DE2611320C2 - Verfahren zur Herstellung von 2,3,6-Trimethylphenol durch Methylierung von 2,6-Xylenol in flüssiger Phase - Google Patents
Verfahren zur Herstellung von 2,3,6-Trimethylphenol durch Methylierung von 2,6-Xylenol in flüssiger PhaseInfo
- Publication number
- DE2611320C2 DE2611320C2 DE2611320A DE2611320A DE2611320C2 DE 2611320 C2 DE2611320 C2 DE 2611320C2 DE 2611320 A DE2611320 A DE 2611320A DE 2611320 A DE2611320 A DE 2611320A DE 2611320 C2 DE2611320 C2 DE 2611320C2
- Authority
- DE
- Germany
- Prior art keywords
- xylenol
- trimethylphenol
- methylation
- liquid phase
- liquid
- 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
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 title claims description 40
- 230000011987 methylation Effects 0.000 title claims description 27
- 238000007069 methylation reaction Methods 0.000 title claims description 27
- 239000007791 liquid phase Substances 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 title description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 21
- 150000002989 phenols Chemical class 0.000 claims description 13
- 239000012071 phase Substances 0.000 claims description 12
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 239000000047 product Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 16
- 239000007858 starting material Substances 0.000 description 15
- FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 description 14
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 14
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 10
- -1 2,6-xylenol Methanol Chemical compound 0.000 description 9
- KLAQSPUVCDBEGF-UHFFFAOYSA-N 2,3,5,6-tetramethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1C KLAQSPUVCDBEGF-UHFFFAOYSA-N 0.000 description 8
- VXSCPERJHPWROZ-UHFFFAOYSA-N 2,4,5-trimethylphenol Chemical compound CC1=CC(C)=C(O)C=C1C VXSCPERJHPWROZ-UHFFFAOYSA-N 0.000 description 8
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- 238000009826 distribution Methods 0.000 description 6
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 4
- GFNZJAUVJCGWLW-UHFFFAOYSA-N 2-methoxy-1,3-dimethylbenzene Chemical compound COC1=C(C)C=CC=C1C GFNZJAUVJCGWLW-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- PXSSNPBEHHJLDH-UHFFFAOYSA-N 2,3,4,5-tetramethylphenol Chemical compound CC1=CC(O)=C(C)C(C)=C1C PXSSNPBEHHJLDH-UHFFFAOYSA-N 0.000 description 3
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000010574 gas phase reaction Methods 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- WALBTDFSFTVXII-UHFFFAOYSA-N 2,3,4,5,6-pentamethylphenol Chemical compound CC1=C(C)C(C)=C(O)C(C)=C1C WALBTDFSFTVXII-UHFFFAOYSA-N 0.000 description 2
- CDRGLMWKDVXKRO-UHFFFAOYSA-N CC1=C(C(=CC=C1C)C)O.CC1=C(C(=CC(=C1)C)C)O Chemical compound CC1=C(C(=CC=C1C)C)O.CC1=C(C(=CC(=C1)C)C)O CDRGLMWKDVXKRO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 241001233037 catfish Species 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 1
- NGXJYKBAHHULFC-UHFFFAOYSA-N 2,3-dimethylphenol;2,5-dimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1.CC1=CC=CC(O)=C1C NGXJYKBAHHULFC-UHFFFAOYSA-N 0.000 description 1
- NBUINIAHJHCKGU-UHFFFAOYSA-N 2,5-dimethylphenol;3,5-dimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1.CC1=CC(C)=CC(O)=C1 NBUINIAHJHCKGU-UHFFFAOYSA-N 0.000 description 1
- ZBVWVXFYNUGPIU-UHFFFAOYSA-N 2,6-dimethylphenol 2-methoxy-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1O.COC1=C(C)C=CC=C1C ZBVWVXFYNUGPIU-UHFFFAOYSA-N 0.000 description 1
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 6-Oxy-pseudocumol Natural products CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 1
