CA1242218A - Process for the preparation of thio-bis-phenols - Google Patents
Process for the preparation of thio-bis-phenolsInfo
- Publication number
- CA1242218A CA1242218A CA000424744A CA424744A CA1242218A CA 1242218 A CA1242218 A CA 1242218A CA 000424744 A CA000424744 A CA 000424744A CA 424744 A CA424744 A CA 424744A CA 1242218 A CA1242218 A CA 1242218A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- thio
- hydroxybenzene
- carboxamide
- sulfur dichloride
- 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
- 238000000034 method Methods 0.000 title claims abstract 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract 12
- 229960003742 phenol Drugs 0.000 claims abstract 6
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000002904 solvent Substances 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 150000003857 carboxamides Chemical class 0.000 claims 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 abstract 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38194082A | 1982-05-26 | 1982-05-26 | |
| US381,940 | 1982-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1242218A true CA1242218A (en) | 1988-09-20 |
Family
ID=23506942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000424744A Expired CA1242218A (en) | 1982-05-26 | 1983-03-29 | Process for the preparation of thio-bis-phenols |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS58216153A (en)) |
| CA (1) | CA1242218A (en)) |
| DE (1) | DE3313440C2 (en)) |
| FR (1) | FR2527603B1 (en)) |
| GB (1) | GB2120656B (en)) |
| IT (1) | IT1172263B (en)) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61151165A (ja) * | 1984-12-24 | 1986-07-09 | Seitetsu Kagaku Co Ltd | ポリチオビスフエノ−ルの製法 |
| CN1053183C (zh) * | 1997-07-22 | 2000-06-07 | 北京燕化石油化工股份有限公司化工三厂 | 一种改进的硫代双酚抗氧剂合成方法 |
| GB2421503B (en) * | 2004-10-05 | 2009-05-27 | John Henry Paul Tyman | A process for the synthesis of thiobisphenols using sulphur dichloride and phenols obtained from Anacardium occidentale and from anacardium giganteum |
| GB2436834B (en) * | 2006-04-07 | 2010-12-29 | John Henry Paul Tyman | The synthesis of di-[4-hydroxy-3-(tetramethylbutyl)phenyl)]-sulphide and t-nonyl analogue effective antioxidants for lubricating oils |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2670382A (en) * | 1950-06-10 | 1954-02-23 | Monsanto Chemicals | Preservatives |
| US3857896A (en) * | 1967-09-13 | 1974-12-31 | R Desjarlais | Substituted diresorcyl sulfide and sulfoxide compounds |
-
1983
- 1983-03-29 CA CA000424744A patent/CA1242218A/en not_active Expired
- 1983-03-29 GB GB08308618A patent/GB2120656B/en not_active Expired
- 1983-04-13 DE DE3313440A patent/DE3313440C2/de not_active Expired
- 1983-05-24 FR FR838308536A patent/FR2527603B1/fr not_active Expired
- 1983-05-25 IT IT48372/83A patent/IT1172263B/it active
- 1983-05-26 JP JP58093282A patent/JPS58216153A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB8308618D0 (en) | 1983-05-05 |
| GB2120656A (en) | 1983-12-07 |
| IT8348372A0 (it) | 1983-05-25 |
| IT1172263B (it) | 1987-06-18 |
| JPH0313229B2 (en)) | 1991-02-22 |
| DE3313440A1 (de) | 1983-12-01 |
| DE3313440C2 (de) | 1985-05-02 |
| JPS58216153A (ja) | 1983-12-15 |
| FR2527603A1 (fr) | 1983-12-02 |
| FR2527603B1 (fr) | 1985-07-26 |
| GB2120656B (en) | 1985-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |