IL30030A - Process for the production of alkyl aryl ethers - Google Patents

Process for the production of alkyl aryl ethers

Info

Publication number: IL30030A
Authority: IL; Israel
Prior art keywords: weight; reaction; process according; alcohol; parts
Prior art date: 1967-09-19

Application number

IL30030A

Other languages

English (en)

Other versions

IL30030A0 (en

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.)

1967-09-19

Filing date

1968-05-20

Publication date

1972-06-28

1968-05-20 Application filed by Bayer Ag filed Critical Bayer Ag

1968-07-25 Publication of IL30030A0 publication Critical patent/IL30030A0/xx

1972-06-28 Publication of IL30030A publication Critical patent/IL30030A/en

Links

238000000034 method Methods 0.000 title claims description 26
150000001346 alkyl aryl ethers Chemical class 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title claims description 7
238000006243 chemical reaction Methods 0.000 claims description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 26
150000001336 alkenes Chemical class 0.000 claims description 22
239000003054 catalyst Substances 0.000 claims description 15
-1 carbalkoxy Chemical group 0.000 claims description 14
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 10
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 4
229920003002 synthetic resin Polymers 0.000 claims description 4
239000000057 synthetic resin Substances 0.000 claims description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
235000019445 benzyl alcohol Nutrition 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
150000001491 aromatic compounds Chemical class 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 26
229960004592 isopropanol Drugs 0.000 description 12
239000002253 acid Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
150000002440 hydroxy compounds Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000004821 distillation Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
229960003742 phenol Drugs 0.000 description 4
ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
APNUQVKSJLIAPO-UHFFFAOYSA-N 1,2-di(propan-2-yloxy)benzene Chemical compound CC(C)OC1=CC=CC=C1OC(C)C APNUQVKSJLIAPO-UHFFFAOYSA-N 0.000 description 2
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
DSTPUJAJSXTJHM-UHFFFAOYSA-N 4-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC(C)=CC=C1O DSTPUJAJSXTJHM-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000011324 bead Substances 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
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000001896 cresols Chemical class 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
ZYNMJJNWXVKJJV-UHFFFAOYSA-N propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC=C1 ZYNMJJNWXVKJJV-UHFFFAOYSA-N 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
238000004062 sedimentation Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-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
VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical class CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000010908 decantation Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001447 polyvinyl benzene Polymers 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
NTUCQKRAQSWLOP-UHFFFAOYSA-N propan-2-yloxymethylbenzene Chemical compound CC(C)OCC1=CC=CC=C1 NTUCQKRAQSWLOP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
150000003739 xylenols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring

Landscapes

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

IL30030A 1967-09-19 1968-05-20 Process for the production of alkyl aryl ethers IL30030A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1967F0053533 DE1643358B2 (de)	1967-09-19	1967-09-19	Verfahren zur herstellung von alkylarylaethern

Publications (2)

Publication Number	Publication Date
IL30030A0 IL30030A0 (en)	1968-07-25
IL30030A true IL30030A (en)	1972-06-28

Family

ID=7106391

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL30030A IL30030A (en)	1967-09-19	1968-05-20	Process for the production of alkyl aryl ethers

Country Status (11)

Country	Link
US (1)	US3584058A (de)
AT (1)	AT282588B (de)
BE (1)	BE720922A (de)
CH (1)	CH495310A (de)
DE (1)	DE1643358B2 (de)
DK (1)	DK118883B (de)
ES (1)	ES358293A1 (de)
FR (1)	FR1581395A (de)
GB (1)	GB1184523A (de)
IL (1)	IL30030A (de)
NL (1)	NL6812843A (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2655826C2 (de) *	1976-12-09	1983-09-01	Haarmann & Reimer Gmbh, 3450 Holzminden	Verfahren zur Herstellung von Alkylaryläthern
DE2903020A1 (de) *	1979-01-26	1980-07-31	Bayer Ag	Verfahren zur herstellung von alkylarylethern
US4292450A (en) *	1979-11-26	1981-09-29	Conoco, Inc.	Selective alkylation of 2,5-xylenol in the presence of 2,4-xylenol
US4249026A (en) *	1979-11-26	1981-02-03	Conoco, Inc.	Separating 2,5-xylenol from a mixture of 2,5-xylenol and 2,4-xylenol
US4406780A (en) *	1981-08-18	1983-09-27	Exxon Research And Engineering Co.	Separation and oxygen-alkylation of phenols from phenol-containing hydrocarbonaceous streams
US4447652A (en) *	1982-05-21	1984-05-08	Uop Inc.	Preparation of alkyl aryl ethers
DK39487A (da) *	1986-02-14	1987-08-15	Givaudan & Cie Sa	Fremgangsmaade til fremstilling af et aldehyd
US5098477A (en) *	1988-12-14	1992-03-24	Ciba-Geigy Corporation	Inks, particularly for ink printing

1967
- 1967-09-19 DE DE1967F0053533 patent/DE1643358B2/de active Granted
1968
- 1968-05-15 CH CH716768A patent/CH495310A/de not_active IP Right Cessation
- 1968-05-20 IL IL30030A patent/IL30030A/en unknown
- 1968-05-31 AT AT524768A patent/AT282588B/de active
- 1968-06-10 US US735535A patent/US3584058A/en not_active Expired - Lifetime
- 1968-06-25 GB GB30184/68A patent/GB1184523A/en not_active Expired
- 1968-09-09 NL NL6812843A patent/NL6812843A/xx unknown
- 1968-09-09 DK DK431568AA patent/DK118883B/da unknown
- 1968-09-16 BE BE720922D patent/BE720922A/xx unknown
- 1968-09-19 ES ES358293A patent/ES358293A1/es not_active Expired
- 1968-09-19 FR FR1581395D patent/FR1581395A/fr not_active Expired

Also Published As

Publication number	Publication date
CH495310A (de)	1970-08-31
DK118883B (da)	1970-10-19
BE720922A (de)	1969-03-17
DE1643358A1 (de)	1971-05-27
NL6812843A (de)	1969-03-21
IL30030A0 (en)	1968-07-25
FR1581395A (de)	1969-09-12
DE1643358B2 (de)	1976-05-06
GB1184523A (en)	1970-03-18
AT282588B (de)	1970-07-10
ES358293A1 (es)	1970-06-01
US3584058A (en)	1971-06-08

Publication	Publication Date	Title
US2775620A (en)	1956-12-25	Production of bis (hydroxyaryl) substituted compounds
US2275312A (en)	1942-03-03	Process of nuclear alkylation in the presence of hydrofluoric acid
EP0210366B1 (de)	1990-01-31	Verfahren zur Herstellung von Bisphenol A
US2802884A (en)	1957-08-13	Alkylation-dealkylation catalysts
US2292205A (en)	1942-08-04	Aluminum phenate
US4153810A (en)	1979-05-08	Process for the preparation of alkyl ethers
US3584058A (en)	1971-06-08	Process for the production of alkyl aryl ethers
US2140782A (en)	1938-12-20	Alkylation of phenols
US2290603A (en)	1942-07-21	Recovery of phenols and olefins
EP0319310B1 (de)	1993-09-15	Verfahren zur Alkylierung von Phenolen
US3200157A (en)	1965-08-10	Buls etal alkylation process
US4202199A (en)	1980-05-13	Manufacture of alkylphenol compounds
US3839470A (en)	1974-10-01	Process for the isomerisation and transalkylation of phenols
US4092367A (en)	1978-05-30	Alkylation of phenols
US2885385A (en)	1959-05-05	Polyphenylol derivatives of olefinic aldehydes
US2671117A (en)	1954-03-02	Hydroxy aromatic hydrocarbonolefin polymer alkylation with alcl2 hso4 catalyst
EP0347835A2 (de)	1989-12-27	Verfahren zur Herstellung von Arylethylphenolen mit einem (oder mehreren) Alkyl-Substituenten in der Ethylgruppe und deren Verwendung
US2353282A (en)	1944-07-11	Preparation of substituted phenols
US4307253A (en)	1981-12-22	Process for the preparation of alkyl aryl ethers
US3422156A (en)	1969-01-14	Nuclear methylation of phenols
US3778481A (en)	1973-12-11	Process for the production of alkyl dihydroxy benzenes
US6255538B1 (en)	2001-07-03	Process for the C-alkylation of aromatic hydroxyl compounds
US2327938A (en)	1943-08-24	Production of phenols and olefins
US2290602A (en)	1942-07-21	Recovery of phenols and olefins
US3711559A (en)	1973-01-16	Monoalkylation of alkylidene bis(phenol)