WO2012009396A2 - Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons - Google Patents
Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons Download PDFInfo
- Publication number
- WO2012009396A2 WO2012009396A2 PCT/US2011/043793 US2011043793W WO2012009396A2 WO 2012009396 A2 WO2012009396 A2 WO 2012009396A2 US 2011043793 W US2011043793 W US 2011043793W WO 2012009396 A2 WO2012009396 A2 WO 2012009396A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrogen sulfide
- scavenger
- alpha
- bis
- fluid
- Prior art date
Links
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 229910000037 hydrogen sulfide Inorganic materials 0.000 title claims abstract description 47
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 21
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 21
- 239000012530 fluid Substances 0.000 claims abstract description 26
- 239000002516 radical scavenger Substances 0.000 claims abstract description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 230000002000 scavenging effect Effects 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- IVETVJOPRZJHDA-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)methoxymethyl]butan-1-amine Chemical compound CCCCN(CCCC)COCN(CCCC)CCCC IVETVJOPRZJHDA-UHFFFAOYSA-N 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 23
- 239000003921 oil Substances 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 6
- -1 tri-substituted-hexahydro-s-triazines Chemical class 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000446 fuel Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical class C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- BVOMRRWJQOJMPA-UHFFFAOYSA-N 1,2,3-trithiane Chemical compound C1CSSSC1 BVOMRRWJQOJMPA-UHFFFAOYSA-N 0.000 description 1
- HUHGPYXAVBJSJV-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyethyl)-1,3,5-triazinan-1-yl]ethanol Chemical compound OCCN1CN(CCO)CN(CCO)C1 HUHGPYXAVBJSJV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001260 acyclic compounds Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WUMYTJKLIVKYST-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)methoxymethoxymethyl]butan-1-amine Chemical compound CCCCN(CCCC)COCOCN(CCCC)CCCC WUMYTJKLIVKYST-UHFFFAOYSA-N 0.000 description 1
- 231100001160 nonlethal Toxicity 0.000 description 1
- 239000010747 number 6 fuel oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/207—Acid gases, e.g. H2S, COS, SO2, HCN
Definitions
- This invention relates generally to the treatment of sour gas and liquid hydrocarbon to remove or reduce the levels of hydrogen sulfide therein.
- the toxicity of hydrogen sulfide in hydrocarbon fluids is well known in the industry. This has caused considerable expense and efforts to be expended annually to reduce its content to a safe level.
- a regenerative system for treating sour gas streams.
- These systems typically employ a compound used in an absorption tower to contact the produced fluids and selectively absorb the hydrogen sulfide and possibly other toxic materials such as carbon dioxide and mercaptans. The absorption compound is then regenerated and reused in the system.
- Typical hydrogen sulfide absorption materials include alkanolamines, PEG, hindered amines, and other species that can be regenerated.
- Nonregenerative scavengers for small plant hydrogen sulfide removal fall into four general categories: 1) aldehyde based, 2) metallic oxide based, 3) caustic based, and 4) other processes.
- the scavenger reacts with the hydrogen sulfide to form a nonlethal compound or a compound, which can be removed from the hydrocarbon.
- a chemical compound known as formthionals e.g., trithiane
- Prior Art aldehyde scavengers typically include low molecular weight aldehydes and ketones and adducts thereof.
- the low molecular weight aldehydes may also be combined with an alkyl or alkanolamine as disclosed in US Patent 4,748,011.
- Other aldehyde derived scavengers include the reaction product of low molecular weight alkanolamines and aldehydes as disclosed in US Patent 4,978,512.
- PCT Application WO 92/01481 discloses a method of reducing sulfides in different applications using certain tri-substituted-hexahydro-s-triazines.
- German reference DE4027300 discloses a regenerative solvent for removing 3 ⁇ 4S and mercaptans.
- US Patent 5,347,004 discloses the use of 1,3,5 alkoxyalkylene hexahydro triazines.
- PCT Application WO 91 US 5232 discloses hydroxyalkyl triazine scavengers, specifically an N,N',N"-tris(2-hydroxyethyl)hexahydro-s-triazine.
- US Patent 5,774,024 discloses the combination of an alkyl triazine scavenger and quaternary ammonium salt, where the quaternary ammonium salt enhances the effectiveness of the alkyl-triazine..
