NO783273L - Fremgangsmaate for fremstilling av o-benzyl-toluener - Google Patents

Fremgangsmaate for fremstilling av o-benzyl-toluener

Info

Publication number: NO783273L
Authority: NO; Norway
Prior art keywords: parts; iron; iii; compound; xylene
Prior art date: 1977-09-28

Application number

NO783273A

Other languages

English (en)

Norwegian (no)

Inventor

John Oswald Morley

Original Assignee

Ici Ltd

Priority date (The priority date 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 date listed.)

1977-09-28

Filing date

1978-09-27

Publication date

1979-03-29

1978-09-27 Application filed by Ici Ltd filed Critical Ici Ltd

1979-03-29 Publication of NO783273L publication Critical patent/NO783273L/no

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)

NO783273A 1977-09-28 1978-09-27 Fremgangsmaate for fremstilling av o-benzyl-toluener NO783273L (no)

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 (fr)
JP (1)	JPS5455555A (fr)
AU (1)	AU520099B2 (fr)
CA (1)	CA1092164A (fr)
DE (1)	DE2840272A1 (fr)
FI (1)	FI782911A7 (fr)
NL (1)	NL7809407A (fr)
NO (1)	NO783273L (fr)
SE (1)	SE7809423L (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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.
FR3115031B1 (fr)	2020-10-08	2023-12-22	Arkema France	Stockage d’hydrogène au moyen de composés liquides organiques
FR3115030B1 (fr)	2020-10-08	2023-12-22	Arkema France	Stockage d’hydrogène au moyen de dérivés de composés d’origine renouvelable

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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/fr not_active Expired
- 1978-09-25 FI FI782911A patent/FI782911A7/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
FI782911A7 (fi)	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
SE7809423L (sv)	1979-03-29
AU3973078A (en)	1980-03-20
CA1092164A (fr)	1980-12-23

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EP0463464B1 (fr)	1995-03-08	Procédé pour la préparation de 2-chloro-5-méthylpyridine
NO783273L (no)	1979-03-29	Fremgangsmaate for fremstilling av o-benzyl-toluener
EP0594658A1 (fr)	1994-05-04	Procede de preparation d'halogenures de magnesium aryle et aralkyle.
Correia	1992	A triphasic brominating/oxidizing system
US3198842A (en)	1965-08-03	Allylation of phenol
EP0006999B1 (fr)	1981-04-01	Procédé pour préparer des dérivés de 2-chlorobenzonitrile
DE69902071T2 (de)	2002-11-14	Verfahren zur Herstellung von 2-substituierten Pyridinen
WO2006001493A1 (fr)	2006-01-05	Procédé pour produire de l’ hydrochlorure de (z)-1-phényl-1-diéthylaminocarbonyl-2-aminométhyl cyclopropane
JP3557624B2 (ja)	2004-08-25	４，６−ジニトロハロベンゼンの製造方法
US4306103A (en)	1981-12-15	Process for the manufacture of 1,3,5-trichlorobenzene
EP0052599B1 (fr)	1985-05-22	Dérivés propargyliques et leur préparation
Young et al.	1937	Allylic Rearrangements. VI. Effect of Solvent and Metal on the Coupling Reaction of Butenyl Bromides
EP0045425B1 (fr)	1983-11-23	Procédé d'halogénation de 4-tert.-butyl-toluènes, le cas échéant substitués, et mélanges tirés de ceux-ci de 4-tert.-butylbenzalhalogénures, 4-tert.-butylbenzylhalogénures et 4-tert.-butylbenzotrihalogénures, le cas échéant substitués
US3751437A (en)	1973-08-07	Batch and continuous process for preparing menadione
EP0022606B1 (fr)	1983-01-12	Procédé de préparation d'hydrocarbures halogénés
US4191711A (en)	1980-03-04	Process for the preparation of certain nuclear chlorinated benzotrichlorides
US4210766A (en)	1980-07-01	Process for producing 2-halo-4-bromophenols
US6156922A (en)	2000-12-05	Method for the synthesis of an aromatic derivative ortho-disubstituted by a halogen atom other than fluorine and by a cyano group
EP0365914B1 (fr)	1992-07-22	Acétophénones contenant du fluor et éventuellement halogénés dans le groupe CH3 et leur préparation à partir de benzonitriles fluorés
US3206516A (en)	1965-09-14	Process for the production of 1, 4-dichloro hydrocarbons
CA1202624A (fr)	1986-04-01	Methode de preparation de cyanures d'alcoyle tertiaire
EP0266544B1 (fr)	1990-12-27	Procédé de préparation d'alcools halogènes
EP0226152B1 (fr)	1989-01-18	Procédé pour la préparation de benzyl-2 toluènes éventuellement substitués
Jewell et al.	1987	Rate constant for chlorine abstraction from CCl4 by the 5-hexenyl radical
US4021443A (en)	1977-05-03	Perchlorodiazafulvene