NO783273L - Fremgangsmaate for fremstilling av o-benzyl-toluener - Google Patents
Fremgangsmaate for fremstilling av o-benzyl-toluenerInfo
- Publication number
- NO783273L NO783273L NO783273A NO783273A NO783273L NO 783273 L NO783273 L NO 783273L NO 783273 A NO783273 A NO 783273A NO 783273 A NO783273 A NO 783273A NO 783273 L NO783273 L NO 783273L
- Authority
- NO
- Norway
- Prior art keywords
- parts
- iron
- iii
- compound
- xylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 claims description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 13
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 7
- -1 benzyl halide Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000002506 iron compounds Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- PQTAUFTUHHRKSS-UHFFFAOYSA-N 1-benzyl-2-methylbenzene Chemical class CC1=CC=CC=C1CC1=CC=CC=C1 PQTAUFTUHHRKSS-UHFFFAOYSA-N 0.000 claims description 4
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 claims description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 4
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000011084 recovery Methods 0.000 description 12
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 10
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 8
- 229940073608 benzyl chloride Drugs 0.000 description 8
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 8
- 238000005292 vacuum distillation Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- LJBGURBFHJJQQU-UHFFFAOYSA-N 2-benzyl-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(CC=2C=CC=CC=2)=C1 LJBGURBFHJJQQU-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical group CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 2
- QCWXDVFBZVHKLV-UHFFFAOYSA-N 1-tert-butyl-4-methylbenzene Chemical compound CC1=CC=C(C(C)(C)C)C=C1 QCWXDVFBZVHKLV-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- LWBPNIJBHRISSS-UHFFFAOYSA-L beryllium dichloride Chemical compound Cl[Be]Cl LWBPNIJBHRISSS-UHFFFAOYSA-L 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- VQRBXYBBGHOGFT-UHFFFAOYSA-N 1-(chloromethyl)-2-methylbenzene Chemical group CC1=CC=CC=C1CCl VQRBXYBBGHOGFT-UHFFFAOYSA-N 0.000 description 1
- CVAMMFFQVDUIEX-UHFFFAOYSA-N 1-benzyl-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1CC1=CC=CC=C1 CVAMMFFQVDUIEX-UHFFFAOYSA-N 0.000 description 1
- OHSBKRHTPKHMQA-UHFFFAOYSA-N 2-benzyl-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1CC1=CC=CC=C1 OHSBKRHTPKHMQA-UHFFFAOYSA-N 0.000 description 1
- 239000005569 Iron sulphate Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 229910001627 beryllium chloride Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002938 p-xylenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4030477 | 1977-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO783273L true NO783273L (no) | 1979-03-29 |
Family
ID=10414230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO783273A NO783273L (no) | 1977-09-28 | 1978-09-27 | Fremgangsmaate for fremstilling av o-benzyl-toluener |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4197417A (ja) |
| JP (1) | JPS5455555A (ja) |
| AU (1) | AU520099B2 (ja) |
| CA (1) | CA1092164A (ja) |
| DE (1) | DE2840272A1 (ja) |
| FI (1) | FI782911A (ja) |
| NL (1) | NL7809407A (ja) |
| NO (1) | NO783273L (ja) |
| SE (1) | SE7809423L (ja) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3544733A1 (de) * | 1985-12-18 | 1987-06-19 | Bayer Ag | Verfahren zur herstellung von gegebenenfalls substituierten 2-benzyl-toluolen |
| US4990716A (en) * | 1989-06-09 | 1991-02-05 | The Dow Chemical Company | Preparation of diphenylmethanes |
| FR2653134B1 (fr) * | 1989-10-13 | 1991-12-13 | Atochem | Procede de synthese de fluides dielectriques. |
| FR2656603B1 (fr) * | 1989-12-28 | 1993-05-21 | Atochem | Procedes de synthese de benzyltoluene et dibenzyltoluene a faible teneur en chlore. |
| FR3115030B1 (fr) | 2020-10-08 | 2023-12-22 | Arkema France | Stockage d’hydrogène au moyen de dérivés de composés d’origine renouvelable |
| FR3115031B1 (fr) | 2020-10-08 | 2023-12-22 | Arkema France | Stockage d’hydrogène au moyen de composés liquides organiques |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2336289A1 (de) * | 1973-07-17 | 1975-02-06 | Basf Ag | Verfahren zur herstellung von o-benzyltoluolen |
-
1978
- 1978-09-05 US US05/939,913 patent/US4197417A/en not_active Expired - Lifetime
- 1978-09-07 SE SE7809423A patent/SE7809423L/xx unknown
- 1978-09-11 AU AU39730/78A patent/AU520099B2/en not_active Expired
- 1978-09-15 NL NL7809407A patent/NL7809407A/xx not_active Application Discontinuation
- 1978-09-15 DE DE19782840272 patent/DE2840272A1/de not_active Withdrawn
- 1978-09-19 CA CA311,551A patent/CA1092164A/en not_active Expired
- 1978-09-25 FI FI782911A patent/FI782911A/fi unknown
- 1978-09-26 JP JP11753878A patent/JPS5455555A/ja active Pending
- 1978-09-27 NO NO783273A patent/NO783273L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7809423L (sv) | 1979-03-29 |
| JPS5455555A (en) | 1979-05-02 |
| NL7809407A (nl) | 1979-03-30 |
| US4197417A (en) | 1980-04-08 |
| AU520099B2 (en) | 1982-01-14 |
| DE2840272A1 (de) | 1979-04-05 |
| AU3973078A (en) | 1980-03-20 |
| FI782911A (fi) | 1979-03-29 |
| CA1092164A (en) | 1980-12-23 |
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