CA1214789A - Preparation of (hydrocarbylthio) phenols - Google Patents
Preparation of (hydrocarbylthio) phenolsInfo
- Publication number
- CA1214789A CA1214789A CA000474017A CA474017A CA1214789A CA 1214789 A CA1214789 A CA 1214789A CA 000474017 A CA000474017 A CA 000474017A CA 474017 A CA474017 A CA 474017A CA 1214789 A CA1214789 A CA 1214789A
- Authority
- CA
- Canada
- Prior art keywords
- phenol
- hydrocarbylthio
- phenols
- methylthio
- alkylthio
- 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.)
- Expired
Links
- 150000002989 phenols Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 3
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 claims abstract description 7
- 239000007858 starting material Substances 0.000 claims abstract description 6
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 9
- SOOARYARZPXNAL-UHFFFAOYSA-N 2-(Methylthio)phenol Chemical compound CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- -1 cycloaliphatic Chemical group 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- GXJRCSYIGYLJOR-UHFFFAOYSA-N 2,4,6-tris(methylsulfanyl)phenol Chemical compound CSC1=CC(SC)=C(O)C(SC)=C1 GXJRCSYIGYLJOR-UHFFFAOYSA-N 0.000 description 2
- ALTBDYBDBRPBGJ-UHFFFAOYSA-N 2,4-bis(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C(SC)=C1 ALTBDYBDBRPBGJ-UHFFFAOYSA-N 0.000 description 2
- XTFWJPDPOBWEFE-UHFFFAOYSA-N 2,6-bis(methylsulfanyl)phenol Chemical compound CSC1=CC=CC(SC)=C1O XTFWJPDPOBWEFE-UHFFFAOYSA-N 0.000 description 2
- LCNLSFRRONIQFX-UHFFFAOYSA-N 3-methylsulfanylphenol Chemical compound CSC1=CC=CC(O)=C1 LCNLSFRRONIQFX-UHFFFAOYSA-N 0.000 description 2
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 2
- IFJYJTCJEGWOHU-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)phenol Chemical compound CSC1=CC(C)=CC(SC)=C1O IFJYJTCJEGWOHU-UHFFFAOYSA-N 0.000 description 2
- AIPNNWIVRIENTH-UHFFFAOYSA-N 4-methyl-2-methylsulfanylphenol Chemical compound CSC1=CC(C)=CC=C1O AIPNNWIVRIENTH-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OYZFFVZQXBXDCT-UHFFFAOYSA-N 4-methyl-3-methylsulfanylphenol Chemical compound CSC1=CC(O)=CC=C1C OYZFFVZQXBXDCT-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US593,562 | 1984-03-26 | ||
| US06/593,562 US4547593A (en) | 1984-03-26 | 1984-03-26 | Preparation of (hydrocarbylthio)phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1214789A true CA1214789A (en) | 1986-12-02 |
Family
ID=24375218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000474017A Expired CA1214789A (en) | 1984-03-26 | 1985-02-11 | Preparation of (hydrocarbylthio) phenols |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4547593A (enExample) |
| EP (1) | EP0156352B1 (enExample) |
| JP (1) | JPS60218370A (enExample) |
| AT (1) | ATE36150T1 (enExample) |
| CA (1) | CA1214789A (enExample) |
| DE (1) | DE3564104D1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792633A (en) * | 1986-05-19 | 1988-12-20 | E. I. Du Pont De Nemours And Company | Preparation of ortho-(alkyl- or arylthio)phenols |
| JPH01149764A (ja) * | 1987-12-07 | 1989-06-12 | Green Cross Corp:The | ビス−ｓ−アルキルベンゼン誘導体 |
| JP7037157B2 (ja) | 2019-06-04 | 2022-03-16 | 学校法人千葉工業大学 | 多孔質セラミックス及び多孔質セラミックスの製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2923743A (en) * | 1958-04-08 | 1960-02-02 | Bayer Ag | Process for the production of arylalkyl thioethers |
| GB1291191A (en) * | 1970-01-08 | 1972-10-04 | Chemische Werke Lowi Ges Mit B | Process for the isomerization and disproportioning of methyl phenols |
| US4324920A (en) * | 1980-07-28 | 1982-04-13 | Ethyl Corporation | Process for the preparation of ortho-(hydrocarbylthio)-phenols |
-
1984
- 1984-03-26 US US06/593,562 patent/US4547593A/en not_active Expired - Fee Related
-
1985
- 1985-02-11 CA CA000474017A patent/CA1214789A/en not_active Expired
- 1985-03-25 AT AT85103534T patent/ATE36150T1/de not_active IP Right Cessation
- 1985-03-25 EP EP85103534A patent/EP0156352B1/en not_active Expired
- 1985-03-25 DE DE8585103534T patent/DE3564104D1/de not_active Expired
- 1985-03-26 JP JP60061749A patent/JPS60218370A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6340782B2 (enExample) | 1988-08-12 |
| EP0156352B1 (en) | 1988-08-03 |
| US4547593A (en) | 1985-10-15 |
| JPS60218370A (ja) | 1985-11-01 |
| EP0156352A2 (en) | 1985-10-02 |
| EP0156352A3 (en) | 1986-02-05 |
| ATE36150T1 (de) | 1988-08-15 |
| DE3564104D1 (en) | 1988-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |