JPS61212554A - 芳香族ジスルホニウム塩の製法 - Google Patents
芳香族ジスルホニウム塩の製法Info
- Publication number
- JPS61212554A JPS61212554A JP5204085A JP5204085A JPS61212554A JP S61212554 A JPS61212554 A JP S61212554A JP 5204085 A JP5204085 A JP 5204085A JP 5204085 A JP5204085 A JP 5204085A JP S61212554 A JPS61212554 A JP S61212554A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic
- bonded
- compound
- sulfuric acid
- sulfide
- 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.)
- Granted
Links
- -1 aromatic sulfonium salt Chemical class 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 150000001555 benzenes Chemical class 0.000 abstract description 4
- 238000010538 cationic polymerization reaction Methods 0.000 abstract description 2
- 239000003505 polymerization initiator Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910021135 KPF6 Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VDCOTRGOYNBXRU-UHFFFAOYSA-N 2,3-difluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(F)=C1F VDCOTRGOYNBXRU-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GYSNTKNTMCAODI-UHFFFAOYSA-L [4-(4-diphenylsulfoniophenyl)sulfanylphenyl]-diphenylsulfanium;dichloride Chemical compound [Cl-].[Cl-].C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC(C=C1)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 GYSNTKNTMCAODI-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KIEKAILMEJNSKU-UHFFFAOYSA-N bis(sulfanyl) sulfate Chemical compound SOS(=O)(=O)OS KIEKAILMEJNSKU-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5204085A JPS61212554A (ja) | 1985-03-15 | 1985-03-15 | 芳香族ジスルホニウム塩の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5204085A JPS61212554A (ja) | 1985-03-15 | 1985-03-15 | 芳香族ジスルホニウム塩の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61212554A true JPS61212554A (ja) | 1986-09-20 |
| JPH0475908B2 JPH0475908B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-12-02 |
Family
ID=12903703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5204085A Granted JPS61212554A (ja) | 1985-03-15 | 1985-03-15 | 芳香族ジスルホニウム塩の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61212554A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002048101A1 (fr) * | 2000-12-15 | 2002-06-20 | San-Apro Limited | Methode de production de sel de sulfonium |
| WO2007061024A1 (ja) | 2005-11-25 | 2007-05-31 | San-Apro Limited | フッ素化アルキルフルオロリン酸スルホニウムの製造方法 |
| JP2014070020A (ja) * | 2012-09-27 | 2014-04-21 | Sumitomo Seika Chem Co Ltd | トリアリールスルホニウム塩の製造方法 |
| WO2017115690A1 (ja) | 2015-12-29 | 2017-07-06 | サンアプロ株式会社 | 感光性組成物 |
| WO2021251035A1 (ja) | 2020-06-12 | 2021-12-16 | サンアプロ株式会社 | 新規オニウム塩、および光酸発生剤 |
| WO2022030139A1 (ja) * | 2020-08-05 | 2022-02-10 | サンアプロ株式会社 | 光酸発生剤 |
| WO2022130796A1 (ja) | 2020-12-14 | 2022-06-23 | サンアプロ株式会社 | 光酸発生剤及びこれを用いた感光性組成物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US663643A (en) * | 1898-09-12 | 1900-12-11 | Frederick Richard Simms | Sparking igniter for explosion-engines. |
| JPS61100557A (ja) * | 1984-10-22 | 1986-05-19 | ゼネラル・エレクトリツク・カンパニイ | トリアリールスルホニウム塩およびその製法 |
-
1985
- 1985-03-15 JP JP5204085A patent/JPS61212554A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US663643A (en) * | 1898-09-12 | 1900-12-11 | Frederick Richard Simms | Sparking igniter for explosion-engines. |
| JPS61100557A (ja) * | 1984-10-22 | 1986-05-19 | ゼネラル・エレクトリツク・カンパニイ | トリアリールスルホニウム塩およびその製法 |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002048101A1 (fr) * | 2000-12-15 | 2002-06-20 | San-Apro Limited | Methode de production de sel de sulfonium |
| US7060858B2 (en) | 2000-12-15 | 2006-06-13 | San-Apro Limited | Method for manufacturing sulfonium salts |
| WO2007061024A1 (ja) | 2005-11-25 | 2007-05-31 | San-Apro Limited | フッ素化アルキルフルオロリン酸スルホニウムの製造方法 |
| JP2014070020A (ja) * | 2012-09-27 | 2014-04-21 | Sumitomo Seika Chem Co Ltd | トリアリールスルホニウム塩の製造方法 |
| WO2017115690A1 (ja) | 2015-12-29 | 2017-07-06 | サンアプロ株式会社 | 感光性組成物 |
| WO2021251035A1 (ja) | 2020-06-12 | 2021-12-16 | サンアプロ株式会社 | 新規オニウム塩、および光酸発生剤 |
| WO2022030139A1 (ja) * | 2020-08-05 | 2022-02-10 | サンアプロ株式会社 | 光酸発生剤 |
| JPWO2022030139A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 2020-08-05 | 2022-02-10 | ||
| KR20230047050A (ko) | 2020-08-05 | 2023-04-06 | 산아프로 가부시키가이샤 | 광산 발생제 |
| WO2022130796A1 (ja) | 2020-12-14 | 2022-06-23 | サンアプロ株式会社 | 光酸発生剤及びこれを用いた感光性組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0475908B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-12-02 |
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