DE2936288A1 - Verfahren zur herstellung von 2,2'-bis- eckige klammer auf 4-(1,1,3,3-tetramethylbutyl)-phenol eckige klammer zu -sulfid - Google Patents
Verfahren zur herstellung von 2,2'-bis- eckige klammer auf 4-(1,1,3,3-tetramethylbutyl)-phenol eckige klammer zu -sulfidInfo
- Publication number
- DE2936288A1 DE2936288A1 DE19792936288 DE2936288A DE2936288A1 DE 2936288 A1 DE2936288 A1 DE 2936288A1 DE 19792936288 DE19792936288 DE 19792936288 DE 2936288 A DE2936288 A DE 2936288A DE 2936288 A1 DE2936288 A1 DE 2936288A1
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- tetramethylbutyl
- organic solvent
- bis
- lewis acid
- 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
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 title claims description 21
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 44
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 20
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 19
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- 235000005074 zinc chloride Nutrition 0.000 claims description 10
- 239000011592 zinc chloride Substances 0.000 claims description 10
- COOCXHSGXWAOHD-UHFFFAOYSA-N 3-(2,4,4-trimethylpentan-2-yl)-7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC2SC21O COOCXHSGXWAOHD-UHFFFAOYSA-N 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 239000002841 Lewis acid Substances 0.000 claims description 7
- -1 alicyclic hydrocarbons Chemical class 0.000 claims description 7
- 150000007517 lewis acids Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 235000011150 stannous chloride Nutrition 0.000 claims description 5
- 239000001119 stannous chloride Substances 0.000 claims description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000011968 lewis acid catalyst Substances 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- TYZWRNYLXYZXAM-UHFFFAOYSA-N chloro thiohypochlorite 4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound S(Cl)Cl.C(C)(C)(CC(C)(C)C)C1=CC=C(C=C1)O TYZWRNYLXYZXAM-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000000047 product Substances 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000001273 butane Substances 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
- 230000003197 catalytic effect Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005486 sulfidation Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical group Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10913678A JPS5536410A (en) | 1978-09-07 | 1978-09-07 | Preparation of 2,2'-bis(4-(1,1,3,3-tetramethylbutyl)phenol)sulfide |
| JP11365178A JPS5540630A (en) | 1978-09-18 | 1978-09-18 | Preparation of 2,2'-bis(4-(1,1,3,3-tetramethylbutyl) phenol) sulfide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2936288A1 true DE2936288A1 (de) | 1980-03-20 |
| DE2936288C2 DE2936288C2 (de) | 1987-05-14 |
Family
ID=26448925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2936288A Expired DE2936288C2 (de) | 1978-09-07 | 1979-09-07 | Verfahren zur Herstellung von 2,2'-bis-[4-(1,1,3,3-Tetramethylbutyl)-phenol]-sulfid |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4248804A (en17) |
| AU (1) | AU530175B2 (en17) |
| DE (1) | DE2936288C2 (en17) |
| FR (1) | FR2435468A1 (en17) |
| GB (1) | GB2031414B (en17) |
| IT (1) | IT1193500B (en17) |
| NL (1) | NL186445C (en17) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2937294A1 (de) * | 1978-09-14 | 1980-04-03 | Mitsui Toatsu Chemicals | Verfahren zur herstellung von 2,2'-bis-(4-substituiertem phenol)-sulfiden |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2145414B (en) * | 1983-08-24 | 1987-04-15 | Ciba Geigy | O-linked polyphenols |
| GB9415624D0 (en) | 1994-08-01 | 1994-09-21 | Exxon Chemical Patents Inc | Preparation of sulfurised phenol additives intermediates and compositions |
| 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 |
| CN114989051B (zh) * | 2022-08-03 | 2022-10-21 | 淄博万科化工有限公司 | 低氯含量抗氧剂323的生产方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB591283A (en) * | 1945-01-15 | 1947-08-13 | Standard Oil Dev Co | Process for the preparation of sulfides of alkylated phenols |
| US2971968A (en) * | 1959-01-29 | 1961-02-14 | Ferro Corp | Ortho, ortho'-bis (para-1, 1, 3, 3-tetramethyl-butylphenol) monosulphide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB731129A (en) * | 1952-12-03 | 1955-06-01 | Standard Oil Dev Co | Improved process for preparing alkyl phenol sulfides |
| GB858890A (en) * | 1959-01-29 | 1961-01-18 | Ferro Corp | Process of producing crystalline ortho, ortho-bis(para-1,1,3,3-tetramethylbutylphenol) monosulphide and nickel derivatives thereof |
| US3726928A (en) * | 1969-11-24 | 1973-04-10 | Ferro Corp | 2,2{40 -thiobis(4,6-di-tert.-butylresourcinol) |
| US3931335A (en) * | 1974-08-26 | 1976-01-06 | Crown Zellerbach Corporation | Process for selectively producing 4,4-monothiodiphenolic compounds in high yields |
-
1979
- 1979-08-22 AU AU50174/79A patent/AU530175B2/en not_active Ceased
- 1979-08-29 US US06/070,614 patent/US4248804A/en not_active Expired - Lifetime
- 1979-09-04 GB GB7930551A patent/GB2031414B/en not_active Expired
- 1979-09-05 FR FR7922178A patent/FR2435468A1/fr active Granted
- 1979-09-06 IT IT25525/79A patent/IT1193500B/it active
- 1979-09-07 DE DE2936288A patent/DE2936288C2/de not_active Expired
- 1979-09-07 NL NLAANVRAGE7906700,A patent/NL186445C/xx not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB591283A (en) * | 1945-01-15 | 1947-08-13 | Standard Oil Dev Co | Process for the preparation of sulfides of alkylated phenols |
| US2971968A (en) * | 1959-01-29 | 1961-02-14 | Ferro Corp | Ortho, ortho'-bis (para-1, 1, 3, 3-tetramethyl-butylphenol) monosulphide |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2937294A1 (de) * | 1978-09-14 | 1980-04-03 | Mitsui Toatsu Chemicals | Verfahren zur herstellung von 2,2'-bis-(4-substituiertem phenol)-sulfiden |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7925525A0 (it) | 1979-09-06 |
| GB2031414A (en) | 1980-04-23 |
| FR2435468B1 (en17) | 1984-03-09 |
| NL186445B (nl) | 1990-07-02 |
| NL7906700A (nl) | 1980-03-11 |
| AU5017479A (en) | 1980-03-13 |
| NL186445C (nl) | 1990-12-03 |
| AU530175B2 (en) | 1983-07-07 |
| US4248804A (en) | 1981-02-03 |
| DE2936288C2 (de) | 1987-05-14 |
| GB2031414B (en) | 1983-01-12 |
| IT1193500B (it) | 1988-07-08 |
| FR2435468A1 (fr) | 1980-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |