BE891076A - Procede pour la preparation d'ethers monoalkyliques de l'hydroquinone et de ses derives - Google Patents

Procede pour la preparation d'ethers monoalkyliques de l'hydroquinone et de ses derives Download PDF

Info

Publication number: BE891076A
Authority: BE; Belgium
Prior art keywords: emi; hydroquinone; reaction; autoclave; oxygen
Prior art date: 1980-11-13

Application number

BE0/206511A

Other languages

English (en)

French (fr)

Inventor

F Rivetti

U Romano

N Di Muzio

Original Assignee

Anic Spa

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.)

1980-11-13

Filing date

1981-11-10

Publication date

1982-05-10

1981-11-10 Application filed by Anic Spa filed Critical Anic Spa

1982-05-10 Publication of BE891076A publication Critical patent/BE891076A/fr

Links

QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims description 29
238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title description 2
150000001346 alkyl aryl ethers Chemical class 0.000 title 1
238000006243 chemical reaction Methods 0.000 claims description 28
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
-1 transition metal salts Chemical class 0.000 claims description 8
239000000758 substrate Substances 0.000 claims description 6
229910052723 transition metal Inorganic materials 0.000 claims description 5
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 4
125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 3
230000005587 bubbling Effects 0.000 claims description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
150000003841 chloride salts Chemical class 0.000 claims 3
229910052742 iron Inorganic materials 0.000 claims 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
229910052802 copper Inorganic materials 0.000 claims 1
239000010949 copper Substances 0.000 claims 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical class [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims 1
239000003456 ion exchange resin Substances 0.000 claims 1
229920003303 ion-exchange polymer Polymers 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
239000003054 catalyst Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical class Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 8
239000000203 mixture Substances 0.000 description 8
229910052500 inorganic mineral Inorganic materials 0.000 description 5
239000011707 mineral Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229960003280 cupric chloride Drugs 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229910010293 ceramic material Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical class Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
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 description 1
229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
239000004250 tert-Butylhydroquinone Substances 0.000 description 1
235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups

Landscapes

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

BE0/206511A 1980-11-13 1981-11-10 Procede pour la preparation d'ethers monoalkyliques de l'hydroquinone et de ses derives BE891076A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT25933/80A IT1134242B (it)	1980-11-13	1980-11-13	Procedimento per la preparazione di monoalchileteri dell'idrochinone e dei suoi derivati

Publications (1)

Publication Number	Publication Date
BE891076A true BE891076A (fr)	1982-05-10

Family

ID=11218178

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/206511A BE891076A (fr)	1980-11-13	1981-11-10	Procede pour la preparation d'ethers monoalkyliques de l'hydroquinone et de ses derives

Country Status (2)

Country	Link
BE (1)	BE891076A (it)
IT (1)	IT1134242B (it)

1980
- 1980-11-13 IT IT25933/80A patent/IT1134242B/it active
1981
- 1981-11-10 BE BE0/206511A patent/BE891076A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1134242B (it)	1986-08-13
IT8025933A0 (it)	1980-11-13

Legal Events

Date

Code

Title

Description

1991-12-31

CH

Change of patent owner

1993-05-31

RE

Patent lapsed

Owner name: ENICHEM SYNTHESISS.P.A.

Effective date: 19921130

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