JP2013516507A - ナフテン酸カルシウムを含む原油中の硫黄化合物により形成される不純物を除去するための添加剤及び方法 - Google Patents
ナフテン酸カルシウムを含む原油中の硫黄化合物により形成される不純物を除去するための添加剤及び方法 Download PDFInfo
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- NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 title claims abstract description 121
- 239000012535 impurity Substances 0.000 title claims abstract description 120
- 150000003464 sulfur compounds Chemical class 0.000 title claims abstract description 104
- 239000000654 additive Substances 0.000 title claims abstract description 96
- 239000010779 crude oil Substances 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 55
- 239000010410 layer Substances 0.000 claims abstract description 92
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical group OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims abstract description 82
- 230000000996 additive effect Effects 0.000 claims abstract description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 74
- 239000011575 calcium Substances 0.000 claims abstract description 65
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 64
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 63
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 52
- 239000012044 organic layer Substances 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000005609 naphthenate group Chemical group 0.000 claims abstract description 4
- 239000012071 phase Substances 0.000 claims description 61
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- 150000002739 metals Chemical class 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 238000002474 experimental method Methods 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 30
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
- 238000009825 accumulation Methods 0.000 description 28
- 239000002253 acid Substances 0.000 description 20
- 238000002329 infrared spectrum Methods 0.000 description 17
- 239000011368 organic material Substances 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 238000009616 inductively coupled plasma Methods 0.000 description 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 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
- C10G17/00—Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge
- C10G17/02—Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge with acids or acid-containing liquids, e.g. acid sludge
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D43/00—Separating particles from liquids, or liquids from solids, otherwise than by sedimentation or filtration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/147—Saturated compounds having only one carboxyl group and containing —CHO groups
- C07C59/153—Glyoxylic acid
-
- 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
- C10G17/00—Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge
- C10G17/02—Refining of hydrocarbon oils in the absence of hydrogen, with acids, acid-forming compounds or acid-containing liquids, e.g. acid sludge with acids or acid-containing liquids, e.g. acid sludge
- C10G17/04—Liquid-liquid treatment forming two immiscible phases
- C10G17/06—Liquid-liquid treatment forming two immiscible phases using acids derived from sulfur or acid sludge thereof
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B37/00—Methods or apparatus for cleaning boreholes or wells
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B43/00—Methods or apparatus for obtaining oil, gas, water, soluble or meltable materials or a slurry of minerals from wells
-
- 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
- C10G2300/205—Metal content
-
- 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
-
- 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
- C10G2300/80—Additives
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- 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
- C10G2300/80—Additives
- C10G2300/805—Water
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- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
表−I
表−II
表−III
表−IV
表−V
表−VI
表−VII
