FR2476078A1 - Procede de fabrication d'un sel complexe de triarylsulfonium - Google Patents
Procede de fabrication d'un sel complexe de triarylsulfonium Download PDFInfo
- Publication number
- FR2476078A1 FR2476078A1 FR8103252A FR8103252A FR2476078A1 FR 2476078 A1 FR2476078 A1 FR 2476078A1 FR 8103252 A FR8103252 A FR 8103252A FR 8103252 A FR8103252 A FR 8103252A FR 2476078 A1 FR2476078 A1 FR 2476078A1
- Authority
- FR
- France
- Prior art keywords
- formula
- metal
- halogen
- diarylsulfide
- metal salt
- 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
- 238000000034 method Methods 0.000 title claims abstract description 17
- 150000003839 salts Chemical class 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 239000002841 Lewis acid Substances 0.000 claims abstract description 10
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 229910052752 metalloid Inorganic materials 0.000 claims abstract description 3
- 150000002738 metalloids Chemical class 0.000 claims abstract description 3
- -1 potassium hexafluoroantimonate Chemical group 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 4
- PWGVOCGNHYMDLS-UHFFFAOYSA-N 3-(2-methoxyethoxy)propan-1-amine Chemical group COCCOCCCN PWGVOCGNHYMDLS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical group ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 17
- 229910017048 AsF6 Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CLPVCAXOQZIJGW-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)sulfanylbenzene Chemical compound C1=CC(Br)=CC=C1SC1=CC=C(Br)C=C1 CLPVCAXOQZIJGW-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 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
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 229910004713 HPF6 Inorganic materials 0.000 description 1
- 229910020261 KBF4 Inorganic materials 0.000 description 1
- 229910019398 NaPF6 Inorganic materials 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 229910001615 alkaline earth metal halide Inorganic materials 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011968 lewis acid catalyst 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
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910001546 potassium hexafluoroantimonate(V) Inorganic materials 0.000 description 1
- 229910001541 potassium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910001542 sodium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical class [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12203680A | 1980-02-19 | 1980-02-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2476078A1 true FR2476078A1 (fr) | 1981-08-21 |
| FR2476078B1 FR2476078B1 (enrdf_load_stackoverflow) | 1984-10-19 |
Family
ID=22400218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8103252A Granted FR2476078A1 (fr) | 1980-02-19 | 1981-02-19 | Procede de fabrication d'un sel complexe de triarylsulfonium |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS56138167A (enrdf_load_stackoverflow) |
| DE (1) | DE3104744A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2476078A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2069486B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10301553B2 (en) | 2017-02-28 | 2019-05-28 | Ecolab Usa Inc. | Use of sulfonium salts as hydrogen sulfide inhibitors |
| US10900128B2 (en) | 2018-08-29 | 2021-01-26 | Championx Usa Inc. | Use of sulfonium salts as corrosion inhibitors |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8330692D0 (en) * | 1983-11-17 | 1983-12-29 | Sericol Group Ltd | Preparation of photoinitiators |
| DE3537401A1 (de) * | 1984-10-22 | 1986-04-24 | General Electric Co., Schenectady, N.Y. | Verfahren zur herstellung von triarylsulfoniumsalzen |
| US20050148679A1 (en) * | 2003-12-29 | 2005-07-07 | Chingfan Chiu | Aryl sulfonium salt, polymerizable composition and polymerization method of the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197174A (en) * | 1979-03-14 | 1980-04-08 | American Can Company | Method for producing bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MX6 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2807648A (en) * | 1955-09-16 | 1957-09-24 | Stauffer Chemical Co | Process for making sulfonium compounds |
| US4173476A (en) * | 1978-02-08 | 1979-11-06 | Minnesota Mining And Manufacturing Company | Complex salt photoinitiator |
| ZA805273B (en) * | 1979-09-28 | 1981-11-25 | Gen Electric | Process of deep section curing photocurable compositions |
-
1981
- 1981-01-14 GB GB8101092A patent/GB2069486B/en not_active Expired
- 1981-02-11 DE DE19813104744 patent/DE3104744A1/de active Granted
- 1981-02-19 JP JP2233581A patent/JPS56138167A/ja active Granted
- 1981-02-19 FR FR8103252A patent/FR2476078A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197174A (en) * | 1979-03-14 | 1980-04-08 | American Can Company | Method for producing bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MX6 |
Non-Patent Citations (3)
| Title |
|---|
| EXBK/65 * |
| EXBK/70 * |
| EXBK/80 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10301553B2 (en) | 2017-02-28 | 2019-05-28 | Ecolab Usa Inc. | Use of sulfonium salts as hydrogen sulfide inhibitors |
| US10900128B2 (en) | 2018-08-29 | 2021-01-26 | Championx Usa Inc. | Use of sulfonium salts as corrosion inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56138167A (en) | 1981-10-28 |
| GB2069486A (en) | 1981-08-26 |
| JPH0139423B2 (enrdf_load_stackoverflow) | 1989-08-21 |
| DE3104744A1 (de) | 1981-11-19 |
| DE3104744C2 (enrdf_load_stackoverflow) | 1990-12-06 |
| GB2069486B (en) | 1984-09-26 |
| FR2476078B1 (enrdf_load_stackoverflow) | 1984-10-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |