US2922801A - Oil-soluble ceric salts and method of preparing the same - Google Patents
Oil-soluble ceric salts and method of preparing the same Download PDFInfo
- Publication number
- US2922801A US2922801A US379458A US37945858A US2922801A US 2922801 A US2922801 A US 2922801A US 379458 A US379458 A US 379458A US 37945858 A US37945858 A US 37945858A US 2922801 A US2922801 A US 2922801A
- Authority
- US
- United States
- Prior art keywords
- ceric
- sulfonate
- oil
- sulfate
- soluble
- 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
- 150000003839 salts Chemical class 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 20
- -1 ALKALI METAL SALT Chemical class 0.000 claims description 34
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 claims description 26
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 10
- 229910002651 NO3 Inorganic materials 0.000 claims description 8
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 8
- VDNBDUGCNUZGGR-UHFFFAOYSA-J cerium(4+);tetraperchlorate Chemical compound [Ce+4].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O VDNBDUGCNUZGGR-UHFFFAOYSA-J 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003871 sulfonates Chemical class 0.000 description 4
- SOSQXPIKTBUEKF-UHFFFAOYSA-N 1,4-dihexoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound CCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCC SOSQXPIKTBUEKF-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- CBCQTCPKFYFJEU-UHFFFAOYSA-N 1,4-dioxo-1,4-dipentoxybutane-2-sulfonic acid Chemical compound CCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCC CBCQTCPKFYFJEU-UHFFFAOYSA-N 0.000 description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RZMWTGFSAMRLQH-UHFFFAOYSA-L disodium;2,2-dihexyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCC RZMWTGFSAMRLQH-UHFFFAOYSA-L 0.000 description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- GQHDQZJQJMDTAS-VAWYXSNFSA-N (E)-1,4-dioxo-1,4-dipentoxybut-2-ene-2-sulfonic acid Chemical compound S(=O)(=O)(O)/C(/C(=O)OCCCCC)=C/C(=O)OCCCCC GQHDQZJQJMDTAS-VAWYXSNFSA-N 0.000 description 1
- ODBFNINCUIRNKD-UHFFFAOYSA-N 1,4-dioxo-1,4-di(pentadecoxy)butane-2-sulfonic acid Chemical compound CCCCCCCCCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCCCCCCCCC ODBFNINCUIRNKD-UHFFFAOYSA-N 0.000 description 1
- GTGJSOCXOWCTAJ-UHFFFAOYSA-N 1,5-diheptoxy-1,5-dioxopentane-2-sulfonic acid Chemical compound S(=O)(=O)(O)C(C(=O)OCCCCCCC)CCC(=O)OCCCCCCC GTGJSOCXOWCTAJ-UHFFFAOYSA-N 0.000 description 1
- KVGOXGQSTGQXDD-UHFFFAOYSA-N 1-decane-sulfonic-acid Chemical compound CCCCCCCCCCS(O)(=O)=O KVGOXGQSTGQXDD-UHFFFAOYSA-N 0.000 description 1
- ZHGIKBCGOGBDFG-UHFFFAOYSA-N 1-icosylnaphthalene Chemical compound C1=CC=C2C(CCCCCCCCCCCCCCCCCCCC)=CC=CC2=C1 ZHGIKBCGOGBDFG-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- UAZLASMTBCLJKO-UHFFFAOYSA-N 2-decylbenzenesulfonic acid Chemical compound CCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O UAZLASMTBCLJKO-UHFFFAOYSA-N 0.000 description 1
- JSFATNQSLKRBCI-NLORQXDXSA-N 73945-47-8 Chemical compound CCCCCC(O)\C=C\C=C\C\C=C\C\C=C\CCCC(O)=O JSFATNQSLKRBCI-NLORQXDXSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ZTHQBROSBNNGPU-UHFFFAOYSA-N Butyl hydrogen sulfate Chemical compound CCCCOS(O)(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- NIKBCKTWWPVAIC-UHFFFAOYSA-N butyl benzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=CC=C1 NIKBCKTWWPVAIC-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- NEXGLIFZDFMSDG-UHFFFAOYSA-N decyl benzenesulfonate;potassium Chemical compound [K].CCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 NEXGLIFZDFMSDG-UHFFFAOYSA-N 0.000 description 1
