IL92702A - טיהור איזותיאזולונים - Google Patents
טיהור איזותיאזולוניםInfo
- Publication number
- IL92702A IL92702A IL9270289A IL9270289A IL92702A IL 92702 A IL92702 A IL 92702A IL 9270289 A IL9270289 A IL 9270289A IL 9270289 A IL9270289 A IL 9270289A IL 92702 A IL92702 A IL 92702A
- Authority
- IL
- Israel
- Prior art keywords
- crystals
- isothiazolone
- salt
- hydrogen chloride
- solution
- Prior art date
Links
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000000746 purification Methods 0.000 title description 13
- 239000013078 crystal Substances 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 43
- -1 2-substituted-3(2H)-isothiazolones Chemical class 0.000 claims abstract description 14
- FKPCCLRWSGMEJU-UHFFFAOYSA-N 1,2-thiazole 1-oxide;hydrochloride Chemical compound Cl.O=S1C=CC=N1 FKPCCLRWSGMEJU-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 47
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 35
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 33
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 238000001816 cooling Methods 0.000 claims description 19
- 238000005660 chlorination reaction Methods 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 8
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000002955 isolation Methods 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 239000012429 reaction media Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000012535 impurity Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 239000003973 paint Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000003755 preservative agent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- CMNSJKWAGPRSRK-UHFFFAOYSA-N 2-octyl-3h-1,2-thiazole 1-oxide Chemical compound CCCCCCCCN1CC=CS1=O CMNSJKWAGPRSRK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000007872 degassing Methods 0.000 description 6
- 238000009849 vacuum degassing Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FDHZSJWAYZGGKD-UHFFFAOYSA-N 3-octyl-1,2-thiazole 1-oxide Chemical compound CCCCCCCCC=1C=CS(=O)N=1 FDHZSJWAYZGGKD-UHFFFAOYSA-N 0.000 description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 238000010900 secondary nucleation Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- XBNMDSSYSMARBF-UHFFFAOYSA-N 2-propyl-3h-1,2-thiazole 1-oxide;hydrochloride Chemical compound Cl.CCCN1CC=CS1=O XBNMDSSYSMARBF-UHFFFAOYSA-N 0.000 description 2
- GJXCLGKEGAGUQC-UHFFFAOYSA-N 3-[(3-amino-3-oxopropyl)disulfanyl]propanamide Chemical class NC(=O)CCSSCCC(N)=O GJXCLGKEGAGUQC-UHFFFAOYSA-N 0.000 description 2
- GODKIWIOTRQOGQ-UHFFFAOYSA-N 3-octan-2-yl-1,2-thiazole 1-oxide Chemical compound CCCCCCC(C)C=1C=CS(=O)N=1 GODKIWIOTRQOGQ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000005452 food preservative Substances 0.000 description 2
- 235000019249 food preservative Nutrition 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- IPLDYJXMZMNUHK-UHFFFAOYSA-N 2-(sulfanylmethyl)decanamide Chemical compound CCCCCCCCC(CS)C(N)=O IPLDYJXMZMNUHK-UHFFFAOYSA-N 0.000 description 1
- CPENFWPCYZNHNK-UHFFFAOYSA-N 2-hexyl-3h-1,2-thiazole 1-oxide Chemical compound CCCCCCN1CC=CS1=O CPENFWPCYZNHNK-UHFFFAOYSA-N 0.000 description 1
- JIPXHYPOQMCLCF-UHFFFAOYSA-N 2-hexyl-3h-1,2-thiazole 1-oxide;hydrochloride Chemical compound Cl.CCCCCCN1CC=CS1=O JIPXHYPOQMCLCF-UHFFFAOYSA-N 0.000 description 1
- ABYMGZBIRXNEIB-UHFFFAOYSA-N 2-methyl-2-sulfanylpropanamide Chemical compound CC(C)(S)C(N)=O ABYMGZBIRXNEIB-UHFFFAOYSA-N 0.000 description 1
- DPGJMCSIMCJAOO-UHFFFAOYSA-N 2-octyl-1,2-thiazol-2-ium-3-ol;chloride Chemical compound Cl.CCCCCCCCN1SC=CC1=O DPGJMCSIMCJAOO-UHFFFAOYSA-N 0.000 description 1
- ACMWXOCNTYNQRQ-UHFFFAOYSA-N 3-[[3-oxo-3-(propylamino)propyl]disulfanyl]-n-propylpropanamide Chemical compound CCCNC(=O)CCSSCCC(=O)NCCC ACMWXOCNTYNQRQ-UHFFFAOYSA-N 0.000 description 1
- UTUAWSZXTSBKRD-UHFFFAOYSA-N 3-chloro-n-octylpropanamide;4,5-dichloro-2-octyl-3h-1,2-thiazole 1-oxide Chemical compound CCCCCCCCNC(=O)CCCl.CCCCCCCCN1CC(Cl)=C(Cl)S1=O UTUAWSZXTSBKRD-UHFFFAOYSA-N 0.000 description 1
- QOSWBBASOQHGPQ-UHFFFAOYSA-N 3-octyl-2h-1,3-thiazole 1-oxide Chemical compound CCCCCCCCN1CS(=O)C=C1 QOSWBBASOQHGPQ-UHFFFAOYSA-N 0.000 description 1
- JLSJEUQOXVVCPN-UHFFFAOYSA-N 3-sulfanylpropanamide Chemical compound NC(=O)CCS JLSJEUQOXVVCPN-UHFFFAOYSA-N 0.000 description 1
- PNCDVHVRKNLUKA-UHFFFAOYSA-N 4,5-dichloro-1,2-thiazole 1-oxide Chemical class ClC=1C=NS(=O)C=1Cl PNCDVHVRKNLUKA-UHFFFAOYSA-N 0.000 description 1
- OYHQMLTXWYBTPL-UHFFFAOYSA-N 4-octan-2-yl-1,2-thiazole 1-oxide Chemical compound CCCCCCC(C)C=1C=NS(=O)C=1 OYHQMLTXWYBTPL-UHFFFAOYSA-N 0.000 description 1
- CDFRIBJXDHLDHP-UHFFFAOYSA-N 5-chloro-2-methyl-3h-1,2-thiazole 1-oxide Chemical compound CN1CC=C(Cl)S1=O CDFRIBJXDHLDHP-UHFFFAOYSA-N 0.000 description 1
- YNJNLZTWVYXZNM-UHFFFAOYSA-N 5-octan-2-yl-1,2-thiazole 1-oxide Chemical compound CCCCCCC(C)C1=CC=NS1=O YNJNLZTWVYXZNM-UHFFFAOYSA-N 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- 206010061619 Deformity Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 229920001218 Pullulan Polymers 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000006280 diesel fuel additive Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- GLGJUDHTWAZGEF-UHFFFAOYSA-N n-hexyl-3-[[3-(hexylamino)-3-oxopropyl]disulfanyl]propanamide Chemical compound CCCCCCNC(=O)CCSSCCC(=O)NCCCCCC GLGJUDHTWAZGEF-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002332 oil field water Substances 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000009928 pasteurization Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/289,069 US5008395A (en) | 1988-12-22 | 1988-12-22 | Purification of isothiazolones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL92702A0 IL92702A0 (en) | 1990-09-17 |
| IL92702A true IL92702A (he) | 1994-02-27 |
Family
ID=23109916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9270289A IL92702A (he) | 1988-12-22 | 1989-12-14 | טיהור איזותיאזולונים |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5008395A (he) |
| EP (1) | EP0375265B1 (he) |
| JP (1) | JP2813394B2 (he) |
| KR (1) | KR0142327B1 (he) |
| AT (1) | ATE88999T1 (he) |
| AU (1) | AU628118B2 (he) |
| BR (1) | BR8906718A (he) |
| CA (1) | CA1332737C (he) |
| DE (1) | DE68906370T2 (he) |
| ES (1) | ES2055108T3 (he) |
| HU (1) | HU204518B (he) |
| IL (1) | IL92702A (he) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5420290A (en) * | 1989-07-03 | 1995-05-30 | Rohm And Haas Company | Nitrosamine-free 3-isothiazolones and process |
| IL97166A (en) | 1991-02-06 | 1995-10-31 | Bromine Compounds Ltd | Process for the preparation of 2-methyl-isothiazolin-3-one compounds |
| JP3732061B2 (ja) * | 1999-12-27 | 2006-01-05 | 株式会社ケミクレア | ２−アルキル−４−イソチアゾリン−３−オン類の製造方法 |
| KR100896517B1 (ko) * | 2002-07-03 | 2009-05-08 | 에스케이케미칼주식회사 | 2-옥틸-3-이소티아졸론의 정제 방법 |
| KR100469064B1 (ko) * | 2002-09-09 | 2005-02-02 | 주식회사 한서켐 | 2-메틸-4-이소티아졸린-3-온 염의 정제 방법 |
| US7893273B2 (en) * | 2006-04-03 | 2011-02-22 | Beijing Tianqing Chemicals Co. Ltd. | Preparation of N-substituted isothiazolinone derivatives |
| CN107151204B (zh) * | 2016-03-04 | 2020-10-23 | 东丽精细化工株式会社 | 1,4-环己烷二甲酰氯的制造方法 |
| CN115232087A (zh) * | 2022-08-18 | 2022-10-25 | 大连百傲化学股份有限公司 | 一种脱除oit盐酸盐中氯化氢的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118901A (en) * | 1962-04-30 | 1964-01-21 | Du Pont | 3, 4-dihalo isothiazolo[4, 5, d]isothiazole and preparation thereof |
| US3452034A (en) * | 1967-03-09 | 1969-06-24 | American Cyanamid Co | Substituted 2-(1,3,4-thiadiazol-2-yl)-4(5)-nitroimidazoles |
| US4053479A (en) * | 1969-09-03 | 1977-10-11 | Rohm And Haas Company | Certain 3-alkoxyisothiazole-4-carboxylic acids and derivatives thereof |
| US4262127A (en) * | 1979-04-16 | 1981-04-14 | Givaudan Corporation | 3-Alkoxy-2-alkylisothiazolium salts and their derivatives |
| AU7639481A (en) * | 1981-10-15 | 1982-01-07 | Nichols, J.T. | Gas cleaning method and apparatus |
| CA1189514A (en) * | 1982-06-01 | 1985-06-25 | Horst O. Bayer | Nitrosamine-free 3-isothiazolones and process |
| DE3643183A1 (de) * | 1986-12-18 | 1988-06-30 | Riedel De Haen Ag | Verfahren zur isolierung von isothiazolinonderivaten |
-
1988
- 1988-12-22 US US07/289,069 patent/US5008395A/en not_active Expired - Fee Related
-
1989
- 1989-09-27 CA CA000613534A patent/CA1332737C/en not_active Expired - Fee Related
- 1989-12-13 AT AT89313046T patent/ATE88999T1/de not_active IP Right Cessation
- 1989-12-13 EP EP89313046A patent/EP0375265B1/en not_active Expired - Lifetime
- 1989-12-13 ES ES89313046T patent/ES2055108T3/es not_active Expired - Lifetime
- 1989-12-13 DE DE89313046T patent/DE68906370T2/de not_active Expired - Fee Related
- 1989-12-14 IL IL9270289A patent/IL92702A/he not_active IP Right Cessation
- 1989-12-19 AU AU46865/89A patent/AU628118B2/en not_active Ceased
- 1989-12-20 JP JP1330936A patent/JP2813394B2/ja not_active Expired - Lifetime
- 1989-12-21 KR KR1019890019074A patent/KR0142327B1/ko not_active Expired - Fee Related
- 1989-12-22 BR BR898906718A patent/BR8906718A/pt not_active IP Right Cessation
- 1989-12-22 HU HU896750A patent/HU204518B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2813394B2 (ja) | 1998-10-22 |
| JPH03128368A (ja) | 1991-05-31 |
| KR900009619A (ko) | 1990-07-05 |
| EP0375265A3 (en) | 1990-09-12 |
| EP0375265B1 (en) | 1993-05-05 |
| ATE88999T1 (de) | 1993-05-15 |
| AU4686589A (en) | 1990-06-28 |
| ES2055108T3 (es) | 1994-08-16 |
| HU896750D0 (en) | 1990-03-28 |
| AU628118B2 (en) | 1992-09-10 |
| IL92702A0 (en) | 1990-09-17 |
| HU204518B (en) | 1992-01-28 |
| DE68906370D1 (de) | 1993-06-09 |
| DE68906370T2 (de) | 1993-11-04 |
| EP0375265A2 (en) | 1990-06-27 |
| CA1332737C (en) | 1994-10-25 |
| HUT52765A (en) | 1990-08-28 |
| BR8906718A (pt) | 1990-09-11 |
| KR0142327B1 (ko) | 1998-06-01 |
| US5008395A (en) | 1991-04-16 |
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Legal Events
| Date | Code | Title | Description |
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| RH | Patent void |