CA2263090A1 - Novel methods for the preparation of trisaryl-o-hydroxyphenyl-s-triazines - Google Patents

Novel methods for the preparation of trisaryl-o-hydroxyphenyl-s-triazines Download PDF

Info

Publication number: CA2263090A1
Authority: CA; Canada
Prior art keywords: formula; compound; carbon atoms; alkyl; halogen
Prior art date: 1998-03-02
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

Application number

CA002263090A

Other languages

English (en)

French (fr)

Inventor

Tyler Arthur Stevenson

Michael Ackerman

Pascal Hayoz

Roger Meuwly

John Francis Oswald

Christian Schregenberger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1998-03-02

Filing date

1999-02-26

Publication date

1999-09-02

1999-02-26 Application filed by Individual filed Critical Individual

1999-09-02 Publication of CA2263090A1 publication Critical patent/CA2263090A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 88
238000002360 preparation method Methods 0.000 title claims description 15
150000001875 compounds Chemical class 0.000 claims abstract description 122
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 91
125000003545 alkoxy group Chemical group 0.000 claims abstract description 45
239000002841 Lewis acid Substances 0.000 claims abstract description 29
150000007517 lewis acids Chemical class 0.000 claims abstract description 29
239000003377 acid catalyst Substances 0.000 claims abstract description 20
239000011968 lewis acid catalyst Substances 0.000 claims abstract description 18
238000004519 manufacturing process Methods 0.000 claims abstract description 11
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 105
125000000217 alkyl group Chemical group 0.000 claims description 58
229910052736 halogen Inorganic materials 0.000 claims description 58
150000002367 halogens Chemical group 0.000 claims description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 32
239000002904 solvent Substances 0.000 claims description 29
125000003884 phenylalkyl group Chemical group 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
229930195733 hydrocarbon Natural products 0.000 claims description 15
150000002989 phenols Chemical class 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 14
239000004215 Carbon black (E152) Substances 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 8
150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
150000001491 aromatic compounds Chemical class 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000000155 melt Substances 0.000 claims description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 27
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 26
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 16
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 abstract description 12
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 12
125000003118 aryl group Chemical group 0.000 abstract description 9
239000000758 substrate Substances 0.000 abstract description 9
230000000269 nucleophilic effect Effects 0.000 abstract description 4
239000000463 material Substances 0.000 abstract description 3
239000006096 absorbing agent Substances 0.000 abstract description 2
230000002411 adverse Effects 0.000 abstract description 2
BEOWAMYAXCGDMK-UHFFFAOYSA-N 4-(1,3,5-triazin-2-yl)benzene-1,2,3-triol Chemical compound Oc1ccc(c(O)c1O)-c1ncncn1 BEOWAMYAXCGDMK-UHFFFAOYSA-N 0.000 abstract 1
238000006073 displacement reaction Methods 0.000 abstract 1
230000000694 effects Effects 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
230000006641 stabilisation Effects 0.000 abstract 1
238000011105 stabilization Methods 0.000 abstract 1
150000003918 triazines Chemical class 0.000 abstract 1
125000005023 xylyl group Chemical group 0.000 abstract 1
239000000203 mixture Substances 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 28
239000007787 solid Substances 0.000 description 28
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
229910000041 hydrogen chloride Inorganic materials 0.000 description 13
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
150000002431 hydrogen Chemical group 0.000 description 12
229940098779 methanesulfonic acid Drugs 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000000047 product Substances 0.000 description 12
239000008096 xylene Substances 0.000 description 12
150000002430 hydrocarbons Chemical class 0.000 description 11
239000012071 phase Substances 0.000 description 11
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
238000003828 vacuum filtration Methods 0.000 description 10
FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-UHFFFAOYSA-N 0.000 description 9
239000007789 gas Substances 0.000 description 9
150000007513 acids Chemical class 0.000 description 8
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 8
239000012043 crude product Substances 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000004305 biphenyl Substances 0.000 description 5
235000010290 biphenyl Nutrition 0.000 description 5
-1 hydrogen halides Chemical class 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000003444 phase transfer catalyst Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
125000004104 aryloxy group Chemical group 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003242 quaternary ammonium salts Chemical class 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000012038 nucleophile Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
WPAYYYDSSCOEHN-UHFFFAOYSA-N 2-chloro-4,6-diphenoxy-1,3,5-triazine Chemical compound N=1C(OC=2C=CC=CC=2)=NC(Cl)=NC=1OC1=CC=CC=C1 WPAYYYDSSCOEHN-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
229910000792 Monel Inorganic materials 0.000 description 2
229920000557 Nafion® Polymers 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
239000011575 calcium Chemical class 0.000 description 2
229910052791 calcium Chemical class 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
238000005580 one pot reaction Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000002572 peristaltic effect Effects 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000011591 potassium Chemical class 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000010792 warming Methods 0.000 description 2
ZQBKITVCWRWZPS-UHFFFAOYSA-N 1,1'-biphenyl 4-(1,3,5-triazin-2-yl)benzene-1,3-diol Chemical compound OC1=C(C=CC(=C1)O)C1=NC=NC=N1.C1=C(C=CC=C1)C1=CC=CC=C1 ZQBKITVCWRWZPS-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
WWASTWQYXXOELT-UHFFFAOYSA-N 2,4-bis(2,4-dimethylphenyl)-4-propoxy-1h-1,3,5-triazine Chemical compound N=1C(OCCC)(C=2C(=CC(C)=CC=2)C)NC=NC=1C1=CC=C(C)C=C1C WWASTWQYXXOELT-UHFFFAOYSA-N 0.000 description 1
LPOJIRJXGOALES-UHFFFAOYSA-N 2,4-bis(2,4-dimethylphenyl)-6-phenoxy-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC(OC=2C=CC=CC=2)=NC(C=2C(=CC(C)=CC=2)C)=N1 LPOJIRJXGOALES-UHFFFAOYSA-N 0.000 description 1
ONJNUTGHRYVYHO-UHFFFAOYSA-N 2,4-dichloro-4-[3-[(2,4-dichloro-1h-1,3,5-triazin-4-yl)oxy]phenoxy]-1h-1,3,5-triazine Chemical compound N1C=NC(Cl)=NC1(Cl)OC1=CC=CC(OC2(Cl)N=C(Cl)N=CN2)=C1 ONJNUTGHRYVYHO-UHFFFAOYSA-N 0.000 description 1
AMEVJOWOWQPPJQ-UHFFFAOYSA-N 2,4-dichloro-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 AMEVJOWOWQPPJQ-UHFFFAOYSA-N 0.000 description 1
UOBCMPHSRPQQIT-UHFFFAOYSA-N 2,4-diphenoxy-6-(2,4,6-trimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC(C)=C1C1=NC(OC=2C=CC=CC=2)=NC(OC=2C=CC=CC=2)=N1 UOBCMPHSRPQQIT-UHFFFAOYSA-N 0.000 description 1
MRGNHBPLBXQZRA-UHFFFAOYSA-N 2-[3-[[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]oxy]phenoxy]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC(OC=2C=C(OC=3N=C(N=C(N=3)C=3C(=CC(C)=CC=3)C)C=3C(=CC(C)=CC=3)C)C=CC=2)=NC(C=2C(=CC(C)=CC=2)C)=N1 MRGNHBPLBXQZRA-UHFFFAOYSA-N 0.000 description 1
LVWOBZPDFCTAOU-UHFFFAOYSA-N 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC(Cl)=NC(C=2C(=CC(C)=CC=2)C)=N1 LVWOBZPDFCTAOU-UHFFFAOYSA-N 0.000 description 1
DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
VQHGZBRYGMNULJ-UHFFFAOYSA-N 4-[4-(2,4-dihydroxyphenyl)-6-(2,4,6-trimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC(C)=C1C1=NC(C=2C(=CC(O)=CC=2)O)=NC(C=2C(=CC(O)=CC=2)O)=N1 VQHGZBRYGMNULJ-UHFFFAOYSA-N 0.000 description 1
GZCHMQTWICRCLR-UHFFFAOYSA-N 4-[4-(2,4-dihydroxyphenyl)-6-phenyl-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C(=CC(O)=CC=2)O)=N1 GZCHMQTWICRCLR-UHFFFAOYSA-N 0.000 description 1
NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical class OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
238000010485 C−C bond formation reaction Methods 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000010842 Sarcandra glabra Nutrition 0.000 description 1
240000004274 Sarcandra glabra Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
229910003074 TiCl4 Inorganic materials 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000011324 bead Substances 0.000 description 1
XMHAFYSAMZJJDN-UHFFFAOYSA-N benzene-1,3-diol;1,3,5-triazine Chemical class C1=NC=NC=N1.OC1=CC=CC(O)=C1.OC1=CC=CC(O)=C1.OC1=CC=CC(O)=C1 XMHAFYSAMZJJDN-UHFFFAOYSA-N 0.000 description 1
PGTXRVQSJHKGSN-UHFFFAOYSA-N benzene-1,3-diol;2-(1,3,5-triazin-2-yl)-1,3,5-triazine Chemical compound OC1=CC=CC(O)=C1.C1=NC=NC(C=2N=CN=CN=2)=N1 PGTXRVQSJHKGSN-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
238000007344 nucleophilic reaction Methods 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

CA002263090A 1998-03-02 1999-02-26 Novel methods for the preparation of trisaryl-o-hydroxyphenyl-s-triazines Abandoned CA2263090A1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3326698A	1998-03-02	1998-03-02
US09/033,266		1998-03-02

Publications (1)

Publication Number	Publication Date
CA2263090A1 true CA2263090A1 (en)	1999-09-02

Family

ID=21869434

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002263090A Abandoned CA2263090A1 (en)	1998-03-02	1999-02-26	Novel methods for the preparation of trisaryl-o-hydroxyphenyl-s-triazines

Country Status (9)

Country	Link
US (1)	US6242598B1 (2)
EP (1)	EP0941989B1 (2)
JP (1)	JP4629814B2 (2)
KR (1)	KR100555072B1 (2)
CN (1)	CN1202090C (2)
CA (1)	CA2263090A1 (2)
DE (1)	DE69941073D1 (2)
IN (1)	IN188425B (2)
TW (1)	TWI236472B (2)

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JP5647872B2 (ja)	2010-01-19	2015-01-07	富士フイルム株式会社	ポリエステル樹脂組成物
JP2012072125A (ja)	2010-08-31	2012-04-12	Fujifilm Corp	トリアジン系化合物、及び紫外線吸収剤
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TWI685524B (zh)	2013-12-17	2020-02-21	美商畢克美國股份有限公司	預先脫層之層狀材料
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KR102580043B1 (ko)	2015-07-20	2023-09-20	바스프 에스이	난연성 폴리올레핀 물품
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1999
- 1999-02-22 EP EP99810156A patent/EP0941989B1/en not_active Expired - Lifetime
- 1999-02-22 DE DE69941073T patent/DE69941073D1/de not_active Expired - Lifetime
- 1999-02-26 CA CA002263090A patent/CA2263090A1/en not_active Abandoned
- 1999-03-01 IN IN251MA1999 patent/IN188425B/en unknown
- 1999-03-02 TW TW088103143A patent/TWI236472B/zh not_active IP Right Cessation
- 1999-03-02 CN CNB991031563A patent/CN1202090C/zh not_active Expired - Lifetime
- 1999-03-02 KR KR1019990006776A patent/KR100555072B1/ko not_active Expired - Fee Related
- 1999-03-02 JP JP05444399A patent/JP4629814B2/ja not_active Expired - Fee Related
2000
- 2000-03-22 US US09/532,222 patent/US6242598B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JP4629814B2 (ja)	2011-02-09
IN188425B (2)	2002-09-21
US6242598B1 (en)	2001-06-05
CN1202090C (zh)	2005-05-18
DE69941073D1 (de)	2009-08-20
KR19990077522A (ko)	1999-10-25
EP0941989B1 (en)	2009-07-08
TWI236472B (en)	2005-07-21
EP0941989A3 (en)	2000-01-12
JPH11315072A (ja)	1999-11-16
EP0941989A2 (en)	1999-09-15
CN1232823A (zh)	1999-10-27
KR100555072B1 (ko)	2006-02-24

