PH26799A - Improved sucrose-6-ester chlorination - Google Patents
Improved sucrose-6-ester chlorination Download PDFInfo
- Publication number
- PH26799A PH26799A PH40800A PH40800A PH26799A PH 26799 A PH26799 A PH 26799A PH 40800 A PH40800 A PH 40800A PH 40800 A PH40800 A PH 40800A PH 26799 A PH26799 A PH 26799A
- Authority
- PH
- Philippines
- Prior art keywords
- sucrose
- ester
- benzoate
- product
- sucralose
- Prior art date
Links
- 238000005660 chlorination reaction Methods 0.000 title claims description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 78
- 239000011541 reaction mixture Substances 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 46
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 45
- 230000008569 process Effects 0.000 claims description 40
- AFHCRQREQZIDSI-OVUASUNJSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate Chemical group O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(=O)C=2C=CC=CC=2)O1 AFHCRQREQZIDSI-OVUASUNJSA-N 0.000 claims description 39
- AFHCRQREQZIDSI-UHFFFAOYSA-N sucrose-6-benzoate Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC(=O)C=2C=CC=CC=2)O1 AFHCRQREQZIDSI-UHFFFAOYSA-N 0.000 claims description 36
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 23
- 239000003960 organic solvent Substances 0.000 claims description 17
- 238000000605 extraction Methods 0.000 claims description 14
- 150000003511 tertiary amides Chemical class 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 10
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 9
- 150000003841 chloride salts Chemical class 0.000 claims description 7
- 150000003839 salts Chemical group 0.000 claims description 6
- 230000003472 neutralizing effect Effects 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 description 46
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 44
- 238000007792 addition Methods 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 239000000047 product Substances 0.000 description 35
- 239000007787 solid Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 229910052786 argon Inorganic materials 0.000 description 22
- 238000004128 high performance liquid chromatography Methods 0.000 description 22
- 239000004376 Sucralose Substances 0.000 description 21
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 21
- 235000019408 sucralose Nutrition 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 15
- 230000008025 crystallization Effects 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 13
- 239000006188 syrup Substances 0.000 description 13
- 235000020357 syrup Nutrition 0.000 description 13
- 239000010410 layer Substances 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
- 239000005720 sucrose Substances 0.000 description 12
- 229930006000 Sucrose Natural products 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000356 contaminant Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 239000012320 chlorinating reagent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 238000007360 debenzoylation reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000413 hydrolysate Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 150000003445 sucroses Chemical class 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- CVTFNNJUXOBPMI-UHFFFAOYSA-N (1,2-dichloro-2-diphenylphosphanylethyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(Cl)C(Cl)P(C=1C=CC=CC=1)C1=CC=CC=C1 CVTFNNJUXOBPMI-UHFFFAOYSA-N 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FACOTAQCKSDLDE-YKEUTPDRSA-N [(2R,3R,4R,5R,6R)-6-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-3-chloro-4,5-dihydroxyoxan-2-yl]methyl acetate Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](COC(=O)C)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 FACOTAQCKSDLDE-YKEUTPDRSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 239000012455 biphasic mixture Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- KNZYMKYLCIPERV-UHFFFAOYSA-N dichloromethanimine;hydrochloride Chemical compound [Cl-].ClC(Cl)=[NH2+] KNZYMKYLCIPERV-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
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- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
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- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
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- 239000011269 tar Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 230000001404 mediated effect Effects 0.000 description 1
- QKZHYYBXLJMLNM-UHFFFAOYSA-N methanimidoyl chloride Chemical class ClC=N QKZHYYBXLJMLNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005866 tritylation reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/382,147 US4980463A (en) | 1989-07-18 | 1989-07-18 | Sucrose-6-ester chlorination |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26799A true PH26799A (en) | 1992-10-13 |
Family
ID=23507711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH40800A PH26799A (en) | 1989-07-18 | 1990-07-06 | Improved sucrose-6-ester chlorination |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4980463A (es) |
| EP (1) | EP0409549B1 (es) |
| JP (1) | JP3183506B2 (es) |
| KR (1) | KR0144344B1 (es) |
| AR (1) | AR247401A1 (es) |
| AT (1) | ATE133175T1 (es) |
| AU (1) | AU625908B2 (es) |
| CA (1) | CA2021632C (es) |
| DE (1) | DE69024868T2 (es) |
| DK (1) | DK0409549T3 (es) |
| ES (1) | ES2088973T3 (es) |
| FI (1) | FI95802C (es) |
| GR (1) | GR1002037B (es) |
| IE (1) | IE69961B1 (es) |
| IL (1) | IL94994A (es) |
| MX (1) | MX164442B (es) |
| NO (1) | NO175532C (es) |
| NZ (1) | NZ234468A (es) |
| PE (1) | PE21591A1 (es) |
| PH (1) | PH26799A (es) |
| PT (1) | PT94719B (es) |
| RU (1) | RU1836377C (es) |
| TR (1) | TR28705A (es) |
| TW (1) | TW219939B (es) |
| YU (1) | YU47948B (es) |
| ZA (1) | ZA905615B (es) |
Families Citing this family (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5136031A (en) * | 1990-07-09 | 1992-08-04 | Tate & Lyle Public Limited Company | Chlorination of sugars |
| US5470969A (en) * | 1990-08-27 | 1995-11-28 | Mcneil-Ppc, Inc. | Catalyzed sucrose-6-ester process |
| GB9110931D0 (en) * | 1991-05-21 | 1991-07-10 | Tate & Lyle Plc | Process for the preparation of sucrose 6-esters |
| US5298611A (en) * | 1993-03-12 | 1994-03-29 | Mcneil-Ppc, Inc. | Sucralose pentaester production |
| US6608039B1 (en) | 1994-07-11 | 2003-08-19 | The United States Of America As Represented By The Secretary Of Agriculture | Chemically synthesized sugar esters for the control of soft-bodied arthropods |
| WO1996001832A1 (en) | 1994-07-11 | 1996-01-25 | The United States Of America, Represented By The Secretary Of The Department Of Agriculture | Chemically synthesized sugar esters for the control of soft-bodied arthropods |
