CA1071179A - Couplage oxydatif d'alkylphenols, d'alkoxyphenols et de naphtols, catalyse par des complexes metalliques d'acide aminocarboxylique et aminosulfonique - Google Patents

Couplage oxydatif d'alkylphenols, d'alkoxyphenols et de naphtols, catalyse par des complexes metalliques d'acide aminocarboxylique et aminosulfonique

Info

Publication number: CA1071179A
Authority: CA; Canada
Prior art keywords: added; alkyl; grams; phenol; reaction
Prior art date: 1974-08-23
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

CA230,971A

Other languages

English (en)

Other versions

CA230971S (en

Inventor

Thomas F. Rutledge

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.)

Zeneca Inc

Original Assignee

ICI United States Inc

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.)

1974-08-23

Filing date

1975-07-08

Publication date

1980-02-05

1975-07-08 Application filed by ICI United States Inc filed Critical ICI United States Inc

1980-02-05 Application granted granted Critical

1980-02-05 Publication of CA1071179A publication Critical patent/CA1071179A/fr

Status Expired legal-status Critical Current

Links

IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 title claims abstract description 17
229910052751 metal Inorganic materials 0.000 title claims description 13
239000002184 metal Substances 0.000 title claims description 13
238000005691 oxidative coupling reaction Methods 0.000 title claims description 13
150000004780 naphthols Chemical class 0.000 title abstract description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 title description 7
239000000203 mixture Substances 0.000 claims abstract description 87
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 60
239000001301 oxygen Substances 0.000 claims abstract description 60
229910052760 oxygen Inorganic materials 0.000 claims abstract description 60
238000000034 method Methods 0.000 claims abstract description 44
239000003054 catalyst Substances 0.000 claims abstract description 41
150000004696 coordination complex Chemical class 0.000 claims abstract description 25
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 20
239000007859 condensation product Substances 0.000 claims abstract description 7
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 124
125000000217 alkyl group Chemical group 0.000 claims description 61
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 53
239000000463 material Substances 0.000 claims description 50
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 29
125000004432 carbon atom Chemical group C* 0.000 claims description 25
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 22
-1 nickelous ions Chemical class 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
239000004471 Glycine Substances 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 14
150000007513 acids Chemical class 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 4
MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 claims description 4
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 claims description 2
150000004782 1-naphthols Chemical class 0.000 claims 1
150000004699 copper complex Chemical group 0.000 claims 1
239000011541 reaction mixture Substances 0.000 abstract description 91
238000006243 chemical reaction Methods 0.000 abstract description 86
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230000008569 process Effects 0.000 abstract description 15
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238000012986 modification Methods 0.000 abstract description 2
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 78
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 69
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 66
150000002500 ions Chemical group 0.000 description 63
239000000243 solution Substances 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
238000004458 analytical method Methods 0.000 description 40
239000007789 gas Substances 0.000 description 35
229910000030 sodium bicarbonate Inorganic materials 0.000 description 33
235000017557 sodium bicarbonate Nutrition 0.000 description 33
229910052757 nitrogen Inorganic materials 0.000 description 27
CZAZXHQSSWRBHT-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-3,4,5,6-tetramethylphenol Chemical compound OC1=C(C)C(C)=C(C)C(C)=C1C1=CC=CC=C1O CZAZXHQSSWRBHT-UHFFFAOYSA-N 0.000 description 23
NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 23
150000002989 phenols Chemical class 0.000 description 23
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238000001030 gas--liquid chromatography Methods 0.000 description 18
DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 14
DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
229940024606 amino acid Drugs 0.000 description 10
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 10
239000011203 carbon fibre reinforced carbon Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 9
235000001014 amino acid Nutrition 0.000 description 9
150000001413 amino acids Chemical class 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 9
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 9
235000019333 sodium laurylsulphate Nutrition 0.000 description 9
239000004094 surface-active agent Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
239000002002 slurry Substances 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
150000007514 bases Chemical class 0.000 description 7
238000005859 coupling reaction Methods 0.000 description 7
229910021645 metal ion Inorganic materials 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
239000010949 copper Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
QSZCGGBDNYTQHH-UHFFFAOYSA-N 2,3-dimethoxyphenol Chemical compound COC1=CC=CC(O)=C1OC QSZCGGBDNYTQHH-UHFFFAOYSA-N 0.000 description 4
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
239000012736 aqueous medium Substances 0.000 description 4
239000000306 component Substances 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 4
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239000008096 xylene Substances 0.000 description 4
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WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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125000003118 aryl group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
230000007423 decrease Effects 0.000 description 3
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HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 3
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WCUDDVOHXLKLQN-UHFFFAOYSA-N 2,3,6-triethylphenol Chemical compound CCC1=CC=C(CC)C(CC)=C1O WCUDDVOHXLKLQN-UHFFFAOYSA-N 0.000 description 2
ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
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108010008488 Glycylglycine Proteins 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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LVIYYTJTOKJJOC-UHFFFAOYSA-N nickel phthalocyanine Chemical compound [Ni+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LVIYYTJTOKJJOC-UHFFFAOYSA-N 0.000 description 1
OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000005502 peroxidation Methods 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 1
238000010992 reflux Methods 0.000 description 1
WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
229910000026 rubidium carbonate Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
AOBMIXQSBXYCFW-UHFFFAOYSA-M sodium;bis(2-ethylhexyl) phosphate Chemical compound [Na+].CCCCC(CC)COP([O-])(=O)OCC(CC)CCCC AOBMIXQSBXYCFW-UHFFFAOYSA-M 0.000 description 1
229940035044 sorbitan monolaurate Drugs 0.000 description 1
239000001589 sorbitan tristearate Substances 0.000 description 1
235000011078 sorbitan tristearate Nutrition 0.000 description 1
229960004129 sorbitan tristearate Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
229940034208 thyroxine Drugs 0.000 description 1
XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/30—Quinones containing groups having oxygen atoms singly bound to carbon atoms with polycyclic non-condensed quinoid structure
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- 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
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
- C07C46/08—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring with molecular oxygen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/08—Quinones with polycyclic non-condensed quinoid structure
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
- C07C50/14—Quinones the quinoid structure being part of a condensed ring system containing two rings with unsaturation outside the ring system, e.g. vitamin K1
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0269—Complexes comprising ligands derived from the natural chiral pool or otherwise having a characteristic structure or geometry
- B01J2531/0275—Complexes comprising ligands derived from the natural chiral pool or otherwise having a characteristic structure or geometry derived from amino acids
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
- B01J2531/72—Manganese
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/08—Aldehydes; Ketones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Inorganic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Polyethers (AREA)

CA230,971A 1974-08-23 1975-07-08 Couplage oxydatif d'alkylphenols, d'alkoxyphenols et de naphtols, catalyse par des complexes metalliques d'acide aminocarboxylique et aminosulfonique Expired CA1071179A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US50021074A	1974-08-23	1974-08-23
US55086075A	1975-02-18	1975-02-18

Publications (1)

Publication Number	Publication Date
CA1071179A true CA1071179A (fr)	1980-02-05

Family

ID=27053449

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA230,971A Expired CA1071179A (fr)	1974-08-23	1975-07-08	Couplage oxydatif d'alkylphenols, d'alkoxyphenols et de naphtols, catalyse par des complexes metalliques d'acide aminocarboxylique et aminosulfonique

Country Status (9)

Country	Link
JP (1)	JPS5168551A (fr)
AR (1)	AR216742A1 (fr)
BR (1)	BR7505247A (fr)
CA (1)	CA1071179A (fr)
DE (1)	DE2536870A1 (fr)
FR (1)	FR2282416A1 (fr)
GB (1)	GB1480460A (fr)
IT (1)	IT1041249B (fr)
NL (1)	NL7509823A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58132204U (ja) *	1982-03-01	1983-09-06	関東自動車工業株式会社	シリンダ装置
JP4908070B2 (ja) *	2006-06-07	2012-04-04	長谷川香料株式会社	ジ−置換ビスフェノールの製造方法
WO2014056736A1 (fr)	2012-10-12	2014-04-17	Evonik Degussa Gmbh	Mélange de biphosphites et leur utilisation en tant que mélange catalytique pour l'hydroformylation

1975
- 1975-07-08 CA CA230,971A patent/CA1071179A/fr not_active Expired
- 1975-08-14 IT IT5096075A patent/IT1041249B/it active
- 1975-08-15 DE DE19752536870 patent/DE2536870A1/de not_active Withdrawn
- 1975-08-15 BR BR7505247D patent/BR7505247A/pt unknown
- 1975-08-18 JP JP9955775A patent/JPS5168551A/ja active Pending
- 1975-08-18 NL NL7509823A patent/NL7509823A/xx not_active Application Discontinuation
- 1975-08-18 FR FR7525564A patent/FR2282416A1/fr active Granted
- 1975-08-18 AR AR26003475A patent/AR216742A1/es active
- 1975-08-19 GB GB3442075A patent/GB1480460A/en not_active Expired

Also Published As

Publication number	Publication date
FR2282416A1 (fr)	1976-03-19
AU8387575A (en)	1977-02-17
IT1041249B (it)	1980-01-10
DE2536870A1 (de)	1976-03-04
FR2282416B1 (fr)	1979-08-03
JPS5168551A (ja)	1976-06-14
GB1480460A (en)	1977-07-20
NL7509823A (nl)	1976-02-25
AR216742A1 (es)	1980-01-31
BR7505247A (pt)	1976-08-03

Legal Events

Date	Code	Title	Description
1997-02-05	MKEX	Expiry

Publication	Publication Date	Title
US4347232A (en)	1982-08-31	Preparation of hydrogen peroxide from its elements
US4008266A (en)	1977-02-15	Coupling of aromatic compounds in the presence of molecular oxygen, a mercuric oxyanion compound, and a group VIII metal or group VIII metal oxyanion compound
Hor et al.	1989	Substituted metal carbonyls XI. 1, 1′-Bis (diphenylphosphino) ferrocene—a bridging, chelating and unidentate ligand in the synthesis of M2 (CO) 10 (μ-P P), M (CO) 4 (η2-P P) and M (CO) 5 (η1-P P)(where M= Cr, Mo, W and P P= Fe (C5H4PPh2) 2)
US4096190A (en)	1978-06-20	Oxidative coupling of alkylphenols catalyzed by metal ammonia complexes
CN1982272A (zh)	2007-06-20	3,3＇,5,5＇,6,6＇－六烷基－2,2＇－联苯酚、3,3＇,4,4＇,5,5＇－六烷基－2,2＇－联苯酚和3,3＇, 4,4＇,5,5＇,6,6＇－八烷基－2,2＇－联苯酚的制备方法
US4132722A (en)	1979-01-02	Oxidative coupling of alkylphenols catalyzed by metal complexes of diimino acid
US4100205A (en)	1978-07-11	Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of aminoketo compounds
US4139544A (en)	1979-02-13	Oxidative coupling of alkylphenols catalyzed by metal complexes of polyimino acids
CA1071179A (fr)	1980-02-05	Couplage oxydatif d'alkylphenols, d'alkoxyphenols et de naphtols, catalyse par des complexes metalliques d'acide aminocarboxylique et aminosulfonique
US4070383A (en)	1978-01-24	Oxidative coupling of phenols and naphthols
US4101561A (en)	1978-07-18	Oxidative coupling of alkylphenols catalyzed by metal complexes of imino acid compounds
US4098830A (en)	1978-07-04	Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of dicarboxylic acid compounds
EP0102341B1 (fr)	1986-11-20	Procédé d'hydroformylation pour la préparation d'aldéhydes glycolliques
US4067890A (en)	1978-01-10	Oxidative coupling of alkylphenols, alkoxyphenols and naphthols catalyzed by metal complexes of amino carboxylic and amino sulfonic acids
US4100202A (en)	1978-07-11	Oxidative coupling of alkylphenols or 1-naphthols catalyzed by cupric complexes
US4147663A (en)	1979-04-03	Oxidative coupling of alkylphenols, alkoxyphenols and naphthols catalyzed by metal complexes of amino carboxylic and amino sulfonic acids
EP3781542A1 (fr)	2021-02-24	Oxydation de p-hydroquinones alkylées dans des solutions aqueuses par peroxyde d'hydrogène
US3968128A (en)	1976-07-06	Magnesium-group VIII transition metal carbonyl and substituted carbonyl complexes
US4130504A (en)	1978-12-19	Oxidative coupling of phenols and naphthols
US4124647A (en)	1978-11-07	Process for the preparation of ethers
Shimizu et al.	1991	A facile synthesis of 4-alkoxymethylphenols by a copper (II)-acetoxime catalyst/O2 system
US4100203A (en)	1978-07-11	Oxidative coupling of alkylphenols or 1-naphthols catalyzed by metal complexes of an oxime of a keto or aldehyde compound
US4164516A (en)	1979-08-14	Preparation of 4-hydroxy-2,4,6-trimethyl-cyclohexa-2,5-diene-1-one
CA1082212A (fr)	1980-07-22	Couplage oxydant d'alkylphenols ou de 1-naphthols catalyse par des complexes metalliques de composes cetohydroxyles
CN110396303B (zh)	2023-11-07	一种三芳基甲烷类化合物的制备及应用