DE2032499C3 - Verfahren zur Orthoalkylierung von Phenolen - Google Patents
Verfahren zur Orthoalkylierung von PhenolenInfo
- Publication number
- DE2032499C3 DE2032499C3 DE2032499A DE2032499A DE2032499C3 DE 2032499 C3 DE2032499 C3 DE 2032499C3 DE 2032499 A DE2032499 A DE 2032499A DE 2032499 A DE2032499 A DE 2032499A DE 2032499 C3 DE2032499 C3 DE 2032499C3
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- magnesium oxide
- phenol
- methanol
- phenols
- 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
- 238000000034 method Methods 0.000 title claims description 17
- 150000002989 phenols Chemical class 0.000 title claims description 11
- 239000003054 catalyst Substances 0.000 claims description 52
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 27
- 239000000395 magnesium oxide Substances 0.000 claims description 24
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000029936 alkylation Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 235000012239 silicon dioxide Nutrition 0.000 claims description 5
- 239000012808 vapor phase Substances 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 21
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000007069 methylation reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000001354 calcination Methods 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical group [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229940031958 magnesium carbonate hydroxide Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic 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
- 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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84696769A | 1969-08-01 | 1969-08-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2032499A1 DE2032499A1 (de) | 1971-03-04 |
| DE2032499B2 DE2032499B2 (de) | 1979-04-12 |
| DE2032499C3 true DE2032499C3 (de) | 1979-12-06 |
Family
ID=25299447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2032499A Expired DE2032499C3 (de) | 1969-08-01 | 1970-07-01 | Verfahren zur Orthoalkylierung von Phenolen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4097411A (enExample) |
| JP (1) | JPS5228784B1 (enExample) |
| BE (1) | BE754105A (enExample) |
| DE (1) | DE2032499C3 (enExample) |
| FR (1) | FR2057794A5 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5412180U (enExample) * | 1977-06-29 | 1979-01-26 | ||
| JPS599530B2 (ja) * | 1978-12-01 | 1984-03-03 | 三井東圧化学株式会社 | オルトアルキル化フェノ−ル類の製造法 |
| JPS58151321A (ja) * | 1982-03-01 | 1983-09-08 | Tokuyama Soda Co Ltd | 無機酸化物 |
| US5097079A (en) * | 1987-11-30 | 1992-03-17 | General Electric Company | Zinc-containing ortho-alkylation catalyst precursor and catalyst, and process of use in alkylation of phenols |
| KR960003790B1 (ko) * | 1992-12-31 | 1996-03-22 | 한국과학기술원 | 신규한 변형 마그네슘 옥사이드 촉매 조성물 및 그의 제조방법 |
| JP4294209B2 (ja) | 2000-09-18 | 2009-07-08 | 旭化成ケミカルズ株式会社 | オルト位アルキル化ヒドロキシ芳香族化合物の製造方法 |
| 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 (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2399261A (en) * | 1942-10-26 | 1946-04-30 | Universal Oil Prod Co | Production of aviation fuel |
| US2544869A (en) * | 1947-07-25 | 1951-03-13 | Universal Oil Prod Co | Preparation of a silica-magnesia catalyst |
| US2800517A (en) * | 1953-06-26 | 1957-07-23 | Publicker Ind Inc | Process for manufacturing butadiene |
| US3446856A (en) * | 1964-05-29 | 1969-05-27 | Gen Electric | Methylation of phenols |
-
0
- BE BE754105D patent/BE754105A/xx unknown
-
1970
- 1970-06-27 JP JP45056432A patent/JPS5228784B1/ja active Pending
- 1970-07-01 DE DE2032499A patent/DE2032499C3/de not_active Expired
- 1970-07-23 FR FR7027292A patent/FR2057794A5/fr not_active Expired
-
1976
- 1976-01-22 US US05/651,251 patent/US4097411A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2032499B2 (de) | 1979-04-12 |
| DE2032499A1 (de) | 1971-03-04 |
| US4097411A (en) | 1978-06-27 |
| FR2057794A5 (enExample) | 1971-05-21 |
| JPS5228784B1 (enExample) | 1977-07-28 |
| BE754105A (fr) | 1970-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |