DE2558522C3 - Verfahren zur kontinuierlichen Herstellung von Di-tertiär-butylkresolen - Google Patents
Verfahren zur kontinuierlichen Herstellung von Di-tertiär-butylkresolenInfo
- Publication number
- DE2558522C3 DE2558522C3 DE2558522A DE2558522A DE2558522C3 DE 2558522 C3 DE2558522 C3 DE 2558522C3 DE 2558522 A DE2558522 A DE 2558522A DE 2558522 A DE2558522 A DE 2558522A DE 2558522 C3 DE2558522 C3 DE 2558522C3
- Authority
- DE
- Germany
- Prior art keywords
- cresol
- isobutene
- tert
- reaction
- sulfuric 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.)
- Expired
Links
- -1 -tert-butyl cresols Chemical class 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 17
- 238000010924 continuous production Methods 0.000 title claims description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 86
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 44
- 229930003836 cresol Natural products 0.000 claims description 33
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 29
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 26
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 15
- 230000009849 deactivation Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 description 19
- 238000002156 mixing Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 229920001083 polybutene Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001896 cresols Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- WYSSJDOPILWQDC-UHFFFAOYSA-N 2,4-ditert-butyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1C(C)(C)C WYSSJDOPILWQDC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- IDGSXMQBQUGSRF-UHFFFAOYSA-N 2,4-dibutyl-3-methylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1C IDGSXMQBQUGSRF-UHFFFAOYSA-N 0.000 description 1
- GTGSYHIBFNHUEQ-UHFFFAOYSA-N 3,4-dibutyl-2-methylphenol Chemical compound CCCCC1=CC=C(O)C(C)=C1CCCC GTGSYHIBFNHUEQ-UHFFFAOYSA-N 0.000 description 1
- JKINPMFPGULFQY-UHFFFAOYSA-N 4-tert-butyl-3-methylphenol Chemical compound CC1=CC(O)=CC=C1C(C)(C)C JKINPMFPGULFQY-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004566 building material 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- C07C37/14—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 addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2558522A DE2558522C3 (de) | 1975-12-24 | 1975-12-24 | Verfahren zur kontinuierlichen Herstellung von Di-tertiär-butylkresolen |
| US05/748,073 US4144400A (en) | 1975-12-24 | 1976-12-06 | Process for the continuous preparation of di-tertiary butylcresols |
| GB53119/76A GB1500356A (en) | 1975-12-24 | 1976-12-20 | Process for the continuous preparation of di-tertiary-butylcresols |
| JP51153504A JPS5926609B2 (ja) | 1975-12-24 | 1976-12-22 | ジ−第三−ブチルクレゾ−ルの製造法 |
| NLAANVRAGE7614276,A NL185838C (nl) | 1975-12-24 | 1976-12-22 | Werkwijze voor de continue bereiding van di-tert-butylcresolen. |
| IT52738/76A IT1066682B (it) | 1975-12-24 | 1976-12-22 | Procedimento per produrre in continuo di terz.butil.cresoli |
| FR7639095A FR2336363A1 (fr) | 1975-12-24 | 1976-12-24 | Procede de preparation continue de di-tert-butylcresols |
| BE2055555A BE849835A (fr) | 1975-12-24 | 1976-12-24 | Procede de preparation continue de di-tert-butylcresols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2558522A DE2558522C3 (de) | 1975-12-24 | 1975-12-24 | Verfahren zur kontinuierlichen Herstellung von Di-tertiär-butylkresolen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2558522A1 DE2558522A1 (de) | 1977-06-30 |
| DE2558522B2 DE2558522B2 (de) | 1980-05-08 |
| DE2558522C3 true DE2558522C3 (de) | 1986-07-31 |
Family