- These prior art attempts however are frequently water-based chemicals and require significant mixing to allow the scavenger to effectively contact the hydrocarbon fluid and remove the hydrogen sulfide.
- At least one embodiment of the invention is directed towards a method for removing hydrogen sulfide from a hydrocarbon fluid.
- the method comprises contacting the fluid with an effective amount of a composition comprising a hydrogen sulfide scavenger.
- the amount of hydrogen sulfide scavenger is sufficient to react with the hydrogen sulfide to reduce the amount hydrogen sulfide released into the vapor space .
- the reaction product of the hydrogen sulfide scavenger and the hydrogen sulfide remain soluble in the hydrocarbon fluid.
- the hydrogen sulfide scavenger contains at least one alpha-amino ether.
- composition may include one item selected from the list consisting of:
- the reaction product of the sulfide scavenging formulation and the hydrogen sulfide may not form a separate fluid layer.
- the method may also further comprise the step of reacting a secondary amine with a formaldehyde equivalent to form at least some of the scavenging formulation.
- the hydrocarbon fluid may be a liquid.
- Alpha-amino ether means a molecule according to the formula:
- R l9 R 2 , R 3 , R4 are carbon containing side chains containing 1 - 20 carbon atoms and includes cyclic and acyclic compounds.
- the cyclic compounds can be aromatic or non-aromatic. Examples include but are not limited to, methyl, ethyl, propyl, tert-butyl, cyclopentyl, cyclohexyl, morpholino, and phenyl, and they all can be the same group or one or more different groups.
- B is an ether group, which is either an oxygen atom or a group having an oxygen atom at both ends (such as -OCH 2 0- or-OCsUtO-).
- Formaldehyde equivalent means a composition of matter containing at least one group according to the formula: ( ⁇ 3 ⁇ 40) ⁇ in which n is an integer greater than or equal to 1, and/or a composition of matter including formaldehyde or related molecules such as
- Hydrocarbon fluid means a liquid or gas predominantly comprising organic material including but not limited to kerosene, crude oil, crude oil emulsions, oilfield condensate, petroleum residua, refined fuels, distillate fuels, fuel oil, heating oils, diesel fuel, gasoline, jet fuel, bunker fuel oils, and any combination thereof.
- Non-Regenerative Scavenger means a scavenger, which is consumed by the process of scavenging.
- Regenerative Scavenger means a scavenger, which is not consumed by the process of scavenging.
- “Scavenger” means a composition of matter, such as but not limited to alpha- amino ethers, useful in reducing the amount of or mitigating the effects of some other composition of matter, such as but not limited to hydrogen sulfide, in a fluid medium.
- the hydrogen sulfide in a hydrocarbon fluid is reduced by the introduction of an alpha-amino ether scavenger into the fluid.
- the alpha-amino ether is a portion of a scavenging formulation is used in a hydrocarbon fluid.
- the formulation comprises alpha-amino ether and can consist of a carrier liquid as well.
- the formulation can be introduced into the hydrocarbon fluid by mechanical means including but not limited to injection pumps or any mechanism disclosed in US Patents 5,744,024 and 5,840,177.
- the gas may be passed through an absorption tower containing a scavenging formulation.
- alpha-amino ether scavenger is soluble in hydrocarbon fluids, since it is not a water-based product.
- the hydrogen sulfide scavenger is produced by reacting a secondary amine with formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane.
- formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane.
- the reaction product also comprises 10-25% of the non-ether diamine (compound A).
- Compound A is an unavoidable side product of the reaction mixture.
- the reaction can be performed by mixing the reactants in solvents such as but not limited to Naphtha (Petroleum) Heavy Aromatic Solvents (such as Aromatic 150 and Solvesso by ExxonMobil) or Naphtha Light Aromatic Solvents (such as (Aromatic 100 by Americhem Sales Corporation).
- solvents such as but not limited to Naphtha (Petroleum) Heavy Aromatic Solvents (such as Aromatic 150 and Solvesso by ExxonMobil) or Naphtha Light Aromatic Solvents (such as (Aromatic 100 by Americhem Sales Corporation).
