FI65422C - Foerfarande foer framstaellning av 2,4,6-tri(3,5-ditert -butyl-4-hydroxibensyl)mesitylen - Google Patents
Foerfarande foer framstaellning av 2,4,6-tri(3,5-ditert -butyl-4-hydroxibensyl)mesitylen Download PDFInfo
- Publication number
- FI65422C FI65422C FI773008A FI773008A FI65422C FI 65422 C FI65422 C FI 65422C FI 773008 A FI773008 A FI 773008A FI 773008 A FI773008 A FI 773008A FI 65422 C FI65422 C FI 65422C
- Authority
- FI
- Finland
- Prior art keywords
- product
- butyl
- mesitylene
- reaction mixture
- ditert
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 24
- 241000257303 Hymenoptera Species 0.000 title 1
- 239000000047 product Substances 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 36
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 34
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 34
- 239000000203 mixture Substances 0.000 description 30
- SCXYLTWTWUGEAA-UHFFFAOYSA-N 2,6-ditert-butyl-4-(methoxymethyl)phenol Chemical compound COCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SCXYLTWTWUGEAA-UHFFFAOYSA-N 0.000 description 16
- 239000002168 alkylating agent Substances 0.000 description 15
- 229940100198 alkylating agent Drugs 0.000 description 15
- 238000003756 stirring Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 8
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical group CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 150000001348 alkyl chlorides Chemical class 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- -1 3,5-ditert-butyl-4-hydroxybenzyl Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RHIVSELDHMBPHG-UHFFFAOYSA-N 2,6-ditert-butyl-4-[[3-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]phenol Chemical group CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=CC(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RHIVSELDHMBPHG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/38—Gaseous or foamed well-drilling compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU762410436A SU749821A1 (ru) | 1976-10-12 | 1976-10-12 | Способ получени 2,4,6-три/3,5дитрет.бутил-4-оксибензил/мезитилена |
| SU2410436 | 1976-10-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773008A7 FI773008A7 (fi) | 1978-04-13 |
| FI65422B FI65422B (fi) | 1984-01-31 |
| FI65422C true FI65422C (fi) | 1984-05-10 |
Family
ID=20679264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773008A FI65422C (fi) | 1976-10-12 | 1977-10-11 | Foerfarande foer framstaellning av 2,4,6-tri(3,5-ditert -butyl-4-hydroxibensyl)mesitylen |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4259534A (da) |
| JP (1) | JPS596293B2 (da) |
| AT (1) | AT353256B (da) |
| BE (1) | BE859577A (da) |
| BR (1) | BR7706813A (da) |
| CA (1) | CA1092612A (da) |
| DE (1) | DE2745879C3 (da) |
| DK (1) | DK145337C (da) |
| ES (1) | ES463106A1 (da) |
| FI (1) | FI65422C (da) |
| FR (1) | FR2367720A1 (da) |
| GB (1) | GB1541766A (da) |
| IE (1) | IE46063B1 (da) |
| IT (1) | IT1143706B (da) |
| NL (1) | NL171573C (da) |
| NO (1) | NO147102C (da) |
| PT (1) | PT67131A (da) |
| SE (1) | SE443134B (da) |
| SU (1) | SU749821A1 (da) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5843983Y2 (ja) * | 1979-12-04 | 1983-10-05 | 三菱電機株式会社 | 太陽熱利用造水装置 |
| US4340767A (en) * | 1981-05-14 | 1982-07-20 | Ethyl Corporation | Antioxidant process using formaldehyde |
| DE3662188D1 (en) * | 1985-10-08 | 1989-04-06 | Mitsui Petrochemical Ind | Triphenol and polycarbonate polymer prepared therefrom |
| US4870214A (en) * | 1988-05-20 | 1989-09-26 | Ethyl Corporation | Antioxidant |
| US4898994A (en) * | 1988-10-14 | 1990-02-06 | Ethyl Corporation | Process for making 3,5-dialkyl-4-hydroxybenzyl-substituted aromatics |
| US4994628A (en) * | 1989-09-25 | 1991-02-19 | Ethyl Corporation | Phenolic antioxidant process |
| US4992597A (en) * | 1989-09-25 | 1991-02-12 | Ethyl Corporation | Antioxidant process |
| US5364895A (en) * | 1993-01-20 | 1994-11-15 | Dover Chemical Corp. | Hydrolytically stable pentaerythritol diphosphites |
| US5292969A (en) * | 1993-04-01 | 1994-03-08 | Ethyl Corporation | Phenolic antioxidant and process |
| KR100413583B1 (ko) * | 1993-08-30 | 2004-05-10 | 도버 케미칼 코포레이션 | 가수분해안정성펜타에리트리톨디포스파이트 |
| CN100567236C (zh) * | 2007-12-24 | 2009-12-09 | 中国科学院新疆理化技术研究所 | Brnsted酸性离子液体催化合成抗氧剂-330的方法 |
| CN102452905A (zh) * | 2010-10-15 | 2012-05-16 | 中国石油化工股份有限公司 | 1,3,5-三甲基-2,4,6-三（3,5-二叔丁基-4-羟基苄基）苯的制备方法 |
| CN102351657B (zh) * | 2011-08-19 | 2013-10-16 | 中国科学院新疆理化技术研究所 | 1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯的制备方法 |
| CN108503512B (zh) * | 2018-03-29 | 2019-02-19 | 江苏极易新材料有限公司 | 一种新型催化剂合成抗氧剂330的方法 |
| CN108623438A (zh) * | 2018-07-05 | 2018-10-09 | 营口风光新材料股份有限公司 | 一种多元受阻酚类抗氧剂330的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2779800A (en) * | 1954-11-30 | 1957-01-29 | Shell Dev | Process for the production of poly-(hydroxyaryl) alkane compounds and new products thereof |
| US3052728A (en) * | 1959-11-30 | 1962-09-04 | Shell Oil Co | Decolorization of cryptophenols by treatment with carbon dioxide |
| BE605948A (da) * | 1960-07-11 | |||
| NL266902A (da) * | 1960-07-11 | |||
| US3309339A (en) * | 1963-11-12 | 1967-03-14 | Allied Chem | New trisphenols and epoxide resins prepared therefrom |
| US3644538A (en) * | 1967-08-22 | 1972-02-22 | Exxon Research Engineering Co | Hindered trisphenols |
| GB1202762A (en) | 1968-06-21 | 1970-08-19 | Shell Int Research | Esters of substituted benzyl alcohols and polyphenols prepared from said esters |
| DE1910793A1 (de) * | 1969-03-04 | 1970-09-17 | F Raschig Gmbh Dr | Verfahren zur Herstellung von substituierten 1,3,5-Trimethyl-2,4,6-tris-(4-hydroxybenzyl)-benzolen |
| US3925488A (en) * | 1971-05-24 | 1975-12-09 | Ethyl Corp | Process for the production of 1,3,5-trimethy-2,4,6-tris(3,5-di-tert-alkyl-4-hydroxybenzyl)benzene |
| US3845142A (en) * | 1972-01-28 | 1974-10-29 | Y Gurvich | Process for producing polycyclic alkylphenols |
-
1976
- 1976-10-10 PT PT67131A patent/PT67131A/pt unknown
- 1976-10-12 SU SU762410436A patent/SU749821A1/ru active
-
1977
- 1977-10-07 US US05/840,329 patent/US4259534A/en not_active Expired - Lifetime
- 1977-10-10 SE SE7711374A patent/SE443134B/xx not_active IP Right Cessation
- 1977-10-11 NO NO773470A patent/NO147102C/no unknown
- 1977-10-11 DK DK450677A patent/DK145337C/da not_active IP Right Cessation
- 1977-10-11 GB GB42251/77A patent/GB1541766A/en not_active Expired
- 1977-10-11 BE BE181617A patent/BE859577A/xx not_active IP Right Cessation
- 1977-10-11 CA CA288,675A patent/CA1092612A/en not_active Expired
- 1977-10-11 IT IT28482/77A patent/IT1143706B/it active
- 1977-10-11 FR FR7730574A patent/FR2367720A1/fr active Granted
- 1977-10-11 FI FI773008A patent/FI65422C/fi not_active IP Right Cessation
- 1977-10-11 ES ES463106A patent/ES463106A1/es not_active Expired
- 1977-10-12 BR BR7706813A patent/BR7706813A/pt unknown
- 1977-10-12 NL NLAANVRAGE7711178,A patent/NL171573C/xx not_active IP Right Cessation
- 1977-10-12 IE IE2082/77A patent/IE46063B1/en unknown
- 1977-10-12 JP JP52121565A patent/JPS596293B2/ja not_active Expired
- 1977-10-12 AT AT729777A patent/AT353256B/de not_active IP Right Cessation
- 1977-10-12 DE DE2745879A patent/DE2745879C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2745879B2 (de) | 1980-05-14 |
| DK145337C (da) | 1983-03-28 |
| ES463106A1 (es) | 1978-10-01 |
| IT1143706B (it) | 1986-10-22 |
| DE2745879C3 (de) | 1981-01-22 |
| NO147102B (no) | 1982-10-25 |
| IE46063B1 (en) | 1983-02-09 |
| FR2367720A1 (fr) | 1978-05-12 |
| NO773470L (no) | 1978-04-13 |
| SU749821A1 (ru) | 1980-07-23 |
| FI773008A7 (fi) | 1978-04-13 |
| NL171573B (nl) | 1982-11-16 |
| DK145337B (da) | 1982-11-01 |
| NL171573C (nl) | 1983-04-18 |
| SE443134B (sv) | 1986-02-17 |
| DK450677A (da) | 1978-04-13 |
| NL7711178A (nl) | 1978-04-14 |
| JPS596293B2 (ja) | 1984-02-10 |
| JPS5368760A (en) | 1978-06-19 |
| BE859577A (fr) | 1978-04-11 |
| CA1092612A (en) | 1980-12-30 |
| IE46063L (en) | 1978-04-12 |
| NO147102C (no) | 1983-02-02 |
| FI65422B (fi) | 1984-01-31 |
| PT67131A (en) | 1977-11-01 |
| SE7711374L (sv) | 1978-04-13 |
| ATA729777A (de) | 1979-04-15 |
| DE2745879A1 (de) | 1978-04-13 |
| GB1541766A (en) | 1979-03-07 |
| US4259534A (en) | 1981-03-31 |
| AT353256B (de) | 1979-11-12 |
| FR2367720B1 (da) | 1980-08-01 |
| BR7706813A (pt) | 1978-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: STERLITAMAXKY OPYTNO-PROMYSHLENNY Owner name: NAUCHNO-ISSLEDOVATELSKY INSTITUT |