# US 10,308,562 B2 · Polymer-supported transition catalyst

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- Number: US 10,308,562 B2
- Document ID: US10308562B2
- Status: Granted
- Kind: B2
- Application number: 15/510,463
- Filed: 2015-09-12
- Published: 2017-10-05
- Granted: 2019-06-04
- Earliest claimed: 2014-09-12
- Assignees: Toyo Gosei Co., Ltd.
- Applicants: Toyo Gosei Co., Ltd.
- Inventors: Takashi Miyazawa; Shin-ya Tashita
- Web page: https://patentgrep.com/patent/US10308562B2

## CPC

- C07B 37/04: Substitution
- B01J 21/04: Alumina
- B01J 21/063: {Titanium; Oxides or hydroxides thereof}
- B01J 21/066: {Zirconium or hafnium; Oxides or hydroxides thereof}
- B01J 21/08: Silica
- B01J 23/40: of the platinum group metals
- B01J 23/42: Platinum
- B01J 23/44: Palladium
- B01J 23/462: {Ruthenium}
- B01J 23/464: {Rhodium}
- B01J 23/52: Gold
- B01J 23/755: Nickel
- B01J 31/06: containing polymers {(organometallic polymers B01J31/123; polymer-bound organometallic complexes B01J31/165; coordination polymers B01J31/1691)}
- B01J 31/069: {Hybrid organic-inorganic polymers, e.g. silica derivatized with organic groups (nitrogen containing groups on mineral substrates B01J31/0254; organometallic polymers B01J31/123; coordination complexes immobilised on an inorganic support B01J31/1616; coordination polymers, e.g. metal-organic frameworks B01J31/1691)}
- B01J 31/127: {the siloxane units, e.g. silsesquioxane units, being grafted onto other polymers or inorganic supports, e.g. via an organic linker}
- B01J 35/59: Membranes
- B01J 37/02: Impregnation, coating or precipitation ({B01J37/0009 and B01J37/0018 take precedence } ; protection by coating B01J33/00)
- B01J 37/035: {Precipitation on carriers}
- B01J 37/06: Washing {(B01J37/0009, B01J37/0018 take precedence)}
- B01J 37/16: Reducing
- B01J 37/18: with gases containing free hydrogen
- C07B 41/06: of carbonyl groups
- C07B 47/00: Formation or introduction of functional groups not provided for in groups C07B39/00 - C07B45/00
- C07B 61/00: Other general methods
- C07C 1/00: Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C 1/321: {the hetero-atom being a non-metal atom}
- C07C 2/00: Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms (redistribution reactions involving splitting C07C6/00)
- C07C 2/861: {the non-hydrocarbon contains only halogen as hetero-atoms}
- C07C 5/08: of carbon-to-carbon triple bonds
- C07C 5/09: to carbon-to-carbon double bonds
- C07C 45/32: with molecular oxygen
- C07C 45/34: in unsaturated compounds
- C07C 49/04: Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C 51/353: by isomerisation; by change of size of the carbon skeleton
- C07C 67/293: by isomerisation; by change of size of the carbon skeleton
- C07C 67/303: by hydrogenation of unsaturated carbon-to-carbon bonds
- C07C 69/157: containing six-membered aromatic rings
- C07C 69/612: Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C 209/36: by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings {in presence of hydrogen-containing gases and a catalyst}
- C07F 7/1876: {by reactions involving the formation of Si-C linkages}
- C08K 3/04: Carbon
- C08K 3/10: Metal compounds
- C08K 3/22: of metals
- C08K 3/36: Silica
- B01J 2231/323: Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
- B01J 2231/4211: Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
- B01J 2231/4261: Heck-type, i.e. RY + C=C, in which R is aryl
- B01J 2231/4266: Sonogashira-type, i.e. RY + HC-CR' triple bonds, in which R=aryl, alkenyl, alkyl and R'=H, alkyl or aryl
- B01J 2231/641: Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J 2231/645: of C=C or C-C triple bonds
- B01J 2231/70: Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- B01J 2531/18: Gold
- B01J 2531/821: Ruthenium
- B01J 2531/822: Rhodium
- B01J 2531/824: Palladium
- B01J 2531/828: Platinum
- B01J 2531/847: Nickel
- C07C 2521/04: Alumina
- C07C 2521/06: Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C 2521/08: Silica
- C07C 2521/10: Magnesium; Oxides or hydroxides thereof
- C07C 2521/18: Carbon
- C07C 2523/42: Platinum
- C07C 2523/44: Palladium
- C07C 2523/46: Ruthenium, rhodium, osmium or iridium
- C07C 2523/52: Gold
- C07C 2523/755: Nickel
- C07C 2531/06: containing polymers
- C08K 2003/222: {Magnesia, i.e. magnesium oxide}
- C08K 2003/2227: {of aluminium}
- C08K 2003/2241: {Titanium dioxide}
- C08K 2003/2244: {of zirconium}
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A long life catalyst is provided that is conveniently and inexpensively capable of being produced and that is highly active and has inhibited metal leakage. According to aspects of the present invention, a catalyst is provided that includes: a polymer including a plurality of first structural units and a plurality of second structural units; and metal acting as a catalytic center, wherein at least part of the metal is covered with the polymer, each of the plurality of first structural units has a first atom constituting a main chain of the polymer and a first substituent group bonded to the first atom, a second atom included in each of the plurality of second structural units is bonded to the first atom, and the second atom is different from the first atom, or at least one of all substituent groups on the second atom is different from the first substituent group.

## Claims

### Claim 1

A catalyst, comprising:
a polysiloxane polymer including a silicon atom and a first substituent group bonded to the silicon atom;
a metal atom acting as a catalytic center; and
an inorganic member or an organic member,
wherein at least a part of the metal is covered with the polymer;
the first substituent group is a hydrogen atom; and
the polysiloxane polymer has a structural unit represented by the following formula

### Claim 2 (depends on 1)

The catalyst of claim 1, wherein the metal is any one of selected from the group consisting of palladium, platinum, ruthenium, rhodium, silver, gold, copper, nickel, cobalt, iron, chromium, manganese, technetium, osmium, molybdenum, tungsten, iridium, rhenium, titanium, zirconium, hafnium, tantalum, niobium, and vanadium.

### Claim 3 (depends on 1)

The catalyst of claim 1, wherein the inorganic member is an alumina or a silicon oxide.

### Claim 4 (depends on 1)

A method of producing the catalyst of claim 1, the method comprising:
preparing a metal compound including a metal atom acting as a catalytic center, a polysiloxane polymer including a silicon atom and a first substituent group bonded to the silicon atom, and an inorganic member or an organic member; and
reacting the metal compound and the polysiloxane polymer to obtain the catalyst of claim 1, wherein:
the first substituent group is a hydrogen atom; and
the polysiloxane polymer has a structural unit represented by the following formula

### Claim 5 (depends on 4)

The method of claim 4, wherein in the reacting the metal compound and the polysiloxane further comprises a reducing agent to reduce a valence of the metal.

### Claim 6 (depends on 1)

A method of producing a compound from a substrate via a catalyzed reaction, the method comprising:
contacting the substrate with the catalyst of claim 1; and
allowing the reaction to occur in the presence of the catalyst;
wherein the reaction is selected from the group consisting of: reduction reaction, oxidation reaction, hydrometalation, carbon-carbon bond forming reaction and carbon-nitrogen bond forming reaction.

### Claim 7 (depends on 4)

The method of claim 4, wherein in the reacting metal compound and the polysiloxane polymer, insertion of the metal atom of the metal compound into a bond between the silicon atom and the hydrogen atom occurs.