- CSMFSDCPJHNZRY-UHFFFAOYSA-M decyl sulfate Chemical compound CCCCCCCCCCOS([O-])(=O)=O CSMFSDCPJHNZRY-UHFFFAOYSA-M 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 229960000878 docusate sodium Drugs 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- SQEDZTDNVYVPQL-UHFFFAOYSA-N dodecylbenzene;sodium Chemical compound [Na].CCCCCCCCCCCCC1=CC=CC=C1 SQEDZTDNVYVPQL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- KGIBGHABTNQVJX-UHFFFAOYSA-N heptadecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCCCCCCOS(O)(=O)=O KGIBGHABTNQVJX-UHFFFAOYSA-N 0.000 description 1
- XWJHULLYLHDLRN-UHFFFAOYSA-N heptadecyl naphthalene-1-sulfonate Chemical compound CCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC2=CC=CC=C12 XWJHULLYLHDLRN-UHFFFAOYSA-N 0.000 description 1
- MIHVYISIUZTFER-UHFFFAOYSA-N heptyl hydrogen sulfate Chemical compound CCCCCCCOS(O)(=O)=O MIHVYISIUZTFER-UHFFFAOYSA-N 0.000 description 1
- CMJSCCWFUCUDJI-UHFFFAOYSA-N heptyl naphthalene-1-sulfonate Chemical compound C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCCCCCCC CMJSCCWFUCUDJI-UHFFFAOYSA-N 0.000 description 1
- SSILHZFTFWOUJR-UHFFFAOYSA-N hexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCS(O)(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-N 0.000 description 1
- LPTIRUACFKQDHZ-UHFFFAOYSA-N hexadecyl sulfate;hydron Chemical compound CCCCCCCCCCCCCCCCOS(O)(=O)=O LPTIRUACFKQDHZ-UHFFFAOYSA-N 0.000 description 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- KTUVYMAZYSSBKC-UHFFFAOYSA-N hexyl benzenesulfonate Chemical compound CCCCCCOS(=O)(=O)C1=CC=CC=C1 KTUVYMAZYSSBKC-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IDUWTCGPAPTSFB-UHFFFAOYSA-N hexyl hydrogen sulfate Chemical compound CCCCCCOS(O)(=O)=O IDUWTCGPAPTSFB-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- JFNAJRJKQQEFNH-UHFFFAOYSA-M lithium;octane-1-sulfonate Chemical compound [Li+].CCCCCCCCS([O-])(=O)=O JFNAJRJKQQEFNH-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- UZZYXUGECOQHPU-UHFFFAOYSA-M n-octyl sulfate Chemical compound CCCCCCCCOS([O-])(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- JKTVUKBHRRIGSI-UHFFFAOYSA-N nonadecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCCCCCCCCOS(O)(=O)=O JKTVUKBHRRIGSI-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- GVRNEIKWGDQKPS-UHFFFAOYSA-N nonyl benzenesulfonate Chemical compound CCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVRNEIKWGDQKPS-UHFFFAOYSA-N 0.000 description 1
- KETHQOOVMIVLCH-UHFFFAOYSA-M nonyl sulfate(1-) Chemical compound CCCCCCCCCOS([O-])(=O)=O KETHQOOVMIVLCH-UHFFFAOYSA-M 0.000 description 1
- CACRRXGTWZXOAU-UHFFFAOYSA-N octadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCS(O)(=O)=O CACRRXGTWZXOAU-UHFFFAOYSA-N 0.000 description 1
- FFQLQBKXOPDGSG-UHFFFAOYSA-N octadecyl benzenesulfonate Chemical compound CCCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 FFQLQBKXOPDGSG-UHFFFAOYSA-N 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- GVMDZMPQYYHMSV-UHFFFAOYSA-N octyl benzenesulfonate Chemical compound CCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVMDZMPQYYHMSV-UHFFFAOYSA-N 0.000 description 1
- 229940067739 octyl sulfate Drugs 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- COUMKTRLCGRAAA-UHFFFAOYSA-M pentadecyl sulfate Chemical compound CCCCCCCCCCCCCCCOS([O-])(=O)=O COUMKTRLCGRAAA-UHFFFAOYSA-M 0.000 description 1
- RJQRCOMHVBLQIH-UHFFFAOYSA-N pentane-1-sulfonic acid Chemical compound CCCCCS(O)(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-N 0.000 description 1
- ZIRHAFGGEBQZKX-UHFFFAOYSA-N pentyl hydrogen sulfate Chemical compound CCCCCOS(O)(=O)=O ZIRHAFGGEBQZKX-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- QFQCYYXEVGXDJR-UHFFFAOYSA-M potassium;decane-1-sulfonate Chemical compound [K+].CCCCCCCCCCS([O-])(=O)=O QFQCYYXEVGXDJR-UHFFFAOYSA-M 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 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 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- URLJMZWTXZTZRR-UHFFFAOYSA-N sodium myristyl sulfate Chemical compound CCCCCCCCCCCCCCOS(O)(=O)=O URLJMZWTXZTZRR-UHFFFAOYSA-N 0.000 description 1
- 229960000776 sodium tetradecyl sulfate Drugs 0.000 description 1
- XQCHMGAOAWZUPI-UHFFFAOYSA-M sodium;butane-1-sulfonate Chemical compound [Na+].CCCCS([O-])(=O)=O XQCHMGAOAWZUPI-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- HRQDCDQDOPSGBR-UHFFFAOYSA-M sodium;octane-1-sulfonate Chemical compound [Na+].CCCCCCCCS([O-])(=O)=O HRQDCDQDOPSGBR-UHFFFAOYSA-M 0.000 description 1
- CSMFSDCPJHNZRY-UHFFFAOYSA-N sulfuric acid monodecyl ester Natural products CCCCCCCCCCOS(O)(=O)=O CSMFSDCPJHNZRY-UHFFFAOYSA-N 0.000 description 1
- UZZYXUGECOQHPU-UHFFFAOYSA-N sulfuric acid monooctyl ester Natural products CCCCCCCCOS(O)(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-N 0.000 description 1
- MYOWBHNETUSQPA-UHFFFAOYSA-N tetradecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCS(O)(=O)=O MYOWBHNETUSQPA-UHFFFAOYSA-N 0.000 description 1
- JLQAXOXQVQGQLG-UHFFFAOYSA-N tetradecyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCCCCCCCCCCCC)=CC=CC2=C1 JLQAXOXQVQGQLG-UHFFFAOYSA-N 0.000 description 1
- QTUIJRIDZOSXHJ-UHFFFAOYSA-M tridecyl sulfate Chemical compound CCCCCCCCCCCCCOS([O-])(=O)=O QTUIJRIDZOSXHJ-UHFFFAOYSA-M 0.000 description 1
- OBYIEPMKXIBQEV-UHFFFAOYSA-N undecyl hydrogen sulfate Chemical compound CCCCCCCCCCCOS(O)(=O)=O OBYIEPMKXIBQEV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
Definitions
- an inorganic ceric salt with an alkali metal salt of a material selected from the group consisting of an alkyl sulfate, an alkyl mono aromaticsulfonate, a sulfonate of an aliphatic polycarboxylic acid dialkyl ester and an aliphatic hydrocarbon sulfonate.
- the inorganic ceric salts may be any one of the following: ceric nitrate, ceric ammonium nitrate, ceric perchlorate and the like. These inorganic ceric salts may be used'either singly or in combination with one another.
- the alkali metal salts used as starting materials in the practice of the process of the present invention may be the sodium salts, potassium salts, lithium salts, and the like. Included in the group of alkali metal salts which may be used are sodium monobutyl acid sulfate, potassium monoamyl acid sulfate, sodium monooctyl acid sulfate, sodium monolauryl acid sulfate, potassium monodecyl acid sulfate, lithium mono-undecyl acid sulfate, sodium octyl benzene sulfonate, potassium decyl benzene sulfonate, sodium dioctyl sulfosuccinate, lithium diheptyl sulfoglutarate, potassium didecyl sulfosuberate, sodium dilauryl sulfosebacate, potassium diamyl sulfomaleate, sodium dimethyl sulfofuma
- ceric alkyl sulfates which may be prepared according to the process of the present invention are those ceric alkyl sulfates in which the alkyl group contains between 4 and 20 carbon atoms and preferably between 8 and 12 carbon atoms. Included in .the group are ceric butyl sulfate, ceric amyl sulfate, ceric hexyl sulfate, ceric heptyl sulfate, ceric octyl sulfate, ceric nonyl sulfate, ceric decyl sulfate, ceric undecyl sulfate,
- ceric dodecyl sulfate ceric tridecyl sulfate, ceric tetradecyl sulfate, ceric pentadecyl sulfate, ceric hexadecyl sulfate, ceric heptadecyl sulfate, ceric octadecyl sulfate, ceric nonadecyl sulfate, and ceric eicosyl sulfate.
- the alkyl groups in these ceric alkyl sulfates may be either a straight chain or a branch chain.
- oil-soluble ceric alkyl mono aromatic sulfonates which may be prepared according to the present invention are those in which the alkyl groups attached to the mono aromatic ring contain between 3 and 20 carbon atoms, and preferably between 8 and 12 carbon atoms.
