CH628343A5 - Process for preparing thioxanthones - Google Patents

Process for preparing thioxanthones Download PDF

Info

Publication number: CH628343A5
Authority: CH; Switzerland
Prior art keywords: formula; compounds; water; mixture; washed
Prior art date: 1977-03-24

Application number

CH375977A

Other languages

German (de)

English (en)

Inventor

Lajos Dr Avar

Evelyne Kalt

Original Assignee

Sandoz 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.)

1977-03-24

Filing date

1977-03-24

Publication date

1982-02-26

1977-03-24 Application filed by Sandoz Ag filed Critical Sandoz Ag

1977-03-24 Priority to CH375977A priority Critical patent/CH628343A5/de

1978-03-17 Priority to DE19782811755 priority patent/DE2811755A1/de

1978-03-17 Priority to IT48479/78A priority patent/IT1104615B/it

1978-03-20 Priority to NL7802977A priority patent/NL7802977A/xx

1978-03-21 Priority to GB11111/78A priority patent/GB1595710A/en

1978-03-22 Priority to BE186193A priority patent/BE865202A/fr

1978-03-22 Priority to ES468218A priority patent/ES468218A1/es

1978-03-22 Priority to JP3182378A priority patent/JPS53119876A/ja

1978-03-24 Priority to FR7808659A priority patent/FR2397412B1/fr

1982-02-26 Publication of CH628343A5 publication Critical patent/CH628343A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 27
238000000034 method Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 3
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
239000000460 chlorine Substances 0.000 description 35
239000000203 mixture Substances 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
229910052801 chlorine Inorganic materials 0.000 description 14
-1 alkyl radical Chemical class 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
239000002244 precipitate Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
239000000178 monomer Substances 0.000 description 8
229910052979 sodium sulfide Inorganic materials 0.000 description 8
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
MKLXVYRSKJSNGW-UHFFFAOYSA-N (2-chlorophenyl)-(2,5-dichlorophenyl)methanone Chemical compound ClC1=CC=C(Cl)C(C(=O)C=2C(=CC=CC=2)Cl)=C1 MKLXVYRSKJSNGW-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000000630 rising effect Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 3
241000251730 Chondrichthyes Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000000976 ink Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
TZBNLXIXLJLJGI-UHFFFAOYSA-N (2,4-dichlorophenyl)-(2,5-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC(Cl)=CC=C1Cl TZBNLXIXLJLJGI-UHFFFAOYSA-N 0.000 description 1
OLHVPJMIHPQGEU-UHFFFAOYSA-N (2-chlorophenyl)-(2,3-dichloro-4-methoxyphenyl)methanone Chemical compound ClC1=C(Cl)C(OC)=CC=C1C(=O)C1=CC=CC=C1Cl OLHVPJMIHPQGEU-UHFFFAOYSA-N 0.000 description 1
CGHHNJUJBNLPHI-UHFFFAOYSA-N (2-chlorophenyl)-(2,4-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1Cl CGHHNJUJBNLPHI-UHFFFAOYSA-N 0.000 description 1
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
HFEASCCDHUVYKU-UHFFFAOYSA-N 1,2-dichloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1Cl HFEASCCDHUVYKU-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
CQJHQLAQUZOKKU-UHFFFAOYSA-N ClC1=C(C(=O)C2=C(C=CC(=C2)Br)Br)C=CC=C1 Chemical compound ClC1=C(C(=O)C2=C(C=CC(=C2)Br)Br)C=CC=C1 CQJHQLAQUZOKKU-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
239000004641 Diallyl-phthalate Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241001244799 Gluta usitata Species 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
229910004874 Na2S 9H2O Inorganic materials 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
125000005396 acrylic acid ester group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
SCBBVCPZAKTFJU-UHFFFAOYSA-N bis(2,4-dichlorophenyl)methanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1Cl SCBBVCPZAKTFJU-UHFFFAOYSA-N 0.000 description 1
DRDRZHJTTDSOPK-UHFFFAOYSA-N bis(2-chlorophenyl)methanone Chemical class ClC1=CC=CC=C1C(=O)C1=CC=CC=C1Cl DRDRZHJTTDSOPK-UHFFFAOYSA-N 0.000 description 1
ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000006757 chemical reactions by type Methods 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
230000002165 photosensitisation Effects 0.000 description 1
239000003504 photosensitizing agent Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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 in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymerisation Methods In General (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH375977A 1977-03-24 1977-03-24 Process for preparing thioxanthones CH628343A5 (en)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
CH375977A CH628343A5 (en)	1977-03-24	1977-03-24	Process for preparing thioxanthones
DE19782811755 DE2811755A1 (de)	1977-03-24	1978-03-17	Verfahren zur herstellung von gegebenenfalls substituierten thioxanthonen
IT48479/78A IT1104615B (it)	1977-03-24	1978-03-17	Procedimento per la preparazione di tioxantoni eventualmente sostituiti(caso 150-4039)
NL7802977A NL7802977A (en)	1977-03-24	1978-03-20	Thioxanthone prepn. from O,O'-di:halo:benzophenone - by reacting with alkali(ne earth) metal sulphide; used as initiators for photopolymerisable compsns.
GB11111/78A GB1595710A (en)	1977-03-24	1978-03-21	Thioxanthones
BE186193A BE865202A (fr)	1977-03-24	1978-03-22	Procede de preparation de thioxanthones eventuellement substituees
ES468218A ES468218A1 (es)	1977-03-24	1978-03-22	Perfeccionamientos en o relacionados con compuestos organi- cos.
JP3182378A JPS53119876A (en)	1977-03-24	1978-03-22	Method of producing thioxanthones
FR7808659A FR2397412B1 (fr)	1977-03-24	1978-03-24	Procede de preparation de thioxanthones eventuellement substituees

