NO312439B1 - Redusering av hydrogensulfid med en aldehyd-ammoniakk-trimer - Google Patents
Redusering av hydrogensulfid med en aldehyd-ammoniakk-trimer Download PDFInfo
- Publication number
- NO312439B1 NO312439B1 NO19962323A NO962323A NO312439B1 NO 312439 B1 NO312439 B1 NO 312439B1 NO 19962323 A NO19962323 A NO 19962323A NO 962323 A NO962323 A NO 962323A NO 312439 B1 NO312439 B1 NO 312439B1
- Authority
- NO
- Norway
- Prior art keywords
- substrate
- aldehyde
- hydrocarbon
- groups
- trimer
- Prior art date
Links
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims description 47
- MZSSRMMSFLVKPK-UHFFFAOYSA-N acetaldehyde ammonia trimer Chemical compound CC1NC(C)NC(C)N1 MZSSRMMSFLVKPK-UHFFFAOYSA-N 0.000 title claims description 14
- 229910000037 hydrogen sulfide Inorganic materials 0.000 title description 40
- 239000000758 substrate Substances 0.000 claims description 35
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 34
- 150000002430 hydrocarbons Chemical class 0.000 claims description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims description 23
- 229930195733 hydrocarbon Natural products 0.000 claims description 23
- 239000003345 natural gas Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 239000012459 cleaning agent Substances 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000012629 purifying agent Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000013638 trimer Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- -1 sulfhydryl compounds Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002802 bituminous coal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003034 coal gas Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000010763 heavy fuel oil Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000010841 municipal wastewater Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
- C10L3/10—Working-up natural gas or synthetic natural gas
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
- C10G21/20—Nitrogen-containing compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treating Waste Gases (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47125895A | 1995-06-06 | 1995-06-06 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO962323D0 NO962323D0 (no) | 1996-06-05 |
| NO962323L NO962323L (no) | 1996-12-09 |
| NO312439B1 true NO312439B1 (no) | 2002-05-13 |
Family
ID=23870898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19962323A NO312439B1 (no) | 1995-06-06 | 1996-06-05 | Redusering av hydrogensulfid med en aldehyd-ammoniakk-trimer |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5958352A (fr) |
| EP (1) | EP0748861B1 (fr) |
| CA (1) | CA2177408C (fr) |
| DK (1) | DK0748861T3 (fr) |
| NO (1) | NO312439B1 (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6367406B1 (en) * | 1999-09-24 | 2002-04-09 | Larson/Glastron Boats, Inc. | Boat and method for manufacturing using resin transfer molding |
| WO2002086021A1 (fr) * | 2001-04-25 | 2002-10-31 | Clearwater International, LLC. | Traitement d'hydrocarbures a base de sulfures |
| US7211665B2 (en) | 2001-11-09 | 2007-05-01 | Clearwater International, L.L.C. | Sulfide scavenger |
| US8562820B2 (en) * | 2001-11-09 | 2013-10-22 | Clearwater International, L.L.C. | Sulfide scavenger |
| US7438877B2 (en) * | 2006-09-01 | 2008-10-21 | Baker Hughes Incorporated | Fast, high capacity hydrogen sulfide scavengers |
| US7985881B2 (en) * | 2007-09-12 | 2011-07-26 | Guard Products Llc | Aromatic imine compounds for use as sulfide scavengers |
| MX2011002377A (es) * | 2008-09-02 | 2011-09-21 | Gen Electric | Procedimiento para remover sulfuro de hidrogeno en petroleo crudo. |
| US8357306B2 (en) | 2010-12-20 | 2013-01-22 | Baker Hughes Incorporated | Non-nitrogen sulfide sweeteners |
| US9463989B2 (en) | 2011-06-29 | 2016-10-11 | Baker Hughes Incorporated | Synergistic method for enhanced H2S/mercaptan scavenging |
| US9278307B2 (en) | 2012-05-29 | 2016-03-08 | Baker Hughes Incorporated | Synergistic H2 S scavengers |
| US10080806B2 (en) | 2015-08-19 | 2018-09-25 | International Business Machines Corporation | Sulfur-containing polymers from hexahydrotriazine and dithiol precursors as a carrier for active agents |
| US9550863B1 (en) | 2015-10-05 | 2017-01-24 | International Business Machines Corporation | Polymers from stabilized imines |
| US9534084B1 (en) | 2015-11-02 | 2017-01-03 | International Business Machines Corporation | High molecular weight polythioaminals from a single monomer |
