CA1223833A - Extraction du petrole brut a l'acide adipeux recycle - Google Patents

Extraction du petrole brut a l'acide adipeux recycle

Info

Publication number: CA1223833A
Authority: CA; Canada
Prior art keywords: acid; acids; fatty acid; group; crude oil
Prior art date: 1984-10-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000466334A

Other languages

English (en)

Inventor

George L. Herter

Christian Herter

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-10-25

Filing date

1984-10-25

Publication date

1987-07-07

1984-10-25 Application filed by Individual filed Critical Individual

1984-10-25 Priority to CA000466334A priority Critical patent/CA1223833A/fr

1987-07-07 Application granted granted Critical

1987-07-07 Publication of CA1223833A publication Critical patent/CA1223833A/fr

Status Expired legal-status Critical Current

Links

235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 75
239000000194 fatty acid Substances 0.000 title claims abstract description 75
229930195729 fatty acid Natural products 0.000 title claims abstract description 75
150000004665 fatty acids Chemical class 0.000 title claims abstract description 75
238000004391 petroleum recovery Methods 0.000 title abstract description 5
239000002253 acid Substances 0.000 claims abstract description 93
238000000034 method Methods 0.000 claims abstract description 52
239000003208 petroleum Substances 0.000 claims abstract description 42
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 34
239000000344 soap Substances 0.000 claims abstract description 27
239000010779 crude oil Substances 0.000 claims abstract description 25
239000000203 mixture Substances 0.000 claims abstract description 25
229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 18
239000001569 carbon dioxide Substances 0.000 claims abstract description 16
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 12
239000008346 aqueous phase Substances 0.000 claims abstract description 11
239000005642 Oleic acid Substances 0.000 claims abstract description 10
230000000269 nucleophilic effect Effects 0.000 claims abstract description 10
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 10
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 9
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 9
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 9
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 9
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052700 potassium Inorganic materials 0.000 claims abstract description 8
239000011591 potassium Substances 0.000 claims abstract description 8
238000004064 recycling Methods 0.000 claims abstract description 8
230000002829 reductive effect Effects 0.000 claims abstract description 6
150000007513 acids Chemical class 0.000 claims description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
229910001868 water Inorganic materials 0.000 claims description 24
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
238000007127 saponification reaction Methods 0.000 claims description 21
239000000243 solution Substances 0.000 claims description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 8
239000007789 gas Substances 0.000 claims description 8
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 7
229960004232 linoleic acid Drugs 0.000 claims description 7
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 6
239000004058 oil shale Substances 0.000 claims description 6
238000007670 refining Methods 0.000 claims description 5
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
235000021353 Lignoceric acid Nutrition 0.000 claims description 4
229940098330 gamma linoleic acid Drugs 0.000 claims description 4
VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims description 4
VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 3
239000002245 particle Substances 0.000 claims description 3
150000003141 primary amines Chemical class 0.000 claims description 3
239000004576 sand Substances 0.000 claims description 3
150000003335 secondary amines Chemical class 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
ZMZINYUKVRMNTG-UHFFFAOYSA-N acetic acid;formic acid Chemical compound OC=O.CC(O)=O ZMZINYUKVRMNTG-UHFFFAOYSA-N 0.000 claims description 2
150000003868 ammonium compounds Chemical class 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
239000000292 calcium oxide Substances 0.000 claims description 2
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 claims description 2
229940005991 chloric acid Drugs 0.000 claims description 2
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 claims description 2
229940077239 chlorous acid Drugs 0.000 claims description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical class N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 6
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 6
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 4
TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 claims 3
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 3
239000005639 Lauric acid Substances 0.000 claims 3
CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 claims 3
235000021360 Myristic acid Nutrition 0.000 claims 3
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims 3
CNVZJPUDSLNTQU-UHFFFAOYSA-N Petroselaidic acid Natural products CCCCCCCCCCCC=CCCCCC(O)=O CNVZJPUDSLNTQU-UHFFFAOYSA-N 0.000 claims 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 claims 3
235000020778 linoleic acid Nutrition 0.000 claims 3
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 3
CNVZJPUDSLNTQU-OUKQBFOZSA-N petroselaidic acid Chemical compound CCCCCCCCCCC\C=C\CCCCC(O)=O CNVZJPUDSLNTQU-OUKQBFOZSA-N 0.000 claims 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 2
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 2
239000000908 ammonium hydroxide Substances 0.000 claims 2
SELIRUAKCBWGGE-UHFFFAOYSA-N hexadecanoic acid;octadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O SELIRUAKCBWGGE-UHFFFAOYSA-N 0.000 claims 2
229960002446 octanoic acid Drugs 0.000 claims 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 2
LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 claims 2