- OBZLBCWOJDSMRT-UHFFFAOYSA-N C1(=CC=CC=C1O)C.C1(=CC=CC=C1)OC Chemical compound C1(=CC=CC=C1O)C.C1(=CC=CC=C1)OC OBZLBCWOJDSMRT-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction 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
- C07C37/16—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/607,732 US3979464A (en) | 1975-08-25 | 1975-08-25 | Methylation of 2,6-xylenol to produce 2,3,6-trimethylphenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2611320A1 DE2611320A1 (de) | 1977-03-10 |
| DE2611320C2 true DE2611320C2 (de) | 1985-01-24 |
Family
ID=24433496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2611320A Expired DE2611320C2 (de) | 1975-08-25 | 1976-03-17 | Verfahren zur Herstellung von 2,3,6-Trimethylphenol durch Methylierung von 2,6-Xylenol in flüssiger Phase |
Country Status (6)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4126750A (en) * | 1977-04-18 | 1978-11-21 | Continental Oil Company | Process for the high pressure methylation of 2,6-xylenol |
| US4258220A (en) * | 1980-01-28 | 1981-03-24 | Conoco, Inc. | Purification of 2,6-xylenol streams |
| US4398048A (en) * | 1981-10-21 | 1983-08-09 | Uop Inc. | Preparation of 2,4,6-trialkylphenols |
| US6897175B2 (en) * | 2001-10-09 | 2005-05-24 | General Electric | Catalyst and method for the alkylation of hydroxyaromatic compounds |
| US7081432B2 (en) * | 2003-07-10 | 2006-07-25 | General Electric Company | Alkylation catalyst and method for making alkylated phenols |
| US7087705B2 (en) * | 2004-03-31 | 2006-08-08 | General Electric Company | Process for the monoalkylation of dihydroxy aromatic compounds |
| US20110152420A1 (en) * | 2009-12-22 | 2011-06-23 | Mark Elkovitch | Poly(arylene ether)/polyamide compositions, methods, and articles |
| US8309655B2 (en) * | 2009-12-22 | 2012-11-13 | Sabic Innovative Plastics Ip B.V. | Methods for the preparation of a poly(arylene ether) polysiloxane multiblock copolymer, multiblock copolymers produced thereby, and associated compositions and articles |
| US8450412B2 (en) * | 2009-12-22 | 2013-05-28 | Sabic Innovative Plastics Ip B.V. | Flame retardant polyamide composition, method, and article |
| US8669332B2 (en) | 2011-06-27 | 2014-03-11 | Sabic Innovative Plastics Ip B.V. | Poly(arylene ether)-polysiloxane composition and method |
| US8722837B2 (en) | 2012-01-31 | 2014-05-13 | Sabic Innovative Plastics Ip B.V. | Poly(phenylene ether)-polysiloxane composition and method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862248A (en) * | 1968-10-02 | 1975-01-21 | Continental Oil Co | Pure 2,3,6-trimethylphenol |
| US3737466A (en) * | 1969-10-20 | 1973-06-05 | Coal Tar Research Asso | Production of cresols |
| BE757374A (fr) * | 1969-11-10 | 1971-03-16 | Union Rheinische Braunkohlen | Procede de preparation de 2,3,6-trimethylphenol |
| US3707569A (en) * | 1970-07-22 | 1972-12-26 | Gen Electric | Alkylation process |
-
1975
- 1975-08-25 US US05/607,732 patent/US3979464A/en not_active Expired - Lifetime
-
1976
- 1976-03-11 CA CA247,739A patent/CA1068726A/en not_active Expired
- 1976-03-17 DE DE2611320A patent/DE2611320C2/de not_active Expired
- 1976-04-12 CH CH463076A patent/CH603517A5/xx not_active IP Right Cessation
- 1976-06-17 GB GB25210/76A patent/GB1490326A/en not_active Expired
- 1976-07-13 JP JP51082615A patent/JPS5227732A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2611320A1 (de) | 1977-03-10 |
| GB1490326A (en) | 1977-11-02 |
| US3979464A (en) | 1976-09-07 |
| CH603517A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-08-15 |
| CA1068726A (en) | 1979-12-25 |
| JPS5227732A (en) | 1977-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: CONOCO INC., 74601 PONCA CITY, OKLA., US |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |