CA1245620A - Catalyseur et precurseur de catalyseur d'ortho- alcoylation contenant du zinc; son utilisation pour l'alcoylation des phenols - Google Patents

Catalyseur et precurseur de catalyseur d'ortho- alcoylation contenant du zinc; son utilisation pour l'alcoylation des phenols

Info

Publication number: CA1245620A
Authority: CA; Canada
Prior art keywords: magnesium; catalyst; process according; ortho; compound
Prior art date: 1984-08-13
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

CA000484892A

Other languages

English (en)

Inventor

James G. Bennett, Jr.

Gregory R. Chambers

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.)

1984-08-13

Filing date

1985-06-21

Publication date

1988-11-29

1985-06-21 Application filed by General Electric Co filed Critical General Electric Co

1988-11-29 Application granted granted Critical

1988-11-29 Publication of CA1245620A publication Critical patent/CA1245620A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 61
238000000034 method Methods 0.000 title claims abstract description 29
230000008569 process Effects 0.000 title claims abstract description 23
238000005804 alkylation reaction Methods 0.000 title claims abstract description 22
150000002989 phenols Chemical class 0.000 title claims abstract description 16
239000012018 catalyst precursor Substances 0.000 title abstract description 5
230000029936 alkylation Effects 0.000 title abstract description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title description 5
239000011701 zinc Substances 0.000 title description 4
229910052725 zinc Inorganic materials 0.000 title description 4
239000000203 mixture Substances 0.000 claims abstract description 49
239000000395 magnesium oxide Substances 0.000 claims abstract description 21
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 21
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
150000003752 zinc compounds Chemical class 0.000 claims abstract description 8
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 20
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 17
239000001095 magnesium carbonate Substances 0.000 claims description 17
229910000021 magnesium carbonate Inorganic materials 0.000 claims description 17
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
239000011787 zinc oxide Substances 0.000 claims description 12
238000001354 calcination Methods 0.000 claims description 9
150000002681 magnesium compounds Chemical class 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
125000005233 alkylalcohol group Chemical group 0.000 claims description 6
239000000463 material Substances 0.000 claims description 6
239000000376 reactant Substances 0.000 claims description 6
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 5
239000000347 magnesium hydroxide Substances 0.000 claims description 5
229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
229920000642 polymer Polymers 0.000 claims description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
-1 poly(2,6-dimethyl-1,4-phenylene) Polymers 0.000 claims description 3
239000012808 vapor phase Substances 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
239000012736 aqueous medium Substances 0.000 claims 1
238000002156 mixing Methods 0.000 claims 1
229920001955 polyphenylene ether Polymers 0.000 claims 1
239000011347 resin Substances 0.000 claims 1
229920005989 resin Polymers 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 7
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
239000010439 graphite Substances 0.000 description 6
229910002804 graphite Inorganic materials 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
238000007493 shaping process Methods 0.000 description 4
239000006200 vaporizer Substances 0.000 description 4
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002243 precursor Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
239000004570 mortar (masonry) Substances 0.000 description 2
239000011148 porous material Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 1
101100204264 Arabidopsis thaliana STR4 gene Proteins 0.000 description 1
125000006539 C12 alkyl 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
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
101150076149 TROL gene Proteins 0.000 description 1
240000004543 Vicia ervilia Species 0.000 description 1
239000004110 Zinc silicate Substances 0.000 description 1
239000005083 Zinc sulfide Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000011324 bead Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl 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])* 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 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
230000000694 effects Effects 0.000 description 1
229920003247 engineering thermoplastic Polymers 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 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
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
229940031958 magnesium carbonate hydroxide Drugs 0.000 description 1
229940099596 manganese sulfate Drugs 0.000 description 1
239000011702 manganese sulphate Substances 0.000 description 1
235000007079 manganese sulphate Nutrition 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001400 nonyl 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])C([H])([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
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
125000000913 palmityl 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])C([H])([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
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229920006380 polyphenylene oxide Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1
LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
229910000165 zinc phosphate Inorganic materials 0.000 description 1
XSMMCTCMFDWXIX-UHFFFAOYSA-N zinc silicate Chemical compound [Zn+2].[O-][Si]([O-])=O XSMMCTCMFDWXIX-UHFFFAOYSA-N 0.000 description 1
235000019352 zinc silicate Nutrition 0.000 description 1
229910052984 zinc sulfide Inorganic materials 0.000 description 1
JQOAZIZLIIOXEW-UHFFFAOYSA-N zinc;chromium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Cr+3].[Cr+3].[Zn+2] JQOAZIZLIIOXEW-UHFFFAOYSA-N 0.000 description 1
ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1

Landscapes

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

CA000484892A 1984-08-13 1985-06-21 Catalyseur et precurseur de catalyseur d'ortho- alcoylation contenant du zinc; son utilisation pour l'alcoylation des phenols Expired CA1245620A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US64008084A	1984-08-13	1984-08-13
US640,080		1984-08-13

Publications (1)

Publication Number	Publication Date
CA1245620A true CA1245620A (fr)	1988-11-29

Family

ID=24566770

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000484892A Expired CA1245620A (fr)	1984-08-13	1985-06-21	Catalyseur et precurseur de catalyseur d'ortho- alcoylation contenant du zinc; son utilisation pour l'alcoylation des phenols

Country Status (1)

Country	Link
CA (1)	CA1245620A (fr)

1985
- 1985-06-21 CA CA000484892A patent/CA1245620A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-11-29	MKEX	Expiry

Publication	Publication Date	Title
US3972836A (en)	1976-08-03	Preparation of ortho-alkylated phenols
US3974229A (en)	1976-08-10	Preparation of ortho-alkylated phenols
US3873628A (en)	1975-03-25	Preparation of ortho-alkylated phenols
US4041085A (en)	1977-08-09	Ortho-alkylation of phenols
US3446856A (en)	1969-05-27	Methylation of phenols
US4201880A (en)	1980-05-06	Preparation of ortho-alkylated phenols
US3843606A (en)	1974-10-22	Preparation of ortho-alkylated phenols
US4418224A (en)	1983-11-29	Preparation of ortho-alkylated phenols using magnesium compound catalysts
EP0146111B1 (fr)	1989-11-02	Précurseur de catalyseur péparé à partir de carbonate de manganèse et dérivé calciné utilisé dans un procédé d'ortho-alcylation
Devi et al.	2002	Vapour phase O-alkylation of phenol over alkali promoted rare earth metal phosphates
US4528407A (en)	1985-07-09	Catalytic process for preparation of ortho-alkylated phenols
US3972828A (en)	1976-08-03	Catalyst comprising magnesium oxide and a cellulosic polymeric binder
EP0509927B1 (fr)	1995-08-09	Procédé pour la production d'éthers monoalkyliques de composés phénoliques dihydriques
US4954475A (en)	1990-09-04	Zinc-containing ortho-alkylation catalyst precursor and catalyst, and process of use in alkylation of phenols
US5097079A (en)	1992-03-17	Zinc-containing ortho-alkylation catalyst precursor and catalyst, and process of use in alkylation of phenols
GB2087383A (en)	1982-05-26	Preparation of 1,1,1,3,3,-hexafluoropropane-2-ol
US4097411A (en)	1978-06-27	Catalyst for preparation of ortho-alkylated phenols
US4590307A (en)	1986-05-20	Catalyst precursor prepared from manganese carbonate, and use of a calcined derivative in an ortho-alkylation process
JPS59228939A (ja)	1984-12-22	銅−マグネシウム触媒およびそれを用いたヒドロキシ芳香族化合物のアルキル化法
US4661638A (en)	1987-04-28	Catalyst derived from mixture of manganese hydroxide and magnesium-containing material, and method of use in ortho-alkylation of phenols
US5847237A (en)	1998-12-08	Catalyst for ortho-alkylation of phenols, a precursor thereof, and production of ortho-alkylated phenols by use of said catalyst
US4900708A (en)	1990-02-13	Ortho-alkylation catalysts based on magnesium and prepared by calcining in presence of feed mixture of reactants
EP0101138A2 (fr)	1984-02-22	Procédé pour méthylation d'un phénol en position ortho
US4677089A (en)	1987-06-30	Catalyst prepared from manganese carbonate and a magnesium compound
EP0119190B1 (fr)	1988-04-27	Composition de catalyseur pour l'ortho-alcoylation d'un phénol