US3013868A - Liquid hydrocarbon compositions - Google Patents
Liquid hydrocarbon compositions Download PDFInfo
- Publication number
- US3013868A US3013868A US816039A US81603959A US3013868A US 3013868 A US3013868 A US 3013868A US 816039 A US816039 A US 816039A US 81603959 A US81603959 A US 81603959A US 3013868 A US3013868 A US 3013868A
- Authority
- US
- United States
- Prior art keywords
- chromium
- conductivity
- copolymer
- methacrylate
- ester
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 91
- 239000007788 liquid Substances 0.000 title claims description 46
- 229930195733 hydrocarbon Natural products 0.000 title claims description 36
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 36
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 28
- 229920001577 copolymer Polymers 0.000 claims description 64
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 38
- 239000011651 chromium Substances 0.000 claims description 38
- 229910052804 chromium Inorganic materials 0.000 claims description 37
- 239000000446 fuel Substances 0.000 claims description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 21
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 12
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 5
- 229960001860 salicylate Drugs 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 description 39
- 229910052751 metal Inorganic materials 0.000 description 31
- 239000002184 metal Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
- 150000003839 salts Chemical class 0.000 description 28
- 230000000996 additive effect Effects 0.000 description 27
- 150000002148 esters Chemical class 0.000 description 27
- -1 aromatic carboxylic acids Chemical class 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000004429 atom Chemical group 0.000 description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- 150000007942 carboxylates Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000008096 xylene Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 12
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 230000008901 benefit Effects 0.000 description 8
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 8
- 239000003502 gasoline Substances 0.000 description 8
- 239000006078 metal deactivator Substances 0.000 description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- JPHRYPDSOKJAQQ-UHFFFAOYSA-N calcium;1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound [Ca].CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC JPHRYPDSOKJAQQ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001844 chromium Chemical class 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000006473 carboxylation reaction Methods 0.000 description 3
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 2
- HXISMZRZHNLOHG-UHFFFAOYSA-N 2-hydroxy-3,4-di(propan-2-yl)benzoic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C(O)=C1C(C)C HXISMZRZHNLOHG-UHFFFAOYSA-N 0.000 description 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000001253 acrylic acids Chemical class 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000021523 carboxylation Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229960000878 docusate sodium Drugs 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000007786 electrostatic charging Methods 0.000 description 2
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- NGYRYRBDIPYKTL-UHFFFAOYSA-N icosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C=C NGYRYRBDIPYKTL-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 2
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- FQHUWSPRTMWLFA-UHFFFAOYSA-N 2-cyclohexylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1CCCCC1 FQHUWSPRTMWLFA-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- GSMYMLZNMQIERY-UHFFFAOYSA-N 2-octadecanoyloxybenzoic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1=CC=CC=C1C(O)=O GSMYMLZNMQIERY-UHFFFAOYSA-N 0.000 description 1
- OBYWYNKFFLAQBD-UHFFFAOYSA-N 2-octadecoxybenzoic acid Chemical compound CCCCCCCCCCCCCCCCCCOC1=CC=CC=C1C(O)=O OBYWYNKFFLAQBD-UHFFFAOYSA-N 0.000 description 1
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 1
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 description 1
- DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 description 1
- WCKMDEHRHUNVEQ-UHFFFAOYSA-N 4-[1-(4-oxopentan-2-ylideneamino)ethylimino]pentan-2-one Chemical compound C(C(=O)C)C(C)=NC(C)N=C(C)CC(=O)C WCKMDEHRHUNVEQ-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 238000006214 Clemmensen reduction reaction Methods 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- YMWGIFNWVJNYCN-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CCCCCCCCCCCCOC(=O)C(C)=C YMWGIFNWVJNYCN-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005421 electrostatic potential Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000000615 nonconductor Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000007965 rubber solvent Substances 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical class [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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- D—TEXTILES; PAPER
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- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
- D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
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- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
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- C09B50/00—Formazane dyes; Tetrazolium dyes
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- 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
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- C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
- C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
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- C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
- C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
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- 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
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- C10L1/2368—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing heterocyclic compounds containing nitrogen in the ring
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- C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
- C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
Definitions
- the conductivity imparted to the liquid by the conductivity additive is much more permanent than in the case of the higher concentrations.
- concentration is l l0 gram atom of metal per liter of flammable liquid, or less
- conductivity benefit is retained for many days in storage.
- conductivity benefit is gradually and sometimes very rapidly decreased, often to a level which is only a small fraction of the initial value.
- composition of the invention is thus a conductivity additive composition (or a flammable liquid containing it) comprising substantial proportions each of (l) a salt of a metal having an atomic number from 22 through 28 and a relatively high molecular weight aromatic carboxylic or sulfonic acid, and (2) a copolymer as described above.
- conductivity additive or a flammable liquid containing it
- a conductivity additive composition comprising substantial proportions each of (l) a salt of a metal having an atomic number from 22 through 28 and a relatively high molecular weight aromatic carboxylic or sulfonic acid, and (2) a copolymer as described above.
- the metal salt conductivity additive in the compositions of the invention is oil soluble and has a molecular weight of at least 200, preferably at least 500, preferably no more than 3000, especially up to about 2500.
- a xylene solution of the carboxylate may be freed from xylene by steam distillation, acidified and extracted with dilute ammonia solution.
- Another method consists in acidifying the carboxylate, and neutralizing it with an alkali metal hydroxide, whereby the alkylsalicylic acids are converted into the alkali metal salts and the alkylphenols remain unconverted; from a solution of a mixture of alkali metal salts of alkylsalicylic acids and alkylphenols in a wateralcohol mixture (e.g. 50% aqueous isopropanol) the alkyl phenols can be extracted by means of a liquid aliphatic hydrocarbon, such as pentane.
- a liquid aliphatic hydrocarbon such as pentane.
- product E-l has a chromium content of 4.78% by weight.
- a special advantage of the chromium salts as conductivity additives in the present invention is due to'the fact that they are not leached from hydrocarbon solutions by water. This is shown in this example.
- Concentrations of suchsynergists are suitably from about 1X10 to about 1 1()- mol per liter, preferably about 1, 10- to about 1 10- mol per liter, .of the flammable liquid.
- the oil-soluble nitrogen-containing copolymer can be selected from a very wide class of such compounds.
- Preferred such copolymers are the copolymers :of a vinylpyridine and at least one ester of an acrylic ;acid and a long chain aliphatic alcohol containing at Eleast carbon atoms, as described in Barnum et al., US. 2,839,512, June 17, 1958.
- the disclosure of this patent is incorporated herein by reference for a complete description of the preferred copolymers.
- oil-soluble nitrogen-containing copolymers particularly suitable in the compositions of the invention are the oil-soluble, basic amino nitrogen-containing addition-type polymers of a plurality of polymerizable ethylenically unsaturated compounds, at least one of which is amine-free and contains from 8 to about 18 carbon atom in an aliphatic hydrocarbon chain which is a side chain in the polymer, and one of which contains a basic amino nitrogen atom in a side chain, as described in Catlin et al,, US. 2,737,452, March '6, 1956.
- the disclosure of this patent is incorporated herein by reference for a complete description of such suitable copolymers.
- Preferred such basic amino nitrogen-containing copolymers are those in which the amino compound is a dialkylaminoalkyl acrylate such as diethylaminoethyl methacrylate,for example the threecomponent copolymer of lauryl methacrylate styrene and diethylaminoethyl methacrylate (45 :45: 10 ratio).
- the amino compound is a dialkylaminoalkyl acrylate such as diethylaminoethyl methacrylate,for example the threecomponent copolymer of lauryl methacrylate styrene and diethylaminoethyl methacrylate (45 :45: 10 ratio).
- oil-soluble nitrogen-containing copolymers particularly suitable in the compositions of the invention are the copolymers of an N-vinyl-Z-pyrrolidone and at least one C (average)-alkyl ester of an acrylic acid, as described in the Belgian patent to Rohm and Haas Company, Belg. 550,442, or in the Canadian patent to Sachs, Can. 560,549, July 22, 1958. Again for the sake of brevity, the disclosures of these patents, too, are incorporated herein by reference for a complete description of such suitable copolymers.
- copolymers are those of N-vinyl-2-pyrrolidone itself and a mixture of alkyl methacrylates the alkyl (esterifying) groups of which are obtained from a commercial mixture of C to C primary alcohols, in which copolymer the 'acids and the long chain aliphatic alcohols.
- ratio of the N-vinyl pyrrolidone structure to the methacrylate ester structure is about 1 to 5 or 6.
- Still other oil-soluble nitrogen-containing copolymers particularly suitable in the compositions of the invention are the copolymers of an alpha olefin having at least 10 carbon atoms and an ester of an acrylic acid and a C alianol, at least 10% of the ester groups of which copolymers have been amidized with an amine containing a substituent polar group, especially NR or Where R is a hydrocarbyl group, as described in Bondi et al., US. 2,800,452, July 23, 1957. Again for the sake of brevity, the disclosure of this patent, too, is incorporated herein by reference for a complete description of such suitable copolymers.
- Still other oil-soluble nitrogen-containing copolymers particularly suitable in the compositions of the invention are the copolymers containing (A) at least one oil-solubilizing compound having an ethylenic linkage and a group of 4 to 30 aliphatic carbon atoms and which is copolymerizable through said linkage and (B) at least one amide of an alpha, beta-unsaturated carboxylic acid of from 3 to 6 carbon atoms, with from 1 to .15 units of the ethylenic component (A) being present in the copolymer for each unit of the amide component (B), as described in the British patent to California Research Corporation, Br. 759,517, published October 17, 1956. Again for the sake of brevity, the disclosure of this patent, too, is incorporated herein by reference for a complete description of such suitable copolymers.
- the oil-soluble nitrogen-containing copolymers should have molecular weights in the range 5000 to 2,500,000 as determined by the light scattering technique described in Chem. Rev., vol. 40, page 319 (1948), preferably from 50,000 to 1,000,000, or most especially from 100,000 to 650,000.
- the nitrogen content of the copolymer is important; it should be at least 0.1% by weight of the copolymer and preferably not more than 8%, but more especially at least 1% and not more than 5% by Weight the copolymer having an inherent viscosity of from about 0.1 to 3.0 as determined at 0.1% weight volume concentration in benzene at 25 C.
- a particularly preferred class of copolymers for the purposes of the present invention are copolymers of the type described in the above Barnum et al. patent but which also contain, as one ofthe monomers, an ester of an acrylic acid and a lower alkanol, viz., special copolymers of 1) a vinylpyridine, (2) a mixture of at least two dissimilar esters of an acrylic acid and long chain alcohols containing at least a pair of esters derived from alcohols which diflFer by at least 4 carbon atoms and which are present in a mol ratio to one another of from 1:10 to 10:1, and (3) at least one ester of an acrylic acid and a lower alkanol containing no more than 6 carbon atoms, such as methyl .methacrylate or butyl methacrylate, in which copolymer the mol ratio of the vinylpyridine to the esters is from 1:15 to 2:1 and the lower alkyl ester is from lO-to 75 mol percent of the total esters.
- the vinylpyridines used in making these special copolymers may be exemplified by 2-vinylpyridine, 3-vinylpyridine, 4-vinylpyridine, 2-methyl-5-vinylpyridine, 4- methyl-Z-vinylpyridine, S-ethyl-Lvinylpyridine and butyl-S-vinylpyridine, and the like.
- Particularly preferred groups comprise 2-, 3- and 4-vinylpyridines and the lower alkyl-substituted derivatives thereof.
- the long chain acrylate esters used in the preparation of these special copolymers include the esters of acrylic
- the acrylic acids include acrylic acid and the alphasubstituted acrylic acids such as methacrylic acid, ethacrylic acid, alpha-phenyl acrylic acid, alpha-cyclohexyl acrylic acid and chloroacrylic acid.
- the long-chain'aliphatic alcohols used in the esterification of these acids may be exemplified by decyl, lauryl, cetyl, stearyl, eicosanyl, nonadecanyl, and the like alcohols and mixtures thereof.
- Particularly preferred esters to be used are the acrylic acid and methacrylic acid esters of aliphatic monohydric alcohols, and especially alkyl alcohols, containing from 14 to 20 carbon atoms.
- these long chain acrylic acid esters include, among others, decyl acrylate, lauryl acrylate, stearyl acrylate, decyl methacrylate, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate, eicosanyl acrylate, docosanyl acrylate and the like, and mixtures thereof.