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH375977A CH628343A5 (en)	1977-03-24	1977-03-24	Process for preparing thioxanthones

Publications (1)

Publication Number	Publication Date
CH628343A5 true CH628343A5 (en)	1982-02-26

Family

ID=4262884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH375977A CH628343A5 (en)	1977-03-24	1977-03-24	Process for preparing thioxanthones

Country Status (8)

Country	Link
JP (1)	JPS53119876A (fr)
BE (1)	BE865202A (fr)
CH (1)	CH628343A5 (fr)
DE (1)	DE2811755A1 (fr)
ES (1)	ES468218A1 (fr)
FR (1)	FR2397412B1 (fr)
GB (1)	GB1595710A (fr)
IT (1)	IT1104615B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH635583A5 (de) *	1978-04-07	1983-04-15	Sandoz Ag	Verfahren zur herstellung von gegebenenfalls substituierten thioxanthonen.
CH640849A5 (de) *	1979-05-18	1984-01-31	Ciba Geigy Ag	Thioxanthoncarbonsaeureester, -thioester und -amide.
US4348530A (en)	1980-02-05	1982-09-07	Ciba-Geigy Corporation	Thioxanthonecarboxylic acids, esters, thioesters and amides with reactive functional groups
US4367324A (en)	1980-02-05	1983-01-04	Ciba-Geigy Corporation	Photocrosslinkable polymers with thioxanthone and imidyl groupings in side chains
DE3010148A1 (de)	1980-03-15	1981-09-24	Merck Patent Gmbh, 6100 Darmstadt	Neue gemische auf basis von aromatisch-aliphatischen ketonen, ihre verwendung als photoinitiatoren sowie photopolymerisierbare systeme enthaltend solche gemische
CH644362A5 (de)	1980-05-06	1984-07-31	Ciba Geigy Ag	3,5-disubstituierte phthalsaeureimide.
CH643552A5 (de)	1980-05-06	1984-06-15	Ciba Geigy Ag	Thioxanthoncarbonsaeuren und thioxanthoncarbonsaeurederivate.
JPS5723602A (en) *	1980-07-17	1982-02-06	Nippon Kayaku Co Ltd	Method for curing photosetting resin composition
JPS57163377A (en) *	1981-03-16	1982-10-07	Nippon Kayaku Co Ltd	Dialkylthioxanthone compound, its preparation, and curing of photopolymerizable resin composition using it
FR2567516B1 (fr) *	1984-07-12	1988-09-16	Sandoz Sa	Procede de preparation de xanthones et de thioxanthones et utilisation de ces composes comme initiateurs de photopolymerisation
DE3606155A1 (de) *	1986-02-26	1987-08-27	Basf Ag	Photopolymerisierbares gemisch, dieses enthaltendes lichtempfindliches aufzeichnungselement sowie verfahren zur herstellung einer flachdruckform mittels dieses lichtempfindlichen aufzeichnungselements
DE59308382D1 (de) *	1992-11-29	1998-05-14	Clariant Gmbh	Neue asymmetrische, halogenierte Benzophenone und Verfahren zu ihrer Herstellung
US5712401A (en) *	1996-04-29	1998-01-27	First Chemical Corporation	Processes for preparing thioxanthone and derivatives thereof
IT1318298B1 (it) *	2000-08-01	2003-07-28	Fiamm Spa	Avvisatore acustico elettromeccanico.
CN108218831B (zh) *	2018-04-17	2020-07-07	吉林大学	具有室温磷光性质的噻吨酮化合物晶体及其制备方法和用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1447031A (en) *	1972-05-19	1976-08-25	Wellcome Found	Tricyclic sulphones and pharmaceutical compositions containing them
US3787212A (en) *	1972-08-04	1974-01-22	Monsanto Co	Polymeric photosensitive compositions and methods using same

1977
- 1977-03-24 CH CH375977A patent/CH628343A5/de not_active IP Right Cessation
1978
- 1978-03-17 IT IT48479/78A patent/IT1104615B/it active
- 1978-03-17 DE DE19782811755 patent/DE2811755A1/de not_active Withdrawn
- 1978-03-21 GB GB11111/78A patent/GB1595710A/en not_active Expired
- 1978-03-22 ES ES468218A patent/ES468218A1/es not_active Expired
- 1978-03-22 BE BE186193A patent/BE865202A/fr not_active IP Right Cessation
- 1978-03-22 JP JP3182378A patent/JPS53119876A/ja active Pending
- 1978-03-24 FR FR7808659A patent/FR2397412B1/fr not_active Expired

Also Published As

Publication number	Publication date
DE2811755A1 (de)	1978-09-28
GB1595710A (en)	1981-08-19
IT7848479A0 (it)	1978-03-17
BE865202A (fr)	1978-09-22
FR2397412B1 (fr)	1987-10-09
FR2397412A1 (fr)	1979-02-09
IT1104615B (it)	1985-10-21
JPS53119876A (en)	1978-10-19
ES468218A1 (es)	1978-12-01

Legal Events

Date	Code	Title	Description
1991-11-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH628343A5 (en)	1982-02-26	Process for preparing thioxanthones
DE69935794T2 (de)	2007-12-27	Alicyclische verbindungen und härtbare harzzusammensetzung
EP0805152B1 (fr)	2005-06-08	Phenyl-alkyl-cétone substitué avec une amine cyclique et procédé pour sa préparation
EP0216884B1 (fr)	1990-08-08	Photo-initiateurs pour la photopolymerisation de systemes insatures
DE69217559T2 (de)	1997-06-05	Uv-härtung von fluorinierten monomeren
EP0007508B1 (fr)	1983-06-01	Acylphosphinoxydes, leur préparation et leur utilisation
EP0192167A1 (fr)	1986-08-27	Utilisation de cétones thiosubstitués comme intiateurs de photopolymérisation
CH640849A5 (de)	1984-01-31	Thioxanthoncarbonsaeureester, -thioester und -amide.
DE3209706A1 (de)	1982-10-07	Dialkylthioxanthon-verbindungen, verfahren zu ihrer herstellung und ihre verwendung
JP2019528331A (ja)	2019-10-10	フルオレン類光開始剤、その製造方法、それを有する光硬化性組成物、及び光硬化分野におけるフルオレン類光開始剤の使用
EP0110832B1 (fr)	1989-12-27	Xanthones et thioxanthones
DE69231351T2 (de)	2001-04-05	Thioxanthonderivate
EP0033720A1 (fr)	1981-08-12	Esters, thioesters et amides de l'acide thioxanthone-carboxylique, leur utilisation comme sensibilisateurs ou photo-amorceurs et polymères
DE10251667A1 (de)	2003-07-10	Photosensitives Polymer mit einer fluorierten Ethylenglykol-Gruppe und dieses umfassende chemisch verstärkte Resist-Zusammensetzung
EP0446717A2 (fr)	1991-09-18	Monomères photochromiques et polymères dérivés de ces monomères
DE2614860B2 (de)	1980-02-28	Durch Lichteinfluß härtbare flüssige Massen
DE69911050T2 (de)	2004-07-08	Für die photopolymerisation geeignete bifunktionelle photoinitiatoren und diese enthaltende photopolymerisierbare systeme
DE112020002202T5 (de)	2022-01-20	Neuartige Diaroylcarbazolverbindung und Verwendung derselben als Sensibilisierungsmittel
DE3820463A1 (de)	1989-12-21	Strahlungsempfindliche, ethylenisch ungesaettigte, copolymerisierbare verbindungen und verfahren zu deren herstellung
DE3523680A1 (de)	1986-01-16	Verfahren zur herstellung von xanthon- und thioxanthonverbindungen
EP0005530A1 (fr)	1979-11-28	Mercaptophénylcétones et leur utilisation comme initiateurs pour la photopolymérisation de composés à insaturation éthylénique
DE2923602A1 (de)	1980-01-10	Verwendung von substituierten alkylarylsulfoxiden und phenylarylsulfoxiden als photoinitiatoren
EP0456040A1 (fr)	1991-11-13	Photo-initiateurs copolymérisables du type cétal-benzilique
DE2452761A1 (de)	1975-05-15	Photographisches aufzeichnungsmaterial
DE2844394A1 (de)	1980-04-30	Neue 4-chloroxazole und verfahren zu deren herstellung