| US5498709A (en) * | 1994-10-17 | 1996-03-12 | Mcneil-Ppc, Inc. | Production of sucralose without intermediate isolation of crystalline sucralose-6-ester |
| KR100405203B1 (ko) * | 1996-05-23 | 2004-02-14 | 비앤티엔지니어링(주) | 암거배수로관 |
| ES2231964T3 (es) * | 1997-02-13 | 2005-05-16 | TATE & LYLE PUBLIC LIMITED COMPANY | Purificacion cromatografica de sucrosa clorada. |
| EP1076661A1 (en) * | 1998-05-15 | 2001-02-21 | Rostislav G. Zhbankov | Method of preparation of 4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose |
| DE19924770A1 (de) * | 1999-05-29 | 2000-12-21 | Buna Sow Leuna Olefinverb Gmbh | Verfahren zur Herstellung von Polyetherpolyolen aus Polysacchariden und deren Verwendung für die Herstellung von PUR-Schäumen |
| US6500973B2 (en) | 2000-06-02 | 2002-12-31 | Eastman Chemical Company | Extractive solution crystallization of chemical compounds |
| DE60133011T2 (de) * | 2000-08-25 | 2009-03-19 | Eastman Chemical Co., Kingsport | Verfahren zur herstellung von disaccharid und trisaccharid c6-c12 fettsäure-estern mit hohem alpha gehalt und materialien davon |
| US6667397B2 (en) * | 2000-08-25 | 2003-12-23 | Eastman Chemical Company | Methods of preparing disaccharide and trisaccharide C6-C12 fatty acid esters with high alpha content and materials therefrom |
| CN1294139C (zh) * | 2000-11-17 | 2007-01-10 | 塔特和莱利有限公司 | 改进的三氯蔗糖组合物及其制备方法 |
| US6998480B2 (en) | 2002-03-08 | 2006-02-14 | Tate & Lyle Public Limited Company | Process for improving sucralose purity and yield |
| US7049435B2 (en) | 2002-03-08 | 2006-05-23 | Tate & Lyle Public Limited Company | Extractive methods for purifying sucralose |
| US6890581B2 (en) * | 2002-04-05 | 2005-05-10 | Tate & Lyle Public Limited Company | Methods for buffer stabilized aqueous deacylation |
| US20040170735A2 (en) * | 2002-04-05 | 2004-09-02 | Mcneil-Ppc, Inc. | Methods and compositions for altering the sweetness delivery profile of sucralose |
| US20040086605A1 (en) * | 2002-10-30 | 2004-05-06 | Sox Thomas E. | Composition for delivering a high intensity sweetener |
| US6943248B2 (en) | 2003-04-30 | 2005-09-13 | Tate & Lyle Public Limited Company | Crystalline form of sucralose, and method for producing it |
| CN1176094C (zh) * | 2003-05-23 | 2004-11-17 | 广东省食品工业研究所 | 一种三氯蔗糖的合成方法 |
| CA2558683A1 (en) * | 2004-03-05 | 2005-09-22 | Sunil Srivastava | High-intensity sweetener-polyol compositions |
| MXPA06010665A (es) * | 2004-03-19 | 2007-03-28 | Pharmed Medicare Pvt Ltd | Un proceso mejorado para producir sacarosa clorada. |
| US20050214425A1 (en) * | 2004-03-23 | 2005-09-29 | Roma Vazirani | Sugar substitute prepared with nutritive and high-intensity sweeteners |
| CN101098971B (zh) * | 2004-12-10 | 2010-04-21 | V.B.医疗保险私人有限公司 | 有助于从含水反应混合物中选择性萃取4,1',6'三氯半乳蔗糖的盐 |
| CN101098970B (zh) * | 2004-12-10 | 2010-05-12 | V.B.医疗保险私人有限公司 | 通过在6-乙酰基-4,1',6'三氯半乳蔗糖和4,1',6'三氯半乳蔗糖的有机溶剂提取物的浓缩过程中直接加入碳酸盐和碳酸氢盐来调节pH的方法 |
| GB2437442B (en) * | 2004-12-10 | 2010-03-31 | Pharmed Medicare Pvt Ltd | Improved process for purification of 6 acetyl 4,1',6' trichlorogalactosucrose and 4,1'6' trichlorogalactosucrose by chromatography on silanized silica gel |
| KR20070113194A (ko) * | 2005-01-03 | 2007-11-28 | 팜드 메디케어 프리베이트 리미티드 | 염소화 시약의 동시 첨가에 의한 수크로스-6-에스테르염소화 |
| US20060188629A1 (en) * | 2005-01-21 | 2006-08-24 | Greg Liesen | Method for the purification of sucralose |
| CN101166748A (zh) * | 2005-02-22 | 2008-04-23 | 法马德医疗保险私人有限公司 | 在生产氯化蔗糖、其前体和衍生物过程的不同步骤中的分子分离方法 |
| US20060205936A1 (en) * | 2005-03-14 | 2006-09-14 | Sl Laboratories, Llc | Chlorination of Sucrose-6-esters |
| US20060247180A1 (en) * | 2005-04-29 | 2006-11-02 | Bergey James L | Purgative composition and uses thereof |
| MX2007013689A (es) * | 2005-05-04 | 2009-02-17 | Pharmed Medicare Pvt Ltd | Generacion de oxicloruro de fosforo como subproducto de pentacloruro de fosforo y dmf y su uso en una reaccion de cloracion al convertirse en reactivo vilsmeier-haack. |
| GB2442619B (en) * | 2005-05-04 | 2010-05-26 | Pharmed Medicare Pvt Ltd | Chlorination of sucrose acylates using triphosgene |
| US20060276639A1 (en) * | 2005-06-01 | 2006-12-07 | Healthy Brands, Llc | Conversion of sucralose-6-ester to sucralose |
| GB2441917A (en) * | 2005-06-01 | 2008-03-19 | Pharmed Medicare Pvt Ltd | Method for purification of chlorinated sucrose derivatives by solvent extraction |
| US20100160625A1 (en) * | 2005-09-22 | 2010-06-24 | Rakesh Ratnam | Novel Preparation of 6-O-Acyl Chlorosucrose from Anhydrous Cholorinated Reaction Mass |
| US20070100139A1 (en) * | 2005-10-31 | 2007-05-03 | Healthy Brands, Llc | Methods for chlorinating sucrose-6-ester |
| US7741477B2 (en) * | 2006-01-10 | 2010-06-22 | Alembic Limited | Process for purification of sucralose |
| EP1996601A4 (en) * | 2006-02-28 | 2010-02-17 | Vb Medicare Pvt Ltd | PROCESS FOR THE PRODUCTION OF A CHLORINATE REAGENT AND THEIR USE IN THE PRODUCTION OF CHLORINE SUGAR |
| CN100418976C (zh) * | 2006-04-03 | 2008-09-17 | 广州科宏食品添加物有限公司 | 一种三氯蔗糖的制备方法 |
| CN100402541C (zh) * | 2006-06-15 | 2008-07-16 | 浙江工业大学 | 一种三氯蔗糖-6-乙酯的合成方法 |
| CN101092438A (zh) * | 2006-06-22 | 2007-12-26 | 南京莱因医药科技有限公司 | 6－o－苯甲酰三氯半乳型蔗糖四乙酯的制备方法 |
| CA2656797A1 (en) * | 2006-07-06 | 2008-01-10 | Alembic Limited | An improved process for the preparation of sucralose of high purity |
| CN100420697C (zh) * | 2006-08-30 | 2008-09-24 | 河北苏科瑞科技有限公司 | 一种制备蔗糖-6-有机酸酯的方法 |
| US8258291B2 (en) * | 2006-10-25 | 2012-09-04 | Mamtek International Limited | Process for the preparation of sucralose by the chlorination of sugar with triphosgene (BTC) |
| US20080103295A1 (en) * | 2006-10-25 | 2008-05-01 | David Losan Ho | Process for the preparation of sucrose-6-ester by esterification in the presence of solid superacid catalyst |
| GB0702857D0 (en) * | 2007-01-19 | 2007-03-28 | Tate & Lyle Plc | Improved sucralose production method |
| US20080227971A1 (en) * | 2007-01-19 | 2008-09-18 | Leinhos Duane A | Deacylation of sucralose-6-acylates |
| CN101260127B (zh) * | 2007-03-06 | 2011-04-20 | 盐城捷康三氯蔗糖制造有限公司 | 由三氯蔗糖-6-乙酯脱乙酰基合成三氯蔗糖的方法 |
| US20080300401A1 (en) * | 2007-06-04 | 2008-12-04 | Polymed Therapeutics, Inc. | Novel chlorination process for preparing sucralose |
| US20080300392A1 (en) * | 2007-06-04 | 2008-12-04 | Polymed Therapeutics, Inc. | Novel chlorination process for preparing sucralose |
| AR070082A1 (es) * | 2008-01-04 | 2010-03-10 | Tate & Lyle Technology Ltd | Metodo para la produccion de sucralosa |
| US7932380B2 (en) * | 2008-03-06 | 2011-04-26 | Wanhe International (Group) Co. Ltd. | Process for the preparation of sucralose |
| US8557976B2 (en) * | 2008-03-13 | 2013-10-15 | Tate & Lyle Technology Limited | Microbial consortia and methods for their use |
| WO2009117317A1 (en) * | 2008-03-20 | 2009-09-24 | Tate & Lyle Technology Ltd | Removal of acids from tertiary amide solvents |
| US8436157B2 (en) * | 2008-03-26 | 2013-05-07 | Tate & Lyle Technology Limited | Method for the production of sucralose |
| AR071134A1 (es) * | 2008-04-03 | 2010-05-26 | Tate & Lyle Technology Ltd | Cristalizacion de sucralosa a partir de chorros que contienen sucralosa |
| JP5653341B2 (ja) * | 2008-04-03 | 2015-01-14 | テート アンド ライル テクノロジー リミテッド | スクラロース抽出効率に対する炭水化物濃度の影響 |
| US20090259036A1 (en) * | 2008-04-03 | 2009-10-15 | Tate & Lyle Technology Limited | Extraction of less polar impurities from sucralose containing aqueous feed streams |
| US8497367B2 (en) * | 2008-04-03 | 2013-07-30 | Tate & Lyle Technology Limited | Sucralose purification process |
| US20090299055A1 (en) * | 2008-04-03 | 2009-12-03 | Tate & Lyle Technology Limited | Purification of Sucralose Containing Feed Streams for Sucralose Crystallization |
| US7862744B2 (en) * | 2008-07-23 | 2011-01-04 | Mamtek International Limited | Methods and systems for preparing materials for sucralose production |
| US20100022765A1 (en) * | 2008-07-23 | 2010-01-28 | David Losan Ho | Methods for extracting and purifying sucralose intermediate |
| GB2468936B (en) * | 2009-03-27 | 2011-09-07 | Mohamad Rami Radwan Jaber | Chlorination of sucrose-6-esters |
| GB2469157B (en) * | 2009-03-30 | 2011-07-06 | John Kerr | Process for removing dimethylamine during sucralose production |
| GB2469158B (en) | 2009-03-31 | 2011-09-28 | Peter J Seaberg | Base-assisted formation of tin-sucrose adducts |
| GB2471348B (en) * | 2009-06-22 | 2011-12-14 | Tate & Lyle Technology Ltd | A method for producing sucralose-6-acylate |
| GB2474310B (en) | 2009-10-12 | 2012-02-29 | Tate & Lyle Technology Ltd | Process for the production of sucrose-6-ester |
| GB2474311B (en) | 2009-10-12 | 2012-10-17 | Tate & Lyle Technology Ltd | Low temperature, single solvent process for the production of sucrose-6-ester |
| WO2012025937A1 (en) * | 2010-08-25 | 2012-03-01 | Ramamohan Rao Davuluri | Improved process for preparation of sugammadex |
| CN103298824B (zh) * | 2010-11-23 | 2016-10-12 | 列克星敦制药实验室 | 碳水化合物的低温氯化 |
| GB201110520D0 (en) | 2011-05-10 | 2011-08-03 | Tate & Lyle Technology Ltd | Extraction of carboxylic acids with tin compounds |
| JP5679447B2 (ja) * | 2011-06-20 | 2015-03-04 | 第一工業製薬株式会社 | ショ糖ベンゾエート組成物の製造方法 |
| US8884004B2 (en) | 2011-09-02 | 2014-11-11 | Divi's Laboratories, Ltd. | Process for the preparation of sucralose |
| DK2646452T3 (da) * | 2011-10-14 | 2016-06-20 | Lexington Pharmaceutical Laboratories Llc | Chlorering af carbohydrater og carbohydratderivater |
| CN102964396B (zh) * | 2012-10-26 | 2015-11-18 | 溧阳维信生物科技有限公司 | 一种三氯蔗糖-6-乙酯重结晶的方法 |
| JP6109531B2 (ja) * | 2012-11-02 | 2017-04-05 | 第一工業製薬株式会社 | 溶媒の除去方法 |
| CN103145772A (zh) * | 2013-03-26 | 2013-06-12 | 山东金城柯瑞化学有限公司 | 三氯蔗糖的制备方法 |
| CN105829332B (zh) | 2013-12-16 | 2018-10-02 | 塔特和莱利技术有限公司 | 蔗糖-6-酯的氯化 |
| US10081651B2 (en) | 2014-08-08 | 2018-09-25 | Tate & Lyle Technology Limited | Chlorination of sucrose-6-esters |
| CN104387427A (zh) * | 2014-10-30 | 2015-03-04 | 安徽金禾实业股份有限公司 | 一种三氯蔗糖的生产方法 |
| GB2536480B (en) | 2015-03-17 | 2019-09-04 | Tate & Lyle Tech Ltd | DMF Distillation |
| CN105131050B (zh) * | 2015-07-22 | 2018-07-31 | 青岛科技大学 | 一种氯化剂的制备方法及其制备三氯蔗糖的方法 |
| CN105859802B (zh) * | 2016-05-14 | 2019-02-12 | 广西科技大学 | 一种三氯蔗糖的结晶和纯化方法 |
| GB2551591B (en) | 2016-06-23 | 2019-08-07 | Tate & Lyle Tech Ltd | Liquid-liquid extraction of DMF |
