BE1005221A3 - Procede pour preparer des melanges de derives hydroxyles d'hydrocarbures aromatiques, avec des proportions reglees des constituants de ces melanges. - Google Patents

Procede pour preparer des melanges de derives hydroxyles d'hydrocarbures aromatiques, avec des proportions reglees des constituants de ces melanges. Download PDF

Info

Publication number: BE1005221A3
Authority: BE; Belgium
Prior art keywords: sep; aromatic hydrocarbons; mixtures; carried out; reaction
Prior art date: 1990-01-19

Application number

BE9100036A

Other languages

English (en)

French (fr)

Inventor

Antonio Esposito

Michele Marinelli

Carlo Calderoni

Original Assignee

Enichem Sintesi

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.)

1990-01-19

Filing date

1991-01-18

Publication date

1993-06-01

1991-01-18 Application filed by Enichem Sintesi filed Critical Enichem Sintesi

1993-06-01 Application granted granted Critical

1993-06-01 Publication of BE1005221A3 publication Critical patent/BE1005221A3/fr

Links

239000000203 mixture Substances 0.000 title claims abstract description 21
238000004519 manufacturing process Methods 0.000 title description 2
-1 hydroxyl aromatic hydrocarbons Chemical class 0.000 title 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 26
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 16
238000006243 chemical reaction Methods 0.000 claims abstract description 16
239000010457 zeolite Substances 0.000 claims abstract description 15
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 14
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 13
239000000758 substrate Substances 0.000 claims abstract description 12
229910052719 titanium Inorganic materials 0.000 claims abstract description 11
239000010936 titanium Substances 0.000 claims abstract description 11
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 10
239000000470 constituent Substances 0.000 claims abstract description 5
239000002904 solvent Substances 0.000 claims abstract description 5
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 4
125000005842 heteroatom Chemical group 0.000 claims abstract description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
239000000463 material Substances 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 3
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
229940090181 propyl acetate Drugs 0.000 claims description 3
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
150000003738 xylenes Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 2
150000002978 peroxides Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract description 44
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 42
238000005805 hydroxylation reaction Methods 0.000 abstract description 8
239000004215 Carbon black (E152) Substances 0.000 abstract description 6
229930195733 hydrocarbon Natural products 0.000 abstract description 6
150000002430 hydrocarbons Chemical class 0.000 abstract description 6
230000033444 hydroxylation Effects 0.000 abstract description 5
239000013078 crystal Substances 0.000 abstract description 2
125000001424 substituent group Chemical group 0.000 abstract description 2
239000000376 reactant Substances 0.000 abstract 1
230000001105 regulatory effect Effects 0.000 abstract 1
239000011269 tar Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
229910002026 crystalline silica Inorganic materials 0.000 description 1
239000000945 filler Substances 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229910019655 synthetic inorganic crystalline material Inorganic materials 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE9100036A 1990-01-19 1991-01-18 Procede pour preparer des melanges de derives hydroxyles d'hydrocarbures aromatiques, avec des proportions reglees des constituants de ces melanges. BE1005221A3 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT01911690A IT1246372B (it)	1990-01-19	1990-01-19	Procedimento per la preparazione di miscele di derivati ossidrilici di idrocarburi aromatici a rapporto controllato dei costituenti

Publications (1)

Publication Number	Publication Date
BE1005221A3 true BE1005221A3 (fr)	1993-06-01

Family

ID=11154816

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE9100036A BE1005221A3 (fr)	1990-01-19	1991-01-18	Procede pour preparer des melanges de derives hydroxyles d'hydrocarbures aromatiques, avec des proportions reglees des constituants de ces melanges.

Country Status (3)

Country	Link
BE (1)	BE1005221A3 (it)
FR (1)	FR2657346B1 (it)
IT (1)	IT1246372B (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3123566B2 (ja) *	1991-12-20	2001-01-15	三菱瓦斯化学株式会社	二価フェノール類の製造方法
CN1049610C (zh) *	1995-06-02	2000-02-23	复旦大学	不含铝的钛(锆、钒)硅五员环沸石催化剂的制备方法
EP3048091B1 (en) *	2013-09-20	2018-08-01	Mitsui Chemicals, Inc.	Method for producing aromatic dihydroxy compound

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4396783A (en) *	1980-09-09	1983-08-02	Anic S.P.A.	Hydroxylating aromatic hydrocarbons
EP0314582A1 (fr) *	1987-10-29	1989-05-03	Rhone-Poulenc Chimie	Procédé d'hydroxylation de phénols et d'éthers de phénols

1990
- 1990-01-19 IT IT01911690A patent/IT1246372B/it active IP Right Grant
1991
- 1991-01-16 FR FR9100442A patent/FR2657346B1/fr not_active Expired - Fee Related
- 1991-01-18 BE BE9100036A patent/BE1005221A3/fr not_active IP Right Cessation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4396783A (en) *	1980-09-09	1983-08-02	Anic S.P.A.	Hydroxylating aromatic hydrocarbons
EP0314582A1 (fr) *	1987-10-29	1989-05-03	Rhone-Poulenc Chimie	Procédé d'hydroxylation de phénols et d'éthers de phénols

Also Published As

Publication number	Publication date
IT9019116A0 (it)	1990-01-19
FR2657346B1 (fr)	1994-11-04
IT1246372B (it)	1994-11-18
IT9019116A1 (it)	1991-07-19
FR2657346A1 (fr)	1991-07-26

Legal Events

Date	Code	Title	Description
1997-12-31	CA	Change of address of the owner of the patent
1997-12-31	CH	Change of patent owner
2007-12-31	RE	Patent lapsed	Effective date: 20060131

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