前記実験2で調製したようにH2Sでパージされたトルエン中のナフテン酸カルシウム溶液が、実験2と同様の方法で処理された。ただしカルシウム濃度に化学量論当量で本発明の添加剤グリオキシル酸の添加を含む同量の水と共に用いた。その結果驚くべきことに予想に反して、不純物は形成されず、従って有機層と水層の境界相に黒色層も蓄積されず、このことはH2S(又は硫黄化合物)と水の存在下でナフテン酸カルシウムが加水分解されるが、しかしグリオキシル酸は不純物形成を防止するため、それにより前記境界相で黒色層の蓄積の防止するために効果的であった、ということを意味する。分離され乾燥された有機層の酸価は約230.01(mgKOH/gm)であり、そのIRスペクトルでは図8に示されるように1538cm−1と1680.7cm−1のピークはなく、1698.6cm−1の強いピークが存在し、このことはまた、ナフテン酸カルシウムの加水分解を示すものであった。以下この実験は実験9と参照される。この実験は、本発明の添加剤グリオキシル酸は、この添加がなければ境界相で黒色層として蓄積され、H2Sを含む硫黄化合物を含む原油のプロセスを妨害する不純物の形成を防止することに効果的である、ことを確認するものである。
表−VIII
Claims (18)
- ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油の混合物中で水の存在下で、ナフテン酸カルシウムとH2Sを含む硫黄化合物との反応による不純物の形成を防止し、前記不純物が、有機層と水層との境界相ですでに形成されて蓄積されている場合、前記不純物を除去する添加剤であり、前記添加剤がグリオキシル酸である、添加剤。
- ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物中で水の存在下で、ナフテン酸カルシウムとH2Sを含む硫黄化合物との反応で不純物の形成を防止する添加剤であり、前記添加剤がグリオキシル酸である、添加剤。
- ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物中で水の存在下で、ナフテン酸カルシウムとH2Sを含む硫黄化合物との反応で形成され、かつ有機層と水層の境界相で蓄積される不純物を除去する添加剤であり、前記添加剤がグリオキシル酸である、添加剤。
- ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油又は原油混合物からカルシウムを含む金属を除去し、かつ同時に、ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物中で水の存在下ナフテン酸カルシウムとH2Sを含む硫黄化合物との間の反応による不純物の形成を防止し、かつすでに形成されて有機層と水層との境界相で蓄積された不純物を除去する添加剤であり、前記添加剤がグリオキシル酸である、添加剤。
- ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物中で水の存在下でナフテン酸カルシウムとH2Sで含む硫黄化合物との反応で不純物の形成を防止し、かつすでに形成され有機層と水層との間の境界相で蓄積された不純物を除去する方法であり、ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む前記混合物をグリオキシル酸で処理することを含む、方法。
- ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物中で水存在下でナフテン酸カルシウムとH2Sを含む硫黄化合物との反応で不純物の形成を防止する方法であり、ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物を、グリオキシル酸で処理するステップを含む、方法。
- ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物中で水存在下でナフテン酸カルシウムとH2Sを含む硫黄化合物との反応ですでに形成されかつ有機層と水層の間の境界相で蓄積された不純物を除去する方法であり、ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む前記原油混合物をグリオキシル酸で処理するステップを含む、方法。
- ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油又は原油混合物からカルシウムを含む金属を除去し、かつ同時に、ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物中で水の存在下ナフテン酸カルシウムとH2Sを含む硫黄化合物との間の反応による不純物の形成を防止し、かつすでに形成されて有機層と水層との境界相で蓄積された不純物を除去する方法であり、ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油混合物をグリオキシル酸で処理することを含む、方法。
- 請求項5、6又は8のいずれか1項に記載の方法であり、不純物の形成を防止するために、前記添加剤が有機層と水層の分離の前に添加される。
- 請求項5、7および8のいずれか1項に記載の方法であり、すでに形成された不純物を除去するために、前記不純物が形成された後に添加剤グリオキシル酸の添加を含む、方法。
- 請求項5、7、8及び10のいずれか1項に記載の方法であり、水層のpHが7以上である、方法。
- 請求項11に記載の方法であり、水層のpHが7から9で変動する、方法。
- 請求項5乃至12のいずれか1項に記載の方法であり、前記添加剤が、水と一緒に添加されるか又は水に溶解させた後添加される、方法。
- 請求項5乃至13のいずれか1項に記載の方法であり、前記添加剤が、カルシウム濃度の化学量論当量で又は2倍当量で添加される、方法。
- 請求項5乃至13のいずれか1項に記載の方法であり、前記添加剤が、カルシウムの化学量論当量で又は小過剰当量で添加される、方法。
- 実質的に前記実施例と添付図面で示される、不純物形成の防止及び除去する添加剤。
- 実質的に前記実施例と添付図面で示される、不純物形成の防止及び除去する方法。
- 実質的に前記実施例と添付図面で示される、ナフテン酸カルシウムとH2Sを含む硫黄化合物を含む原油又は原油混合物からカルシウムを含む金属を除去する方法。
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PCT/IN2010/000858 WO2011080759A1 (en) | 2009-12-31 | 2010-12-28 | Additive and method for removal of impurities formed due to sulfur compounds in crude oils containing calcium naphthenate |
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PE20130057A1 (es) | 2009-12-31 | 2013-02-04 | Dorf Ketal Chemicals India Private Ltd | Aditivo y metodo para la eliminacion de impurezas formadas debido a compuestos de azufre en petroleos crudos que contienen naftenato de calcio |
WO2013049027A1 (en) * | 2011-09-27 | 2013-04-04 | General Electric Company | Hydrogen sulfide scavenger compositions, methods for making and processes for removing hydrogen sulfide from liquid hydrocarbon media |
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AU2010337845B2 (en) | 2015-01-15 |
AU2010337845A1 (en) | 2012-08-09 |
US20120285865A1 (en) | 2012-11-15 |
CL2012001751A1 (es) | 2012-11-30 |
CN102753658A (zh) | 2012-10-24 |
SG181995A1 (en) | 2012-08-30 |
CA2786077C (en) | 2014-09-30 |
BR112012016218A2 (pt) | 2019-11-12 |
CN102753658B (zh) | 2015-05-20 |
CO6541644A2 (es) | 2012-10-16 |
WO2011080759A1 (en) | 2011-07-07 |
KR20120112642A (ko) | 2012-10-11 |
US8679324B2 (en) | 2014-03-25 |
ZA201205704B (en) | 2015-01-28 |
MX2012007716A (es) | 2012-12-05 |
CA2786077A1 (en) | 2011-07-07 |
MY156528A (en) | 2016-02-26 |
EP2519608A1 (en) | 2012-11-07 |
PE20130057A1 (es) | 2013-02-04 |
KR101555479B1 (ko) | 2015-09-24 |
JP5716041B2 (ja) | 2015-05-13 |
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