235000021314 Palmitic acid Nutrition 0.000 claims 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
150000001345 alkine derivatives Chemical group 0.000 claims 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 1
XEMZLVDIUVCKGL-UHFFFAOYSA-N hydrogen peroxide;sulfuric acid Chemical compound OO.OS(O)(=O)=O XEMZLVDIUVCKGL-UHFFFAOYSA-N 0.000 claims 1
150000002500 ions Chemical group 0.000 claims 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims 1
230000001376 precipitating effect Effects 0.000 claims 1
238000011084 recovery Methods 0.000 abstract description 19
238000006243 chemical reaction Methods 0.000 abstract description 15
125000001931 aliphatic group Chemical group 0.000 abstract description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 6
239000006227 byproduct Substances 0.000 abstract description 6
239000011734 sodium Substances 0.000 abstract description 6
229910052708 sodium Inorganic materials 0.000 abstract description 6
150000001735 carboxylic acids Chemical class 0.000 abstract description 4
238000002347 injection Methods 0.000 abstract description 3
239000007924 injection Substances 0.000 abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract description 2
238000007796 conventional method Methods 0.000 abstract 1
238000000746 purification Methods 0.000 abstract 1
239000003921 oil Substances 0.000 description 16
230000008569 process Effects 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 10
238000005755 formation reaction Methods 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
238000013019 agitation Methods 0.000 description 9
239000012071 phase Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
235000021313 oleic acid Nutrition 0.000 description 8
235000011121 sodium hydroxide Nutrition 0.000 description 7
239000000126 substance Substances 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
235000011118 potassium hydroxide Nutrition 0.000 description 6
238000000926 separation method Methods 0.000 description 6
239000011269 tar Substances 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000005086 pumping Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
-1 steam Substances 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
238000000605 extraction Methods 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
238000005065 mining Methods 0.000 description 4
239000011435 rock Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000004809 Teflon Substances 0.000 description 3
229920006362 Teflon® Polymers 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000010426 asphalt Substances 0.000 description 3
239000000356 contaminant Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000021588 free fatty acids Nutrition 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
150000002889 oleic acids Chemical class 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000002441 reversible effect Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000003158 alcohol group Chemical group 0.000 description 2
150000001299 aldehydes Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000011109 contamination Methods 0.000 description 2
238000010586 diagram Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000005553 drilling Methods 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
230000035699 permeability Effects 0.000 description 2
239000008149 soap solution Substances 0.000 description 2
241000894007 species Species 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
239000011275 tar sand Substances 0.000 description 2
WLNBMPZUVDTASE-HXIISURNSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO WLNBMPZUVDTASE-HXIISURNSA-N 0.000 description 1
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910018954 NaNH2 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000015076 Shorea robusta Nutrition 0.000 description 1
244000166071 Shorea robusta Species 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
241000009298 Trigla lyra Species 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
239000012445 acidic reagent Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001336 alkenes Chemical group 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000012658 bimolecular nucleophilic substitution Methods 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000005323 carbonate salts Chemical class 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000002036 drum drying Methods 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000004571 lime Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003027 oil sand Substances 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000002407 reforming Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
229940095696 soap product Drugs 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000007614 solvation Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000466334A 1984-10-25 1984-10-25 Extraction du petrole brut a l'acide adipeux recycle Expired CA1223833A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000466334A CA1223833A (fr)	1984-10-25	1984-10-25	Extraction du petrole brut a l'acide adipeux recycle

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000466334A CA1223833A (fr)	1984-10-25	1984-10-25	Extraction du petrole brut a l'acide adipeux recycle

Publications (1)

Publication Number	Publication Date
CA1223833A true CA1223833A (fr)	1987-07-07

Family

ID=4129006

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000466334A Expired CA1223833A (fr)	1984-10-25	1984-10-25	Extraction du petrole brut a l'acide adipeux recycle

Country Status (1)

Country	Link
CA (1)	CA1223833A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116556909A (zh) *	2023-04-19	2023-08-08	中国石油天然气股份有限公司	一种二氧化碳驱高效分离及循环回注利用装置及方法

1984
- 1984-10-25 CA CA000466334A patent/CA1223833A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116556909A (zh) *	2023-04-19	2023-08-08	中国石油天然气股份有限公司	一种二氧化碳驱高效分离及循环回注利用装置及方法
CN116556909B (zh) *	2023-04-19	2024-05-28	中国石油天然气股份有限公司	一种二氧化碳驱高效分离及循环回注利用装置及方法

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Date	Code	Title	Description
2004-10-25	MKEX	Expiry

Publication	Publication Date	Title
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