- the mono aromatic grouping in said sulfonates may be phenyl, naphthyl, anthracyl, triphenylyl, perylyl, and the like.
- these compounds include ceric butyl benzene sulfonate, ceric hexyl benzene sulfonate, ceric octyl benzene sulfonate, ceric nonyl benzene sulfonate, ceric decyl benzene sulfonate, ceric dodecyl benzene sulfonate, ceric octadecyl benzene sulfonate, ceric isopropyl naphthalene sulfonate, ceric heptyl naphthalene sulfonate, ceric tetradecyl naphthalene sulfonate, ceric heptadecyl naphthalene sulfonate, ceric eicosyl naphthalene sulfonate, and the like.
- oil-soluble ceric sulfonates of an aliphatic polycarboxylic acid dialkyl ester which may be prepared from the process of the present invention are those prepared from the sodium salts of a sulfonate of an aliphatic polycarboxylic acid dialkyl ester.
- These sodium salts and other alkali metal salts are shown in considerable detail in the US. Patent 2,028,091.
- the aliphatic dicarboxylic acids which may be used as starting materials include malonic, succinic, glutaric, sebacic, adipic, pimelic, suberic, azelaic, citric, tartaric, malic, maleic, fumaric, aconitic, itaconic, and the like.
- the diesters of these acids are prepared by reacting an aliphatic monohydric alcohol containing from 1 to 15 carbon atoms and preferably containing from 4 to 8 carbon atoms so as to form the dialkyl ester of said polycarboxylic acid. More specifically the following oil-soluble ceric salts may be prepared by the process of the present invention: ceric dihexyl sulfosuccinate, ceric dioctyl sulfosuccinate, ceric diheptyl sulfoglutarate, ceric didecyl sulfosubarate, ceric dilauryl sulfosebacate, ceric diamyl sulfomaleate, ceric diceric dibutyl sulfodimethyl succinate, ceric dilauryl sulfomethyl glutarate, ceric dipentadecyl sulfosuccinate, and the like.
- oil-soluble ceric aliphatic hydrocarbon sulfonates which may be prepared in keeping with the process of the present invention are those in which the aliphatic hydrocarbon contains between 4 and 20 carbon atoms and preferably those containing between 8 and 12 carbon atoms.
- the oil-soluble ceric aliphatic hydrocarbon sulfonates of the present invention include ceric butyl sulfonate, ceric amyl sulfonate, ceric hexyl sulfonate, ceric octyl sulfonate, ceric decyl sulfonate, ceric dodecyl sulfonate, ceric tetradecyl sulfonate, ceric hexadecyl sulfonate, ceric octadecyl sulfonate, ceric eicosyl sulfonate, and the like.
- the inorganic ceric salt is introduced into the reaction sphere with an alkali metal salt of an alkyl sulfate or an alkyl mono aromatic sulfonate or a sulfonate of an aliphatic polycarboxylic acid dialkyl ester or an aliphatic hydrocarbon sulfonate in an aqueous medium.
- the temperature of the reaction may be controlled between about 0 C. and 40 C. and preferably between 20 and 25 C .
- the pH of the system should be adjusted to 3.5 or below and preferably between about 1 and 2.
- the system will be rendered acidic by the use of an acid material and preferably an inorganic acid material such as nitric acid,
- perchloric acid perchloric acid, and the like.
- agitation is preferred as contrasted with quiescence in the course of reaction.
- the alkali metal sulfate or sulfonate may be used such as 5 mols or even 6 but no appreciable advantage is to be gained. It is preferred that the mol ratio of the alkali metal sulfates or sulfonates per mol of ceric inorganic salt be controlled between about 1.521 and 2:1, respectively.
- novel oil-soluble ceric salts'of the present invention will find utility in the polymerization of polymerizable monomeric compounds such as styrene, acrylonitrile, vinyl acetate, acrylamide, and the like, and particularly in a system in which a grafting mechanism is being carried out with a polymeric organic reducing agent such as when an aqueous emulsion system is utilized.
- Example 1 Into a suitable reaction vessel equipped with a mechanical stirrer, there is introduced a solution of 11 parts of ceric ammonium nitrate in 100 parts of water at room temperature. With constant stirring, there is added thereto a solution of 15.4-parts of sodium dihexyl sulfosuccinate in 100 parts of water. The stirring is continued even after the addition is completed and is stopped only when all of the precipitate has come out of the blended solutions. The precipitate is separated from the water by a simple filtration producing a yield of 14 parts of ceric dihexyl sulfosuccinate. 7
- Example 2 parts of a 0.1 molar solution of nitric acid at 15 C.