- the ratio of amine to formaldehyde in the reaction mixture is inclusively within the range of 1.5:1 to 1:1.5 and is preferably between 1.2:1 and 1:1.2.
- any of the R and R' groups correspond to any of the Ri, R 2 , R , and R4, groups described in the definition of "alpha-amino ether".
- Compound A is ⁇ , ⁇ , ⁇ ', ⁇ '-tetrabutylmethanediamine
- Compound B is N,N'-oxybis(methylene)bis(N,N-dibutylene), and
- Compound C is N 5 N'-(methylenebis(oxy)bis(methylene))bis(N,N'-dibutylamine).
- compositions comprising:
- Table 1 compares the inventive composition in naphtha at 22 degrees C
- Table 2 kerosene at 22 degrees C, and Table 3 slurry oil (such as carbon black oil, decant oil, and clarified slurry oil produced in a refinery) at 97 degrees C.
- slurry oil such as carbon black oil, decant oil, and clarified slurry oil produced in a refinery
- Tat le 2 tes 22 °C
- the amount of H 2 S present in the vapor space was determined by measuring the vapor space hydrogen sulfide levels according to ASTM D5705-03. test procedure was modified by running at temperatures other than 60°C. A one-gallon sample was divided into multiple 500 milliliter samples for testing. The treated containers were pre-dosed with Compounds A-C and then the fluid being tested was poured into the container. In each example, the dose ratio was the number used to determine the ppm treat rate for the sample. For table 1 the untreated sample resulted in a vapor space
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Gas Separation By Absorption (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020137003671A KR20130047739A (ko) | 2010-07-14 | 2011-07-13 | 탄화수소로부터 황화수소를 제거하기 위한 알파-아미노 에테르의 용도 |
| BR112013000890A BR112013000890A2 (pt) | 2010-07-14 | 2011-07-13 | método para reduzir a quantidade de sulfeto de hidrogênio em um fluido de hidrocarboneto |
| RU2013102414/04A RU2563633C2 (ru) | 2010-07-14 | 2011-07-13 | Использование простых альфа-аминоэфиров для удаления сероводорода из углеводородов |
| JP2013519783A JP5890409B2 (ja) | 2010-07-14 | 2011-07-13 | 炭化水素から硫化水素を除去するためのアルファ−アミノエーテルの使用 |
| CN201180034667.8A CN103403129B (zh) | 2010-07-14 | 2011-07-13 | α-氨基醚用于从烃中除去硫化氢的用途 |
| EP20110807425 EP2593535A4 (en) | 2010-07-14 | 2011-07-13 | USE OF ALPHA AMINO ETHERS FOR THE REMOVAL OF HYDROGEN SULPHIDE FROM HYDROCARBONS |
| CA2805404A CA2805404C (en) | 2010-07-14 | 2011-07-13 | Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons |
| MX2013000507A MX2013000507A (es) | 2010-07-14 | 2011-07-13 | Uso de alfa-amino eteres para eliminacion de sulfuro de hidrogeno a partir de hidrocarburos. |
| SG2013002993A SG187078A1 (en) | 2010-07-14 | 2011-07-13 | Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/836,037 US20120012507A1 (en) | 2010-07-14 | 2010-07-14 | Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons |
| US12/836,037 | 2010-07-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2012009396A2 true WO2012009396A2 (en) | 2012-01-19 |
| WO2012009396A3 WO2012009396A3 (en) | 2012-05-18 |
Family
ID=45466088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2011/043793 WO2012009396A2 (en) | 2010-07-14 | 2011-07-13 | Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons |
Country Status (12)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013077965A1 (en) * | 2011-11-23 | 2013-05-30 | General Electric Company | Methods and compounds for improving sulfide scavenging activity |
| WO2018207657A1 (ja) | 2017-05-12 | 2018-11-15 | 株式会社クラレ | 含硫黄化合物除去装置および含硫黄化合物除去方法 |
| WO2018218641A1 (en) * | 2017-06-02 | 2018-12-06 | General Electric Company | Method of mitigation of tramp amines in application of h2s scavengers |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9108899B2 (en) | 2011-12-30 | 2015-08-18 | General Electric Company | Sulfide scavengers, methods for making and methods for using |
| US9278307B2 (en) | 2012-05-29 | 2016-03-08 | Baker Hughes Incorporated | Synergistic H2 S scavengers |
| US9638018B2 (en) * | 2012-12-19 | 2017-05-02 | Ecolab Usa Inc. | Scavenging hydrogen sulfide |
| AU2013361683B2 (en) * | 2012-12-19 | 2018-06-14 | Nalco Company | Functionalized hydrogen sulfide scavengers |
| BR112015011232B1 (pt) | 2012-12-19 | 2021-07-06 | Ecolab Usa Inc | método de tratamento por compressão para eliminação de sulfeto de hidrogênio em um fluido de produção |
| EP3470390B1 (en) | 2013-01-30 | 2023-06-07 | Ecolab USA Inc. | Hydrogen sulfide scavengers |
| US9663390B2 (en) | 2013-05-10 | 2017-05-30 | Ecolab Usa Inc. | Reduction of hydrogen sulfide and/or malodor gassing from water via the addition of peroxyacetic acid/hydrogen peroxide product |
| US9719030B2 (en) | 2013-06-27 | 2017-08-01 | Ecolab Usa Inc. | Epoxide-based hydrogen sulfide scavengers |
| US9273254B2 (en) | 2013-12-20 | 2016-03-01 | Ecolab Usa Inc. | Amino acetals and ketals as hydrogen sulfide and mercaptan scavengers |
| US9458393B2 (en) | 2014-04-15 | 2016-10-04 | Ecolab Usa Inc. | Hydantoins as hydrogen sulfide and mercaptan scavengers |
| CN107438601B (zh) | 2015-04-22 | 2020-11-13 | 艺康美国股份有限公司 | 开发用于去除硫化氢的高温稳定清除剂 |
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- 2011-07-13 CN CN201180034667.8A patent/CN103403129B/zh active Active
- 2011-07-13 RU RU2013102414/04A patent/RU2563633C2/ru active
- 2011-07-13 BR BR112013000890A patent/BR112013000890A2/pt not_active Application Discontinuation
- 2011-07-13 SG SG2013002993A patent/SG187078A1/en unknown
- 2011-07-13 MX MX2013000507A patent/MX2013000507A/es active IP Right Grant
- 2011-07-13 KR KR1020137003671A patent/KR20130047739A/ko not_active Ceased
- 2011-07-13 JP JP2013519783A patent/JP5890409B2/ja active Active
- 2011-07-13 CA CA2805404A patent/CA2805404C/en active Active
- 2011-07-13 EP EP20110807425 patent/EP2593535A4/en not_active Ceased
- 2011-07-13 WO PCT/US2011/043793 patent/WO2012009396A2/en active Application Filing
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013077965A1 (en) * | 2011-11-23 | 2013-05-30 | General Electric Company | Methods and compounds for improving sulfide scavenging activity |
| US8663457B2 (en) | 2011-11-23 | 2014-03-04 | General Electric Company | Methods and compounds for improving sulfide scavenging activity |
| WO2018207657A1 (ja) | 2017-05-12 | 2018-11-15 | 株式会社クラレ | 含硫黄化合物除去装置および含硫黄化合物除去方法 |
| WO2018218641A1 (en) * | 2017-06-02 | 2018-12-06 | General Electric Company | Method of mitigation of tramp amines in application of h2s scavengers |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20130047739A (ko) | 2013-05-08 |
| WO2012009396A3 (en) | 2012-05-18 |
| JP5890409B2 (ja) | 2016-03-22 |
| AR082165A1 (es) | 2012-11-14 |
| EP2593535A4 (en) | 2014-04-23 |
| BR112013000890A2 (pt) | 2016-05-17 |
| JP2013531728A (ja) | 2013-08-08 |
| RU2013102414A (ru) | 2014-08-20 |
| RU2563633C2 (ru) | 2015-09-20 |
| US20120012507A1 (en) | 2012-01-19 |
| CN103403129B (zh) | 2015-05-20 |
| EP2593535A2 (en) | 2013-05-22 |
| CN103403129A (zh) | 2013-11-20 |
| SG187078A1 (en) | 2013-02-28 |
| CA2805404A1 (en) | 2012-01-19 |
| CA2805404C (en) | 2018-11-27 |
| MX2013000507A (es) | 2013-02-27 |
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