BE1003840A3 - Procede d'oxydation des ethers. - Google Patents

Procede d'oxydation des ethers. Download PDF

Info

Publication number: BE1003840A3
Authority: BE; Belgium
Prior art keywords: oxidation; reaction; carried out; ethers; ethers according
Prior art date: 1990-05-25

Application number

BE9100501A

Other languages

English (en)

French (fr)

Inventor

Federico Maspero

Ugo Romano

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.)

1990-05-25

Filing date

1991-05-24

Publication date

1992-06-23

1991-05-24 Application filed by Enichem Sintesi filed Critical Enichem Sintesi

1992-06-23 Application granted granted Critical

1992-06-23 Publication of BE1003840A3 publication Critical patent/BE1003840A3/fr

Links

238000000034 method Methods 0.000 title claims abstract description 22
150000002170 ethers Chemical class 0.000 title claims abstract description 15
238000007254 oxidation reaction Methods 0.000 title claims description 19
230000003647 oxidation Effects 0.000 title claims description 16
238000006243 chemical reaction Methods 0.000 claims abstract description 13
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
125000005842 heteroatom Chemical group 0.000 claims abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
239000010457 zeolite Substances 0.000 claims description 10
229910021536 Zeolite Inorganic materials 0.000 claims description 7
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
235000012239 silicon dioxide Nutrition 0.000 claims description 3
229910052719 titanium Inorganic materials 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
229910052787 antimony Inorganic materials 0.000 claims description 2
229910052790 beryllium Inorganic materials 0.000 claims description 2
229910052796 boron Inorganic materials 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
229910052681 coesite Inorganic materials 0.000 claims description 2
229910052906 cristobalite Inorganic materials 0.000 claims description 2
239000013078 crystal Substances 0.000 claims description 2
229910002026 crystalline silica Inorganic materials 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052748 manganese Inorganic materials 0.000 claims description 2
239000011148 porous material Substances 0.000 claims description 2
229910052703 rhodium Inorganic materials 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
229910052682 stishovite Inorganic materials 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
229910052905 tridymite Inorganic materials 0.000 claims description 2
229910052720 vanadium Inorganic materials 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
229910052726 zirconium Inorganic materials 0.000 claims description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 18
150000001241 acetals Chemical class 0.000 abstract description 4
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
-1 alkyl radical Chemical class 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical class CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229920002994 synthetic fiber Polymers 0.000 description 2
239000010936 titanium Substances 0.000 description 2
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
MATDIXOGHXOZDW-UHFFFAOYSA-N 2-butoxyoxolane Chemical group CCCCOC1CCCO1 MATDIXOGHXOZDW-UHFFFAOYSA-N 0.000 description 1
LCQZTTHYFOMGKL-UHFFFAOYSA-N 2-methoxy-1,4-dioxane Chemical compound COC1COCCO1 LCQZTTHYFOMGKL-UHFFFAOYSA-N 0.000 description 1
XTDKZSUYCXHXJM-UHFFFAOYSA-N 2-methoxyoxane Chemical compound COC1CCCCO1 XTDKZSUYCXHXJM-UHFFFAOYSA-N 0.000 description 1
RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
MSKQCZTZWBEWQH-UHFFFAOYSA-N 4-hydroxybutanal;oxolan-2-ol Chemical compound OCCCC=O.OC1CCCO1 MSKQCZTZWBEWQH-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
ZYNMJJNWXVKJJV-UHFFFAOYSA-N propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC=C1 ZYNMJJNWXVKJJV-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
- 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
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

Landscapes

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

BE9100501A 1990-05-25 1991-05-24 Procede d'oxydation des ethers. BE1003840A3 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT02043190A IT1248644B (it)	1990-05-25	1990-05-25	Procedimento per l'oissidazione di eteri

Publications (1)

Publication Number	Publication Date
BE1003840A3 true BE1003840A3 (fr)	1992-06-23

Family

ID=11166852

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE9100501A BE1003840A3 (fr)	1990-05-25	1991-05-24	Procede d'oxydation des ethers.

Country Status (2)

Country	Link
BE (1)	BE1003840A3 (it)
IT (1)	IT1248644B (it)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997041087A1 (en) *	1996-04-26	1997-11-06	Exxon Chemical Patents Inc.	Process for the manufacture of hydroxycarbonyl compounds
WO1997041086A1 (en) *	1996-04-26	1997-11-06	Exxon Chemical Patents Inc.	Process for the manufacture of oxygenates
US6191308B1 (en)	1996-04-26	2001-02-20	Exxon Chemical Patents Inc.	Process for the manufacture of oxygenates
CN107056732A (zh) *	2017-05-05	2017-08-18	南京师范大学	一种铁催化醇和醚的脱氢交叉偶联反应合成醚的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3139443A (en) *	1961-02-13	1964-06-30	Iit Res Inst	Method of making acetals and compositions resulting therefrom
EP0100118A1 (en) *	1982-07-28	1984-02-08	ANIC S.p.A.	Process for the synthesis of glycol monomethylethers
EP0266825B1 (en) *	1986-10-22	1990-12-05	ENIRICERCHE S.p.A.	Synthetic, crystalline, porous material containing oxides of silicon, titanium and gallium

1990
- 1990-05-25 IT IT02043190A patent/IT1248644B/it active IP Right Grant
1991
- 1991-05-24 BE BE9100501A patent/BE1003840A3/fr not_active IP Right Cessation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3139443A (en) *	1961-02-13	1964-06-30	Iit Res Inst	Method of making acetals and compositions resulting therefrom
EP0100118A1 (en) *	1982-07-28	1984-02-08	ANIC S.p.A.	Process for the synthesis of glycol monomethylethers
EP0266825B1 (en) *	1986-10-22	1990-12-05	ENIRICERCHE S.p.A.	Synthetic, crystalline, porous material containing oxides of silicon, titanium and gallium

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TETRAHEDRON LETTERS. no. 33, 1970, OXFORD GB pages 2885 - 2888; K.KARIYONE ET AL.: 'Oxidative Cleavage of Beta,Gamma-Unsaturated Ether.' *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997041087A1 (en) *	1996-04-26	1997-11-06	Exxon Chemical Patents Inc.	Process for the manufacture of hydroxycarbonyl compounds
WO1997041086A1 (en) *	1996-04-26	1997-11-06	Exxon Chemical Patents Inc.	Process for the manufacture of oxygenates
US6107525A (en) *	1996-04-26	2000-08-22	Exxon Chemical Patents Inc.	Process for the manufacture of hydroxycarbonyl compounds
US6191308B1 (en)	1996-04-26	2001-02-20	Exxon Chemical Patents Inc.	Process for the manufacture of oxygenates
CN107056732A (zh) *	2017-05-05	2017-08-18	南京师范大学	一种铁催化醇和醚的脱氢交叉偶联反应合成醚的方法
CN107056732B (zh) *	2017-05-05	2019-10-29	南京师范大学	一种铁催化醇和醚的脱氢交叉偶联反应合成醚的方法

Also Published As

Publication number	Publication date
IT1248644B (it)	1995-01-26
IT9020431A1 (it)	1991-11-25
IT9020431A0 (it)	1990-05-25

Legal Events

Date

Code

Title

Description

2011-05-31

RE20

Patent expired

Owner name: *ENICHEM SYNTHESIS S.P.A.

Effective date: 20110524

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