# US 2014/0155670 A1 · Catalysts and methods of using the same

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- Number: US 2014/0155670 A1
- Document ID: US20140155670A1
- Status: Published application
- Kind: A1
- Application number: 14/015,206
- Filed: 2013-08-30
- Published: 2014-06-05
- Earliest claimed: 2012-11-30
- Assignees: Iowa State University Research Foundation, Inc.
- Inventors: Igor Ivan Slowing; Kapil Kandel
- Web page: https://patentgrep.com/patent/US20140155670A1

## CPC

- C07C 1/22: by reduction
- B01J 21/08: Silica
- B01J 23/745: Iron
- B01J 23/755: Nickel
- B01J 23/881: and iron
- B01J 23/8906: {Iron and noble metals}
- B01J 29/0308: {Mesoporous materials not having base exchange properties, e.g. Si-MCM-41}
- B01J 35/393: {Metal or metal oxide crystallite size}
- B01J 35/45: Nanoparticles
- B01J 35/615: {100-500 m2/g}
- B01J 35/635: {0.5-1.0 ml/g}
- B01J 35/647: {2-50 nm}
- B01J 37/0018: {Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)}
- B01J 37/0201: {Impregnation}
- B01J 37/0207: {Pretreatment of the support}
- B01J 37/10: in the presence of water, e.g. steam
- C07C 1/2078: {by a transformation in which at least one -C(=O)-O- moiety is eliminated}
- B01J 37/18: with gases containing free hydrogen
- B01J 2235/10: Infrared [IR]
- B01J 2235/15: X-ray diffraction
- B01J 2235/30: Scanning electron microscopy; Transmission electron microscopy
- C07C 2521/08: Silica
- C07C 2523/745: Iron
- C07C 2523/755: Nickel
- Y02P 20/50: Improvements relating to the production of bulk chemicals
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present invention provides a catalyst including a mesoporous silica nanoparticle and a catalytic material comprising iron. In various embodiments, the present invention provides methods of using and making the catalyst. In some examples, the catalyst can be used to hydrotreat fatty acids or to selectively remove fatty acids from feedstocks.

## Claims

### Claim 1

A method comprising:
combining a catalyst with at least one first molecule comprising at least one of a fatty acid, a fatty acid ester, a monoglyceride, a diglyceride, and a triglyceride, to provide a mixture, the catalyst comprising a mesoporous silica nanoparticle comprising a catalytic material comprising iron; and
combining the mixture with a hydrogen gas under conditions so that the catalytic material in the catalyst catalyzes a chemical transformation of the first molecule.

### Claim 2 (depends on 1)

The method of claim 1, wherein the chemical transformation of the first molecule comprises hydrotreatment.

### Claim 3 (depends on 1)

The method of claim 1, wherein the catalytic material has a particle size equal to or less than a pore size of the catalytic material.

### Claim 4 (depends on 1)

The method of claim 1, wherein the catalytic material has a particle size of about 5 nm to about 15 nm.

### Claim 5 (depends on 1)

The method of claim 1, wherein the catalytic material is located at least partially within pores of the mesoporous silica nanoparticle.

### Claim 6 (depends on 1)

The method of claim 1, wherein about 0.1 wt % to about 30 wt % of the catalyst comprises the catalytic material.

### Claim 7 (depends on 1)

The method of claim 1, wherein the catalyst has a particle size of about 50 nm-1200 nm.

### Claim 8 (depends on 1)

The method of claim 1, wherein the catalyst has a pore size of about 5 nm to about 15 nm.

### Claim 9 (depends on 1)

The method of claim 1, wherein the catalyst is an adsorbent catalyst, wherein the catalyst comprises at least one adsorbent functional group comprising a functional group selected from the group consisting of an amino(C1-C20)alkyl group or a salt thereof, a (C1-C20)alkyl carboxylic acid group or a salt thereof, a (C1-C20)alkyl sulfonic acid group or a salt thereof, and a perfluoro(C1-C20)alkyl group, wherein the alkyl unit of the aminoalkyl group, the alkyl carboxylic acid group, the alkyl sulfonic acid group, and of the perfluoroalkyl group is covalently bound to the mesoporous silica nanoparticle, and wherein the C1-C20 alkyl groups of the amino(C1-C20)alkyl group are independently optionally interrupted by one or two —NH— groups.

### Claim 10 (depends on 9)

The method of claim 9, wherein the first molecule is selectively adsorbed by the adsorbent functional group.

### Claim 11

A catalyst comprising:
a mesoporous silica nanoparticle; and
a catalytic material comprising iron nanoparticles;
wherein the iron nanoparticles are at least partially within pores of the mesoporous silica nanoparticle.

### Claim 12 (depends on 11)

The catalyst of claim 11, wherein the catalyst is sufficient to catalyze hydrocracking in the presence of H2 at a lower rate than the catalyst catalyzes at least one of hydrogenation, reduction, decarboxylation, and hydrodeoxygenation.

### Claim 13 (depends on 11)

The catalyst of claim 11, wherein the catalyst is sufficient to catalyze hydrocracking of a (C5-C50) fatty acid in the presence of H2 such that, at about 100% conversion of the fatty acid, at a temperature of about 200° C. to about 400° C., about 0.01-15% of the yield of the reaction is hydrocracking product.

### Claim 14 (depends on 11)

The catalyst of claim 11, wherein the catalyst is sufficient to catalyze at least one of hydrogenation, reduction, decarboxylation, and hydrodeoxygenation of at least one of a C5-50 fatty acid C1-50 ester and a triglyceride having C5-50 fatty acid groups in the presence of H2 at a temperature of about 200° C. to about 400° C.

### Claim 15 (depends on 11)

The catalyst of claim 11, further comprising
at least one adsorbent functional group comprising a functional group selected from the group consisting of an amino(C1-C20)alkyl group or a salt thereof, a (C1-C20)alkyl carboxylic acid group or a salt thereof, a (C1-C20)alkyl sulfonic acid group or a salt thereof, and a perfluoro(C1-C20)alkyl group,
wherein the alkyl unit of the aminoalkyl group, the alkyl carboxylic acid group, the alkyl sulfonic acid group, and of the perfluoroalkyl group is covalently bound to the mesoporous silica nanoparticle, wherein the C1-C20 alkyl groups of the amino(C1-C20)alkyl group are independently optionally interrupted by one or two —NH— groups, and wherein the catalyst is an adsorbent catalyst.

### Claim 16 (depends on 15)

The adsorbent catalyst of claim 15, wherein the adsorbent functional group adsorbs fatty acids at a higher rate than it adsorbs at least one of fatty acid esters and triglycerides.

### Claim 17 (depends on 15)

The adsorbent catalyst of claim 15, wherein the adsorbent functional group comprises at least one of an amino(C1-10)alkyl group and a salt thereof wherein the alkyl unit is covalently bound to the mesoporous silica nanoparticle.

### Claim 18 (depends on 15)

The adsorbent catalyst of claim 15, wherein the adsorbent functional group is present in a concentration of about 0.01 mmol to about 50 mmol per gram of the mesoporous silica nanoparticle.

### Claim 19 (depends on 15)

The adsorbent catalyst of claim 15, wherein the adsorbent catalyst is sufficient to catalyze decarboxylation and hydrodeoxygenation of a fatty acid at a higher rate than a corresponding mesoporous silica nanoparticle not having the adsorbent functional group bound thereto.

### Claim 20

A catalyst comprising:
a mesoporous silica nanoparticle comprising a particle size of about 50 nm to about 1200 nm, a pore size of about 5 nm to about 15 nm, and a pore volume of about 0.5 to about 1.5 cm3/g; and
a catalytic material comprising iron nanoparticles having a particle size of about 5 nm to about 15 nm at least partially within pores of the mesoporous silica nanoparticle, the iron nanoparticles comprising about 1-10 wt % of the catalyst;
wherein the catalyst has a surface area of about 150 m2/g to about 375 m2/g.