 | 具有增高羧基含量的低粘度牛皮纸纤维及其制造和使用方法 |
| CZ2014150A3 (cs) | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití |
| MX2016011467A (es) * | 2014-03-11 | 2016-11-16 | Du Pont | Poli alfa-1,3-glucano oxidado como mejorador de detergente. |
| CZ2014451A3 (cs) | 2014-06-30 | 2016-01-13 | Contipro Pharma A.S. | Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití |
| CZ309295B6 (cs) | 2015-03-09 | 2022-08-10 | Contipro A.S. | Samonosný, biodegradabilní film na bázi hydrofobizované kyseliny hyaluronové, způsob jeho přípravy a použití |
| CZ2015398A3 (cs) | 2015-06-15 | 2017-02-08 | Contipro A.S. | Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin |
| CZ306662B6 (cs) | 2015-06-26 | 2017-04-26 | Contipro A.S. | Deriváty sulfatovaných polysacharidů, způsob jejich přípravy, způsob jejich modifikace a použití |
| WO2017020237A1 (zh) * | 2015-08-04 | 2017-02-09 | 江南大学 | 三重响应型淀粉基微凝胶及其制备方法 |
| US11350640B1 (en) | 2016-08-12 | 2022-06-07 | Zee Company I, Llc | Methods and related apparatus for increasing antimicrobial efficacy in a poultry chiller tank |
| US10974211B1 (en) | 2016-02-17 | 2021-04-13 | Zee Company, Inc. | Peracetic acid concentration and monitoring and concentration-based dosing system |
| CZ308106B6 (cs) | 2016-06-27 | 2020-01-08 | Contipro A.S. | Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití |
| US10865519B2 (en) | 2016-11-16 | 2020-12-15 | Gp Cellulose Gmbh | Modified cellulose from chemical fiber and methods of making and using the same |
| CN106832018A (zh) * | 2017-01-20 | 2017-06-13 | 青岛大学 | 一种高羧基含量氧化淀粉的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5334756A (en) * | 1991-03-26 | 1994-08-02 | Sandoz Ltd. | Carboxylate of certain polyoxyalkylene amines |
| US5362868A (en) * | 1993-06-18 | 1994-11-08 | Degussa Aktiengesellshaft | Thinning of granular starch |
| US5739352A (en) * | 1995-10-19 | 1998-04-14 | United Carbide Chemicals & Plastics Technology Corporation | Process for preparing carboxylic acids |
-
1999
- 1999-05-04 ES ES99919713T patent/ES2174605T3/es not_active Expired - Lifetime
- 1999-05-04 PL PL99343940A patent/PL188781B1/pl not_active IP Right Cessation
- 1999-05-04 NZ NZ507873A patent/NZ507873A/en not_active IP Right Cessation
- 1999-05-04 BR BR9910274-9A patent/BR9910274A/pt not_active IP Right Cessation
- 1999-05-04 DK DK99919713T patent/DK1093467T3/da active
- 1999-05-04 IL IL13934699A patent/IL139346A/he not_active IP Right Cessation
- 1999-05-04 CA CA002331701A patent/CA2331701C/en not_active Expired - Fee Related
- 1999-05-04 JP JP2000547126A patent/JP2002513809A/ja active Pending
- 1999-05-04 KR KR1020007012356A patent/KR20010071212A/ko active IP Right Grant
- 1999-05-04 AT AT99919713T patent/ATE215097T1/de active
- 1999-05-04 CN CNB998058637A patent/CN1141322C/zh not_active Expired - Fee Related
- 1999-05-04 EP EP99919713A patent/EP1093467B1/en not_active Expired - Lifetime
- 1999-05-04 AU AU37369/99A patent/AU746462B2/en not_active Ceased
- 1999-05-04 WO PCT/NL1999/000272 patent/WO1999057158A1/en active IP Right Grant
- 1999-05-04 DE DE69901117T patent/DE69901117T2/de not_active Expired - Lifetime
- 1999-05-04 HU HU0101777A patent/HUP0101777A3/hu unknown
-
2000
- 2000-11-03 ZA ZA200006305A patent/ZA200006305B/en unknown
- 2000-11-07 US US09/706,767 patent/US6518419B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6518419B1 (en) | 2003-02-11 |
| NZ507873A (en) | 2002-05-31 |
| EP1093467A1 (en) | 2001-04-25 |
| HUP0101777A3 (en) | 2003-04-28 |
| ZA200006305B (en) | 2001-11-05 |
| IL139346A0 (en) | 2001-11-25 |
| DK1093467T3 (da) | 2002-04-29 |
| DE69901117T2 (de) | 2002-09-05 |
| AU3736999A (en) | 1999-11-23 |
| CA2331701A1 (en) | 1999-11-11 |
| AU746462B2 (en) | 2002-05-02 |
| ATE215097T1 (de) | 2002-04-15 |
| PL188781B1 (pl) | 2005-04-29 |
| EP1093467B1 (en) | 2002-03-27 |
| CA2331701C (en) | 2008-11-18 |
| CN1141322C (zh) | 2004-03-10 |
| ES2174605T3 (es) | 2002-11-01 |
| WO1999057158A1 (en) | 1999-11-11 |
| DE69901117D1 (de) | 2002-05-02 |
| HUP0101777A2 (hu) | 2001-12-28 |
| PL343940A1 (en) | 2001-09-10 |
| JP2002513809A (ja) | 2002-05-14 |
| KR20010071212A (ko) | 2001-07-28 |
| CN1299373A (zh) | 2001-06-13 |
| BR9910274A (pt) | 2001-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL139346A (he) | תהליך לחמצון סלקטיבי של אלכוהולים ראשוניים | |
| US6498269B1 (en) | Method for the oxidation of aldehydes, hemiacetals and primary alcohols | |
| US6936710B2 (en) | Process for oxidizing primary alcohols | |
| US6770755B1 (en) | Process of oxidizing primary alcohols | |
| De Nooy et al. | On the use of stable organic nitroxyl radicals for the oxidation of primary and secondary alcohols | |
| EP1173409A1 (en) | Process for producing nitrosonium ions | |
| US5417755A (en) | Amphoteric starch containing carboxyl and cationic groups | |
| EP1149846B1 (en) | Oxidation of polysaccharides with nitroxyls | |
| WO1994021690A2 (en) | Method for the oxidation of vicinal diols, including carbohydrates | |
| US20100152435A1 (en) | Compositions and processes for the selective catalytic oxidation of alcohols | |
| EP3253772B1 (en) | Process for the preparation of diosmin | |
| JP4852689B2 (ja) | オリゴ糖の第一級アルコールの選択的酸化プロセス | |
| MXPA00010829A (en) | Process for selective oxidation of primary alcohols | |
| JP2000302740A (ja) | 有機アジドの製造方法 | |
| Choudhury et al. | Communication: Chemoselective Glycosylation Based on Difference in the Reactivities of Ethyl and p-Tolyl Thioglycosides | |
| Inoue et al. | Phosphorylation of D-glucose derivatives with inorganic monoimido-cyclo-triphosphate | |
| EP1349876A1 (en) | Process for oxidising primary alcohols | |
| MXPA99007427A (es) | Proceso para oxidacion selectiva de alcoholes primarios de oligosacaridos | |
| JPH10265505A (ja) | メチル化γ−シクロデキストリンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |