ES2276765T3 - Procedimiento para producir compuestos organicos halogenos en n. - Google Patents
Procedimiento para producir compuestos organicos halogenos en n. Download PDFInfo
- Publication number
- ES2276765T3 ES2276765T3 ES01906581T ES01906581T ES2276765T3 ES 2276765 T3 ES2276765 T3 ES 2276765T3 ES 01906581 T ES01906581 T ES 01906581T ES 01906581 T ES01906581 T ES 01906581T ES 2276765 T3 ES2276765 T3 ES 2276765T3
- Authority
- ES
- Spain
- Prior art keywords
- procedure
- accordance
- reaction mixture
- bromine
- base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 238
- 229910052736 halogen Inorganic materials 0.000 title claims description 67
- -1 HALOGEN ORGANIC COMPOUNDS Chemical class 0.000 title claims description 32
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 151
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 127
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 106
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 79
- 239000000047 product Substances 0.000 claims abstract description 77
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 60
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 60
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 54
- 239000002244 precipitate Substances 0.000 claims abstract description 41
- 239000012320 chlorinating reagent Substances 0.000 claims abstract description 37
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 25
- 230000008569 process Effects 0.000 claims abstract description 21
- 229940091173 hydantoin Drugs 0.000 claims abstract description 20
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003368 amide group Chemical group 0.000 claims abstract description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 11
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 188
- 239000011541 reaction mixture Substances 0.000 claims description 177
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 153
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 114
- 239000002585 base Substances 0.000 claims description 99
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims description 88
- 229910052757 nitrogen Inorganic materials 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 81
- 239000000243 solution Substances 0.000 claims description 77
- 239000000460 chlorine Substances 0.000 claims description 54
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 50
- 150000001408 amides Chemical class 0.000 claims description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 45
- 239000007864 aqueous solution Substances 0.000 claims description 43
- 239000007791 liquid phase Substances 0.000 claims description 42
- 239000007787 solid Substances 0.000 claims description 34
- 150000001768 cations Chemical class 0.000 claims description 30
- 239000000725 suspension Substances 0.000 claims description 28
- 239000007900 aqueous suspension Substances 0.000 claims description 27
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 18
- 238000005660 chlorination reaction Methods 0.000 claims description 18
- 230000026030 halogenation Effects 0.000 claims description 17
- 238000011065 in-situ storage Methods 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 17
- 230000031709 bromination Effects 0.000 claims description 16
- 238000005893 bromination reaction Methods 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 150000001340 alkali metals Chemical class 0.000 claims description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 14
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 13
- 229910001513 alkali metal bromide Inorganic materials 0.000 claims description 12
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 12
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 11
- 239000012452 mother liquor Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 150000003949 imides Chemical class 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 8
- 229910001503 inorganic bromide Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 claims description 7
- 150000003842 bromide salts Chemical class 0.000 claims description 7
- 239000012527 feed solution Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 7
- 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
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 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
- 150000003950 cyclic amides Chemical class 0.000 claims description 4
- 239000011736 potassium bicarbonate Substances 0.000 claims description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 235000011181 potassium carbonates Nutrition 0.000 claims description 4
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims description 4
- 229910001948 sodium oxide Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 235000012255 calcium oxide Nutrition 0.000 claims description 3
- 229910001509 metal bromide Inorganic materials 0.000 claims description 3
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 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 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000001246 bromo group Chemical group Br* 0.000 claims 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 239000002184 metal Substances 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 239000012071 phase Substances 0.000 claims 3
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 claims 2
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical class O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- JFBJUMZWZDHTIF-UHFFFAOYSA-N chlorine chlorite Inorganic materials ClOCl=O JFBJUMZWZDHTIF-UHFFFAOYSA-N 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 abstract description 46
- 239000002245 particle Substances 0.000 abstract description 41
- 239000000376 reactant Substances 0.000 abstract description 13
- 238000005979 thermal decomposition reaction Methods 0.000 abstract description 3
- 230000035611 feeding Effects 0.000 description 23
- 239000000126 substance Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 150000002366 halogen compounds Chemical class 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 9
- 150000001469 hydantoins Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 230000002411 adverse Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- 239000003643 water by type Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000002140 halogenating effect Effects 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 238000012423 maintenance Methods 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
- 238000009826 distribution Methods 0.000 description 4
- 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 3
- 229910014265 BrCl Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- PQRDTUFVDILINV-UHFFFAOYSA-N bcdmh Chemical compound CC1(C)N(Cl)C(=O)N(Br)C1=O PQRDTUFVDILINV-UHFFFAOYSA-N 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
- 239000007789 gas Substances 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 description 2
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 238000013019 agitation Methods 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
- 239000006184 cosolvent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000002609 medium Substances 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
- 230000009467 reduction Effects 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 241000894007 species Species 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 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
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- YRNLEENWMPRRPU-UHFFFAOYSA-M [Cl-].[Br+] Chemical compound [Cl-].[Br+] YRNLEENWMPRRPU-UHFFFAOYSA-M 0.000 description 1
- 238000009825 accumulation Methods 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
- 239000011230 binding agent Substances 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- 238000010908 decantation Methods 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
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000006251 dihalogenation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation 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
- 238000002474 experimental method 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
- 235000013305 food Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 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
- 230000001590 oxidative effect Effects 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
- 235000020030 perry Nutrition 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
- 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
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005507 spraying 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US484844 | 2000-01-18 | ||
| US09/484,844 US6809205B1 (en) | 2000-01-18 | 2000-01-18 | Process for producing N-halogenated organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2276765T3 true ES2276765T3 (es) | 2007-07-01 |
Family
ID=23925854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01906581T Expired - Lifetime ES2276765T3 (es) | 2000-01-18 | 2001-01-17 | Procedimiento para producir compuestos organicos halogenos en n. |
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 |
| US2920997A (en) | 1955-02-14 | 1960-01-12 | Pittsburgh Coke And Chemical C | Fungicidal composition of a hydantoin selected from the group consisting of 5, 5 polymethylene and 5, 5 diaryl, and 5, 5 aryl, alky hydantion |
| US3147259A (en) | 1956-06-22 | 1964-09-01 | Drug Res Inc | Process of preparing halogen carriers |
| US3121715A (en) | 1957-05-10 | 1964-02-18 | Thomas D Waugh | Production of n-brominated organic compounds |
| US2971959A (en) | 1958-04-14 | 1961-02-14 | Thomas D Waugh | Production of nu-brominated organic nitrogen compounds |
| US2971960A (en) | 1958-12-29 | 1961-02-14 | Thomas D Waugh | Production of nu-brominated imides and hydantoins |
| US3345371A (en) | 1961-04-07 | 1967-10-03 | Drug Res Inc | N-brominated-n-chlorinated organic compounds and process for preparing same |
| US4327151A (en) | 1976-08-25 | 1982-04-27 | Lever Brothers Company | Encapsulated bleaches and methods for their preparation |
| US4078099A (en) | 1976-08-25 | 1978-03-07 | Lever Brothers Company | Encapsulated bleaches and methods for their preparation |
| GB1600289A (en) | 1978-05-31 | 1981-10-14 | Fisons Ltd | Sterilisation of water for nutrient film systems |
| US4242216A (en) | 1979-09-27 | 1980-12-30 | Chemed Corporation | Stabilized dichlorodimethyl hydantoin |
| US4465839A (en) | 1981-11-11 | 1984-08-14 | Bayer Aktiengesellschaft | Process for the production of hydantoins |
| US4427692A (en) | 1981-12-15 | 1984-01-24 | Glyco, Inc. | Agglomerated halo-hydantoins |
| US4532330A (en) | 1982-09-30 | 1985-07-30 | Great Lakes Chemical Corporation | Process for producing densified halogenated dimethylhydantoins |
| US4621096A (en) | 1982-09-30 | 1986-11-04 | Great Lakes Chemical Corporation | Densified halogenated dimethylhydantoins |
| CA1230825A (en) | 1982-11-08 | 1987-12-29 | Bristol-Myers Squibb Company | Apparatus and method for disinfecting water and hydantoin disinfectant tablets therefor |
| US4560766A (en) | 1983-02-02 | 1985-12-24 | Glyco Chemicals, Inc. | Shaped halogenated hydantoins |
| US4654424A (en) | 1983-02-02 | 1987-03-31 | Glyco Inc. | Method for preparing halogenated hydantoins |
| US4571333A (en) | 1983-06-14 | 1986-02-18 | Syntex (U.S.A.) Inc. | Controlled release naproxen and naproxen sodium tablets |
| US4537697A (en) | 1983-12-16 | 1985-08-27 | Glyco, Inc. | Method of enhancing solubility of halogenated hydantoins |
| US4597941A (en) | 1984-03-28 | 1986-07-01 | The Drackett Company | Toilet cleaning article and method for codispensing disinfectant and dye having resistance to spectral degradation |
| ATE70055T1 (de) | 1984-09-13 | 1991-12-15 | Lonza Ag | Verfahren zur hestellung halogenierter hydantoine. |
| GB8515181D0 (en) | 1985-06-14 | 1985-07-17 | Jeyes Group Ltd | Lavatory cleansing compositions |
| US4677130A (en) | 1985-10-07 | 1987-06-30 | Great Lakes Chemical Corporation | Process of densification of N-halohydantoin compositions and products thereof |
| US4698165A (en) | 1985-10-18 | 1987-10-06 | Glyco Inc. | Shock treatment of aqueous systems |
| EP0228593A3 (en) | 1985-12-10 | 1989-10-18 | Chesebrough-Pond's Inc. | Composition for cleaning water-containing devices |
| US4713079A (en) | 1985-12-31 | 1987-12-15 | Lever Brothers Company | Particles containing dihalohydantoin bleach in a diluted core |
| US4745189A (en) | 1986-06-23 | 1988-05-17 | Ethyl Corporation | Method of preparing N-halogenated organic heterocyclic compounds |
| US4925866A (en) | 1986-10-31 | 1990-05-15 | Great Lakes Chemical Corporation | Method for controlling plant diseases and microoganisms in the presence of plants |
| US4728453A (en) | 1987-01-13 | 1988-03-01 | The Clorox Company | Timed-release bleach coated with an inorganic salt and an amine with reduced dye damage |
| US4867895A (en) | 1987-01-13 | 1989-09-19 | The Clorox Company | Timed-release bleach coated with an amine with reduced dye damage |
| EP0417144A4 (en) | 1988-05-05 | 1992-05-13 | Great Lakes Chemical Corporation | Biocidal composition |
| US4919841A (en) | 1988-06-06 | 1990-04-24 | Lever Brothers Company | Wax encapsulated actives and emulsion process for their production |
| MX173174B (es) | 1989-11-06 | 1994-02-04 | Bio Lab Inc | Composiciones de n-halogeno con pigmento azul estable |
| CA2042430A1 (en) | 1990-05-29 | 1991-11-30 | Charles G. Parsons | Water treatment blend in solid form |
| GB9108574D0 (en) | 1991-04-22 | 1991-06-05 | Jeyes Ltd | Lavatory cleansing blocks |
| US5614528A (en) | 1991-09-06 | 1997-03-25 | Bio-Lab, Inc. | Compositions and methods for inhibiting the formation of chloramines and trihalomethanes in aqueous media |
| US5670451A (en) | 1994-12-13 | 1997-09-23 | Bio-Lab, Inc. | Compositions and methods for controlling the growth of microbials in aqueous media |
| ZA926651B (en) | 1991-09-06 | 1993-03-16 | Bio Lab Inc | Compositions and methods for controlling the growth of microbials in aqueous media. |
| US5339889A (en) | 1992-08-19 | 1994-08-23 | Bigham Fred L | Controlled biocide feeder for cooling water systems |
| GB9225338D0 (en) | 1992-12-03 | 1993-01-27 | Jeyes Group Plc | Lavatory cleansing blocks |
| US5422126A (en) | 1993-03-24 | 1995-06-06 | Great Lakes Chemical Corporation | Halogen compositions for water treatment and method of preparation thereof |
| US5578559A (en) | 1993-05-14 | 1996-11-26 | Block Drug Company, Inc. | Lavatory cleaning block |
| US5603941A (en) | 1994-05-03 | 1997-02-18 | Lonza, Inc. | Multifunctional biodispersant/biocidal compositions |
| US5565109B1 (en) | 1994-10-14 | 1999-11-23 | Lonza Ag | Hydantoin-enhanced halogen efficacy in pulp and paper applications |
| US5565576A (en) | 1994-10-27 | 1996-10-15 | Lonza Inc. | Halohydantoin and fatty amide composition for compaction, process of compacting and product produced thereby |
| US6055679A (en) | 1995-03-03 | 2000-05-02 | S. C. Johnson & Son, Inc. | Passive lavatory cleanser dispensing system |
| GB2300423A (en) | 1995-03-27 | 1996-11-06 | Jeyes Group Plc | Lavatory cleansing |
| US6124251A (en) | 1995-10-27 | 2000-09-26 | The Clorox Company | Toilet bowl cleaning tablet |
| US5750061A (en) | 1995-11-07 | 1998-05-12 | Lonza Inc. | Halohydantoin forms produced by melt extrusion and method for making |
| EP0778341A1 (en) | 1995-12-07 | 1997-06-11 | The Procter & Gamble Company | Use of amido compounds in halogen bleach-comprising compositions for improved mildness to the skin |
| CA2239586C (en) | 1995-12-07 | 2005-07-26 | The Procter & Gamble Company | Process for manufacturing bleaching compositions |
| IL116545A (en) | 1995-12-25 | 2000-12-06 | Bromine Compounds Ltd | Method for stabilizing halogenated alkyl hydantoins and compositions containing them |
| WO1997043264A1 (en) | 1996-05-14 | 1997-11-20 | Great Lakes Chemical Corporation | Compositions and methods utilizing 1,3-bromochloro-5-methyl-5-propylhydantoin |
| EP0912695A1 (en) | 1996-05-15 | 1999-05-06 | The Procter & Gamble Company | Process for manufacturing bleaching compositions comprising chlorine and bromine sources and product thereof |
| US5942153A (en) | 1996-08-14 | 1999-08-24 | Bush Boake Allen Inc. | Stable fragrances for bleaching compounds |
| BR9714511A (pt) | 1996-12-12 | 2001-09-25 | Lonza Ag | Composições de limpeza contendo um agente alvejante com halgênio e um sal de sulfosuccinato |
| US5859060A (en) | 1997-01-15 | 1999-01-12 | Platt; Chris | Timed release tablet comprising naproxen and pseudoepherine |
| US5972864A (en) | 1997-02-14 | 1999-10-26 | Lonza Inc. | Bleaching and cleaning compositions containing fragrances |
| US5756440A (en) | 1997-05-27 | 1998-05-26 | The Clorox Company | Solid, water-degradable disinfectant and cleanser composition, and associated methods of manufacture and use |
| US6447722B1 (en) | 1998-12-04 | 2002-09-10 | Stellar Technology Company | Solid water treatment composition and methods of preparation and use |
-
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 |
|---|---|
| WO2001053270A2 (en) | 2001-07-26 |
| CA2397423A1 (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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