EP2947134A1 - Method for reducing friction in the transport of ethanol - Google Patents
Method for reducing friction in the transport of ethanol Download PDFInfo
- Publication number
- EP2947134A1 EP2947134A1 EP15168058.4A EP15168058A EP2947134A1 EP 2947134 A1 EP2947134 A1 EP 2947134A1 EP 15168058 A EP15168058 A EP 15168058A EP 2947134 A1 EP2947134 A1 EP 2947134A1
- Authority
- EP
- European Patent Office
- 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 121
- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000001603 reducing effect Effects 0.000 title claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 76
- 239000000178 monomer Substances 0.000 claims abstract description 41
- -1 N-substituted methacrylamide Chemical class 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 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 25
- 230000008569 process Effects 0.000 claims description 24
- 229920001577 copolymer Polymers 0.000 claims description 16
- 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 10
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- 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 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 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-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-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
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 2
- 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 1
- 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
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 claims 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-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
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-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
- BRXCDHOLJPJLLT-UHFFFAOYSA-N butane-2-sulfonic acid Chemical compound CCC(C)S(O)(=O)=O BRXCDHOLJPJLLT-UHFFFAOYSA-N 0.000 claims 1
- FCSHDIVRCWTZOX-DVTGEIKXSA-N clobetasol Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O FCSHDIVRCWTZOX-DVTGEIKXSA-N 0.000 claims 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- 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 1
- 230000032258 transport Effects 0.000 description 29
- 239000012530 fluid Substances 0.000 description 14
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 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
- 238000011156 evaluation Methods 0.000 description 4
- 239000002551 biofuel Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000011161 development Methods 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
- 238000003786 synthesis reaction Methods 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
- 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
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 230000006872 improvement Effects 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
- 238000012544 monitoring process 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
- 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
- VHJXEURRAPYRDU-UHFFFAOYSA-N trimethyl(3-oxopent-4-enyl)azanium Chemical compound C[N+](C)(C)CCC(=O)C=C VHJXEURRAPYRDU-UHFFFAOYSA-N 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
Definitions
- the present invention relates to the field of ethanol transport.
- the invention relates to the use of a specific polymer as a friction reducer for the transport of ethanol.
- water-soluble polymers of high molecular weight can act as friction reducers of aqueous solutions.
- the stretching of the polymeric chains in solution makes it possible to delay the turbulent regime established during the transport of the fluid at high speed. The consequence is a reduction in the energy required to transport the aqueous solution.
- the state of the art relating to biofuels concerns the development of specific polymers for biodiesels (mixtures of fatty acid esters) making it possible to reduce their viscosity, especially at low temperature, to improve their transport by pipeline.
- biodiesels mixtures of fatty acid esters
- the polymers described are mainly hydrophobic polymers belonging to the categories of polyalkyl (meth) acrylates, polyalkyl (meth) acrylamide, polyesters, and polyolefins.
- bioethanol does not have a problem of viscosity to be transported but it is subject to friction.
- the polymers conventionally used to reduce friction during the transport of aqueous solutions can not be used for lack of solubility in bioethanol.
- the document BR PI0 900 355 mentions that polymers of the polyethylene glycol (PEG) type are effective in reducing friction during the transport of bioethanol.
- a polymer will be all the more effective in reducing friction phenomena as its molecular weight is important.
- PEGs are not known to have very large molecular masses because of their synthetic processes.
- the polymers with the largest masses are the polyacrylamide derivatives but the existing products are not soluble in ethanol. Indeed, ethanol is commonly used as a counter-solvent for precipitating polyacrylamides.
- the problem to be solved by the invention is therefore to develop a polymer to reduce friction and thus improve the transport of ethanol.
- the subject of the present invention is a process for reducing the friction of ethanol during its transportation in a pipe consisting in putting the ethanol in contact with a polymer-based composition, characterized in that the polymer is obtained at from at least one monomer selected from the group consisting of N-substituted acrylamide, N-substituted methacrylamide, N, N-substituted acrylamide, N, N-substituted methacrylamide, substituted acrylate, and substituted methacrylate.
- the polymer is contacted with ethanol during transport.
- it is advantageously introduced into the pipe which transports the ethanol.
- the contacting of the ethanol with the polymer or a polymer-based composition may in particular be carried out by introducing or injecting the polymer or a composition based on said polymer into a pipe allowing the transport of a fluid (ethanol). .
- the contacting between the polymer and the ethanol can be carried out before the introduction of ethanol into the transport pipe. It can be carried out in a storage tank for example.
- ethanol and fluids whose transport is improved designate ethanol, especially bioethanol, and also fluids composed essentially of ethanol, said fluids containing at least 50%, preferably at least 80% by weight ethanol.
- Ethanol is advantageously bioethanol. It is preferably derived from biomass.
- the polymer used in the transport of ethanol is obtained from at least 50 mol% of at least one monomer chosen from the group comprising the (meth) acrylamide N monomers. -substituted or N, N-substituted, and substituted (meth) acrylate monomers.
- N-substituted or N, N-substituted (meth) acrylamide monomers and / or substituted (meth) acrylate monomers makes it possible to obtain not only soluble polymers in high concentration both in and in ethanol, but also made it possible to obtain polymers with friction reducing performance in the transport of ethanol-based fluids.
- These monomers are advantageously nonionic.
- the polymer used to reduce friction in the process which is the subject of the invention has a molecular weight preferably of between 0.5 and 25 million g / mol, more preferably greater than 2 million g / mol, and even more preferentially greater than 5 million g / mol.
- the polymer used to reduce friction in the process which is the subject of the invention comprises at least 80 mol% of monomers N-substituted or N, N-substituted (meth) acrylamide and / or substituted (meth) acrylate monomers, preferably at least 90 mol%.
- the polymer may especially be a homopolymer of N-substituted or N, N-substituted (meth) acrylamide monomers or substituted (meth) acrylate monomers.
- the N-substituted or N, N-substituted (meth) acrylamide monomers are preferably chosen from N-ethylacrylamide, N-isopropylacrylamide, N-tert-butylacrylamide, diacetoneacrylamide, N-hydroxyethylacrylamide, N- hydroxymethylacrylamide, N-alkyl acrylamide (C 3 -C 22 alkyl), N- [tris (hydroxymethyl) methyl] acrylamide, N-acryloylmorpholine, N, N-dimethylacrylamide, N, N-diethylacrylamide, N, N-dialkylacrylamide (alkyl: C3 to C22).
- the substituted (meth) acrylate monomers are preferably chosen from methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, (meth) acrylate and the like.
- the carbon chain of the substituted part of the monomers mentioned above allows good solubility of the polymer in water and in alcohol.
- the substituted chains of the N-substituted or N, N-substituted (meth) acrylamide monomers and / or substituted (meth) acrylate monomers preferably contain less than 30 carbon atoms, more preferably less than 10 carbon atoms, and still more preferably less than 5 carbon atoms.
- the friction reducing polymer according to the invention may further comprise at least one ionic monomer in an amount of less than 40 mol%, preferably less than 20 mol%, very preferably less than 10 mol%.
- the ionic monomer is preferably an anionic monomer.
- This anionic monomer is preferably chosen from acrylic acid, methacrylic acid, itaconic acid, maleic acid, 2-acrylamido-2-methylpropanesulphonic acid (ATBS), vinylsulphonic acid, and acid. vinylphosphonic, said anionic monomer being uns-salified, partially or totally salified, and salts of 3-sulfopropyl methacrylate.
- the ionic monomer may be a cationic monomer.
- This cationic monomer is preferably chosen from diallyl dimethyl ammonium chloride (DADMAC) dialkylaminoethyl acrylate (ADAME) and dialkylaminoethyl methacrylate (MADAME), acrylamido dialkylamino propyl, meth acrylamido dialkylamino propyl, and their acidified or quaternized salts.
- DADMAC diallyl dimethyl ammonium chloride
- ADAME dialkylaminoethyl acrylate
- MADAME dialkylaminoethyl methacrylate
- the polymer used in the process which is the subject of the invention is a homopolymer of N-substituted or N-substituted (meth) acrylamide, a substituted (meth) acrylate homopolymer, a copolymer of (meth) acrylate and acrylic acid, or a copolymer of N, N-di (m) ethylacrylamide and 2-acrylamido-2-methylpropanesulphonic acid (ATBS).
- the polymer is a polymer chosen from the group comprising the homopolymer of N, N-dimethylacrylamide, the homopolymer of N, N-diethylacrylamide, the copolymer of N, N-dimethylacrylamide and acrylic acid. , the copolymer of N, N-diethylacrylamide and of acrylic acid, the copolymer of N, N-dimethylacrylamide and of 2-acrylamido-2-methylpropanesulphonic acid, and the copolymer of N, N-diethylacrylamide and of acid 2 -acrylamido-2-methylpropanesulphonic acid.
- the polymer used in the friction reduction method according to the invention may further comprise at least one nonionic monomer such as acrylamide.
- the polymer used does not require development of a particular polymerization process. Indeed, it can be obtained by any of the polymerization techniques well known to those skilled in the art, that is to say by solution polymerization, suspension polymerization, gel or bulk polymerization, precipitation polymerization, emulsion polymerization. (Aqueous or inverse) followed or not by a step of spray drying, micellar polymerization followed or not by a precipitation step, post-hydrolysis polymerization or co-hydrolysis, polymerization called "template", radical, or radical controlled.
- the polymer may be in liquid or solid form when its preparation includes a drying step such as spray drying, drum drying or microwave drying.
- the polymer is preferably obtained according to a method of synthesis in the gel route which makes it possible to obtain polymers of very high molecular weight in an economical and ecological manner (because without solvent).
- the method of synthesis in the gel process consists in polymerizing monomers in aqueous solution in order to obtain a gel which is then ground and dried to obtain a powder.
- the method which is the subject of the present invention comprises a step of contacting the ethanol to be transported with at least one friction-reducing polymer obtained from N-substituted or N, N-substituted (meth) acrylamide monomers. and / or substituted (meth) acrylate monomers.
- the process according to the invention is particularly advantageous when large volumes of ethanol are transported over long distances. More particularly, the process according to the invention relates to the transport of ethanol over a distance greater than 1 km, preferably greater than 5 km, and possibly exceeding 20 to 50 km.
- the flow rate is generally high and greater than 10 liters per second, preferably greater than 100 liters per second.
- the polymer is used in a composition comprising water or ethanol or a mixture of both.
- the polymer for reducing friction during the transport of ethanol in a pipe can be implemented in a solution or a concentrated dispersion (of the order of 1,000 to 20,000 ppm). This solution may be diluted beforehand or not before it comes into contact with ethanol. This dilution is advantageously carried out in ethanol, or in an ethanol-based fluid as described above. The only concentration limit of this solution or Concentrated dispersion corresponds to the manipulability limit due to the increase in viscosity as the polymer concentration increases.
- the polymer is generally introduced into an ethanol-carrying conduit by any means known to those skilled in the art allowing a polymer or a solution / composition to come into contact with the fluid (ethanol), preferably in a pipe carrying the fluid (ethanol).
- the systems for injecting a fluid into a pipe are quite appropriate.
- the composition comprises water and / or ethanol.
- the amount of polymer used in the process according to the invention is between 5 and 5,000 ppm by weight relative to ethanol, preferably less than 1,000 ppm and very preferably between 10 and 500 ppm by weight relative to ethanol.
- the introduction of the polymer can be made throughout the transport, in one or more additions.
- the process according to the invention offers undeniable advantages in the transport of ethanol (in particular bioethanol).
- ethanol in particular bioethanol.
- the polymers described above effectively reduce friction during the transportation of ethanol and thus facilitate the transport of large quantities over long distances. The energy required for the transport of ethanol is thus significantly reduced.
- An aqueous phase is prepared by mixing 520 g of N, N-dimethylacrylamide (DMA) and 978.2 g of deionized water. The pH is adjusted to 5 by adding 1.8 g of acetic acid. Several additives are added to the aqueous phase: 0.04 g of a solution of 40% sodium diethylenetriaminepentaacetate, 0.01 g of sodium hypophosphite and 1.5 g of azobis-isobutyronitrile. The polymerization is conducted under adiabatic conditions by adding an oxido-reducing pair (typically sodium persulfate / iron salt II). The temperature rises 70 ° C in 4h. The finished product is a gel which is chopped, dried and milled to yield the desired product in powder form.
- DMA N, N-dimethylacrylamide
- Example 1 The protocol used for Example 1 was repeated but the composition of the aqueous phase was modified: 494 g of N, N-dimethylacrylamide (DMA), 120.25 g of a 50% solution of the sodium salt of the acrylamidomethylpropylsulfonic acid (ATBSNa), 2.25 g of acetic acid to reach a pH of 4 and 883.5 g of deionized water.
- DMA N, N-dimethylacrylamide
- ATBSNa acrylamidomethylpropylsulfonic acid
- acetic acid to reach a pH of 4 and 883.5 g of deionized water.
- Example 1 The protocol used for Example 1 was repeated but the composition of the aqueous phase was modified: 493.75 g of N, N-dimethylacrylamide (DMA), 63.55 g of a solution containing 80% of acryloylethyltrimethylammonium (ADAMQUAT), 9.125 g of acetic acid to reach a pH of 4.2 and 933.575 g of deionized water.
- DMA N, N-dimethylacrylamide
- ADAMQUAT a solution containing 80% of acryloylethyltrimethylammonium
- acetic acid 9.125 g of acetic acid to reach a pH of 4.2 and 933.575 g of deionized water.
- the friction reduction evaluation was evaluated in turbulent ethanol using a flow loop.
- a 3 meter tube with a diameter of 1/8 "(1/8") is used At 20 ° C and at a rate of 60 l / h, the Reynolds number applied is 12,000.
- the monitoring of the friction reducing effect is obtained by measuring the pressure drop in the tube.
- the tested polymers were first dissolved in ethanol at 10,000 ppm (stock solution). This makes it possible to verify that all the polymers prepared have a good solubility in ethanol.
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Abstract
La présente invention concerne un procédé pour réduire la friction de l'éthanol pendant son transport dans une canalisation. Ce procédé consiste 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 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.The present invention relates to a method for reducing the friction of ethanol during its transportation in a pipeline. This method comprises contacting ethanol with a polymer-based composition, characterized in that the polymer is obtained from at least 50 mol% of at least one monomer chosen from the group comprising N-acrylamide. substituted, N-substituted methacrylamide, N, N-substituted acrylamide, N, N-substituted methacrylamide, substituted acrylate, and substituted methacrylate.
Description
La présente invention concerne le domaine du transport de l'éthanol. L'invention se rapporte à l'utilisation d'un polymère spécifique comme réducteur de friction pour le transport de l'éthanol.The present invention relates to the field of ethanol transport. The invention relates to the use of a specific polymer as a friction reducer for the transport of ethanol.
Le transport de l'éthanol, et particulièrement le bioéthanol, est un sujet d'importance dans un contexte de transition énergétique où les énergies fossiles sont progressivement remplacées par des technologies alternatives. L'éthanol (bioéthanol) produit à partir de la biomasse connait un fort développement et la question de son transport efficace sur de longues distances se pose.The transport of ethanol, and particularly bioethanol, is a subject of importance in a context of energy transition where fossil fuels are gradually being replaced by alternative technologies. Ethanol (bioethanol) produced from biomass is experiencing a strong development and the question of its efficient transport over long distances arises.
En
Il est connu que les polymères hydrosolubles de forte poids moléculaire peuvent jouer le rôle de réducteur de friction de solutions aqueuses. L'étirement des chaînes polymériques en solution permet de retarder le régime turbulent s'établissant lors du transport du fluide à grande vitesse. La conséquence est une réduction de l'énergie nécessaire au transport de la solution aqueuse.It is known that water-soluble polymers of high molecular weight can act as friction reducers of aqueous solutions. The stretching of the polymeric chains in solution makes it possible to delay the turbulent regime established during the transport of the fluid at high speed. The consequence is a reduction in the energy required to transport the aqueous solution.
Le transport à grande vitesse d'autres fluides que l'eau est également sujet à ces problématiques de friction. La difficulté réside cependant dans le fait que les polymères développés pour le transport des solutions aqueuses ne peuvent pas être utilisés du fait de leur piètre solubilité dans ces fluides.High-speed transport of fluids other than water is also subject to these friction problems. The difficulty however lies in the fact that the polymers developed for the transport of aqueous solutions can not be used because of their poor solubility in these fluids.
Par autres fluides, on entend des solvants organiques, des huiles ou des biocombustibles.Other fluids are organic solvents, oils or biofuels.
L'état de l'art relatif aux biocombustibles concerne le développement de polymères spécifiques pour les biodiesels (mélanges d'esters d'acide gras) permettant de réduire leur viscosité, surtout à basse température, pour améliorer leur transport par pipeline. Nous pouvons notamment citer les documents
Parmi les biocombustibles, nous pouvons citer le bioéthanol. Ce dernier ne présente pas de problème de viscosité pour être transporté mais il est soumis aux frictions. Les polymères classiquement utilisés pour réduire les frictions lors du transport de solutions aqueuses (dérivés de polyacrylamide) ne peuvent être utilisés par manque de solubilité dans le bioéthanol. En revanche, le document
Un polymère sera d'autant plus efficace pour réduire les phénomènes de friction que son poids moléculaire est important. Or les PEG ne sont pas connus pour présenter de très grandes masses moléculaires du fait de leurs procédés de synthèse.A polymer will be all the more effective in reducing friction phenomena as its molecular weight is important. PEGs are not known to have very large molecular masses because of their synthetic processes.
Les polymères possédant les plus grandes masses sont les dérivés de polyacrylamide mais les produits existant ne sont pas solubles dans l'éthanol. En effet, l'éthanol est couramment utilisé en tant que contre-solvant pour précipiter des polyacrylamides.The polymers with the largest masses are the polyacrylamide derivatives but the existing products are not soluble in ethanol. Indeed, ethanol is commonly used as a counter-solvent for precipitating polyacrylamides.
La préparation d'un polymère apte à réduire les frictions dans le transport de l'éthanol nécessite de synthétiser un polymère de très haute poids moléculaire soluble dans l'éthanol.The preparation of a polymer capable of reducing friction in the transport of ethanol requires the synthesis of a very high molecular weight polymer soluble in ethanol.
Le problème que se propose de résoudre l'invention est donc de développer un polymère permettant de réduire les frictions et ainsi améliorer le transport de l'éthanol.The problem to be solved by the invention is therefore to develop a polymer to reduce friction and thus improve the transport of ethanol.
De manière tout à fait surprenante, la Demanderesse a découvert que l'utilisation de polymères obtenus à partir de monomères (méth)acrylamide N-substitués ou N,N-substitués et/ou de monomères (méth)acrylate substitués permet de résoudre ce problème.Surprisingly, the Applicant has discovered that the use of polymers obtained from N-substituted or N, N-substituted (meth) acrylamide monomers and / or substituted (meth) acrylate monomers makes it possible to solve this problem. .
Plus précisément, la présente invention a pour objet un 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.More specifically, the subject of the present invention is a process for reducing the friction of ethanol during its transportation in a pipe consisting in putting the ethanol in contact with a polymer-based composition, characterized in that the polymer is obtained at from at least one monomer selected from the group consisting of N-substituted acrylamide, N-substituted methacrylamide, N, N-substituted acrylamide, N, N-substituted methacrylamide, substituted acrylate, and substituted methacrylate.
De manière avantageuse, le polymère est mis en contact avec l'éthanol pendant le transport. En d'autres termes, il est avantageusement introduit dans la canalisation qui transporte l'éthanol.Advantageously, the polymer is contacted with ethanol during transport. In other words, it is advantageously introduced into the pipe which transports the ethanol.
La mise en contact de l'éthanol avec le polymère ou une composition à base de polymère peut notamment être réalisée par introduction ou injection du polymère ou d'une composition à base dudit polymère dans une canalisation permettant le transport d'un fluide (éthanol).The contacting of the ethanol with the polymer or a polymer-based composition may in particular be carried out by introducing or injecting the polymer or a composition based on said polymer into a pipe allowing the transport of a fluid (ethanol). .
Selon un mode de réalisation particulier, la mise en contact entre le polymère et l'éthanol peut être réalisée avant l'introduction de l'éthanol dans la canalisation de transport. Elle peut être réalisée dans une cuve de stockage par exemple.According to a particular embodiment, the contacting between the polymer and the ethanol can be carried out before the introduction of ethanol into the transport pipe. It can be carried out in a storage tank for example.
Dans la présente invention, l'éthanol et les fluides dont le transport est amélioré désignent l'éthanol, notamment le bioéthanol, et également des fluides composés essentiellement d'éthanol, lesdits fluides contenant au moins 50%, préférentiellement au moins 80% en poids d'éthanol.In the present invention, ethanol and fluids whose transport is improved designate ethanol, especially bioethanol, and also fluids composed essentially of ethanol, said fluids containing at least 50%, preferably at least 80% by weight ethanol.
L'éthanol est avantageusement du bioéthanol. Il est préférentiellement issu de la biomasse.Ethanol is advantageously bioethanol. It is preferably derived from biomass.
Selon un premier aspect de l'invention, le polymère mis en oeuvre dans le transport de l'éthanol est obtenu à partir d'au moins 50 mol% d'au moins un monomère choisi dans le groupe comprenant les monomères (méth)acrylamide N-substitués ou N,N-substitués, et les monomères (méth)acrylate substitués.According to a first aspect of the invention, the polymer used in the transport of ethanol is obtained from at least 50 mol% of at least one monomer chosen from the group comprising the (meth) acrylamide N monomers. -substituted or N, N-substituted, and substituted (meth) acrylate monomers.
La Demanderesse a découvert que l'utilisation de monomères (méth)acrylamide N-substitués ou N,N-substitués et/ou de monomères (méth)acrylate substitués, permettait d'obtenir non seulement des polymères solubles en forte concentration à la fois dans l'eau et dans l'éthanol, mais permettait également d'obtenir des polymères ayant des performances de réduction des frictions dans le transport de fluides à base d'éthanol. Ces monomères sont avantageusement non-ioniques.The Applicant has discovered that the use of N-substituted or N, N-substituted (meth) acrylamide monomers and / or substituted (meth) acrylate monomers makes it possible to obtain not only soluble polymers in high concentration both in and in ethanol, but also made it possible to obtain polymers with friction reducing performance in the transport of ethanol-based fluids. These monomers are advantageously nonionic.
Comme déjà évoqué, les polymères de haut poids moléculaire sont particulièrement efficaces. Le polymère mis en oeuvre pour réduire les frictions dans le procédé objet de l'invention a un poids moléculaire préférentiellement compris entre 0.5 et 25 millions de g/mol, plus préférentiellement supérieur à 2 millions de g/mol, et encore plus préférentiellement supérieur à 5 millions de g/mol.As already mentioned, high molecular weight polymers are particularly effective. The polymer used to reduce friction in the process which is the subject of the invention has a molecular weight preferably of between 0.5 and 25 million g / mol, more preferably greater than 2 million g / mol, and even more preferentially greater than 5 million g / mol.
Selon un mode de réalisation avantageux, le polymère mis en oeuvre pour réduire les frictions dans le procédé objet de l'invention comprend au moins 80 mol% de monomères (méth)acrylamide N-substitués ou N,N-substitués et/ou de monomères (méth)acrylate substitués, préférentiellement au moins 90 mol%.According to an advantageous embodiment, the polymer used to reduce friction in the process which is the subject of the invention comprises at least 80 mol% of monomers N-substituted or N, N-substituted (meth) acrylamide and / or substituted (meth) acrylate monomers, preferably at least 90 mol%.
Le polymère peut notamment être un homopolymère de monomères (méth)acrylamide N-substitués ou N,N-substitués ou de monomères (méth)acrylate substitués.The polymer may especially be a homopolymer of N-substituted or N, N-substituted (meth) acrylamide monomers or substituted (meth) acrylate monomers.
Selon un autre mode de réalisation avantageux, les monomères (méth)acrylamide N-substitués ou N,N-substitués sont préférentiellement choisis parmi le N-éthylacrylamide, N-isopropylacrylamide, N-ter-butylacrylamide, diacetoneacrylamide, N-hydroxyéthylacrylamide, N-hydroxyméthylacrylamide, N-alkyl acrylamide (alkyl: C3 à C22), N-[tris(hydroxyméthyl)méthyl]acrylamide, N-acryloylmorpholine, le N,N-diméthylacrylamide, N,N-diéthylacrylamide, N,N-dialkylacrylamide (alkyl: C3 à C22).According to another advantageous embodiment, the N-substituted or N, N-substituted (meth) acrylamide monomers are preferably chosen from N-ethylacrylamide, N-isopropylacrylamide, N-tert-butylacrylamide, diacetoneacrylamide, N-hydroxyethylacrylamide, N- hydroxymethylacrylamide, N-alkyl acrylamide (C 3 -C 22 alkyl), N- [tris (hydroxymethyl) methyl] acrylamide, N-acryloylmorpholine, N, N-dimethylacrylamide, N, N-diethylacrylamide, N, N-dialkylacrylamide (alkyl: C3 to C22).
Selon un autre mode de réalisation avantageux, les monomères (méth)acrylate substitués sont préférentiellement choisis parmi le (méth)acrylate de méthyle, le (méth)acrylate d'éthyle, le (méth)acrylate de propyle, le (méth)acrylate de butyle, le (méth)acrylate d'alkyle (C5 à C22), le (méth)acrylate d'isobornyle et (méth)acrylate de 2-éthylhexyle, le (méth)acrylate d'hydroxyéthyle et (méth)acrylate d'hydroxypropyle, le (méth)acrylate de furfuryle et (méth)acrylate de tétrahydrofurfuryle, le (méth)acrylate de glycéryle, le (méth)acrylate de glycidyle.According to another advantageous embodiment, the substituted (meth) acrylate monomers are preferably chosen from methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, (meth) acrylate and the like. butyl, (C 5 -C 22) alkyl (meth) acrylate, isobornyl (meth) acrylate and 2-ethylhexyl (meth) acrylate, hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate , furfuryl (meth) acrylate and tetrahydrofurfuryl (meth) acrylate, glyceryl (meth) acrylate, glycidyl (meth) acrylate.
Dans un mode préféré de l'invention, la chaîne carbonée de la partie substituée des monomères mentionnés ci-dessus permet une bonne solubilité du polymère dans l'eau et dans l'alcool. Ainsi, les chaînes substituées des monomères (méth)acrylamide N-substitués ou N,N-substitués et/ou de monomères (méth)acrylate substitués contiennent de préférence moins de 30 atomes de carbone, plus préférentiellement moins de 10 atomes de carbone, et encore plus préférentiellement moins de 5 atomes de carbone.In a preferred embodiment of the invention, the carbon chain of the substituted part of the monomers mentioned above allows good solubility of the polymer in water and in alcohol. Thus, the substituted chains of the N-substituted or N, N-substituted (meth) acrylamide monomers and / or substituted (meth) acrylate monomers preferably contain less than 30 carbon atoms, more preferably less than 10 carbon atoms, and still more preferably less than 5 carbon atoms.
Il est connu que l'introduction de charges sur le squelette de polymère (i.e. polyélectrolyte) est largement défavorable à la solubilité du polymère dans l'éthanol (qui est généralement un solvant de précipitation du polymère). Pourtant les chaînes de polyélectrolyte, du fait des répulsions électrostatiques s'établissant, sont très étirées et rajoute à l'efficacité du polymère.It is known that introducing charges onto the polymer backbone (i.e., polyelectrolyte) is largely unfavorable to the solubility of the polymer in ethanol (which is generally a polymer precipitation solvent). However, the polyelectrolyte chains, because electrostatic repulsions are established, are very stretched and adds to the effectiveness of the polymer.
La Demanderesse a ainsi découvert de manière surprenante qu'il était possible d'incorporer un certain pourcentage de charges dans le polymère mis en oeuvre dans le procédé objet de l'invention sans pour autant affecter la solubilité du polymère.The Applicant has thus surprisingly found that it was possible to incorporate a certain percentage of charges into the polymer used in the process which is the subject of the invention without affecting the solubility of the polymer.
Dans un mode particulier, le polymère réducteur de friction selon l'invention peut comprendre en outre au moins un monomère ionique dans une quantité inférieure à 40 mol%, préférentiellement inférieure à 20 mol%, très préférentiellement inférieure à 10 mol%.In a particular embodiment, the friction reducing polymer according to the invention may further comprise at least one ionic monomer in an amount of less than 40 mol%, preferably less than 20 mol%, very preferably less than 10 mol%.
Le monomère ionique est préférentiellement un monomère anionique. Ce monomère anionique est préférentiellement choisi parmi l'acide acrylique, l'acide méthacrylique, l'acide itaconique, l'acide maléique, l'acide 2-acrylamido-2-méthylpropane sulfonique (ATBS), l'acide vinylsulphonique, l'acide vinylphosphonic, ledit monomère anionique étant non salifié, partiellement ou totalement salifié, et les sels du méthacrylate de 3-sulfopropyle.The ionic monomer is preferably an anionic monomer. This anionic monomer is preferably chosen from acrylic acid, methacrylic acid, itaconic acid, maleic acid, 2-acrylamido-2-methylpropanesulphonic acid (ATBS), vinylsulphonic acid, and acid. vinylphosphonic, said anionic monomer being uns-salified, partially or totally salified, and salts of 3-sulfopropyl methacrylate.
Selon un autre mode de réalisation, le monomère ionique peut être un monomère cationique. Ce monomère cationique est préférentiellement choisi parmi le chlorure de diallyl diméthyl ammonium (DADMAC) l'acrylate de dialkylaminoéthyle (ADAME) et le méthacrylate de dialkylaminoéthyle (MADAME), l'acrylamido dialkyl amino propyle, le méth acrylamido dialkyl amino propyle, ainsi que leurs sels acidifiés ou quaternisés.In another embodiment, the ionic monomer may be a cationic monomer. This cationic monomer is preferably chosen from diallyl dimethyl ammonium chloride (DADMAC) dialkylaminoethyl acrylate (ADAME) and dialkylaminoethyl methacrylate (MADAME), acrylamido dialkylamino propyl, meth acrylamido dialkylamino propyl, and their acidified or quaternized salts.
Dans un mode de réalisation préféré, le polymère mis en oeuvre dans le procédé objet de l'invention est un homopolymère de (méth)acrylamide N-substitués ou N,N-substitués, un homopolymère de (méth)acrylate substitués, un copolymère de (méth)acrylate substitués et d'acide acrylique, ou un copolymère de N,N-di(m)éthylacrylamide et d'acide 2-acrylamido-2-méthylpropane sulfonique (ATBS).In a preferred embodiment, the polymer used in the process which is the subject of the invention is a homopolymer of N-substituted or N-substituted (meth) acrylamide, a substituted (meth) acrylate homopolymer, a copolymer of (meth) acrylate and acrylic acid, or a copolymer of N, N-di (m) ethylacrylamide and 2-acrylamido-2-methylpropanesulphonic acid (ATBS).
