IP Library Granted Patent US 12,215,070
Granted Patent B2
US 12,215,070 · App. 16/953,521 · Granted Feb 4, 2025

Cyanocarbon compositions

Inventors: Todd R. Boehlow (Houston, TX); Benjamin Haseltine (Houston, TX); Jefferson Thomas Ebert (Houston, TX); Sanjay Dube (Houston, TX); Darrick Elmore (Houston, TX)
Assignee: Ascend Performance Materials Operations LLC
C07C255/05
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Quick Facts
Patent No.
US 12,215,070
App. No.
16/953,521
Granted
Feb 4, 2025
Kind
B2
Abstract

The disclosure relates to the cyanocarbon compositions and processes for producing the same. The cyanocarbon compositions comprise tricyanohexane and one or more coproducts of the tricyanohexane production reaction. Exemplary coproducts include tetracyano compounds, cyanoalkenes, cyanooximes, cyanoamides, and combinations thereof.

Claims (20)

1. A cyanocarbon composition comprising:

1,3,6-tricyanohexane; and

from 0.2 wt. % to 10 wt. % of a tricyanohexane coproduct selected from the group consisting of a tetracyano compound, a cyanoalkene, a cyanoamine, a cyanooxime, a cyanoamide, 1,2,3-tricyanohexane, 1,2,6-tricyanohexane, 1,3,4-tricyanohexane, 1,3,5-tricyanohexane, 1,4,5-tricyanohexane, 2,3,5-tricyanohexane, and combinations thereof.

2. The cyanocarbon composition of claim 1 , wherein the tricyanohexane coproduct comprises an isomer of tricyanohexane selected from the group consisting of 1,2,3-tricyanohexane, 1,2,6-tricyanohexane, 1,3,4-tricyanohexane, 1,3,5-tricyanohexane, 1,4,5-tricyanohexane, 2,3,5-tricyanohexane, and combinations thereof.

3. The cyanocarbon composition of claim 2 , wherein the weight ratio of tricyanohexane to the isomer is at least 5:1.

4. The cyanocarbon composition of claim 1 , wherein the tricyanohexane coproduct comprises a tetracyano compound having the chemical formula C x H 2x-2 (CN) 4 ;

wherein x is from 5 to 10.

5. The cyanocarbon composition of claim 4 , wherein the composition comprises from 0.2 wt. % to 10 wt. % tricyanohexane coproduct.

6. The cyanocarbon composition of claim 1 , wherein the tricyanohexane coproduct comprises a tricyanoalkene.

7. The cyanocarbon composition of claim 1 , wherein the tricyanohexane coproduct comprises a (cyanoethyl)amine.

8. The cyanocarbon composition of claim 7 , wherein the cyanoethylamine comprises tri-(cyanoethyl)amine.

9. The cyanocarbon composition of claim 1 , wherein the tricyanohexane coproduct comprises adiponitrile.

10. The cyanocarbon composition of claim 1 , wherein the tricyanohexane coproduct comprises a cyanooxime having the chemical structure

wherein a is 0 to 3, b is 1 to 3, and c is 1 to 4.

11. The cyanocarbon composition of claim 1 , wherein the tricyanohexane coproduct comprises a cyano-compound having the chemical structure

wherein a is from 1 to 3, and b is from 1 to 4.

12. The cyanocarbon composition of claim 1 , wherein the tricyanohexane coproduct has a molecular weight ranging from 105 amu to 215 amu.

13. The cyanocarbon composition of claim 1 , wherein the cyanocarbon composition comprises at least 92 wt. % 1,3,6-tricyanohexane.

14. The cyanocarbon composition of claim 2 , wherein the cyanocarbon composition comprises at least 92 wt. % 1,3,6-tricyanohexane, from from 0.5 wt % to 7 wt % of the isomer of tricyanohexane, wherein the weight ratio of tricyanohexane to the isomer is at least 5:1, and from 500 ppm to 1 wt % adiponitrile.

15. The cyanocarbon composition of claim 2 , wherein the cyanocarbon composition comprises at least 92 wt. % 1,3,6-tricyanohexane, from 0.5 wt % to 7 wt % of the isomer of tricyanohexane, and from 0.01 wt. % to 2 wt. % of a tetracyano compound.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Dec 23, 2025
From: WILMINGTON SAVINGS FUND SOCIETY, FSB
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 074050/0090 →
SECURITY INTEREST Recorded Dec 23, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 074056/0183 →
SECURITY INTEREST Recorded Dec 19, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 074007/0183 →
SECURITY INTEREST Recorded Apr 10, 2025
From: BANK OF AMERICA, N.A.
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 070811/0705 →
SECURITY INTEREST Recorded Dec 8, 2022
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC
Reel/Frame 062094/0172 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 20, 2020
From: BOEHLOW, TODD R.; HASELTINE, BENJAMIN; EBERT, JEFFERSON THOMAS; DUBE, SANJE; ELMORE, DARRICK
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 054488/0871 →