JPS6032740A - オルソベンジルフエノ−ルの製法 - Google Patents
オルソベンジルフエノ−ルの製法Info
- Publication number
- JPS6032740A JPS6032740A JP58142084A JP14208483A JPS6032740A JP S6032740 A JPS6032740 A JP S6032740A JP 58142084 A JP58142084 A JP 58142084A JP 14208483 A JP14208483 A JP 14208483A JP S6032740 A JPS6032740 A JP S6032740A
- Authority
- JP
- Japan
- Prior art keywords
- benzyl alcohol
- phenol
- catalyst
- reaction
- orthobenzylphenol
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 title 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 75
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 235000019445 benzyl alcohol Nutrition 0.000 claims abstract description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 4
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PGEBXGLGFFYYFX-UHFFFAOYSA-N 2,3-dibenzylphenol Chemical compound C=1C=CC=CC=1CC=1C(O)=CC=CC=1CC1=CC=CC=C1 PGEBXGLGFFYYFX-UHFFFAOYSA-N 0.000 description 1
- 241001377695 Polygonum arenastrum Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58142084A JPS6032740A (ja) | 1983-08-03 | 1983-08-03 | オルソベンジルフエノ−ルの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58142084A JPS6032740A (ja) | 1983-08-03 | 1983-08-03 | オルソベンジルフエノ−ルの製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6032740A true JPS6032740A (ja) | 1985-02-19 |
| JPS6217980B2 JPS6217980B2 (enrdf_load_stackoverflow) | 1987-04-21 |
Family
ID=15307054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58142084A Granted JPS6032740A (ja) | 1983-08-03 | 1983-08-03 | オルソベンジルフエノ−ルの製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6032740A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62162285U (enrdf_load_stackoverflow) * | 1985-12-04 | 1987-10-15 | ||
| WO2007027375A3 (en) * | 2005-08-29 | 2010-05-06 | General Electric Company | Method of making benzylated phenols |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013034454A1 (en) | 2011-09-06 | 2013-03-14 | British American Tobacco (Investments) Limited | Heating smokeable material |
| GB201207039D0 (en) | 2012-04-23 | 2012-06-06 | British American Tobacco Co | Heating smokeable material |
| WO2015062983A2 (en) | 2013-10-29 | 2015-05-07 | British American Tobacco (Investments) Limited | Apparatus for heating smokable material |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093667A (en) * | 1977-03-14 | 1978-06-06 | Continental Oil Company | Preparation of 4-n-hexylresorcinol |
| US4105699A (en) * | 1977-02-16 | 1978-08-08 | Continental Oil Company | Preparation of o-benzylphenol |
| US4108909A (en) * | 1976-01-19 | 1978-08-22 | Continental Oil Company | N-alkylated cresylic acids via direct alkylation in a liquid phase |
| US4117243A (en) * | 1977-03-07 | 1978-09-26 | Continental Oil Company | Preparation of o-benzylphenol |
-
1983
- 1983-08-03 JP JP58142084A patent/JPS6032740A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4108909A (en) * | 1976-01-19 | 1978-08-22 | Continental Oil Company | N-alkylated cresylic acids via direct alkylation in a liquid phase |
| US4105699A (en) * | 1977-02-16 | 1978-08-08 | Continental Oil Company | Preparation of o-benzylphenol |
| US4117243A (en) * | 1977-03-07 | 1978-09-26 | Continental Oil Company | Preparation of o-benzylphenol |
| US4093667A (en) * | 1977-03-14 | 1978-06-06 | Continental Oil Company | Preparation of 4-n-hexylresorcinol |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62162285U (enrdf_load_stackoverflow) * | 1985-12-04 | 1987-10-15 | ||
| WO2007027375A3 (en) * | 2005-08-29 | 2010-05-06 | General Electric Company | Method of making benzylated phenols |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6217980B2 (enrdf_load_stackoverflow) | 1987-04-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Johnson | 218. 2-butyne-1: 4-diol. Part I. Reactions of the hydroxyl groups | |
| JP3041703B2 (ja) | カルバミン酸エステルの製法 | |
| US4140716A (en) | Process for making an amide of formic acid and forming nitrodiarylamine therefrom | |
| HU185896B (en) | New process for producing 7-hydroxy-2,2-dimethyl-2,3-dihydro-bracket-benzo-furane-bracket closed | |
| JPH0710811A (ja) | ジアルキルカーボネートの製造方法 | |
| JPS6032740A (ja) | オルソベンジルフエノ−ルの製法 | |
| JPH0135809B2 (enrdf_load_stackoverflow) | ||
| US5371270A (en) | Method of manufacturing chlorine-free cyclopropanecarboxylic acid methyl ester | |
| US6162946A (en) | Processing for producing allyl 2-hydroxyisobutyrate | |
| US2651659A (en) | Preparation of 2, 4-dichlorophenoxyacetic acid | |
| JPH02172924A (ja) | オクタン誘導体の製造法 | |
| US4518785A (en) | Malondialdehyde tetraalkylacetals and their preparation | |
| US3418378A (en) | Production of diphenylol propane | |
| US3984475A (en) | Process for the production of substituted ketones | |
| EP0625519B1 (en) | Method for the production of alkylene carbonates | |
| US5463111A (en) | Process for preparing dialkyl 2-haloethyl malonates | |
| US3079396A (en) | Process for making n-vinyl-5-methyl-2-oxazolidinone and 5-methyl-2-oxazolidinone | |
| JPH0648993A (ja) | ジアルキルカーボネートの製造法 | |
| JP3814943B2 (ja) | 炭酸ジアルキルの製法 | |
| JPH0920751A (ja) | ジスルフィド類の製造方法 | |
| US2870221A (en) | Production of 1:1:3-trialkoxyprop-2-ene | |
| JPS61286346A (ja) | ２，２−ビス（４′−アクリロイルオキシ−３′，５′−ジブロモフエニル）プロパンの製造法 | |
| US2338569A (en) | Preparation of coumarin-3-carboxylic acid | |
| JPS6019755A (ja) | ２−アルカリホルミル−３，３−ジアルコキシプロパンニトリル類の製法 | |
| JPS5917099B2 (ja) | グリコ−ルモノエステルの製造法 |