ID=5965528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2558522A Expired DE2558522C3 (de) | 1975-12-24 | 1975-12-24 | Verfahren zur kontinuierlichen Herstellung von Di-tertiär-butylkresolen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4144400A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5926609B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE849835A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2558522C3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2336363A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1500356A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1066682B (cg-RX-API-DMAC7.html) |
| NL (1) | NL185838C (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4229598A (en) * | 1978-12-14 | 1980-10-21 | Conoco, Inc. | Chemicals for treatment of PVC |
| CN1072638C (zh) * | 1998-08-25 | 2001-10-10 | 义县精细化工总厂 | 加压制备2,6－二叔丁基对甲酚方法 |
| CN104496758B (zh) * | 2014-12-02 | 2017-02-08 | 安徽海华科技股份有限公司 | 一种间、对甲酚烷基化连续反应的方法 |
| CN105315133B (zh) * | 2015-11-17 | 2017-12-15 | 安徽海华科技股份有限公司 | 一种百里香酚合成工艺 |
| CN108285406A (zh) * | 2018-02-07 | 2018-07-17 | 常州大学 | 一种抗氧剂bht的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1035779A (fr) * | 1950-04-11 | 1953-08-31 | Ici Ltd | Production de phénols |
| FR1089570A (fr) * | 1952-12-01 | 1955-03-18 | Standard Oil Dev Co | Procédé continu d'alcoylation des phénols |
| BE531727A (cg-RX-API-DMAC7.html) * | 1953-09-08 | |||
| US2793239A (en) * | 1955-03-14 | 1957-05-21 | California Research Corp | Alkylation of aromatic compounds |
| FR1209863A (fr) * | 1956-07-19 | 1960-03-04 | Ct De Technologie Chimique | Procédé perfectionné d'alcoylation des phénols |
| DE1156083B (de) * | 1958-12-09 | 1963-10-24 | Wingfoot Corp | Verfahren zur Herstellung von trialkylierten Phenolen |
| DE1145629B (de) * | 1961-08-18 | 1963-03-21 | Ruetgerswerke Ag | Verfahren zur Herstellung von reinem m- und p-Kresol aus technischen Gemischen aus m- und p-Kresol |
| FR1417031A (fr) * | 1963-12-10 | 1965-11-05 | Rohm & Haas | Préparation de dialcoyl-phénols |
| FR1419289A (fr) * | 1963-12-31 | 1965-11-26 | Basf Ag | Procédé pour la production en continu d'alcoylphénols |
| US3534111A (en) * | 1967-02-06 | 1970-10-13 | Koppers Co Inc | Butylated cresol preparation |
| DE1668984A1 (de) * | 1968-01-04 | 1971-09-23 | Union Rheinische Braunkohlen | Verfahren zur Herstellung von Ditert.butyl-Kresolen |
| JPS49822B1 (cg-RX-API-DMAC7.html) * | 1970-04-15 | 1974-01-10 | ||
| AU453928B2 (en) * | 1972-08-15 | 1974-10-17 | Sterlitamaxky Opytno-Promyshlenny Zavod Po Proizvodstvu Izoprenovogo Kadokura | Process forr isolating isobutylene from butane butylene fraction |
-
1975
- 1975-12-24 DE DE2558522A patent/DE2558522C3/de not_active Expired
-
1976
- 1976-12-06 US US05/748,073 patent/US4144400A/en not_active Expired - Lifetime
- 1976-12-20 GB GB53119/76A patent/GB1500356A/en not_active Expired
- 1976-12-22 NL NLAANVRAGE7614276,A patent/NL185838C/xx not_active IP Right Cessation
- 1976-12-22 JP JP51153504A patent/JPS5926609B2/ja not_active Expired
- 1976-12-22 IT IT52738/76A patent/IT1066682B/it active
- 1976-12-24 BE BE2055555A patent/BE849835A/xx not_active IP Right Cessation
- 1976-12-24 FR FR7639095A patent/FR2336363A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL185838B (nl) | 1990-03-01 |
| JPS5926609B2 (ja) | 1984-06-29 |
| BE849835A (fr) | 1977-06-24 |
| DE2558522A1 (de) | 1977-06-30 |
| NL185838C (nl) | 1990-08-01 |
| IT1066682B (it) | 1985-03-12 |
| JPS5283340A (en) | 1977-07-12 |
| FR2336363A1 (fr) | 1977-07-22 |
| NL7614276A (nl) | 1977-06-28 |
| DE2558522B2 (de) | 1980-05-08 |
| GB1500356A (en) | 1978-02-08 |
| US4144400A (en) | 1979-03-13 |
| FR2336363B1 (cg-RX-API-DMAC7.html) | 1982-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8281 | Inventor (new situation) |
Free format text: FIEGE, HELMUT, DIPL.-CHEM. DR. HAYDN, JOSEF, DIPL.-CHEM. DR. RENNER, JOHANN, DR., 5090 LEVERKUSEN, DE WEDEMEYER, KARLFRIED, DIPL.-CHEM. DR., 5000 KOELN, DE |
|
| C3 | Grant after two publication steps (3rd publication) |