CN1202090C - 用于制备三－芳基－o－羟苯基－s－三嗪的新方法 - Google Patents

用于制备三－芳基－o－羟苯基－s－三嗪的新方法 Download PDF

Info

Publication number: CN1202090C
Authority: CN; China
Prior art keywords: formula; compound; acid; resorcinol; triazine
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.): Expired - Lifetime

Application number

CNB991031563A

Other languages

English (en)

Chinese (zh)

Other versions

CN1232823A (zh

Inventor

T·A·史蒂文森

R·穆吕里

M·阿克曼

J·F·奥斯沃尔特

P·海厄兹

C·施雷让伯杰

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

Ciba Spezialitaetenchemie Holding AG

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

1999-03-02

Publication date

2005-05-18

1999-03-02 Application filed by Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG

1999-10-27 Publication of CN1232823A publication Critical patent/CN1232823A/zh

2005-05-18 Application granted granted Critical

2005-05-18 Publication of CN1202090C publication Critical patent/CN1202090C/zh

2019-03-02 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 100
238000002360 preparation method Methods 0.000 title claims description 23
150000001875 compounds Chemical class 0.000 claims abstract description 132
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 90
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 20
239000002841 Lewis acid Substances 0.000 claims abstract description 19
150000007517 lewis acids Chemical class 0.000 claims abstract description 19
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 19
239000011968 lewis acid catalyst Substances 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 15
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims description 75
125000004432 carbon atom Chemical group C* 0.000 claims description 62
229960001755 resorcinol Drugs 0.000 claims description 47
238000006243 chemical reaction Methods 0.000 claims description 43
239000002253 acid Substances 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 21
229910052801 chlorine Inorganic materials 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 19
239000003513 alkali Substances 0.000 claims description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
239000003054 catalyst Substances 0.000 claims description 10
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000007848 Bronsted acid Substances 0.000 claims description 5
239000012747 synergistic agent Substances 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims 4
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 abstract description 32
238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 28
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 abstract description 12
239000003377 acid catalyst Substances 0.000 abstract description 11
238000004519 manufacturing process Methods 0.000 abstract description 10
239000000758 substrate Substances 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 6
239000006096 absorbing agent Substances 0.000 abstract description 3
230000000269 nucleophilic effect Effects 0.000 abstract description 3
230000002411 adverse Effects 0.000 abstract 1
238000006073 displacement reaction Methods 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
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
229910052736 halogen Inorganic materials 0.000 description 41
150000002367 halogens Chemical class 0.000 description 41
239000000203 mixture Substances 0.000 description 38
239000007787 solid Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
229910000041 hydrogen chloride Inorganic materials 0.000 description 13
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 13
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
239000000047 product Substances 0.000 description 12
238000003828 vacuum filtration Methods 0.000 description 12
238000003756 stirring Methods 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
239000007789 gas Substances 0.000 description 9
239000012071 phase Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000012043 crude product Substances 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
229930195733 hydrocarbon Natural products 0.000 description 8
150000002430 hydrocarbons Chemical class 0.000 description 8
150000002989 phenols Chemical class 0.000 description 8
125000002924 primary amino group Chemical group [H]N([H])* 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 7
239000012074 organic phase Substances 0.000 description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
235000011121 sodium hydroxide Nutrition 0.000 description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
238000001035 drying Methods 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000004305 biphenyl Substances 0.000 description 5
235000010290 biphenyl Nutrition 0.000 description 5
239000003444 phase transfer catalyst Substances 0.000 description 5
235000015320 potassium carbonate Nutrition 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
238000005406 washing Methods 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 4
125000004104 aryloxy group Chemical group 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
239000000463 material Substances 0.000 description 4
125000000896 monocarboxylic acid group Chemical group 0.000 description 4
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003242 quaternary ammonium salts Chemical class 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012434 nucleophilic reagent Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
229910000792 Monel Inorganic materials 0.000 description 2
229920000557 Nafion® Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
238000013459 approach Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000011876 fused mixture Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000012423 maintenance Methods 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
238000007344 nucleophilic reaction Methods 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
229920001296 polysiloxane Polymers 0.000 description 2
239000011591 potassium Substances 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
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000001308 synthesis method 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
NXUSAAVIBFYTQA-UHFFFAOYSA-N 1,1'-biphenyl 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1.C1=CC=CC=C1C1=CC=CC=C1 NXUSAAVIBFYTQA-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
HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 1
MVDYXUKNMGWCKS-UHFFFAOYSA-N 2-chloro-4-phenyl-1,3,5-triazine Chemical class ClC1=NC=NC(C=2C=CC=CC=2)=N1 MVDYXUKNMGWCKS-UHFFFAOYSA-N 0.000 description 1
NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical compound OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 description 1
-1 Cl or F Chemical class 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
235000001018 Hibiscus sabdariffa Nutrition 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000003140 Panax quinquefolius Nutrition 0.000 description 1
240000005373 Panax quinquefolius Species 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
235000005291 Rumex acetosa Nutrition 0.000 description 1
240000007001 Rumex acetosella Species 0.000 description 1
235000010842 Sarcandra glabra Nutrition 0.000 description 1
240000004274 Sarcandra glabra Species 0.000 description 1
239000004990 Smectic liquid crystal Substances 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
CTDZTTNWEGAVGL-UHFFFAOYSA-M [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.CC1=C(C=CC=C1)C Chemical compound [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.CC1=C(C=CC=C1)C CTDZTTNWEGAVGL-UHFFFAOYSA-M 0.000 description 1
238000004026 adhesive bonding Methods 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 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
238000005516 engineering process Methods 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
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
239000010410 layer Substances 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
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000012856 packing Methods 0.000 description 1
QCBWLIQQQBXUOU-UHFFFAOYSA-N phenol;1,3-xylene Chemical compound OC1=CC=CC=C1.CC1=CC=CC(C)=C1 QCBWLIQQQBXUOU-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940072033 potash Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
238000010926 purge Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007790 scraping Methods 0.000 description 1
235000003513 sheep sorrel Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000001052 transient effect Effects 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)

CNB991031563A 1998-03-02 1999-03-02 用于制备三－芳基－o－羟苯基－s－三嗪的新方法 Expired - Lifetime CN1202090C (zh)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US3326698A	1998-03-02	1998-03-02
US09/033266		1998-03-02
US09/033,266		1998-03-02

Publications (2)

Publication Number	Publication Date
CN1232823A CN1232823A (zh)	1999-10-27
CN1202090C true CN1202090C (zh)	2005-05-18

Family

ID=21869434

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CNB991031563A Expired - Lifetime CN1202090C (zh)	1998-03-02	1999-03-02	用于制备三－芳基－o－羟苯基－s－三嗪的新方法

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)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI259182B (en)	1998-11-17	2006-08-01	Cytec Tech Corp	Process for preparing triazines using a combination of Lewis acids with reaction promoters
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1999
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- 1999-02-22 DE DE69941073T patent/DE69941073D1/de not_active Expired - Lifetime
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IN188425B (2)	2002-09-21
US6242598B1 (en)	2001-06-05
CA2263090A1 (en)	1999-09-02
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

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