# US 2017/0282193 A1 · Mercaptanized Dicyclopentadiene Compositions and Use Thereof as a Mining Chemical Collector

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- Number: US 2017/0282193 A1
- Document ID: US20170282193A1
- Status: Published application
- Kind: A1
- Application number: 15/090,654
- Filed: 2016-04-05
- Published: 2017-10-05
- Earliest claimed: 2016-04-05
- Assignees: Chevron Phillips Chemical Company LP
- Applicants: Chevron Phillips Chemical Company LP
- Inventors: Jim D. Byers; Michael S. Matson; Jason L. Kreider; Kenneth M. Lassen
- Web page: https://patentgrep.com/patent/US20170282193A1

## CPC

- B03D 1/012: containing sulfur
- B03D 1/02: Froth-flotation processes
- C07C 319/02: of thiols
- C08F 36/04: conjugated
- B03D 2201/007: Modifying reagents for adjusting pH or conductivity
- B03D 2201/02: Collectors
- B03D 2201/04: Frothers
- B03D 2203/02: Ores
- B03D 2203/025: Precious metal ores
- B03D: FLOTATION; DIFFERENTIAL SEDIMENTATION (sedimentation in general B01D21/00; in combination with other separation of solids B03B; sink-float separation B03B5/28; detergents, soaps C11D)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

The present invention discloses thiol compositions containing monothiotricyclodecenes, dithiotricyclodecanes, and intermolecular sulfide compounds, as well as mining chemical collector compositions containing such thiol compositions. Flotation processes for recovering metals, such as copper and molybdenum, from ores using the mining chemical collector compositions also are disclosed.

## Claims

### Claim 1

A flotation process for the recovery of molybdenum from an ore, the process comprising:
contacting the ore with a collector composition, wherein the collector composition comprises a thiol composition comprising sulfur-containing compounds, the sulfur-containing compounds comprising:
(i) at least 80 wt. % monothiotricyclodecene compounds;
(ii) less than 10 wt. % dithiotricyclodecane compounds; and
(iii) less than 10 wt. % of a heavy fraction comprising intermolecular sulfide compounds having at least one intermolecular sulfide group (—S—), at least two groups independently selected from a tricyclodecenyl group and a tricyclodecanyl group, and optionally at least one thiol sulfur group (—SH); wherein:
the ore comprises chalcopyrite and/or chalcocite; and
a percent recovery of molybdenum from the ore is at least about 70 wt. %.

### Claim 2 (depends on 1)

The process of claim 1, wherein the monothiotricyclodecene compounds comprise a compound having the structure:

### Claim 3 (depends on 1)

The process of claim 1, wherein the dithiotricyclodecane compounds comprise a compound having the structure:

### Claim 4 (depends on 1)

The process of claim 1, wherein the heavy fraction comprises at least one of the following compounds:
or combinations thereof.

### Claim 5 (depends on 1)

The process of claim 1, wherein the sulfur-containing compounds comprise:
(i) at least 90 wt. % of monothiotricyclodecene compounds;
(ii) less than or equal to 5 wt. % of dithiotricyclodecane compounds; and
(iii) less than or equal to 5 wt. % of the heavy fraction.

### Claim 6 (depends on 1)

The process of claim 1, wherein the thiol composition contains less than or equal to 1 wt. % sulfur-free olefin-containing compounds.

### Claim 7 (depends on 1)

The process of claim 1, wherein the sulfur-containing compounds are characterized by:
an average of less than 1 wt. % sulfide sulfur; and
an average of from 19 wt. % to 20 wt. % thiol sulfur.

### Claim 8 (depends on 1)

The process of claim 1, wherein a percent recovery of molybdenum from the ore is at least about 85 wt. %.

### Claim 9 (depends on 1)

The process of claim 1, wherein the collector composition and the ore are contacted at an amount of the collector composition, excluding water, per ton of ore in a range from about 0.01 lb to about 5 lb.

### Claim at position 10

10-12. (canceled)

### Claim 13 (depends on 1)

The process of claim 1, wherein the process is characterized by a percent recovery of molybdenum from the ore that is greater than or within about 5 wt. % of a percent recovery using a collector composition containing 600 g of lime, 1637 μL of a 1% sodium ethyl xanthate solution in water, 32.5 μL of diesel, and 56 μL of pine oil/methyl isobutyl carbinol, per ton of the ore, under the same flotation conditions.