Selon un mode de réalisation particulier, le polymère est un polymère choisi dans le groupe comprenant l'homopolymère de N,N-diméthylacrylamide, l'homopolymère de N,N-diéthylacrylamide, le copolymère de N,N-diméthylacrylamide et d'acide acrylique, le copolymère de N,N-diéthylacrylamide et d'acide acrylique, le copolymère de N,N-diméthylacrylamide et d'acide 2-acrylamido-2-méthylpropane sulfonique, et le copolymère de N,N-diéthylacrylamide et d'acide 2-acrylamido-2-méthylpropane sulfonique.According to a particular embodiment, the polymer is a polymer chosen from the group comprising the homopolymer of N, N-dimethylacrylamide, the homopolymer of N, N-diethylacrylamide, the copolymer of N, N-dimethylacrylamide and acrylic acid. , the copolymer of N, N-diethylacrylamide and of acrylic acid, the copolymer of N, N-dimethylacrylamide and of 2-acrylamido-2-methylpropanesulphonic acid, and the copolymer of N, N-diethylacrylamide and of acid 2 -acrylamido-2-methylpropanesulphonic acid.
D'autre part, le polymère mis en oeuvre dans le procédé de réduction de friction selon l'invention peut comprendre en outre au moins un monomère non ionique comme l'acrylamide.On the other hand, the polymer used in the friction reduction method according to the invention may further comprise at least one nonionic monomer such as acrylamide.
De manière générale, le polymère mis en oeuvre ne nécessite pas de développement de procédé de polymérisation particulier. En effet, il peut être obtenu par toutes les techniques de polymérisation bien connues par l'homme du métier, c'est à dire par polymérisation en solution, polymérisation en suspension, polymérisation en gel ou en masse, polymérisation par précipitation, polymérisation en émulsion (aqueuse ou inverse) suivie ou non d'une étape de spray drying, polymérisation micellaire suivie ou non d'une étape de précipitation, polymérisation post-hydrolyse ou co-hydrolyse, polymérisation dite « template », radicalaire, ou encore radicalaire contrôlée.In general, the polymer used does not require development of a particular polymerization process. Indeed, it can be obtained by any of the polymerization techniques well known to those skilled in the art, that is to say by solution polymerization, suspension polymerization, gel or bulk polymerization, precipitation polymerization, emulsion polymerization. (Aqueous or inverse) followed or not by a step of spray drying, micellar polymerization followed or not by a precipitation step, post-hydrolysis polymerization or co-hydrolysis, polymerization called "template", radical, or radical controlled.
Le polymère peut se présenter sous forme liquide ou solide lorsque sa préparation inclut une étape de séchage tel que le spray drying, le séchage sur tambour ou encore le séchage micro-ondes.The polymer may be in liquid or solid form when its preparation includes a drying step such as spray drying, drum drying or microwave drying.
Le polymère est préférentiellement obtenu selon un procédé de synthèse en voie gel ce qui permet d'obtenir des polymères de très haut poids moléculaire d'une manière économique et écologique (car sans solvant). Le procédé de synthèse en voie gel consiste à polymériser des monomères en solution aqueuse afin d'obtenir un gel qui est ensuite broyé et séché pour obtenir une poudre.The polymer is preferably obtained according to a method of synthesis in the gel route which makes it possible to obtain polymers of very high molecular weight in an economical and ecological manner (because without solvent). The method of synthesis in the gel process consists in polymerizing monomers in aqueous solution in order to obtain a gel which is then ground and dried to obtain a powder.
Comme déjà indiqué, le procédé objet de la présente invention comprend une étape de mise en contact de l'éthanol à transporter avec au moins un polymère réducteur de friction obtenu à partir de monomères (méth)acrylamide N-substitués ou N,N-substitués et/ou de monomères (méth)acrylate substitués.As already indicated, the method which is the subject of the present invention comprises a step of contacting the ethanol to be transported with at least one friction-reducing polymer obtained from N-substituted or N, N-substituted (meth) acrylamide monomers. and / or substituted (meth) acrylate monomers.
Généralement, le procédé selon l'invention est particulièrement intéressant lorsque des volumes important d'éthanol sont transportés sur de longues distances. Plus particulièrement le procédé selon l'invention concerne le transport d'éthanol sur une distance supérieure à 1 km, préférentiellement supérieure à 5 km, et pouvant excéder 20 à 50 km. Le débit est généralement élevé et supérieur à 10 litres par seconde, préférentiellement supérieur à 100 litres par seconde.Generally, the process according to the invention is particularly advantageous when large volumes of ethanol are transported over long distances. More particularly, the process according to the invention relates to the transport of ethanol over a distance greater than 1 km, preferably greater than 5 km, and possibly exceeding 20 to 50 km. The flow rate is generally high and greater than 10 liters per second, preferably greater than 100 liters per second.
Généralement, le polymère est mis en oeuvre dans une composition comprenant de l'eau ou de l'éthanol ou un mélange des deux. Le polymère permettant de réduire les frictions lors du transport de l'éthanol dans une canalisation peut être mis en oeuvre dans une solution ou une dispersion concentrée (de l'ordre de 1.000 à 20.000 ppm). Cette solution peut être préalablement diluée ou pas avant sa mise en contact avec l'éthanol. Cette dilution est avantageusement réalisée dans de l'éthanol, ou dans un fluide à base d'éthanol tel que décrit ci-dessus. La seule limite de concentration de cette solution ou dispersion concentrée correspond à la limite de manipulabilité due à l'augmentation de viscosité lorsque la concentration en polymère augmente.Generally, the polymer is used in a composition comprising water or ethanol or a mixture of both. The polymer for reducing friction during the transport of ethanol in a pipe can be implemented in a solution or a concentrated dispersion (of the order of 1,000 to 20,000 ppm). This solution may be diluted beforehand or not before it comes into contact with ethanol. This dilution is advantageously carried out in ethanol, or in an ethanol-based fluid as described above. The only concentration limit of this solution or Concentrated dispersion corresponds to the manipulability limit due to the increase in viscosity as the polymer concentration increases.
Le polymère est généralement introduit dans un conduit transportant l'éthanol par tout moyen connu de l'homme de l'art permettant la mise en contact d'un polymère ou d'une solution/composition avec le fluide (éthanol), de préférence dans une canalisation transportant le fluide (éthanol). Parmi ces moyens, les systèmes d'injection d'un fluide dans une canalisation sont tout à fait appropriés.The polymer is generally introduced into an ethanol-carrying conduit by any means known to those skilled in the art allowing a polymer or a solution / composition to come into contact with the fluid (ethanol), preferably in a pipe carrying the fluid (ethanol). Among these means, the systems for injecting a fluid into a pipe are quite appropriate.
Le procédé pour transporter de l'éthanol peut ainsi comprendre les étapes suivantes :
- Préparation d'une composition comprenant au moins un polymère apte à réduire les frictions, obtenu à partir d'au moins un monomère N-alkylacrylamide ou N,N-dialkylacrylamide,
- Mise en contact de cette composition avec l'éthanol, de préférence, par introduction de la composition dans un conduit transportant de l'éthanol.
- Preparation of a composition comprising at least one polymer capable of reducing friction, obtained from at least one N-alkylacrylamide or N, N-dialkylacrylamide monomer,
- Contacting this composition with ethanol, preferably, by introducing the composition into a conduit carrying ethanol.
Dans un mode préféré, la composition comprend de l'eau et/ou de l'éthanol.In a preferred embodiment, the composition comprises water and / or ethanol.
La quantité de polymère utilisée dans le procédé selon l'invention est comprise entre 5 et 5.000 ppm en poids par rapport à l'éthanol, préférentiellement inférieure 1.000 ppm et très préférentiellement comprise entre 10 et 500 ppm en poids par rapport à l'éthanol.The amount of polymer used in the process according to the invention is between 5 and 5,000 ppm by weight relative to ethanol, preferably less than 1,000 ppm and very preferably between 10 and 500 ppm by weight relative to ethanol.
L'introduction du polymère peut être faite tout au long du transport, en un ou plusieurs ajouts.The introduction of the polymer can be made throughout the transport, in one or more additions.
Le procédé selon l'invention offre des avantages indéniables dans le transport de l'éthanol (notamment le bioéthanol). Les polymères décrits ci-dessus réduisent efficacement les frictions lors du transport de l'éthanol et permettent ainsi de faciliter le transport de grandes quantités sur de longues distances. L'énergie nécessaire pour le transport de l'éthanol est ainsi réduite de manière significative.The process according to the invention offers undeniable advantages in the transport of ethanol (in particular bioethanol). The polymers described above effectively reduce friction during the transportation of ethanol and thus facilitate the transport of large quantities over long distances. The energy required for the transport of ethanol is thus significantly reduced.
Les modes spécifiques ou préférés décrits dans la présente invention peuvent être combinés entre eux pour donner un mode particulier préféré sauf si il est clairement indiqué que cette combinaison n'est pas souhaité.The specific or preferred modes described in the present invention may be combined with each other to give a particular preferred mode unless it is clearly indicated that this combination is not desired.
L'invention et les avantages qui en découlent ressortiront bien des exemples de réalisation suivants qui n'ont pas un caractère limitatif.The invention and the advantages thereof will emerge from the following examples of embodiments which are not limiting in nature.
Une phase aqueuse est préparée en mélangeant 520 g de N,N-diméthylacrylamide (DMA) et 978,2 g d'eau permutée. Le pH est ajusté à 5 en ajoutant 1,8 g d'acide acétique. Plusieurs additifs sont ajoutés à la phase aqueuse : 0,04 g d'une solution de diéthylenetriaminepentaacetate de sodium à 40%, 0,01 g d'hypophosphite de sodium et 1,5 g d'azo-bis-isobutyronitrile. La polymérisation est conduite dans des conditions adiabatiques en ajoutant un couple oxydo-réducteur (typiquement persulfate de sodium / sel de fer II). La température s'élève de 70°C en 4h. Le produit fini est un gel qui est haché, séché et broyé pour conduire au produit recherché sous forme de poudre.An aqueous phase is prepared by mixing 520 g of N, N-dimethylacrylamide (DMA) and 978.2 g of deionized water. The pH is adjusted to 5 by adding 1.8 g of acetic acid. Several additives are added to the aqueous phase: 0.04 g of a solution of 40% sodium diethylenetriaminepentaacetate, 0.01 g of sodium hypophosphite and 1.5 g of azobis-isobutyronitrile. The polymerization is conducted under adiabatic conditions by adding an oxido-reducing pair (typically sodium persulfate / iron salt II). The temperature rises 70 ° C in 4h. The finished product is a gel which is chopped, dried and milled to yield the desired product in powder form.
Le protocole utilisé pour l'exemple 1 a été répété mais la composition de la phase aqueuse a été modifiée : 494 g de N,N-diméthylacrylamide (DMA), 120.25g d'une solution à 50% du sel de sodium de l'acide acrylamidométhylpropylsulfonique (ATBSNa), 2,25g d'acide acétique pour atteindre un pH de 4 et 883,5g d'eau permutée.The protocol used for Example 1 was repeated but the composition of the aqueous phase was modified: 494 g of N, N-dimethylacrylamide (DMA), 120.25 g of a 50% solution of the sodium salt of the acrylamidomethylpropylsulfonic acid (ATBSNa), 2.25 g of acetic acid to reach a pH of 4 and 883.5 g of deionized water.
Le protocole utilisé pour l'exemple 1 a été répété mais la composition de la phase aqueuse a été modifiée : 493,75 g de N,N-diméthylacrylamide (DMA), 63,55 g d'une solution à 80% du chlorure de l'acryloyléthyltriméthylammonium (ADAMQUAT), 9,125g d'acide acétique pour atteindre un pH de 4,2 et 933,575 g d'eau permutée.The protocol used for Example 1 was repeated but the composition of the aqueous phase was modified: 493.75 g of N, N-dimethylacrylamide (DMA), 63.55 g of a solution containing 80% of acryloylethyltrimethylammonium (ADAMQUAT), 9.125 g of acetic acid to reach a pH of 4.2 and 933.575 g of deionized water.
L'évaluation de la réduction de friction a été évaluée dans l'éthanol en régime turbulent en utilisant une flow loop. Un tube de 3 mètres avec un diamètre de 1/8 de pouce (1/8") est utilisé. A 20°C et à un débit de 60l/h, le nombre Reynolds appliqué est de 12 000.The friction reduction evaluation was evaluated in turbulent ethanol using a flow loop. A 3 meter tube with a diameter of 1/8 "(1/8") is used At 20 ° C and at a rate of 60 l / h, the Reynolds number applied is 12,000.
