CA2397423A1 - Process for producing n-halogenated organic compounds - Google Patents
Process for producing n-halogenated organic compounds Download PDFInfo
- Publication number
- CA2397423A1 CA2397423A1 CA002397423A CA2397423A CA2397423A1 CA 2397423 A1 CA2397423 A1 CA 2397423A1 CA 002397423 A CA002397423 A CA 002397423A CA 2397423 A CA2397423 A CA 2397423A CA 2397423 A1 CA2397423 A1 CA 2397423A1
- Authority
- CA
- Canada
- Prior art keywords
- reaction mixture
- fed
- bromine
- range
- moles
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 230
- 230000008569 process Effects 0.000 title claims abstract description 224
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 168
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 123
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 98
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 98
- 125000003368 amide group Chemical group 0.000 claims abstract description 96
- 239000000047 product Substances 0.000 claims abstract description 82
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 80
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 65
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 60
- 239000012320 chlorinating reagent Substances 0.000 claims abstract description 55
- 239000002244 precipitate Substances 0.000 claims abstract description 40
- 229940091173 hydantoin Drugs 0.000 claims abstract description 29
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 27
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims description 230
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 144
- 238000006243 chemical reaction Methods 0.000 claims description 135
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 103
- 229910052757 nitrogen Inorganic materials 0.000 claims description 93
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims description 88
- 239000000243 solution Substances 0.000 claims description 76
- 239000002585 base Substances 0.000 claims description 71
- 239000000460 chlorine Substances 0.000 claims description 53
- 239000002002 slurry Substances 0.000 claims description 53
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 52
- 239000007791 liquid phase Substances 0.000 claims description 46
- 239000007864 aqueous solution Substances 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 39
- 150000001768 cations Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 26
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 23
- 239000012452 mother liquor Substances 0.000 claims description 20
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 238000011065 in-situ storage Methods 0.000 claims description 14
- 150000001447 alkali salts Chemical class 0.000 claims description 13
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 229910001513 alkali metal bromide Inorganic materials 0.000 claims description 12
- 150000001340 alkali metals Chemical class 0.000 claims description 12
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 claims description 12
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 12
- -1 cyclic imide Chemical class 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 150000003842 bromide salts Chemical class 0.000 claims description 11
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 230000026030 halogenation Effects 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 8
- 229910001503 inorganic bromide Inorganic materials 0.000 claims description 8
- 239000012527 feed solution Substances 0.000 claims description 7
- 230000000977 initiatory effect Effects 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 5
- 239000000920 calcium hydroxide Substances 0.000 claims description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 5
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 5
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000292 calcium oxide Substances 0.000 claims description 5
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 5
- 235000012255 calcium oxide Nutrition 0.000 claims description 5
- 239000011736 potassium bicarbonate Substances 0.000 claims description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 235000011181 potassium carbonates Nutrition 0.000 claims description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 5
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 5
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 claims description 5
- 229910001950 potassium oxide Inorganic materials 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims description 5
- 229910001948 sodium oxide Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003950 cyclic amides Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- JFBJUMZWZDHTIF-UHFFFAOYSA-N chlorine chlorite Inorganic materials ClOCl=O JFBJUMZWZDHTIF-UHFFFAOYSA-N 0.000 claims 2
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 abstract description 44
- 239000002245 particle Substances 0.000 abstract description 40
- 239000000376 reactant Substances 0.000 abstract description 8
- 238000005979 thermal decomposition reaction Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000000463 material Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 10
- 150000001469 hydantoins Chemical class 0.000 description 9
- 238000004448 titration Methods 0.000 description 9
- 230000002411 adverse Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 230000002140 halogenating effect Effects 0.000 description 7
- 150000003949 imides Chemical class 0.000 description 7