| US9862802B2 (en) | 2015-11-30 | 2018-01-09 | International Business Machines Corporation | Poly(thioaminal) probe based lithography |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1951992A (en) * | 1931-07-15 | 1934-03-20 | Carbide & Carbon Chem Corp | Separation of acid gases |
| US2596273A (en) * | 1947-09-11 | 1952-05-13 | Cities Service Oil Co | Method of inhibiting hydrogen sulfide corrosion of metals |
| US2596425A (en) * | 1947-09-11 | 1952-05-13 | Cities Service Oil Co | Method of inhibiting hydrogen sulfide corrosion of metals |
| US2496354A (en) * | 1947-09-11 | 1950-02-07 | Cities Service Oil Co | Method of inhibiting hydrogen sulfide corrosion of metals |
| US2783205A (en) * | 1950-05-12 | 1957-02-26 | Socony Mobil Oil Co Inc | Suppression of acidic gas evolution |
| US2729679A (en) * | 1951-11-19 | 1956-01-03 | Du Pont | Preparation of methylenimines |
| US3770377A (en) * | 1971-03-08 | 1973-11-06 | Celanese Corp | Process for inhibiting corrosion |
| US4022785A (en) * | 1976-01-08 | 1977-05-10 | Petrolite Corporation | Substituted pyridines and dihydropyridines |
| US4112049A (en) * | 1977-03-18 | 1978-09-05 | The Dow Chemical Company | Absorption of sulfur compounds from gas streams |
| US4266054A (en) * | 1979-04-23 | 1981-05-05 | The Dow Chemical Company | N-Substituted perhydro-s-triazines |
| US4523947A (en) * | 1983-06-06 | 1985-06-18 | Ciba-Geigy Corporation | Use of triazine derivatives for protecting maize and sorghum plants |
| US4748011A (en) * | 1983-07-13 | 1988-05-31 | Baize Thomas H | Method and apparatus for sweetening natural gas |
| US4877578A (en) * | 1985-03-29 | 1989-10-31 | Petrolite Corporation | Corrosion inhibitors |
| US4680127A (en) * | 1985-12-13 | 1987-07-14 | Betz Laboratories, Inc. | Method of scavenging hydrogen sulfide |
| US4894178A (en) * | 1987-10-13 | 1990-01-16 | Exxon Research And Engineering Company | Absorbent composition containing severely-hindered amine mixture for the absorption of H2 S |
| US4978512B1 (en) * | 1988-12-23 | 1993-06-15 | Composition and method for sweetening hydrocarbons | |
| CA2017047C (fr) * | 1989-08-01 | 1999-08-17 | Jerry J. Weers | Methode d'elimination du sulfure d'hydrogene des hydrocarbures |
| DE4002132A1 (de) * | 1990-01-25 | 1991-08-01 | Hoechst Ag | Verfahren zum abfangen von schwefelwasserstoff mit glyoxal |
| MX9100361A (es) * | 1990-07-24 | 1992-02-28 | Quaker Chem Corp | Metodos para reducir sulfuros en gas de aguas negras |
| US5128049A (en) * | 1991-01-22 | 1992-07-07 | Gatlin Larry W | Hydrogen sulfide removal process |
| US5488103A (en) * | 1991-07-11 | 1996-01-30 | Gatlin; Larry W. | Hydrogen sulfide converter |
| US5213680A (en) * | 1991-12-20 | 1993-05-25 | Baker Hughes Incorporated | Sweetening of oils using hexamethylenetetramine |
| US5347004A (en) * | 1992-10-09 | 1994-09-13 | Baker Hughes, Inc. | Mixtures of hexahydrotriazines useful as H2 S scavengers |
| US5387393A (en) * | 1992-12-11 | 1995-02-07 | Nalco Chemical Company | Prevention of cracking and blistering of refinery steels by cyanide scavenging in petroleum refining processes |
| US5347003A (en) * | 1993-03-05 | 1994-09-13 | Quaker Chemical Corporation | Methods for regenerating a sulfur scavenging compound from a product of a sulfur scavenging reaction |
| US5498707A (en) * | 1993-04-22 | 1996-03-12 | Gatlin; Larry W. | Hydrogen sulfide converter |
| CA2125513A1 (fr) * | 1993-07-30 | 1995-01-31 | Kishan Bhatia | Methode pour traiter des circuits de gaz acides et d'hydrocarbures liquides |
| CA2148849A1 (fr) * | 1994-06-23 | 1995-12-24 | Kishan Bhatia | Methode pour traiter des hydrocarbures gazeux et liquides acides |
-
1996
- 1996-05-27 CA CA002177408A patent/CA2177408C/fr not_active Expired - Fee Related
- 1996-05-30 EP EP96108645A patent/EP0748861B1/fr not_active Expired - Lifetime
- 1996-05-30 DK DK96108645T patent/DK0748861T3/da active
- 1996-06-05 NO NO19962323A patent/NO312439B1/no not_active IP Right Cessation
-
1997
- 1997-01-24 US US08/792,961 patent/US5958352A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO962323D0 (no) | 1996-06-05 |
| DK0748861T3 (da) | 2000-08-21 |
| US5958352A (en) | 1999-09-28 |
| CA2177408C (fr) | 2001-12-11 |
| CA2177408A1 (fr) | 1996-12-07 |
| NO962323L (no) | 1996-12-09 |
| EP0748861B1 (fr) | 2000-04-05 |
| EP0748861A1 (fr) | 1996-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |