FR3021327A1 - Procede de reduction de friction dans le transport de l'ethanol - Google Patents
Procede de reduction de friction dans le transport de l'ethanol Download PDFInfo
- Publication number
- FR3021327A1 FR3021327A1 FR1454595A FR1454595A FR3021327A1 FR 3021327 A1 FR3021327 A1 FR 3021327A1 FR 1454595 A FR1454595 A FR 1454595A FR 1454595 A FR1454595 A FR 1454595A FR 3021327 A1 FR3021327 A1 FR 3021327A1
- Authority
- FR
- France
- Prior art keywords
- substituted
- acrylate
- polymer
- methacrylate
- ethanol
- Prior art date
- 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.)
- Granted
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 123
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000001603 reducing effect Effects 0.000 title claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 74
- 239000000178 monomer Substances 0.000 claims abstract description 40
- -1 N-substituted acrylamide Chemical class 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 15
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 11
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 11
- 229920001519 homopolymer Polymers 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims description 6
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 5
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 claims description 3
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 claims description 3
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 claims description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 2
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 2
- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims description 2
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims 2
- DWXAVNJYFLGAEF-UHFFFAOYSA-N furan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CO1 DWXAVNJYFLGAEF-UHFFFAOYSA-N 0.000 claims 2
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims 1
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims 1
- 229940119545 isobornyl methacrylate Drugs 0.000 claims 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims 1
- 239000012530 fluid Substances 0.000 description 14
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000002551 biofuel Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229920002401 polyacrylamide Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920000867 polyelectrolyte Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DOGQRRGVLIGIEG-UHFFFAOYSA-N 1-(prop-2-enoylamino)butane-2-sulfonic acid Chemical compound CCC(S(O)(=O)=O)CNC(=O)C=C DOGQRRGVLIGIEG-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- LPNSCOVIJFIXTJ-UHFFFAOYSA-N 2-methylidenebutanamide Chemical compound CCC(=C)C(N)=O LPNSCOVIJFIXTJ-UHFFFAOYSA-N 0.000 description 1
- KFNGWPXYNSJXOP-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propane-1-sulfonic acid Chemical class CC(=C)C(=O)OCCCS(O)(=O)=O KFNGWPXYNSJXOP-UHFFFAOYSA-N 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LQPLDXQVILYOOL-UHFFFAOYSA-I pentasodium;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O LQPLDXQVILYOOL-UHFFFAOYSA-I 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000000710 polymer precipitation Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ICKIMNNCJKMGAT-UHFFFAOYSA-M trimethyl(3-oxopent-4-enyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCC(=O)C=C ICKIMNNCJKMGAT-UHFFFAOYSA-M 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
- C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
-
- 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
- C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
-
- 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0461—Fractions defined by their origin
- C10L2200/0469—Renewables or materials of biological origin
-
- 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
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/14—Function and purpose of a components of a fuel or the composition as a whole for improving storage or transport of the fuel
-
- 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
- C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
- C10L2250/04—Additive or component is a polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Medicinal Preparation (AREA)
- Lubricants (AREA)
Abstract
Description
Claims (6)
- REVENDICATIONS1- Procédé pour réduire la friction de l'éthanol pendant son transport dans une canalisation consistant à mettre l'éthanol en contact avec une composition à base de polymère, caractérisé en ce que le polymère est obtenu à partir d'au moins un monomère choisi dans le groupe comprenant les acrylamide N-substitués, les méthacrylamide N-substitués, les acrylamide N,N-substitués, les méthacrylamide N,N-substitués, les acrylate substitués, et les méthacrylate substitués. Procédé selon la revendication 1, caractérisé en ce que le polymère a un poids moléculaire compris entre 0.5 et 25 millions g/mol. Procédé selon la revendication 1 ou 2, caractérisé en ce que le polymère comprend au moins 50 mol% d'au moins un monomère choisi dans le groupe comprenant les acrylamide N-substitués, les méthacrylamide N-substitués, les acrylamide N,N-substitués, les méthacrylamide N,N-substitués, les acrylate substitués, et les méthacrylate substitués. Procédé selon l'une des revendications 1 à 3, caractérisé en ce que les monomères du polymère présentent des chaînes substituées contenant moins de 30 atomes de carbone. Procédé selon l'une des revendications 1 à 4, caractérisé en ce que les monomères acrylamide N-substitués, méthacrylamide N-substitués, acrylamide N,Nsubstitués, et méthacrylamide N,N-substitués sont choisis dans le groupe comprenant le N-éthylacrylamide, N-isopropylacrylamide, N-ter-butylacrylamide, diacetoneacrylamide, N-hydroxyéthylacrylamide, N-hydroxyméthylacrylamide, N-alkyl acrylamide, N-[Tris(hydroxyméthyl)méthyl]acrylamide, N- acryloylmorpholine, N,N-diméthylacrylamide, N,N-diéthylacrylamide, et N,Ndialkylacrylamide ; alkyl désignant un groupe alkyle comprenant 3 à 22 atomes de carbone. Procédé selon les revendications 1 à 5, caractérisé en ce que les monomères acrylate substitués, méthacrylate substitués sont choisis dans le groupe comprenant l'acrylate d'alkyle, le méthacrylate d'alkyle, l'acrylate d'isobornyle, le méthacrylate d'isobornyle, l'acrylate de
- 2-éthylhexyle, le méthacrylate de 2- éthylhexyle, acrylate d'hydroxyéthyle, le méthacrylate d'hydroxyéthyle, l'acrylate d'hydroxypropyle, le méthacrylate d'hydroxypropyle, l'acrylate de 10 2-
- 3- 15
- 4- 20
- 5- 25 30
- 6- 35 - 3021327 12 57- 8- 15 9- 20 10- 25 11- 12- 30 13- 35 furfuryle, le méthacrylate de furfuryle, l'acrylate de tetrahydrofurfuryle, le méthacrylate de tetrahydrofurfuryle, l'acrylate de glyceryle, le méthacrylate de glyceryle, l'acrylate de glycidyle, le méthacrylate de glycidyle ; alkyle désignant un groupe alkyle comprenant 5 à 22 atomes de carbone. Procédé selon les revendications 1 à 6, caractérisé en ce que le polymère comprend en outre moins de 40 mol% d'au moins un monomère ionique. Procédé selon la revendication 7, caractérisé en ce que le monomère ionique est un monomère anionique choisi dans le groupe comprenant l'acide acrylique, l'acide méthacrylique, l'acide itaconique, l'acide maléique, l'acide 2-acrylamido2-méthylpropane sulfonique (ATBS), ledit monomère anionique étant sous sa forme acide, partiellement salifié ou totalement salifié. Procédé selon l'une des revendications 1 à 8, caractérisé en ce que le polymère est un polymère choisi dans le groupe comprenant l'homopolymère de N,Ndiméthylacrylamide, l'homopolymère de N,N-diéthylacrylamide, le copolymère de N,N-diméthylacrylamide et d'acide acrylique, le copolymère de N,Ndiéthylacrylamide et d'acide acrylique, le copolymère de N,N-diméthylacrylamide et d'acide 2-acrylamido-2-méthylpropane sulfonique, et le copolymère de N,Ndiéthylacrylamide et d'acide 2-acrylamido-2-méthylpropane sulfonique. Procédé selon l'une des revendications 1 à 9, caractérisé en ce que le polymère est obtenu selon un procédé de synthèse en voie gel. Procédé selon l'une des revendications 1 à 10, caractérisé en ce que la composition comprend en outre de l'eau et/ou de l'éthanol. Procédé selon la revendication 11, caractérisé en ce que la quantité de polymère mis en contact avec l'éthanol est comprise entre 5 et 5.000 ppm en poids par rapport au poids de l'éthanol. Procédé selon l'une des revendications 1 à 12, caractériSé én ce que l'éthanol est le bioéthanol.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1454595A FR3021327B1 (fr) | 2014-05-21 | 2014-05-21 | Procede de reduction de friction dans le transport de l'ethanol |
BR102015011015-4A BR102015011015B1 (pt) | 2014-05-21 | 2015-05-13 | Processo para a redução da fricção durante o transporte de etanol através de oleodutos |
US14/713,532 US9822325B2 (en) | 2014-05-21 | 2015-05-15 | Process for friction reduction during ethanol transport |
CN201510249523.4A CN105085751B (zh) | 2014-05-21 | 2015-05-15 | 乙醇运输过程中减少摩擦的方法 |