Legal Events

Date	Code	Title	Description
2003-11-13	EEER	Examination request
2008-02-26	FZDE	Discontinued

Publication	Publication Date	Title
CA2263090A1 (en)	1999-09-02	Novel methods for the preparation of trisaryl-o-hydroxyphenyl-s-triazines
KR0143990B1 (ko)	1998-07-15	2-(2',4'-디하이드록시페닐)-4,6-디아릴-s-트리아진의 제조방법
CA2133938A1 (en)	1995-04-23	Process for the preparation of hydroxyphenyl-1,3,5- triazines
CA2348749A1 (en)	2000-05-25	Process for preparing triazines using a combination of lewis acids and reaction promoters
KR870001382B1 (ko)	1987-07-24	트리아진유도체의 제조방법
EP0770599B1 (en)	2002-08-07	Process for the preparation of aromatic or heteroaromatic sulfonyl halides
CA2192774A1 (en)	1997-06-15	Process for the preparation of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine
BR0007982B1 (pt)	2010-11-30	processo para a preparação de um composto pesticida ou intermediário pesticida, e, composto pesticida ou intermediário pesticida.
KR100470862B1 (ko)	2005-08-23	비대칭4,6-비스(아릴옥시)피리미딘화합물의제조방법
FI111543B (fi)	2003-08-15	Menetelmä epäsymmetrisesti substituoitujen triatsiinien valmistamiseksi
MXPA99001978A (en)	2000-06-05	Novedous methods for the preparation of tris-aril-o-hydroxypenyl-s-triaci
KR20250025456A (ko)	2025-02-21	히드록시페닐-1,3,5-트리아진 화합물을 제조하는 방법
KR100555053B1 (ko)	2006-06-13	비대칭4,6-비스(아릴옥시)피리미딘화합물의개량된제조방법
KR101207668B1 (ko)	2012-12-03	세미카르바존의 제조 방법
HU199101B (en)	1990-01-29	Process for producing fluoro-formiate derivatives
US4220765A (en)	1980-09-02	Process for the preparation of 4,6-dihalogeno-triazines
CA1164878A (en)	1984-04-03	Process for the preparation of pyrazole
CA2175420C (en)	2007-04-10	Process for the preparation of optionally 2-substituted 5-chloroimidazole-4-carbaldehydes
KR0152518B1 (ko)	1998-10-15	히드록실아민 유도체
KR100920291B1 (ko)	2009-10-08	모노페놀-비스아릴 트리아진의 분리 방법
JPH08231497A (ja)	1996-09-10	２−クロロ−６−ニトロフエニルアルキルスルフイド類の製造方法および新規な２−クロロ−６−ニトロフエニルアルキルスルフイド類
Nakhmanovich et al.	2005	Synthesis of 1, 3, 4-oxadiazinium bromides from 1, 1-dimethylhydrazine derivatives and 1, 3-dibromopropyne
EP0562576B1 (en)	2003-01-22	Process for the preparation of phenyl (1,3,5-triazin-2-yl) carbamates
US3522280A (en)	1970-07-28	Hindered phenols and process of producing the same
US5380843A (en)	1995-01-10	Process for the preparation of phenyl (1,3,5-triazin-2-yl)carbamates