JPH0260655B2 - - Google Patents
Info
- Publication number
- JPH0260655B2 JPH0260655B2 JP63040906A JP4090688A JPH0260655B2 JP H0260655 B2 JPH0260655 B2 JP H0260655B2 JP 63040906 A JP63040906 A JP 63040906A JP 4090688 A JP4090688 A JP 4090688A JP H0260655 B2 JPH0260655 B2 JP H0260655B2
- Authority
- JP
- Japan
- Prior art keywords
- acetate
- toluene
- diacetate
- mmol
- acetic anhydride
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 81
- BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical compound CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 claims description 24
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 229940049953 phenylacetate Drugs 0.000 claims description 20
- -1 benzylidene acetate Chemical compound 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000003377 acid catalyst Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 20
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 11
- 239000007791 liquid phase Substances 0.000 description 11
- 229940007550 benzyl acetate Drugs 0.000 description 10
- CDJJKTLOZJAGIZ-UHFFFAOYSA-N Tolylacetate Chemical compound CC(=O)OC1=CC=C(C)C=C1 CDJJKTLOZJAGIZ-UHFFFAOYSA-N 0.000 description 8
- HPHGBTNBRGYFGO-UHFFFAOYSA-N acetyloxymethyl acetate phenyl acetate Chemical compound CC(=O)OCOC(C)=O.CC(=O)OC1=CC=CC=C1 HPHGBTNBRGYFGO-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- AMZORBZSQRUXNC-UHFFFAOYSA-N o-Tolyl acetate Chemical compound CC(=O)OC1=CC=CC=C1C AMZORBZSQRUXNC-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- XRYSDRCNTMEYFH-UHFFFAOYSA-N [acetyloxy(phenyl)methyl] acetate Chemical compound CC(=O)OC(OC(C)=O)C1=CC=CC=C1 XRYSDRCNTMEYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 5
- 238000000197 pyrolysis Methods 0.000 description 5
- 238000005979 thermal decomposition reaction Methods 0.000 description 5
- AKOGNYJNGMLDOA-UHFFFAOYSA-N (4-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C=C1 AKOGNYJNGMLDOA-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 3
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- GXXXUZIRGXYDFP-UHFFFAOYSA-M 2-(4-methylphenyl)acetate Chemical compound CC1=CC=C(CC([O-])=O)C=C1 GXXXUZIRGXYDFP-UHFFFAOYSA-M 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007233 catalytic pyrolysis Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OTGAHJPFNKQGAE-UHFFFAOYSA-N cresatin Chemical compound CC(=O)OC1=CC=CC(C)=C1 OTGAHJPFNKQGAE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000003244 pro-oxidative effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/035—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with saturated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/890,180 US4156783A (en) | 1978-03-27 | 1978-03-27 | Conversion of benzylidene diacetate to phenyl acetate and methylene diacetate |
| US94574778A | 1978-09-25 | 1978-09-25 | |
| US05/957,273 US4260808A (en) | 1978-11-03 | 1978-11-03 | Catalytic process for the conversion of toluene to equimolar amounts of phenol acetate and methylene diacetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6445339A JPS6445339A (en) | 1989-02-17 |
| JPH0260655B2 true JPH0260655B2 (enrdf_load_stackoverflow) | 1990-12-17 |
Family
ID=27420538
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3384579A Pending JPS54130510A (en) | 1978-03-27 | 1979-03-24 | Catalytic method of converving toluene to equal mol quantity of phenol and formaldehyde |
| JP63040906A Granted JPS6445339A (en) | 1978-03-27 | 1988-02-25 | Manufacture of phenylacetate and methylenediacetate from benzylideneacetate |
| JP63040905A Granted JPS6445323A (en) | 1978-03-27 | 1988-02-25 | Catalytic process for converting m- or p-credylacetate to equal mol of hydroquinone or resolcinol and formaldehyde |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3384579A Pending JPS54130510A (en) | 1978-03-27 | 1979-03-24 | Catalytic method of converving toluene to equal mol quantity of phenol and formaldehyde |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63040905A Granted JPS6445323A (en) | 1978-03-27 | 1988-02-25 | Catalytic process for converting m- or p-credylacetate to equal mol of hydroquinone or resolcinol and formaldehyde |
Country Status (7)
| Country | Link |
|---|---|
| JP (3) | JPS54130510A (enrdf_load_stackoverflow) |
| CA (1) | CA1146966A (enrdf_load_stackoverflow) |
| DE (1) | DE2912098A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2421162A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2017098B (enrdf_load_stackoverflow) |
| IT (1) | IT1113044B (enrdf_load_stackoverflow) |
| NL (1) | NL7902258A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2015119167A1 (ja) * | 2014-02-07 | 2017-03-23 | 住友化学株式会社 | 触媒、及び酸化生成物の製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1595299A (en) * | 1924-01-07 | 1926-08-10 | Dow Chemical Co | Manufacture of phenols |
| US2799698A (en) * | 1954-12-30 | 1957-07-16 | Hercules Powder Co Ltd | Oxidation of alkyl-substituted aromatic compounds to phenolic compounds |
| FR1489679A (fr) * | 1965-08-18 | 1967-07-21 | Ici Ltd | Procédé de production de composés organiques contenant de l'oxygène |
| US3590081A (en) * | 1966-07-21 | 1971-06-29 | Asahi Chemical Ind | Process for the preparation and recovery of acetic anhydride |
| FR2068133A5 (en) * | 1969-11-28 | 1971-08-20 | Inst Neftechimichesk | Preparation of phenyl esters and phenols |
| NL151976B (nl) * | 1969-12-02 | 1977-01-17 | Inst Neftechimicheskogo Sintez | Werkwijze voor het bereiden van fenolen. |
| DE1960520C3 (de) * | 1969-12-02 | 1974-04-25 | Institut Neftechimitscheskowo Sintesa Imeni A.W. Toptschijewa Akademii Nauk, Moskau | Verfahren zur Herstellung von Phenolen |
| JPS5343941B2 (enrdf_load_stackoverflow) * | 1975-01-31 | 1978-11-24 | ||
| CA1146585A (en) * | 1978-11-03 | 1983-05-17 | Sun Tech, Inc. | Co-oxidation of methyl benzenes and benzaldehyde |
-
1979
- 1979-03-15 CA CA000323630A patent/CA1146966A/en not_active Expired
- 1979-03-20 GB GB7909740A patent/GB2017098B/en not_active Expired
- 1979-03-22 NL NL7902258A patent/NL7902258A/xx not_active Application Discontinuation
- 1979-03-24 JP JP3384579A patent/JPS54130510A/ja active Pending
- 1979-03-26 IT IT21301/79A patent/IT1113044B/it active
- 1979-03-27 DE DE2912098A patent/DE2912098A1/de active Granted
- 1979-03-27 FR FR7907648A patent/FR2421162A1/fr active Granted
-
1988
- 1988-02-25 JP JP63040906A patent/JPS6445339A/ja active Granted
- 1988-02-25 JP JP63040905A patent/JPS6445323A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2017098B (en) | 1983-02-16 |
| JPS6445323A (en) | 1989-02-17 |
| DE2912098C2 (enrdf_load_stackoverflow) | 1989-03-23 |
| JPS6445339A (en) | 1989-02-17 |
| GB2017098A (en) | 1979-10-03 |
| NL7902258A (nl) | 1979-10-01 |
| FR2421162A1 (fr) | 1979-10-26 |
| IT1113044B (it) | 1986-01-20 |
| IT7921301A0 (it) | 1979-03-26 |
| JPS54130510A (en) | 1979-10-09 |
| FR2421162B1 (enrdf_load_stackoverflow) | 1983-01-28 |
| DE2912098A1 (de) | 1979-10-18 |
| CA1146966A (en) | 1983-05-24 |
| JPH036128B2 (enrdf_load_stackoverflow) | 1991-01-29 |
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