DE2612075C2 - Verfahren zur Herstellung von 2,6-Xylenol und 2,3,6-Trimethylphenol durch Methylierung von o-Kresol - Google Patents
Verfahren zur Herstellung von 2,6-Xylenol und 2,3,6-Trimethylphenol durch Methylierung von o-KresolInfo
- Publication number
- DE2612075C2 DE2612075C2 DE2612075A DE2612075A DE2612075C2 DE 2612075 C2 DE2612075 C2 DE 2612075C2 DE 2612075 A DE2612075 A DE 2612075A DE 2612075 A DE2612075 A DE 2612075A DE 2612075 C2 DE2612075 C2 DE 2612075C2
- Authority
- DE
- Germany
- Prior art keywords
- cresol
- methylation
- xylenol
- trimethylphenol
- catalyst
- 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
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 28
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 title claims description 22
- 230000011987 methylation Effects 0.000 title claims description 15
- 238000007069 methylation reaction Methods 0.000 title claims description 15
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000007791 liquid phase Substances 0.000 claims description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000012808 vapor phase Substances 0.000 description 5
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 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 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- 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 2
- 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 2
- VXSCPERJHPWROZ-UHFFFAOYSA-N 2,4,5-trimethylphenol Chemical compound CC1=CC(C)=C(O)C=C1C VXSCPERJHPWROZ-UHFFFAOYSA-N 0.000 description 2
- FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002672 m-cresols Chemical class 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- -1 metal oxide Pentamethylphenols Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002931 p-cresols Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 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 1
- PXSSNPBEHHJLDH-UHFFFAOYSA-N 2,3,4,5-tetramethylphenol Chemical class CC1=CC(O)=C(C)C(C)=C1C PXSSNPBEHHJLDH-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-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
- RCORZSOEOGHWCD-UHFFFAOYSA-N 2,6-dimethylphenol;2-methylphenol Chemical compound CC1=CC=CC=C1O.CC1=CC=CC(C)=C1O RCORZSOEOGHWCD-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 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 1
- 230000005484 gravity Effects 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 150000003739 xylenols Chemical class 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 |
|---|---|---|---|
| US05/607,733 US4022843A (en) | 1975-08-25 | 1975-08-25 | Liquid phase methylation of ortho cresol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2612075A1 DE2612075A1 (de) | 1977-03-10 |
| DE2612075C2 true DE2612075C2 (de) | 1984-12-20 |
Family
ID=24433499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2612075A Expired DE2612075C2 (de) | 1975-08-25 | 1976-03-22 | Verfahren zur Herstellung von 2,6-Xylenol und 2,3,6-Trimethylphenol durch Methylierung von o-Kresol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4022843A (enExample) |
| JP (1) | JPS5239635A (enExample) |
| CA (1) | CA1077063A (enExample) |
| CH (1) | CH609023A5 (enExample) |
| DE (1) | DE2612075C2 (enExample) |
| GB (1) | GB1490327A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197613A (ja) * | 1985-02-28 | 1986-09-01 | Mitsubishi Rayon Co Ltd | 耐熱性共重合体の製造方法 |
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB717588A (en) * | 1951-10-01 | 1954-10-27 | Ici Ltd | Improvements in and relating to the production of 2,6-xylenol |
| DE1265755B (de) * | 1965-07-23 | 1968-04-11 | Chemisches Werk Lowi | Verfahren zur Kernmethylierung von Phenolen |
| US3426358A (en) * | 1965-11-19 | 1969-02-04 | Hooker Chemical Corp | Alkylation of phenols |
| US3624163A (en) * | 1968-02-12 | 1971-11-30 | Consolidation Coal Co | Process for the preparation of meta-, para-cresol mixtures with high meta to para ratio |
| US3716589A (en) * | 1968-11-27 | 1973-02-13 | Agency Ind Science Techn | Process for the synthesis of 2,6-dimethylphenols |
| US3737466A (en) * | 1969-10-20 | 1973-06-05 | Coal Tar Research Asso | Production of cresols |
| US3707569A (en) * | 1970-07-22 | 1972-12-26 | Gen Electric | Alkylation process |
-
1975
- 1975-08-25 US US05/607,733 patent/US4022843A/en not_active Expired - Lifetime
-
1976
- 1976-03-11 CA CA247,733A patent/CA1077063A/en not_active Expired
- 1976-03-22 DE DE2612075A patent/DE2612075C2/de not_active Expired
- 1976-04-22 CH CH505876A patent/CH609023A5/xx not_active IP Right Cessation
- 1976-06-17 GB GB25212/76A patent/GB1490327A/en not_active Expired
- 1976-08-18 JP JP51097825A patent/JPS5239635A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US4022843A (en) | 1977-05-10 |
| CA1077063A (en) | 1980-05-06 |
| CH609023A5 (enExample) | 1979-02-15 |
| GB1490327A (en) | 1977-11-02 |
| JPS5239635A (en) | 1977-03-28 |
| DE2612075A1 (de) | 1977-03-10 |
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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 |