- a mixture of two or more of these long chain acrylate esters is used in making the new copolymers.
- Illustrative examples of these mixtures include, among others dodecyl methacrylate/octadecyl methacrylate, tetradecyl acrylate/octadecyl methacrylate, decyl methacrylate/octadecyl methacrylate, tetradecyl methacrylate/ hexadecyl methacrylate, tetradecyl acrylate/octadecyl methacrylate, dodecyl methacrylate/eicosanyl acrylate, and the like.
- an ester of acrylic acid or methacrylic acid and technical lauryl alcohol which is a mixture of straight chain alcohols, should not be considered such a mixture as described above since copolymers of lauryl (technical) methacrylate and a vinylpyridine will not havethe required ratio of dissimilar alkyl chains or the average alkyl chain length which is required of such preferred special copolymers.
- the third type of component used in making these special copolymers is an ester of an acrylic acid and a lower aliphatic alcohol of not more than 6 carbon atoms.
- these lower acrylates include, among others, the acrylic acid and methacrylic acid esters of methanol, ethanol, butanol, hexanol, isobutyl alcohol and propanol.
- This third component is used only in certain specific amounts. It has been found that the ester of the acrylic acids and the aliphatic alcohol containing not more than 6 carbon atoms should be employed in no more than 75 mol percent of the total acrylate ester mixture, i.e. the total of the mixture of long chain esters and the lower aliphatic monohydric alcohol containing not more than 6 carbon atoms. Preferably the lower acrylate ester is employed in amounts varying from 15% to 60% by weight of the total acrylate ester mixture.
- EXAMPLE VI A mixture of 2.52 mol of stearyl methacrylate, 5.04 mol of lauryl methacrylate, 0.83 mol of methyl methacrylate and 1 mol of Z-methyl-S-vinyl pyridine and 0.2% wt. of alpha, alpha aodiisobutyronitrile dissolved in a minor amount of acetate for solubility was placed in a reaction vessel and reacted for about 2448 hours at 65 C. with stirring in a nitrogen atmosphere. The polymer was then dispersed in equal volumes of benzene and thereafter precipitated with 5-10 volumes of a mixture of acetone and methanol.
- SMA stearyl methacrylatc
- LMA laury1 mcthacrylate
- MMA methyl mcthaerylate
- BMA butyl methacrylate
- MVP 2-methyl-5- viuylpyridinc EVP fi-ethyhZ-viuylpyridine.
- EXAMPLE XXI 29.3% stearyl methacrylate, 49.7% lauryl methacrylate, 16% methyl methacrylate and 5.0% methyl Vinylpyridine were charged to a 300-gallon stainless steel autoclave. A 50/ 50 mixture of benzene and neutral petroleum oil was then added to the autoclave so as to furnish 1 part of the mixture per 3 parts of the total monomer. 0.25% of ditert-butyl peroxide was then added and the mixture heated at 120 C. for about seven hours. At the completion of the reaction, the benzene was stripped off to final conditions of 120 C. and 10 mm. Hg with nitrogen sparging. The benzene-free product was then diluted with neutral oil to a polymer content of about 30% by weight and filtered at 120 C.
- the conductivity additive composition of the invention must contain very substantial amounts of the copolymer in proportion to the metal salt. It is generally necessary that the weight ratio of copolymer to metal in the metal salt conductivity additive be at least 20:1, more especially at least 50:1, and preferably even at least 200:1. On the other hand it will rarely be necessary that a weight ratio greater than 5000:1 of copolymer to metal in the metal salt be used, and, in order to minimize water sensi tivity of hydrocarbon liquids, especially fuels, into which the composition is incorporated, it is desirable that this ratio be no greater than 2000:1. It .is particularly preferred that this ratio be no greater than 1500:1.
- Suitable hydrocarbon base liquids into which the conductivity additive composition'of the invention can be advantageously incorporated are those normally boiling Within the range of from about -40 F. to about 700 F., i.e., those which are generally referred toas hydrocarbon distillates.
- the invention is particularly applicable to petroleum distillates in the gasoline and kerosene boiling ranges, such as gasoline (both automotive and aviation), aviation turbine fuel of the JP-l, JP4 and JP-S mineral spirits, rubber solvent, lacquer diluent, insecticide base, kersosene, and special boiling range solvents of all kinds such as direct cuts of xylenes and non-aromatics boiling in or near the xylene range, or similar toluene or benzene cuts, and also extracts and rafiinates (e.g. from S or furfural extraction) obtained from such cuts.
- the invention is of greatest benefit and importance in the case of aviation turbine fuels, especially of the kerosene type, because of the extreme danger of static electrical charges in such fuels.
- the concentration of the metal-containing salt necessary to adequately protect a hydrocarbon liquid from electrostatic phenomena is extremely minute. In general it is only necessary to provide in the hydr0- carbon liquid a concentration of the metal salt equivalent to at least l lO gram atom of the metal per liter of the hydrocarbon liquid, although in some cases no more than 1X 10* gram atom will be needed. On the other hand, because it is not desirable to incorporate in a hydrocarbon liquid too much of an ash-containing additive, it is preferred to use no more than l 10- or preferably no more than 1 10 gram atom of the metal in the form of the metal salt per liter of hydrocarbon liquid.
- Especially suitable concentrations are from about 1X10 to about 1 l0- gram atom of the metal per liter of hydrocarbon liquid.
- concentrations for example 1 l() to l 10- gram atom of metal.
- the conductivity benefits while relatively smaller are nevertheless relatively well retained by the hydrocarbon liquid.
- Example IV where there was no loss of conductivity in the case of 1X 10 mols and even 1X l0 mols chromium per liter of gasoline after 4 days.
- the loss became very significant at 1X 10* mols chromium per liter of gasoline, and as will be shown in Example XXII below, becomes very large in the case of higher concentrations and in a heavier hydrocarbon liquid.
- Fuel composition B thus contained the copolymer and metal of the metal salt conductivity additive in a weight raito of copolymer to metal (i.e., chromium) of about 450:1.
- R is an alkylene radical containing from 1 through 4 carbon atoms, preferably ethylene or 1,2-propylene.
- metal deactivators thus include, and are preferably, the compounds described in Downing et al., US. 2,181,121, November 28, 1939, and in White et al., US. 2,285,878, June 9, 1942. It is preferred that the metal deactivators, except for the oxygen and nitrogen atoms in the above structural group, be entirely hydrocarbon and that the molecular weight thereof be not more than 300.
- the especially preferred metal deactivator in the compositions of the invention is the compound N,N-disalicyiidene-1,2-propanediamine; however, another preferred compound is bis(l-acetonyl-ethylidene)-ethanediamine, which through keto-enol tautomerism contains the above group.
- the concentration of such metal deactivators in the compositions of the invention should *be at least one gram mol thereof per gram atom of metal in the metal salt conductivity additive. It is preferred that at least 5, and more especially at least gram mols of the meta] deactivator be present per gram atom of metal of the metal salt conductivity additive. Much higher concentrations of the metal deactivator can effectively be present without adversely affecting the conductivity benefits of the metal salt, even up to about 1000 or more gram mols of the metal deactivator per gram atom of metal in the conductivity additive. In general, however, economics and other considerations will dictate the use of no more than about 100, or preferably no more than about 80 gram mols of metal deactivator per gram atom of metal in the metal salt.
- the conductivity additive composition of the invention can advantageously contain sufficient mineral oil, such as kerosene, xylene, gasoline, naphtha, etc., to give the additive composition sufiicient fluidity for easy handling.
- a particularly preferred conductivity additive composition in accordance with the invention is one containing product E-2, i.e. chromium C -alkylsalicylate prepared as described in Example II above, and additionally, 450 parts by weight (for each part by weight chromium in the chromium material present) of the copolymer of Example XXt, and 50 gram mols of N,N'disalicylidene-l, Z-propanediamine per gram atom of chromium in the chromium material present.
- a particularly preferred hydrocarbon fuel composition in accordance with the invention is a jet fuel of the kerosene type containing a sufficient quantity of the additive composition of Example XXV that the concentration of chromium metal in the jet fuel is 0.03 part per million by weight.
- a conductivity composition consisting essentially of (1) a chromium alkyl salicylate having a molecular weight of 5002500 and (2) a copolymer of a vinyl pyridine and at least one ester of an acrylic acid and a long chain aliphatic alcohol containing at least 10 carbon atoms, the mol ratio of the vinyl pyridine to ester being from 1:15 to 2:1, said copolymer having an average molecular Weight between 5 10 to 25 10 the weight and 5000:1.
- the oil soluble nitrogen-containing copolymer is a copolymer of (1) a monovinyl-substituted pyridine of the group consisting of pyridines substituted on one of the ring carbon atoms with, as the sole substituted substituent, a vinyl group, and derivatives of the aforedescribed vinylpyridines having a lower alkyl group substituted on a ring carbon atom and (2) a mixture of a C to C alkyl ester of an acrylic acid of the group consisting of acrylic acid and methacrylic acid and a C to C alkyl ester of an acrylic acid of the group consisting of acrylic acid and methacrylic acid.
- a liquid hydrocarbon fuel composition consisting essentially of hydrocarbons boiling in the range of from -40 F. to 700 F. and a composition according to claim 1, in an amount suificient to provide said fuel composition with 1X10 to 1 10 gram atoms of chromium in the form of the salicylate per liter of hydrocarbon.
- liquid hydrocarbon fuel composition according to claim 3 containing in addition 1 10 to 1 10- mols per liter of a calcium dialkyl sulfosuccinate.
- the liquid hydrocarbon fuel composition according to claim 3 wherein the copolymer is one formed by copolymerization of 29.3% stearyl methacrylate, 49.7% lauryl methacrylate, 16% methyl methacrylate and 5.0% 2-methyl-5-vinyl pyridine.
- a conductivity additive composition consisting essentially of (1) a chromium alkylsalicylate having a molecular weight of from about 500 to about 2500 and (2) a copolymer of a vinylpyridine, a mixture of at least two dissimilar esters of an acrylic acid and long chain alcohols which mixture contains at least one pair of esters derived from alcohols differing by at least 4 carbon atoms and being present in a mol ratio to one another of from 1:10 to 10: 1, and at least one ester of an acrylic acid and a lower aikanol containing no more than 6 carbon atoms, in which copolymer the mol ratio of the vinylpyridine to the total esters is from 1:15 to 2:1 and the ester of the lower alkanol is from 10 to mol percent of the total esters, the weight ratio of copolymer to chromium being between 20:1 and 5000:1.
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Carbonaceous Fuels (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL120317D NL120317C (de) | 1959-05-27 | ||
NL251969D NL251969A (de) | 1959-05-27 | ||
US816039A US3013868A (en) | 1959-05-27 | 1959-05-27 | Liquid hydrocarbon compositions |
DES68679A DE1279267B (de) | 1959-05-27 | 1960-05-25 | Stabilisierung und Erhoehung der elektrischen Leitfaehigkeit von fluessigen Kohlenwasserstoffen oder deren Gemischen |
FR828239A FR1269640A (fr) | 1959-05-27 | 1960-05-25 | Liquides organiques ayant une conductivité électrique accrue |
BE591230A BE591230A (de) | 1959-05-27 | 1960-05-25 | |
GB18466/60A GB938118A (en) | 1959-05-27 | 1960-05-25 | Organic liquids having increased electrical conductivity |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US816039A US3013868A (en) | 1959-05-27 | 1959-05-27 | Liquid hydrocarbon compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US3013868A true US3013868A (en) | 1961-12-19 |
Family
ID=25219541
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US816039A Expired - Lifetime US3013868A (en) | 1959-05-27 | 1959-05-27 | Liquid hydrocarbon compositions |
Country Status (6)
Country | Link |
---|---|
US (1) | US3013868A (de) |
BE (1) | BE591230A (de) |
DE (1) | DE1279267B (de) |
FR (1) | FR1269640A (de) |
GB (1) | GB938118A (de) |
NL (2) | NL120317C (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3126260A (en) * | 1959-05-28 | 1964-03-24 | Qgganic liquid composition | |
US3210169A (en) * | 1960-12-30 | 1965-10-05 | Shell Oil Co | Hydrocarbon compositions containing salts of certain nitrogen-containing polymers with sulfodicarboxylates |
US3250113A (en) * | 1963-11-27 | 1966-05-10 | Shell Oil Co | Expendable pipeline plug |
US3256073A (en) * | 1963-03-22 | 1966-06-14 | Cities Service Oil Co | Liquid hydrocarbon compositions having antistatic properties |
US3807977A (en) * | 1972-06-30 | 1974-04-30 | Du Pont | Antistatic additive compositions |
US3995097A (en) * | 1975-09-15 | 1976-11-30 | Phillips Petroleum Company | Prevention of fouling in polymerization reactors |
US3996023A (en) * | 1968-04-11 | 1976-12-07 | Imperial Chemical Industries Limited | Aviation fuel containing dissolved polymer and having reduced tendency to particulate dissemination under shock |
RU2796997C2 (ru) * | 2020-12-27 | 2023-05-30 | ООО "Технологии синтетических ПАВ" | Способ получения антистатической присадки для углеводородных топлив и растворителей |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9522359D0 (en) * | 1995-11-01 | 1996-01-03 | Bp Chemicals Additives | Alkylation process |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2737452A (en) * | 1952-04-07 | 1956-03-06 | Du Pont | Stabilized fuel oils |
GB749898A (en) * | 1952-12-30 | 1956-06-06 | Bataafsche Petroleum | Organic liquids having increased electrical conductivity |
US2800452A (en) * | 1954-07-12 | 1957-07-23 | Shell Dev | Stabilized hydrocarbon compositions |
US2839512A (en) * | 1955-12-30 | 1958-06-17 | Shell Dev | Vinylpyridine long chain acrylic ester copolymers and their preparation |
-
0
- NL NL251969D patent/NL251969A/xx unknown
- NL NL120317D patent/NL120317C/xx active
-
1959
- 1959-05-27 US US816039A patent/US3013868A/en not_active Expired - Lifetime
-
1960
- 1960-05-25 FR FR828239A patent/FR1269640A/fr not_active Expired
- 1960-05-25 DE DES68679A patent/DE1279267B/de active Pending
- 1960-05-25 GB GB18466/60A patent/GB938118A/en not_active Expired
- 1960-05-25 BE BE591230A patent/BE591230A/xx unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2737452A (en) * | 1952-04-07 | 1956-03-06 | Du Pont | Stabilized fuel oils |
GB749898A (en) * | 1952-12-30 | 1956-06-06 | Bataafsche Petroleum | Organic liquids having increased electrical conductivity |
US2800452A (en) * | 1954-07-12 | 1957-07-23 | Shell Dev | Stabilized hydrocarbon compositions |
US2839512A (en) * | 1955-12-30 | 1958-06-17 | Shell Dev | Vinylpyridine long chain acrylic ester copolymers and their preparation |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3126260A (en) * | 1959-05-28 | 1964-03-24 | Qgganic liquid composition | |
US3210169A (en) * | 1960-12-30 | 1965-10-05 | Shell Oil Co | Hydrocarbon compositions containing salts of certain nitrogen-containing polymers with sulfodicarboxylates |
US3256073A (en) * | 1963-03-22 | 1966-06-14 | Cities Service Oil Co | Liquid hydrocarbon compositions having antistatic properties |
US3250113A (en) * | 1963-11-27 | 1966-05-10 | Shell Oil Co | Expendable pipeline plug |
US3996023A (en) * | 1968-04-11 | 1976-12-07 | Imperial Chemical Industries Limited | Aviation fuel containing dissolved polymer and having reduced tendency to particulate dissemination under shock |
US3807977A (en) * | 1972-06-30 | 1974-04-30 | Du Pont | Antistatic additive compositions |
US3995097A (en) * | 1975-09-15 | 1976-11-30 | Phillips Petroleum Company | Prevention of fouling in polymerization reactors |
RU2796997C2 (ru) * | 2020-12-27 | 2023-05-30 | ООО "Технологии синтетических ПАВ" | Способ получения антистатической присадки для углеводородных топлив и растворителей |
Also Published As
Publication number | Publication date |
---|---|
FR1269640A (fr) | 1961-08-18 |
DE1279267B (de) | 1968-10-03 |
NL251969A (de) | |
BE591230A (de) | 1960-11-25 |
NL120317C (de) | |
GB938118A (en) | 1963-10-02 |
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