EP15168058.4A EP2947134B1 (fr) | 2014-05-21 | 2015-05-19 | Procede de reduction de friction dans le transport de l'ethanol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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FR1454595A FR3021327B1 (fr) | 2014-05-21 | 2014-05-21 | Procede de reduction de friction dans le transport de l'ethanol |
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FR3021327A1 true FR3021327A1 (fr) | 2015-11-27 |
FR3021327B1 FR3021327B1 (fr) | 2016-06-03 |
Family
ID=51383831
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FR1454595A Expired - Fee Related FR3021327B1 (fr) | 2014-05-21 | 2014-05-21 | Procede de reduction de friction dans le transport de l'ethanol |
Country Status (5)
Country | Link |
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US (1) | US9822325B2 (fr) |
EP (1) | EP2947134B1 (fr) |
CN (1) | CN105085751B (fr) |
BR (1) | BR102015011015B1 (fr) |
FR (1) | FR3021327B1 (fr) |
Families Citing this family (2)
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CN105504160A (zh) * | 2015-12-07 | 2016-04-20 | 南京工业大学 | 一种针对阳离子染料染色织物新型高分子皂洗剂的制备方法 |
CN111379971B (zh) * | 2018-12-29 | 2023-01-03 | 中润油新能源股份有限公司 | 一种降低甲醇汽油气阻性的生产装置 |
Citations (4)
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US4637418A (en) * | 1983-03-20 | 1987-01-20 | Henkel Corporation | Fluid friction reduction |
US20050049327A1 (en) * | 2003-09-02 | 2005-03-03 | Vladimir Jovancicevic | Drag reducing agents for multiphase flow |
US20100029843A1 (en) * | 2008-07-31 | 2010-02-04 | Conocophillips Company | Drag reducing copolymers for cold fluid applications |
BRPI0900355A2 (pt) * | 2009-01-21 | 2011-08-16 | Unicamp | redutores de atrito hidrodinámico para biocombustìveis |
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US4522733A (en) * | 1983-01-31 | 1985-06-11 | American Polywater Corporation | Substantially neutral aqueous lubricant |
CN100460448C (zh) * | 2007-04-09 | 2009-02-11 | 中国石油化工集团公司 | 一种多功能减阻聚合物悬浮液的制备方法 |
US7888407B2 (en) * | 2007-10-26 | 2011-02-15 | Conocophillips Company | Disperse non-polyalphaolefin drag reducing polymers |
CN101638569B (zh) * | 2008-07-31 | 2012-07-18 | 中国石油天然气股份有限公司 | 一种油酸及其酯类衍生物减阻剂及其制备方法 |
US9234631B2 (en) * | 2008-12-18 | 2016-01-12 | Lubrizol Speciality Products, Inc. | Drag reducing polymers for low molecular weight liquids applications |
US20110180759A1 (en) * | 2010-01-22 | 2011-07-28 | Midcontinental Chemical Company, Inc. | Methods and compositions for reducing stress corrosion cracking |
JP5810576B2 (ja) | 2010-04-22 | 2015-11-11 | 日油株式会社 | バイオディーゼル燃料油用流動性向上剤 |
CN102453297B (zh) * | 2010-10-28 | 2013-10-16 | 中国石油天然气股份有限公司 | 一种超分子聚合物油品减阻剂及其制备方法 |
CN102002355B (zh) * | 2010-11-01 | 2013-05-01 | 中国石油化工股份有限公司西北油田分公司工程技术研究院 | 一种压裂液降阻剂及其制备方法 |
US20130212931A1 (en) | 2012-02-16 | 2013-08-22 | Baker Hughes Incorporated | Biofuel having improved cold flow properties |
US20150059238A1 (en) | 2012-04-27 | 2015-03-05 | Evonik Oil Additives Gmbh | Use of cold flow improver compositions for fuels, blends thereof with biofuels and formulations thereof |
GB201208795D0 (en) | 2012-05-18 | 2012-07-04 | Dupont Nutrition Biosci Aps | Compound |
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CN103694984B (zh) * | 2013-12-20 | 2016-09-07 | 西南石油大学 | 一种页岩气酸化压裂减阻剂及其制备方法 |
-
2014
- 2014-05-21 FR FR1454595A patent/FR3021327B1/fr not_active Expired - Fee Related
-
2015
- 2015-05-13 BR BR102015011015-4A patent/BR102015011015B1/pt active IP Right Grant
- 2015-05-15 US US14/713,532 patent/US9822325B2/en active Active
- 2015-05-15 CN CN201510249523.4A patent/CN105085751B/zh active Active
- 2015-05-19 EP EP15168058.4A patent/EP2947134B1/fr not_active Not-in-force
Patent Citations (4)
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US4637418A (en) * | 1983-03-20 | 1987-01-20 | Henkel Corporation | Fluid friction reduction |
US20050049327A1 (en) * | 2003-09-02 | 2005-03-03 | Vladimir Jovancicevic | Drag reducing agents for multiphase flow |
US20100029843A1 (en) * | 2008-07-31 | 2010-02-04 | Conocophillips Company | Drag reducing copolymers for cold fluid applications |
BRPI0900355A2 (pt) * | 2009-01-21 | 2011-08-16 | Unicamp | redutores de atrito hidrodinámico para biocombustìveis |
Also Published As
Publication number | Publication date |
---|---|
CN105085751A (zh) | 2015-11-25 |
EP2947134A1 (fr) | 2015-11-25 |
US9822325B2 (en) | 2017-11-21 |
BR102015011015B1 (pt) | 2022-02-01 |
EP2947134B1 (fr) | 2017-10-11 |
CN105085751B (zh) | 2020-01-10 |
BR102015011015A2 (pt) | 2016-01-05 |
US20150337232A1 (en) | 2015-11-26 |
FR3021327B1 (fr) | 2016-06-03 |
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