DE2027610A1 - Verfahren zur kontinuierlichen Herstellung von m-Alkylphenolen - Google Patents
Verfahren zur kontinuierlichen Herstellung von m-AlkylphenolenInfo
- Publication number
- DE2027610A1 DE2027610A1 DE19702027610 DE2027610A DE2027610A1 DE 2027610 A1 DE2027610 A1 DE 2027610A1 DE 19702027610 DE19702027610 DE 19702027610 DE 2027610 A DE2027610 A DE 2027610A DE 2027610 A1 DE2027610 A1 DE 2027610A1
- Authority
- DE
- Germany
- Prior art keywords
- alkylphenols
- isopropylphenol
- continuous production
- phenol
- isomerization
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 238000010924 continuous production Methods 0.000 title claims description 3
- 238000006317 isomerization reaction Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 4
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims description 3
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 6
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- -1 aluminum silicates Chemical class 0.000 description 3
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical class CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZEFOXNBIQIPHOP-UHFFFAOYSA-N 2,3-di(propan-2-yl)phenol Chemical class CC(C)C1=CC=CC(O)=C1C(C)C ZEFOXNBIQIPHOP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
-
- 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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702027610 DE2027610A1 (de) | 1970-06-05 | 1970-06-05 | Verfahren zur kontinuierlichen Herstellung von m-Alkylphenolen |
| BE767822A BE767822A (fr) | 1970-06-05 | 1971-05-28 | Procede de preparation en continu de m-alcoylphenols |
| GB07787/71A GB1300877A (en) | 1970-06-05 | 1971-05-28 | A process for the continuous production of m-alkyl phenols |
| NL7107413A NL7107413A (enExample) | 1970-06-05 | 1971-05-28 | |
| FR7120384A FR2095954A5 (enExample) | 1970-06-05 | 1971-06-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702027610 DE2027610A1 (de) | 1970-06-05 | 1970-06-05 | Verfahren zur kontinuierlichen Herstellung von m-Alkylphenolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2027610A1 true DE2027610A1 (de) | 1971-12-09 |
Family
ID=5773082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702027610 Pending DE2027610A1 (de) | 1970-06-05 | 1970-06-05 | Verfahren zur kontinuierlichen Herstellung von m-Alkylphenolen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE767822A (enExample) |
| DE (1) | DE2027610A1 (enExample) |
| FR (1) | FR2095954A5 (enExample) |
| GB (1) | GB1300877A (enExample) |
| NL (1) | NL7107413A (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5059338A (enExample) * | 1973-10-01 | 1975-05-22 | ||
| US3968173A (en) * | 1972-08-30 | 1976-07-06 | Bayer Aktiengesellschaft | Process for the preparation of 5-isopropyl-3-methyl-phenol |
| US4237259A (en) * | 1978-12-06 | 1980-12-02 | General Electric Company | Organic materials having meta, para-isopropylidene diphenoxy units and method |
| US4268647A (en) * | 1978-12-06 | 1981-05-19 | General Electric Company | Organic materials having meta, para-isopropylidene diphenoxy units and method |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE296276T1 (de) | 1999-02-02 | 2005-06-15 | Akzo Nobel Nv | Verfahren zur isomerisierung von alkylphenolen in gegenwart eines festen säurekatalysators |
| JP7414171B1 (ja) | 2023-03-10 | 2024-01-16 | 東洋インキＳｃホールディングス株式会社 | カーボンナノチューブ分散組成物およびその利用 |
-
1970
- 1970-06-05 DE DE19702027610 patent/DE2027610A1/de active Pending
-
1971
- 1971-05-28 BE BE767822A patent/BE767822A/xx unknown
- 1971-05-28 GB GB07787/71A patent/GB1300877A/en not_active Expired
- 1971-05-28 NL NL7107413A patent/NL7107413A/xx unknown
- 1971-06-04 FR FR7120384A patent/FR2095954A5/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968173A (en) * | 1972-08-30 | 1976-07-06 | Bayer Aktiengesellschaft | Process for the preparation of 5-isopropyl-3-methyl-phenol |
| JPS5059338A (enExample) * | 1973-10-01 | 1975-05-22 | ||
| US4237259A (en) * | 1978-12-06 | 1980-12-02 | General Electric Company | Organic materials having meta, para-isopropylidene diphenoxy units and method |
| US4268647A (en) * | 1978-12-06 | 1981-05-19 | General Electric Company | Organic materials having meta, para-isopropylidene diphenoxy units and method |
Also Published As
| Publication number | Publication date |
|---|---|
| BE767822A (fr) | 1971-10-18 |
| NL7107413A (enExample) | 1971-12-07 |
| FR2095954A5 (enExample) | 1972-02-11 |
| GB1300877A (en) | 1972-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH422739A (de) | Verfahren zum Alkylieren aromatischer Kohlenwasserstoffe | |
| DE2027610A1 (de) | Verfahren zur kontinuierlichen Herstellung von m-Alkylphenolen | |
| DE2745589A1 (de) | Verfahren zur herstellung von p-alkylphenolen | |
| US2428745A (en) | Alkylation of phenols | |
| DE1768411A1 (de) | Verfahren zum Isomerisieren und Transalkylieren von Phenolen | |
| DE2139622A1 (de) | Verfahren zur herstellung von thymol | |
| DE1252692C2 (de) | Verfahren zur kontinuierlichen herstellung von p-alkylphenolen | |
| DE2440950A1 (de) | Verfahren zur herstellung von 2,6di-tert.-butyl-4-cumylphenol | |
| DE2421168C3 (de) | Verfahren zur Herstellung von Cumol und bzw. oder sek.-Butylbenzol | |
| DE2039600A1 (de) | Verfahren zur Herstellung von Isothymol | |
| US3928471A (en) | Method for the separation of 5-isopropyl-m-cresol | |
| DE1222491B (de) | Verfahren zur Herstellung von Olefinen | |
| DE2021526A1 (de) | Verfahren zur Herstellung von Alkylphenolgemischen | |
| DE638756C (enExample) | ||
| DE1493365A1 (de) | Verfahren zur Herstellung von alkyliertem Benzol | |
| DE1668185C (enExample) | ||
| DE1935750B2 (de) | Verfahren zur Herstellung von Alkylbenzolen | |
| DE2346498C3 (de) | Verfahren zur Herstellung von o-Äthylphenol | |
| DE1228597C2 (de) | Verfahren zum Alkylieren von p-Xylol mit Propen zwecks Herstellung von 1, 4-Dimethyl-2, 5-diisopropylbenzol | |
| DE1222071B (de) | Verfahren zum Alkylieren von Phenolen, Phenolaethern oder Thiophenolen | |
| DE1618014A1 (de) | Verfahren zur Alkylierung von Phenolen | |
| DE1518407A1 (de) | Verfahren zur Herstellung von vorwiegend o-Kresol enthaltenden Methylierungsprodukten des Phenols durch Methylierung von Phenol mit Methanol oder Dimethylaether | |
| DE2208363A1 (de) | Verfahren zur alkylierung von naphthalin | |
| DE1275037B (de) | Verfahren zur kontinuierlichen Alkylierung von aromatischen Kohlenwasserstoffen | |
| DE1811443A1 (de) | Verfahren zur Herstellung von Alkylphenolen |