- 238000012423 maintenance Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000015107 ale Nutrition 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical class NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000001046 glycoluril group Chemical class [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical class NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 2
- 125000005543 phthalimide group Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000006251 dihalogenation reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000012840 feeding operation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000007793 ph indicator Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
- C07D233/82—Halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/484,844 | 2000-01-18 | ||
| US09/484,844 US6809205B1 (en) | 2000-01-18 | 2000-01-18 | Process for producing N-halogenated organic compounds |
| PCT/US2001/001544 WO2001053270A2 (en) | 2000-01-18 | 2001-01-17 | Process for producing n-halogenated organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2397423A1 true CA2397423A1 (en) | 2001-07-26 |
Family
ID=23925854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002397423A Abandoned CA2397423A1 (en) | 2000-01-18 | 2001-01-17 | Process for producing n-halogenated organic compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6809205B1 (enExample) |
| EP (1) | EP1250327B1 (enExample) |
| JP (1) | JP5170927B2 (enExample) |
| AT (1) | ATE346048T1 (enExample) |
| CA (1) | CA2397423A1 (enExample) |
| DE (1) | DE60124668T2 (enExample) |
| ES (1) | ES2276765T3 (enExample) |
| PT (1) | PT1250327E (enExample) |
| WO (1) | WO2001053270A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050049420A1 (en) * | 2000-01-18 | 2005-03-03 | Elnagar Hassan Y. | Process for producing N-halogenated organic compounds |
| US6565868B1 (en) * | 2000-01-18 | 2003-05-20 | Albemarle Corporation | Methods for microbiological control in aqueous systems |
| US7999118B2 (en) * | 2000-01-18 | 2011-08-16 | Albemarle Corporation | Process for producing N-halogenated hydantoins |
| US6986910B2 (en) | 2001-06-28 | 2006-01-17 | Albemarle Corporation | Microbiological control in poultry processing |
| US6908636B2 (en) | 2001-06-28 | 2005-06-21 | Albermarle Corporation | Microbiological control in poultry processing |
| US20040086463A1 (en) * | 2002-05-06 | 2004-05-06 | Hansen Richard L. | Nasal solution containing a broad spectrum microbicide and a method for its use |
| US7901276B2 (en) | 2003-06-24 | 2011-03-08 | Albemarle Corporation | Microbiocidal control in the processing of meat-producing four-legged animals |
| US9629376B2 (en) | 2007-01-12 | 2017-04-25 | Albemarle Corporation | Microbiocidal treatment of edible fruits and vegetables |
| AR064779A1 (es) * | 2007-01-12 | 2009-04-22 | Albemarle Corp | Tratamiento microbicida de frutas y verduras comestibles |
| AR064778A1 (es) * | 2007-01-12 | 2009-04-22 | Albemarle Corp | Biocidas a base de bromo adecuados para el procesamiento de alimentos |
| MX2012001211A (es) * | 2009-07-27 | 2012-05-29 | Lonza Ag | Soluciones de halogeno activas estabilizadas. |
| CN102285922B (zh) * | 2011-08-22 | 2013-07-17 | 河北亚光精细化工有限公司 | 用作医药中间体合成的二氯海因的生产方法 |
| US9028807B2 (en) * | 2012-04-05 | 2015-05-12 | Ues, Inc. | Synthesis models for antimicrobial agents via the halogenation of organic/inorganic composites |
| CA2891350A1 (en) | 2013-01-11 | 2014-07-17 | Albemarle Corporation | Microbiocidal treatment of edible fruits and vegetables |
| US9656967B2 (en) | 2013-03-19 | 2017-05-23 | Nippoh Chemicals Co., Ltd. | Method for producing halohydantoin compound |
| CN110305065B (zh) * | 2019-07-26 | 2022-05-17 | 河北利仕化学科技有限公司 | 溴氯海因连续式生产设备及生产方法 |
Family Cites Families (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2969360A (en) * | 1961-01-24 | Continuous chlorination of cyan uric | ||
| GB1054243A (enExample) | 1900-01-01 | |||
| US2130805A (en) | 1936-02-26 | 1938-09-20 | Du Pont | Sterilizing agent |
| US2398598A (en) | 1942-10-14 | 1946-04-16 | Du Pont | 1, 3-dichloro-5-methyl-5-isobutyl hydantoin and method of preparation |
| US2392505A (en) | 1944-06-06 | 1946-01-08 | Du Pont | Monochlorohydantions and salts thereof |
| US2868787A (en) | 1956-08-06 | 1959-01-13 | Drug Res Inc | Process of preparing n-brominated halogen compounds |
| US2779764A (en) | 1954-06-22 | 1957-01-29 | Drug Res Inc | Halogenated hydantoins |
| US2795556A (en) | 1954-07-26 | 1957-06-11 | Theobald Ind | Composition providing available chlorine and process of making same |
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-
2000
- 2000-01-18 US US09/484,844 patent/US6809205B1/en not_active Expired - Fee Related
-
2001
- 2001-01-17 JP JP2001553272A patent/JP5170927B2/ja not_active Expired - Lifetime
- 2001-01-17 EP EP01906581A patent/EP1250327B1/en not_active Revoked
- 2001-01-17 WO PCT/US2001/001544 patent/WO2001053270A2/en not_active Ceased
- 2001-01-17 ES ES01906581T patent/ES2276765T3/es not_active Expired - Lifetime
- 2001-01-17 DE DE60124668T patent/DE60124668T2/de not_active Revoked
- 2001-01-17 AT AT01906581T patent/ATE346048T1/de not_active IP Right Cessation
- 2001-01-17 PT PT01906581T patent/PT1250327E/pt unknown
- 2001-01-17 CA CA002397423A patent/CA2397423A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ES2276765T3 (es) | 2007-07-01 |
| WO2001053270A2 (en) | 2001-07-26 |
| EP1250327B1 (en) | 2006-11-22 |
| US6809205B1 (en) | 2004-10-26 |
| JP5170927B2 (ja) | 2013-03-27 |
| DE60124668T2 (de) | 2007-09-13 |
| WO2001053270A3 (en) | 2002-02-14 |
| EP1250327A2 (en) | 2002-10-23 |
| JP2003520275A (ja) | 2003-07-02 |
| PT1250327E (pt) | 2007-01-31 |
| ATE346048T1 (de) | 2006-12-15 |
| DE60124668D1 (de) | 2007-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |