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CA-3130142-C - HYDROGEN SULFIDE SCAVENGERS FOR ASPHALT

CA3130142CCA 3130142 CCA3130142 CCA 3130142CCA-3130142-C

Abstract

Scavenging compounds and compositions useful in reducing sulfide emissions from asphalt, such as polymer-treated asphalt, are disclosed. The scavenger compositions may include sulfide-scavenging agents. The scavenger compositions also include a metal-containing compound and optionally a solvent. Any of the compositions, sulfide-scavenging agents and metal-containing compounds may be anhydrous. Methods of using the compositions to reduce hydrogen sulfide emissions from asphalt are also disclosed.

Inventors

  • Xiaowei Tong
  • Jennifer L. Sorrells
  • Elizabeth Balapitiya
  • Ravindranath Mukkamala

Assignees

  • ECOLAB USA INC.

Dates

Publication Date
20260505
Application Date
20200226
Priority Date
20190228

Claims (20)

  1. CLAIMS What is claimed is: 1. A composition for reducing hydrogen sulfide emission from asphalt, comprising: (a) a metal-containing compound being a metal carboxylate, a metal carbonate, or any combination thereof; and (b) a sulfide-scavenging agent selected from the group consisting of hexamethylenetetramine and a 1,3,5-triazine derivative of Formula I: R 1 ' /"-.... ,., R2 N N lN) I R3 wherein each of R1, R2, and R3 is independently selected at each occurrence from hydrogen, straight or branched C1-C30 alkyl, hydroxyl substituted straight or branched C1-C30 alkyl, and straight or branched C1-C30 alkyl substituted with straight or branched C1-C30 alkoxy, wherein the metal-containing compound is free from zinc.
  2. 2. The composition of claim 1, further comprising asphalt.
  3. 3. The composition of claim 2, wherein the asphalt is polymer-treated asphalt.
  4. 4. The composition of claim 2 or 3, wherein the asphalt comprises polyphosphoric acid.
  5. 5. The composition of any one of claims 1 to 4, wherein the sulfide-scavenging agent comprises Formula I, and each of R1, R2, and R3 is independently selected from straight or branched Cs-C30 alkyl, hydroxyl substituted straight or branched CsC3o alkyl, and straight or branched Cs-C30 alkoxy substituted with straight or branched C1-C30 alkoxy. Date Rei;ue/Date Received 2024-04-19
  6. 6. The composition of any one of claims 1 to 4, wherein the sulfide-scavenging agent comprises Formula I, and each of R1, R2, and R3 is selected from C1-Ca straight or branched alkyl.
  7. 7. The composition of any one of claims 1 to 6, wherein the sulfide-scavenging agent comprises Formula I, and each of R1, R2, and R3 is the same substituent.
  8. 8. The composition of any one of claims 1, 2, 3, 4, 5 or 7, wherein R1 is -CH2CH2OH, R2 is-CH2CH2OH, and R3 is-CH2CH2OH.
  9. 9. The composition of any one of claims 1 to 4, wherein the sulfide-scavenging agent is hexamethylenetetramine.
  10. 10. The composition of any one of claims 1 to 9, further comprising a polar solvent being diethylene glycol, 2-butoxyethanol, propylene glycol, monoethanol amine, or any combination thereof.
  11. 11. The composition of claim 1, wherein the composition comprises about 10 weight% to about 90 weight% of the sulfide-scavenging agent, and about 1 weight % to about 50 weight % of the metal-containing compound.
  12. 12. The composition of claim 11, wherein the composition comprises about 10 weight % to about 90 weight % of a solvent.
  13. 13. The composition of claim 3, wherein the asphalt comprises about 0.1 weight % to about 10 weight% of the polymer.
  14. 14. The composition of any one of claims 1 to 13, wherein the metal of the metal-containing compound is Cu (II}, Fe (II}, Ni (II}, Co (II}, Mn (II}, Ca (II}, Mg (II}, or any combination thereof.
  15. 15. The composition of any one of claims 1 to 13, wherein the metal-containing compound is copper carboxylate, iron carboxylate, or any combination thereof. Date Rei;ue/Date Received 2024-04-19
  16. 16. The composition of any one of claims 1 to 13, wherein the metal-containing compound is copper acetate, copper bis-glycinate, copper 2-ethylhexanoate, iron 2- ethylhexanoate, or any combination thereof.
  17. 17. The composition of any one of claims 1 to 13, wherein the metal-containing compound is copper acetate.
  18. 18. The composition of any one of claims 1 to 17, wherein the composition, the metal-containing compound and/or the sulfide-scavenging agent is anhydrous.
  19. 19. A method of reducing hydrogen sulfide emission from asphalt, comprising: combining asphalt with a composition, the composition comprising: a metalcontaining compound being a metal carboxylate, a metal carbonate, or any combination thereof; and a sulfide-scavenging agent selected from the group consisting of hexamethylenetetramine and a 1,3,5-triazine derivative of Formula I: R1, /"--... .,,R2 N N ~N) I R3 wherein each of R1, R2, and R3 is independently selected at each occurrence from hydrogen, straight or branched C1-C30 alkyl, hydroxyl substituted straight or branched C1-C30 alkyl, and straight or branched C1-C30 alkyl substituted with straight or branched C1-C30 alkoxy.
  20. 20. The method of claim 19, wherein the asphalt is polymer-treated asphalt.

