CA1096405A - Ortho-alkylation de phenols catalysee par une substance contenant de l'oxyde de calcium - Google Patents

Ortho-alkylation de phenols catalysee par une substance contenant de l'oxyde de calcium

Info

Publication number: CA1096405A
Authority: CA; Canada
Prior art keywords: calcium oxide; alkanol; phenol; ortho; catalyst
Prior art date: 1977-02-09
Legal status (The legal status 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 status listed.): Expired

Application number

CA271,397A

Other languages

English (en)

Inventor

John E. Dabrowski

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

General Electric Co

Original Assignee

General Electric Co

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.)

1977-02-09

Filing date

1977-02-09

Publication date

1981-02-24

1977-02-09 Application filed by General Electric Co filed Critical General Electric Co

1977-02-09 Priority to CA271,397A priority Critical patent/CA1096405A/fr

1981-02-24 Application granted granted Critical

1981-02-24 Publication of CA1096405A publication Critical patent/CA1096405A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 29
150000002989 phenols Chemical class 0.000 title claims abstract description 16
238000005804 alkylation reaction Methods 0.000 title claims description 14
230000029936 alkylation Effects 0.000 title claims description 7
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title description 3
229910052791 calcium Inorganic materials 0.000 title description 3
239000011575 calcium Substances 0.000 title description 3
238000000034 method Methods 0.000 claims abstract description 39
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims abstract description 28
239000000292 calcium oxide Substances 0.000 claims abstract description 27
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims abstract description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
239000012808 vapor phase Substances 0.000 claims description 9
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
-1 methyl-substituted phenyl Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229920002472 Starch Polymers 0.000 claims description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000008107 starch Substances 0.000 claims description 4
235000019698 starch Nutrition 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
229910002804 graphite Inorganic materials 0.000 claims description 3
239000010439 graphite Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000000377 silicon dioxide Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 18
229910000019 calcium carbonate Inorganic materials 0.000 claims 9
230000002152 alkylating effect Effects 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 description 7
150000002085 enols Chemical class 0.000 description 6
239000000376 reactant Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000008188 pellet Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
229930003836 cresol Natural products 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
150000003739 xylenols Chemical class 0.000 description 2
QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
235000006696 Catha edulis Nutrition 0.000 description 1
240000007681 Catha edulis Species 0.000 description 1
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
101100001347 Mus musculus Akt1s1 gene Proteins 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000007654 immersion Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical class O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
238000000465 moulding Methods 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
235000015927 pasta Nutrition 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA271,397A 1977-02-09 1977-02-09 Ortho-alkylation de phenols catalysee par une substance contenant de l'oxyde de calcium Expired CA1096405A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA271,397A CA1096405A (fr)	1977-02-09	1977-02-09	Ortho-alkylation de phenols catalysee par une substance contenant de l'oxyde de calcium

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA271,397A CA1096405A (fr)	1977-02-09	1977-02-09	Ortho-alkylation de phenols catalysee par une substance contenant de l'oxyde de calcium

Publications (1)

Publication Number	Publication Date
CA1096405A true CA1096405A (fr)	1981-02-24

Family

ID=4107894

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA271,397A Expired CA1096405A (fr)	1977-02-09	1977-02-09	Ortho-alkylation de phenols catalysee par une substance contenant de l'oxyde de calcium

Country Status (1)

Country	Link
CA (1)	CA1096405A (fr)

1977
- 1977-02-09 CA CA271,397A patent/CA1096405A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-02-24	MKEX	Expiry

Publication	Publication Date	Title
US3974229A (en)	1976-08-10	Preparation of ortho-alkylated phenols
US4260845A (en)	1981-04-07	Alcohol dehydration employing a zinc aluminate catalyst
US4201880A (en)	1980-05-06	Preparation of ortho-alkylated phenols
US4041085A (en)	1977-08-09	Ortho-alkylation of phenols
EP0333076B1 (fr)	1993-08-04	Procédé en une seule opération pour la synthèse de l'oxyde de méthyle et de tertiobutyle
US4227023A (en)	1980-10-07	Process for the selective ortho-alkylation of phenolic compounds
US6060035A (en)	2000-05-09	Addition reaction of hydroxyl-containing compounds with alkynes or allenes
EP0333077B1 (fr)	1993-03-17	Procédé en une seule opération pour la synthèse de l'oxyde de méthyle et de tertiobutyle
US4359591A (en)	1982-11-16	Process for the o-substitution of phenols
US4208537A (en)	1980-06-17	Process for the selective ortho-alkylation of phenolic compounds
US5817886A (en)	1998-10-06	Process for production of alkyl ether of phenol and catalyst used therein
US4533758A (en)	1985-08-06	Alkylation of phenols to alkyl aryl ethers using phosphate catalysts
US3972828A (en)	1976-08-03	Catalyst comprising magnesium oxide and a cellulosic polymeric binder
EP0394682B1 (fr)	1993-06-23	Procédé pour l'ortho-alkylation de phénol
US4048239A (en)	1977-09-13	Process for the ortho alkylation of phenols using aldehydes and hydrogen in the presence of a copper-chromium catalyst
CA1096405A (fr)	1981-02-24	Ortho-alkylation de phenols catalysee par une substance contenant de l'oxyde de calcium
US4482753A (en)	1984-11-13	Catalyst for use in the hydrogenolysis of methyl glycol formals
US4429171A (en)	1984-01-31	Method for manufacture of orthomethylated phenol compounds
US4097411A (en)	1978-06-27	Catalyst for preparation of ortho-alkylated phenols
US4675454A (en)	1987-06-23	Catalytic etherification of phenols to alkyl aryl ethers
US4450306A (en)	1984-05-22	Selective catalytic alkylation of phenols to alkyl aryl ethers
US3707569A (en)	1972-12-26	Alkylation process
US4100207A (en)	1978-07-11	Preparation of methyl-substituted phenols
EP0017852A1 (fr)	1980-10-29	Procédé pour dissocier les alkylènebisphénols
CA1090828A (fr)	1980-12-02	Procede d'ortho-alkylation selective d'un phenol en presence d'un catalyseur de type cuivre-chrome