Le suivi de l'effet réducteur de friction est obtenu en mesurant la perte de charge dans le tube.The monitoring of the friction reducing effect is obtained by measuring the pressure drop in the tube.
Les polymères testés ont été au préalable dissous dans l'éthanol à 10 000 ppm (solution mère). Cela permet de vérifier que tous les polymères préparés présentent une bonne solubilité dans l'éthanol.The tested polymers were first dissolved in ethanol at 10,000 ppm (stock solution). This makes it possible to verify that all the polymers prepared have a good solubility in ethanol.
Les résultats sont rassemblés dans le tableau 1 ci-après.
Les résultats des expériences montrent que les polymères selon l'invention (exemples 1 et 2) permettent de réduire efficacement les frictions lors du transport d'éthanol.The results of the experiments show that the polymers according to the invention (Examples 1 and 2) make it possible to effectively reduce friction during the transport of ethanol.
Quand bien même les polymères comprenant de l'ATBS (contre-exemples du tableau 1) peuvent également réduire les frictions, l'amélioration est nettement inférieure à celle résultant de la présence de polymères selon l'invention.Even though the polymers comprising ATBS (counterexamples of Table 1) can also reduce friction, the improvement is significantly less than that resulting from the presence of polymers according to the invention.
Une nouvelle série d'expériences a été reproduite en étudiant la stabilité du polymère en fonction du temps. A titre de comparaison un PEG (polyéthylèneglycol) de masse moléculaire 900 000, réputé efficace comme réducteur de friction de l'éthanol (
Il apparait que le polymère selon l'invention (exemple 3) reste stable en fonction du temps, son pouvoir réducteur de friction n'est pas affecté après 10 minutes. La référence PEG ne présente pas ce type de stabilité. Après seulement 5 minutes, son efficacité est réduite d'un facteur 3.It appears that the polymer according to the invention (Example 3) remains stable as a function of time, its friction reducing power is not affected after 10 minutes. The PEG reference does not exhibit this type of stability. After only 5 minutes, its effectiveness is reduced by a factor of 3.
Les résultats des expériences montrent que les polymères selon l'invention (exemples 1 à 3) permettent de réduire efficacement les frictions lors du transport d'éthanol.The results of the experiments show that the polymers according to the invention (Examples 1 to 3) make it possible to effectively reduce friction during the transport of ethanol.
Claims (13)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1454595A FR3021327B1 (en) | 2014-05-21 | 2014-05-21 | METHOD OF REDUCING FRICTION IN THE TRANSPORT OF ETHANOL |
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| EP2947134A1 true EP2947134A1 (en) | 2015-11-25 |
| EP2947134B1 EP2947134B1 (en) | 2017-10-11 |
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| EP15168058.4A Not-in-force EP2947134B1 (en) | 2014-05-21 | 2015-05-19 | Method for reducing friction in the transport of ethanol |
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| US (1) | US9822325B2 (en) |
| EP (1) | EP2947134B1 (en) |
| CN (1) | CN105085751B (en) |
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| FR (1) | FR3021327B1 (en) |
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| CN105504160A (en) * | 2015-12-07 | 2016-04-20 | 南京工业大学 | Preparation method of novel high-molecular soaping agent for cationic dye dyed fabric |
| CN111379971B (en) * | 2018-12-29 | 2023-01-03 | 中润油新能源股份有限公司 | Production device for reducing resistance of methanol gasoline gas |
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| US20050049327A1 (en) * | 2003-09-02 | 2005-03-03 | Vladimir Jovancicevic | Drag reducing agents for multiphase flow |
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| US4522733A (en) * | 1983-01-31 | 1985-06-11 | American Polywater Corporation | Substantially neutral aqueous lubricant |
| CN100460448C (en) * | 2007-04-09 | 2009-02-11 | 中国石油化工集团公司 | Preparation method of multifunctional resistance-reducing polymer suspension |
| US7888407B2 (en) * | 2007-10-26 | 2011-02-15 | Conocophillips Company | Disperse non-polyalphaolefin drag reducing polymers |
| CN101638569B (en) * | 2008-07-31 | 2012-07-18 | 中国石油天然气股份有限公司 | Drag reducer for oleic acid and ester derivatives thereof and preparation method thereof |
| 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 |
| CN102453297B (en) * | 2010-10-28 | 2013-10-16 | 中国石油天然气股份有限公司 | Supermolecular polymer drag reducer for oil products and preparation method thereof |
| CN102002355B (en) * | 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 | Friction-reducing agent of fracturing fluid and preparation method thereof |
| CN102977877B (en) * | 2012-12-04 | 2014-08-06 | 西南石油大学 | Drag reducer for shale gas fracture and preparation method of drag reducer |
| CN103694984B (en) * | 2013-12-20 | 2016-09-07 | 西南石油大学 | A kind of shale gas acid fracturing drag reducer and preparation method thereof |
-
2014
- 2014-05-21 FR FR1454595A patent/FR3021327B1/en not_active Expired - Fee Related
-
2015
- 2015-05-13 BR BR102015011015-4A patent/BR102015011015B1/en active IP Right Grant
- 2015-05-15 CN CN201510249523.4A patent/CN105085751B/en active Active
- 2015-05-15 US US14/713,532 patent/US9822325B2/en active Active
- 2015-05-19 EP EP15168058.4A patent/EP2947134B1/en not_active Not-in-force
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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 (en) | 2009-01-21 | 2011-08-16 | Unicamp | hydrodynamic friction reducers for biofuels |
| EP2383327A1 (en) | 2010-04-22 | 2011-11-02 | NOF Corporation | Flow improver for biodiesel fuels |
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| WO2013171319A1 (en) | 2012-05-18 | 2013-11-21 | Dupont Nutrition Biosciences Aps | Ester compound of a polyoly and fatty acid oligomer for use as a cold flow improver in fuel compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BR102015011015B1 (en) | 2022-02-01 |
| US9822325B2 (en) | 2017-11-21 |
| CN105085751B (en) | 2020-01-10 |
| BR102015011015A2 (en) | 2016-01-05 |
| CN105085751A (en) | 2015-11-25 |
| FR3021327A1 (en) | 2015-11-27 |
| EP2947134B1 (en) | 2017-10-11 |
| FR3021327B1 (en) | 2016-06-03 |
| US20150337232A1 (en) | 2015-11-26 |
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