DE2039062A1 - Verfahren zur Herstellung von 2,6-Ditert.-butylphenol - Google Patents
Verfahren zur Herstellung von 2,6-Ditert.-butylphenolInfo
- Publication number
- DE2039062A1 DE2039062A1 DE19702039062 DE2039062A DE2039062A1 DE 2039062 A1 DE2039062 A1 DE 2039062A1 DE 19702039062 DE19702039062 DE 19702039062 DE 2039062 A DE2039062 A DE 2039062A DE 2039062 A1 DE2039062 A1 DE 2039062A1
- Authority
- DE
- Germany
- Prior art keywords
- butylphenol
- tert
- phenol
- approx
- isobutene
- 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.)
- Pending
Links
- 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 title claims description 9
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 10
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- -1 alkyl hydroxide Chemical compound 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 5
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 3
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JJULABXIXFRDCQ-UHFFFAOYSA-N 2,3,4-tritert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C JJULABXIXFRDCQ-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- SDNSCTVFEDLPNC-UHFFFAOYSA-N 2,4,4-tritert-butylcyclohexa-1,5-dien-1-ol Chemical compound CC(C)(C)C1=C(O)C=CC(C(C)(C)C)(C(C)(C)C)C1 SDNSCTVFEDLPNC-UHFFFAOYSA-N 0.000 description 1
- SQVNEBWOVQKOHH-UHFFFAOYSA-N C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)O.C(C)(C)(C)C1=CC=C(C=C1)O.C(C)(C)(C)C1=C(C=CC=C1)O Chemical compound C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)O.C(C)(C)(C)C1=CC=C(C=C1)O.C(C)(C)(C)C1=C(C=CC=C1)O SQVNEBWOVQKOHH-UHFFFAOYSA-N 0.000 description 1
- 101000651298 Homo sapiens TRAF-interacting protein with FHA domain-containing protein A Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 102100027651 TRAF-interacting protein with FHA domain-containing protein A Human genes 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702039062 DE2039062A1 (de) | 1970-08-06 | 1970-08-06 | Verfahren zur Herstellung von 2,6-Ditert.-butylphenol |
| GB3567271A GB1338709A (en) | 1970-08-06 | 1971-07-29 | Process for the preparation of 2,6-di-tert-butyl phenol |
| NL7110559A NL7110559A (OSRAM) | 1970-08-06 | 1971-07-30 | |
| CH1141971A CH558767A (de) | 1970-08-06 | 1971-08-03 | Verfahren zur herstellung von 2,6-di-tert.-butylphenol. |
| BE770917A BE770917A (fr) | 1970-08-06 | 1971-08-04 | Procede de preparation de 2,6-di-tertiobutyl phenol |
| IT2717771A IT941652B (it) | 1970-08-06 | 1971-08-04 | Processo per la produzione di 2 6 di tert butilfenolo |
| FR7128753A FR2104011A5 (OSRAM) | 1970-08-06 | 1971-08-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702039062 DE2039062A1 (de) | 1970-08-06 | 1970-08-06 | Verfahren zur Herstellung von 2,6-Ditert.-butylphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2039062A1 true DE2039062A1 (de) | 1972-02-10 |
Family
ID=5779002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702039062 Pending DE2039062A1 (de) | 1970-08-06 | 1970-08-06 | Verfahren zur Herstellung von 2,6-Ditert.-butylphenol |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE770917A (OSRAM) |
| CH (1) | CH558767A (OSRAM) |
| DE (1) | DE2039062A1 (OSRAM) |
| FR (1) | FR2104011A5 (OSRAM) |
| GB (1) | GB1338709A (OSRAM) |
| IT (1) | IT941652B (OSRAM) |
| NL (1) | NL7110559A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2712530A1 (de) * | 1976-03-22 | 1977-10-06 | Sterlitamaxky O Promyshlenny | Verfahren zur herstellung von 2,6- di-tert.butylphenol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100387563C (zh) * | 2005-05-28 | 2008-05-14 | 淄博万昌科威化工有限公司 | 烷基酚联产生产工艺 |
| US10196334B2 (en) | 2015-09-11 | 2019-02-05 | Basf Se | Process for the alkylation of phenols |
-
1970
- 1970-08-06 DE DE19702039062 patent/DE2039062A1/de active Pending
-
1971
- 1971-07-29 GB GB3567271A patent/GB1338709A/en not_active Expired
- 1971-07-30 NL NL7110559A patent/NL7110559A/xx unknown
- 1971-08-03 CH CH1141971A patent/CH558767A/xx not_active IP Right Cessation
- 1971-08-04 BE BE770917A patent/BE770917A/xx unknown
- 1971-08-04 IT IT2717771A patent/IT941652B/it active
- 1971-08-05 FR FR7128753A patent/FR2104011A5/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2712530A1 (de) * | 1976-03-22 | 1977-10-06 | Sterlitamaxky O Promyshlenny | Verfahren zur herstellung von 2,6- di-tert.butylphenol |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1338709A (en) | 1973-11-28 |
| FR2104011A5 (OSRAM) | 1972-04-14 |
| IT941652B (it) | 1973-03-10 |
| CH558767A (de) | 1975-02-14 |
| BE770917A (fr) | 1972-02-04 |
| NL7110559A (OSRAM) | 1972-02-08 |
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