| EP4206211A4 (en) | 2020-09-30 | 2023-10-11 | Anhui Jinhe Industrial Co., Ltd. | METHOD FOR PURIFYING SUCRALOSE |
| CN113699196A (zh) * | 2021-08-17 | 2021-11-26 | 安徽金禾实业股份有限公司 | 一种蔗糖-6-乙酸酯的无水酶法催化合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435440A (en) * | 1976-01-08 | 1984-03-06 | Tate & Lyle Limited | Sweeteners |
| EP0010410B1 (en) * | 1978-10-18 | 1982-03-03 | TATE & LYLE PATENT HOLDINGS LIMITED | A method for the preparation of 2-chloro-2-deoxy saccharides and some 2-chloro-2-deoxy saccharides |
| CA1138443A (en) * | 1979-03-09 | 1982-12-28 | Tate & Lyle Patent Holdings Limited | Process for the preparation of chloro-deoxysugars |
| EP0031651B1 (en) * | 1979-12-20 | 1983-03-23 | TATE & LYLE PUBLIC LIMITED COMPANY | Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose |
| US4345933A (en) * | 1980-01-28 | 1982-08-24 | Velsicol Chemical Corporation | Sucrose ester of 2-methoxy-3,6-dichlorobenzoic acid |
| US4291158A (en) * | 1980-01-28 | 1981-09-22 | Velsicol Chemical Corporation | Sucrose ester of 2-methoxy-3,6-dichlorobenzoic acid |
| EP0043649B1 (en) * | 1980-07-08 | 1984-09-12 | TATE & LYLE PUBLIC LIMITED COMPANY | Process for the preparation of 4, 1',6'-trichloro-4,1',6'-trideoxygalactosucrose (tgs) |
| GR81281B (es) * | 1982-09-13 | 1984-12-11 | Tate & Lyle Plc | |
| GB8316790D0 (en) * | 1983-06-21 | 1983-07-27 | Tate & Lyle Plc | Chemical process |
| GB8622345D0 (en) * | 1986-09-17 | 1986-10-22 | Tate & Lyle Plc | Sucrose derivatives |
-
1989
- 1989-07-18 US US07/382,147 patent/US4980463A/en not_active Expired - Lifetime
-
1990
- 1990-07-06 PH PH40800A patent/PH26799A/en unknown
- 1990-07-06 IL IL9499490A patent/IL94994A/en unknown
- 1990-07-11 NZ NZ234468A patent/NZ234468A/en unknown
- 1990-07-12 GR GR900100537A patent/GR1002037B/el not_active IP Right Cessation
- 1990-07-16 PE PE1990172224A patent/PE21591A1/es not_active Application Discontinuation
- 1990-07-16 CA CA002021632A patent/CA2021632C/en not_active Expired - Lifetime
- 1990-07-17 IE IE260390A patent/IE69961B1/en not_active IP Right Cessation
- 1990-07-17 JP JP18732890A patent/JP3183506B2/ja not_active Expired - Fee Related
- 1990-07-17 PT PT94719A patent/PT94719B/pt not_active IP Right Cessation
- 1990-07-17 NO NO903190A patent/NO175532C/no not_active IP Right Cessation
- 1990-07-17 RU SU4830726A patent/RU1836377C/ru active
- 1990-07-17 AU AU59069/90A patent/AU625908B2/en not_active Expired
- 1990-07-17 DK DK90307784.0T patent/DK0409549T3/da active
- 1990-07-17 EP EP90307784A patent/EP0409549B1/en not_active Expired - Lifetime
- 1990-07-17 ES ES90307784T patent/ES2088973T3/es not_active Expired - Lifetime
- 1990-07-17 AR AR90317395A patent/AR247401A1/es active
- 1990-07-17 ZA ZA905615A patent/ZA905615B/xx unknown
- 1990-07-17 FI FI903603A patent/FI95802C/fi not_active IP Right Cessation
- 1990-07-17 AT AT90307784T patent/ATE133175T1/de not_active IP Right Cessation
- 1990-07-17 DE DE69024868T patent/DE69024868T2/de not_active Expired - Lifetime
- 1990-07-18 MX MX21634A patent/MX164442B/es unknown
- 1990-07-18 KR KR1019900010857A patent/KR0144344B1/ko not_active IP Right Cessation
- 1990-07-18 TR TR00678/90A patent/TR28705A/xx unknown
- 1990-07-18 YU YU141190A patent/YU47948B/sh unknown
- 1990-07-26 TW TW079106171A patent/TW219939B/zh active
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