### Claim 14 (depends on 1)

The process of claim 1, wherein the process is characterized by:
a percent recovery of molybdenum from the ore that is greater than or within about 5 wt. % of a percent recovery using tertiary dodecyl mercaptan instead of the thiol composition, under the same flotation conditions;
a percent recovery of molybdenum from the ore that is greater than or within about 5 wt. % of a percent recovery using n-dodecyl mercaptan instead of the thiol composition, under the same flotation conditions; or
both.

### Claim 15 (depends on 1)

The process of claim 1, wherein the sulfur-containing compounds comprise:
(i) at least 95 wt. % of monothiotricyclodecene compounds;
(ii) less than or equal to 2 wt. % of dithiotricyclodecane compounds; and
(iii) less than or equal to 2 wt. % of the heavy fraction.

### Claim 16 (depends on 15)

The process of claim 15, wherein the collector composition further comprises a pH control agent, a frothing agent, and water.

### Claim 17 (depends on 16)

The process of claim 16, wherein a percent recovery of molybdenum from the ore is at least about 90 wt. %.

### Claim 18 (depends on 16)

The process of claim 16, wherein the process is characterized by a percent recovery of molybdenum from the ore that is greater than or within about 5 wt. % of a percent recovery using a collector composition containing 600 g of lime, 1637 μL of a 1% sodium ethyl xanthate solution in water, 32.5 μL of diesel, and 56 μL of pine oil/methyl isobutyl carbinol, per ton of the ore, under the same flotation conditions.

### Claim 19 (depends on 16)

The process of claim 16, wherein the process is characterized by:
a percent recovery of molybdenum from the ore that is greater than or within about 5 wt. % of a percent recovery using tertiary dodecyl mercaptan instead of the thiol composition, under the same flotation conditions; and
a percent recovery of molybdenum from the ore that is greater than or within about 5 wt. % of a percent recovery using n-dodecyl mercaptan instead of the thiol composition, under the same flotation conditions.

### Claim 20

(canceled)

### Claim 21

A flotation process for the recovery of molybdenum from an ore, the process comprising:
contacting the ore with a collector composition, wherein the collector composition comprises a thiol composition comprising sulfur-containing compounds, the sulfur-containing compounds comprising:
(i) at least 80 wt. % monothiotricyclodecene compounds;
(ii) less than 10 wt. % dithiotricyclodecane compounds; and
(iii) less than 10 wt. % of a heavy fraction comprising intermolecular sulfide compounds having at least one intermolecular sulfide group (—S—), at least two groups independently selected from a tricyclodecenyl group and a tricyclodecanyl group, and optionally at least one thiol sulfur group (—SH); wherein:
the ore comprises chalcopyrite and/or chalcocite;
a percent recovery of molybdenum from the ore is greater than or within about 5 wt. % of a percent recovery using n-dodecyl mercaptan instead of the thiol composition, under the same flotation conditions.

### Claim 22 (depends on 21)

The process of claim 21, wherein the collector composition further comprises a pH control agent, a frothing agent, and water.

### Claim 23 (depends on 22)

The process of claim 22, wherein the percent recovery of molybdenum from the ore is greater than a percent recovery using n-dodecyl mercaptan instead of the thiol composition, under the same flotation conditions.

### Claim 24 (depends on 22)

The process of claim 22, wherein the sulfur-containing compounds comprise:
(i) at least 95 wt. % of monothiotricyclodecene compounds;
(ii) less than or equal to 2 wt. % of dithiotricyclodecane compounds; and
(iii) less than or equal to 2 wt. % of the heavy fraction.

### Claim 25 (depends on 22)

The process of claim 22, wherein a percent recovery of molybdenum from the ore is at least about 90 wt. %.

### Claim 26

A flotation process comprising:
contacting an ore comprising chalcopyrite and/or chalcocite with a collector composition, wherein the ore comprises more copper than molybdenum, and wherein the collector composition comprises a thiol composition comprising sulfur-containing compounds, the sulfur-containing compounds comprising:
(i) at least 80 wt. % monothiotricyclodecene compounds;
(ii) less than 10 wt. % dithiotricyclodecane compounds; and
(iii) less than 10 wt. % of a heavy fraction comprising intermolecular sulfide compounds having at least one intermolecular sulfide group (—S—), at least two groups independently selected from a tricyclodecenyl group and a tricyclodecanyl group, and optionally at least one thiol sulfur group (—SH); and
recovering molybdenum from the ore in an amount greater than about 75 wt. %, based on the amount of molybdenum in the ore prior to the contacting with the collector composition.