IT1264075B1 - Process for the production of sulphurated antioxidants from derivatives of cashew nut shell oil - Google Patents
Process for the production of sulphurated antioxidants from derivatives of cashew nut shell oilInfo
- Publication number
- IT1264075B1 IT1264075B1 IT93RM000605A ITRM930605A IT1264075B1 IT 1264075 B1 IT1264075 B1 IT 1264075B1 IT 93RM000605 A IT93RM000605 A IT 93RM000605A IT RM930605 A ITRM930605 A IT RM930605A IT 1264075 B1 IT1264075 B1 IT 1264075B1
- Authority
- IT
- Italy
- Prior art keywords
- pentadecylphenol
- tert
- bis
- amyl
- butyl
- Prior art date
Links
- 244000226021 Anacardium occidentale Species 0.000 title abstract 2
- 235000020226 cashew nut Nutrition 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000003963 antioxidant agent Substances 0.000 title 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical class CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000010586 diagram Methods 0.000 abstract 3
- KAHCOHPCVDRPLX-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)-5-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=C(C(C)(C)CC)C(O)=C1 KAHCOHPCVDRPLX-UHFFFAOYSA-N 0.000 abstract 2
- TUWLHUWKVRSCPR-UHFFFAOYSA-N 2-tert-butyl-5-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=C(C(C)(C)C)C(O)=C1 TUWLHUWKVRSCPR-UHFFFAOYSA-N 0.000 abstract 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 abstract 2
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 abstract 2
- JEXFOYWXBUUAFJ-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-pentadecylphenyl)sulfanyl-5-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1CCCCCCCCCCCCCCC JEXFOYWXBUUAFJ-UHFFFAOYSA-N 0.000 abstract 1
- ATZDLURSDXNXSV-UHFFFAOYSA-N 2-tert-butyl-4-[(5-tert-butyl-4-hydroxy-2-pentadecylphenyl)disulfanyl]-5-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC(O)=C(C(C)(C)C)C=C1SSC1=CC(C(C)(C)C)=C(O)C=C1CCCCCCCCCCCCCCC ATZDLURSDXNXSV-UHFFFAOYSA-N 0.000 abstract 1
- GEPLJWXQXWHWAD-UHFFFAOYSA-N 4-(4-hydroxy-2-pentadecylphenyl)sulfanyl-3-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC(O)=CC=C1SC1=CC=C(O)C=C1CCCCCCCCCCCCCCC GEPLJWXQXWHWAD-UHFFFAOYSA-N 0.000 abstract 1
- QIZRXLZXQMXXKT-UHFFFAOYSA-N 4-[(4-hydroxy-2-pentadecylphenyl)disulfanyl]-3-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC(O)=CC=C1SSC1=CC=C(O)C=C1CCCCCCCCCCCCCCC QIZRXLZXQMXXKT-UHFFFAOYSA-N 0.000 abstract 1
- XDKHFMZQQOBPTC-UHFFFAOYSA-N 4-[4-hydroxy-5-(2-methylbutan-2-yl)-2-pentadecylphenyl]sulfanyl-2-(2-methylbutan-2-yl)-5-pentadecylphenol Chemical compound S(C1=CC(=C(C=C1CCCCCCCCCCCCCCC)O)C(C)(C)CC)C1=CC(=C(C=C1CCCCCCCCCCCCCCC)O)C(C)(C)CC XDKHFMZQQOBPTC-UHFFFAOYSA-N 0.000 abstract 1
- UVNIHABLXOQRHG-UHFFFAOYSA-N 4-[[4-hydroxy-5-(2-methylbutan-2-yl)-2-pentadecylphenyl]disulfanyl]-2-(2-methylbutan-2-yl)-5-pentadecylphenol Chemical compound C(C)(C)(CC)C1=C(C=C(C(=C1)SSC1=CC(=C(C=C1CCCCCCCCCCCCCCC)O)C(C)(C)CC)CCCCCCCCCCCCCCC)O UVNIHABLXOQRHG-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000014571 nuts Nutrition 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
Abstract
Process for the production of sulphurated derivatives of 3-n-pentadecylphenol (diagram 1), 2-tert-butyl-5-n- pentadecylphenol and 2-tert-amyl-5-n-pentadecylphenol in which said compounds are caused to react with sulphur dichloride and sulphur monochloride. New sterically hindered thioether or dithioether bisphenol compounds derived from the sulphuration of 3-n- pentadecylphenol 1a, 2-tert-butyl-5-n-pentadecylphenol 1b and 2-tert-amyl-5-n-pentadecylphenol 1c in the 4 position in which one or two sulphur atoms form a bridge between two of said molecules depending upon whether the sulphuration is performed with sulphur dichloride (diagram 1) or sulphur monochloride (diagram 2) respectively. According to the international nomenclature these compounds have the following names: 4,4'-thio-bis- (3-n-pentadecylphenol) 2a, 4,4'-thio-bis-(2-tert-butyl-5- n-pentadecylphenol) 2b, 4,4'-thio-bis-(2-tert-amyl-5-n- pentadecylphenol) 2c, 4,4'-dithio-bis-(3-n- pentadecylphenol) 2d, 4,4'-dithio-bis-(2-tert-butyl-5-n- pentadecylphenol) 2e, 4,4'-dithio-bis-(2-tert-amyl-5- pentadecylphenol) 2f. The problem solved is that of obtaining organic chemical compounds of wide industrial application from low-cost products deriving from the processing of cashew nuts for food purposes. The invention lies in the technical field of the chemical industry and finds application above all in the field of lubricants, in particular in the field of additives for mineral oils. <IMAGE>
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT93RM000605A IT1264075B1 (en) | 1993-09-09 | 1993-09-09 | Process for the production of sulphurated antioxidants from derivatives of cashew nut shell oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT93RM000605A IT1264075B1 (en) | 1993-09-09 | 1993-09-09 | Process for the production of sulphurated antioxidants from derivatives of cashew nut shell oil |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| ITRM930605A0 ITRM930605A0 (en) | 1993-09-09 |
| ITRM930605A1 ITRM930605A1 (en) | 1995-03-09 |
| IT1264075B1 true IT1264075B1 (en) | 1996-09-10 |
Family
ID=11401942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT93RM000605A IT1264075B1 (en) | 1993-09-09 | 1993-09-09 | Process for the production of sulphurated antioxidants from derivatives of cashew nut shell oil |
Country Status (1)
| Country | Link |
|---|---|
| IT (1) | IT1264075B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114058077B (en) * | 2020-08-03 | 2023-10-13 | 中国石油化工股份有限公司 | SBS thermoplastic elastomer, preparation method thereof, anti-aging agent and application thereof |
-
1993
- 1993-09-09 IT IT93RM000605A patent/IT1264075B1/en active IP Right Grant
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| ITRM930605A1 (en) | 1995-03-09 |
| ITRM930605A0 (en) | 1993-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 0001 | Granted | ||
| TA | Fee payment date (situation as of event date), data collected since 19931001 |
Effective date: 19970929 |