CS215127B2 - Method of making the elkylarylethers - Google Patents

Method of making the elkylarylethers Download PDF

Info

Publication number: CS215127B2
Authority: CS; Czechoslovakia
Prior art keywords: ether; reaction; phenols; ethers; parts
Prior art date: 1979-01-26

Application number

CS80540A

Other languages

Czech (cs)

English (en)

Inventor

Rainer Neumann

Hans-Helmut Schwarz

Dieter Nachtsheim

Original Assignee

Bayer Ag

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.)

1979-01-26

Filing date

1980-01-25

Publication date

1982-07-30

1980-01-25 Application filed by Bayer Ag filed Critical Bayer Ag

1982-07-30 Publication of CS215127B2 publication Critical patent/CS215127B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 4
238000000034 method Methods 0.000 claims description 28
-1 aliphatic alcohols Chemical group 0.000 claims description 17
150000001768 cations Chemical class 0.000 claims description 16
150000002989 phenols Chemical class 0.000 claims description 13
239000002168 alkylating agent Substances 0.000 claims description 9
229940100198 alkylating agent Drugs 0.000 claims description 9
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 8
238000005804 alkylation reaction Methods 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 13
230000002378 acidificating effect Effects 0.000 description 12
150000001346 alkyl aryl ethers Chemical class 0.000 description 11
239000000203 mixture Substances 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
238000004821 distillation Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000003054 catalyst Substances 0.000 description 3
238000006266 etherification reaction Methods 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
150000001983 dialkylethers Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical group CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical group CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
229940005642 polystyrene sulfonic acid Drugs 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000002699 waste material Substances 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
QZYDOKBVZJLQCK-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical compound CCOC1=CC=CC=C1OCC QZYDOKBVZJLQCK-UHFFFAOYSA-N 0.000 description 1
MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical group CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
GMVPRGQOIOIIMI-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DODZYUBVSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000006057 Non-nutritive feed additive Substances 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000003717 m-cresyl group Chemical group [H]C1=C([H])C(O*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
150000008442 polyphenolic compounds Chemical class 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1
150000003739 xylenols Chemical group 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
- C07C41/14—Preparation of ethers by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials

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)

CS80540A 1979-01-26 1980-01-25 Method of making the elkylarylethers CS215127B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792903020 DE2903020A1 (de)	1979-01-26	1979-01-26	Verfahren zur herstellung von alkylarylethern

Publications (1)

Publication Number	Publication Date
CS215127B2 true CS215127B2 (en)	1982-07-30

Family

ID=6061471

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS80540A CS215127B2 (en)	1979-01-26	1980-01-25	Method of making the elkylarylethers

Country Status (8)

Country	Link
US (1)	US4307253A (da)
EP (1)	EP0013924B1 (da)
JP (1)	JPS55100330A (da)
BR (1)	BR8000485A (da)
CS (1)	CS215127B2 (da)
DE (2)	DE2903020A1 (da)
DK (1)	DK32580A (da)
IL (1)	IL59201A0 (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1209617B (it) *	1985-03-01	1989-08-30	Eniricerche Spa	Procedimento per la preparazione di alchilarileteri.
GB8515179D0 (en) *	1985-06-14	1985-07-17	Bp Chem Int Ltd	Preparation of phenolic ethers
FR2635103B1 (fr) *	1988-08-05	1990-11-02	Rhone Poulenc Chimie	Procede de monomethylation de composes phenoliques
DE19949319A1 (de) *	1999-10-13	2001-06-13	Ruetgers Vft Ag	Verfahren zur Herstellung von Arylalkylethern
EP2313357A2 (en) *	2008-06-27	2011-04-27	Futurefuel Chemical Company	Systems and methods for the preparation of alkyl aryl ethers

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2782239A (en) *		1957-02-19		mavity
US2487832A (en) *	1946-11-02	1949-11-15	Du Pont	Process for preparing anisole
US2781404A (en) *	1953-12-28	1957-02-12	Universal Oil Prod Co	Synthesis of ortho-alkyl-p-alkoxyphenols
AT251561B (de) *	1964-04-20	1967-01-10	Efim Biller	Verfahren zur Herstellung von Aryläthern
DE1643358B2 (de) *	1967-09-19	1976-05-06	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von alkylarylaethern
DE2655826C2 (de) *	1976-12-09	1983-09-01	Haarmann & Reimer Gmbh, 3450 Holzminden	Verfahren zur Herstellung von Alkylaryläthern

1979
- 1979-01-26 DE DE19792903020 patent/DE2903020A1/de not_active Withdrawn
1980
- 1980-01-07 US US06/110,034 patent/US4307253A/en not_active Expired - Lifetime
- 1980-01-14 DE DE8080100159T patent/DE3060082D1/de not_active Expired
- 1980-01-14 EP EP80100159A patent/EP0013924B1/de not_active Expired
- 1980-01-23 IL IL59201A patent/IL59201A0/xx unknown
- 1980-01-24 JP JP641380A patent/JPS55100330A/ja active Pending
- 1980-01-25 CS CS80540A patent/CS215127B2/cs unknown
- 1980-01-25 BR BR8000485A patent/BR8000485A/pt unknown
- 1980-01-25 DK DK32580A patent/DK32580A/da unknown

Also Published As

Publication number	Publication date
US4307253A (en)	1981-12-22
DE3060082D1 (en)	1982-01-28
IL59201A0 (en)	1980-05-30
JPS55100330A (en)	1980-07-31
DE2903020A1 (de)	1980-07-31
DK32580A (da)	1980-07-27
EP0013924A1 (de)	1980-08-06
BR8000485A (pt)	1980-10-21
EP0013924B1 (de)	1981-11-25

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