Description

HYDROGEN SULFIDE SCAVENGERS FOR ASPHALT TECHNICAL FIELD [0001] The present disclosure relates generally to scavengers of sulfur-based species, and more particularly to compounds that scavenge hydrogen sulfide and/or mercaptan vapors released from asphalt. BACKGROUND [0002] Asphalt is commonly used in the construction and paving of roads. Asphalt is a mixture of aggregate material, such as sand, gravel, and crushed stone, with hot bitumen. The bitumen coats the aggregate material to give the asphalt, which may be spread as a uniform layer upon a road bed and compacted and smoothed with heavy rolling equipment. [0003] Asphalt invariably contains sulfur. The amount of sulfur will depend on the origin of the crude oil, as well as the processes used to refine the crude oil, into asphalt. The sulfur may exist in different forms. For example, sulfur may be in the form of hydrogen sulfide. Hydrogen sulfide, or dihydrogen sulfide, is a chemical compound with the formula H2S. It is a colorless, poisonous, flammable gas with the characteristically regarded foul odor. [0004] Hydrogen sulfide may be released from asphalt, in particular when the asphalt is heated to a certain temperature. For example, hydrogen sulfide results from the dehydrogenation reactions that occur between bitumen and sulfur at the hot mixing temperatures, for example temperatures greater than 140 °C. Hydrogen sulfide emissions are regulated. Therefore, there exists a need to reduce the amount of hydrogen sulfide in asphalt. [0005] A variety of polymers are used to treat/ modify asphalt. The degree to which a polymer improves an asphalt's properties depends on the compatibility of the polymer and the asphalt; e.g., a polymer that does not separate in a mixture of asphalt and polymer during storage. Highly compatible or compatibilized polymers are more effective in providing property improvements. An extensive range of additives has been used for the purpose of "crosslinking" polymers and asphalts, WO 2020/176604 PCT /0S2020/019866 thereby rendering the mixture compatible. For example, sulfur is a well-known crosslinking agent. [0006] Polyphosphoric acid (PPA) (Hn+2 PnO3n+1) is a polymer of orthophosphoric acid (H3PQ4). PPA offered commercially is a mixture of orthophosphoric acid with pyrophosphoric acid, triphosphoric and higher acids. Superphosphoric acid is a similar mixture sold at 105% H3PQ4. Other grades of phosphoric acid may contain water, but are not typically used in asphalt modification. This eliminates issues of foaming and corrosion at the refinery or terminal. PPA's major applications are surfactant production, water treatment, pharmaceutical synthesis, pigment production, flame proofing, metals finishing and asphalt modification. [0007] PPA has been widely used in refineries to modify the performance properties of asphalt. Due to its strong acidity, however, the PPA would revert most H2S scavengers and allow undesirable release the hydrogen sulfide from scavenger treated asphalt. BRIEF SUMMARY [0008] The present disclosure relates generally to scavengers of sulfur-based species and methods of using the scavengers. In some embodiments, the disclosure provides a composition for reducing hydrogen sulfide emission from asphalt. The composition comprises a metal-containing compound; and a sulfidescavenging agent selected from the group consisting of hexamethylenetetramine and a 1,3,5-triazine derivative of Formula I: R1, ............... .,..R2 N N ~N) I R3 wherein each of R1, R2, and R3 is independently selected at each occurrence from hydrogen, straight or branched C1-C30 alkyl, hydroxyl substituted straight or branched C1-C30 alkyl, and straight or branched C1-C30 alkyl substituted with straight or branched C1-C30 alkoxy. [0009] The composition may further comprise asphalt. The asphalt may be polymer-treated asphalt. The asphalt may comprise PPA. WO 2020/176604 PCT /0S2020/019866 [0010] In some embodiments, the sulfide-scavenging agent comprises Formula I, and each of R1, R2, and R3 is independently selected from straight or branched CeC30 alkyl, hydroxyl substituted straight or branched Ce-C30 alkyl, and straight or branched Ce-C30 alkoxy substituted with straight or branched C1-C30 alkoxy. In certain embodiments, the sulfide-scavenging agent comprises Formula I, and each of R1, R2, and R3 is selected from C1-Ce straight or branched alkyl. In some embodiments, the sulfide-scavenging agent comprises Formula I, and each of R1, R2, and R3 is the same substituent, such as -CH2CH2OH. In certain embodiments, the sulfide-scavenging agent is hexamethylenetetramine. [0011] In some embodiments, the composition further comprises a polar solvent. The polar solvent may be selected from the group consisting of diethylene glycol, 2- butoxyethanol, propylene glycol, monoethanol amine, and any combination thereof. [0012] The composition may comprise about 1 0 weight % to about 90 weight % of the sulfide-scavenging agent, about 1 weight % to about 50 we