- Example 3 11 parts of ceric ammonium nitrate are dissolved in 100 parts of a 0.1 molar solution of nitric acid at 25 C. To this solution there is added, with rapid stirring,
- oil soluble is one frequently used in the art and signifies solubility in an organic solvent, which sol: vent is itself not miscible with water.
- solvents A plurality of these solvents have been recited hereinabove and a substantial plurality of said solvents are well known in the art.
- An oil-soluble ceric salt selected from the group consisting of (1) a ceric alkyl sulfate, (2) a ceric alkyl arene sulfonate, (3) a ceric sulfonate of an unsubstituted aliphatic polycarboxylic acid dialkyl ester and (4) a ceric aliphatic hydrocarbon sulfonate.
- a method for preparing an .oil-soluble ceric salt which comprises reacting an inorganic ceric salt selected from the group consisting of ceric nitrate, ceric ammonium nitrate and ceric perchlorate with an alkali metal salt of a material selected from the group consisting of (1) an alkyl sulfate, (2) an alkyl arene sulfonate, (3) a sulfonate of an unsubstituted aliphatic polycarboxylic acid dialkyl ester and (4) an aliphatic hydrocarbon sulfonate.
- a method for preparing an oil-soluble ceric comprising reacting an inorganic ceric salt selected from the group consisting of ceric nitrate, ceric ammonium comprising reactlng an inorganic ceric salt selected from the group consisting of'ceric nitrate, ceric ammonium nitrate and ceric perchlorate with an alkali metal salt of an alkyl arene sulfonate.
- a method for preparing an oil-soluble ceric salt comprising reacting an inorganic ceric salt selected from the group consisting of ceric nitrate, ceric ammonium nitrate and ceric perchlorate with an alkali metal salt of a sulfonate of an unsubstituted aliphaticpolycarboxylic acid dialkyl ester.
- a method for preparing an oil-soluble ceric salt comprising reacting an inorganic ceric salt selected from the group consisting of ceric nitrate, ceric ammonium nitrate and ceric perchlorate with an alkali metal salt of an aliphati hydrocarbon .sulfonate.
- a method comprising reacting ceric ammonium nitrate with sodium dihexyl sulfosuccinate.
- a process comprising reacting cetjic ammonium nitrate with sodium dodecyl benzene sulfona'te.
- a process comprising reacting ceric ammonium nitrate with sodium dodecyl sulfate.
- a process comprising reacting ceric ammonium nitrate with'sodium dodecyl'sulfonate.
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Description
Unite States OIL-SOLUBLE CERIC SALTS AND METHOD F PREPARING THE SAME Samuel Kaizerman, North Plainfield, and Guido Mino,
Plainfield, N.J., assignors to American Cyanamid Company, New York, N.Y., a corporation of Maine No Drawing. Application June 3, 1958 Serial No. 739,458
20 Claims. (Cl. 260-4292) utility particularly as graft polymerization initiators in a vinyl polymerization system. These and other objects of the'present invention will be discussed in greater detail hereinbelow.
This application is a continuation-in-part of our earlier application having the Serial No. 628,212, filed December 14, 1956, entitled Process for Polymerization and the Products Produced Thereby. Said application is a continuation-in-part of our parent case having the Serial No.
577,641, filed April 12, 1956, entitled Process for Polymerization and the Products Produced Thereby, now abandoned.
In producing the novel oil-soluble ceric salts of the present invention, one may react an inorganic ceric salt with an alkali metal salt of a material selected from the group consisting of an alkyl sulfate, an alkyl mono aromaticsulfonate, a sulfonate of an aliphatic polycarboxylic acid dialkyl ester and an aliphatic hydrocarbon sulfonate. The inorganic ceric salts may be any one of the following: ceric nitrate, ceric ammonium nitrate, ceric perchlorate and the like. These inorganic ceric salts may be used'either singly or in combination with one another.
The alkali metal salts used as starting materials in the practice of the process of the present invention may be the sodium salts, potassium salts, lithium salts, and the like. Included in the group of alkali metal salts which may be used are sodium monobutyl acid sulfate, potassium monoamyl acid sulfate, sodium monooctyl acid sulfate, sodium monolauryl acid sulfate, potassium monodecyl acid sulfate, lithium mono-undecyl acid sulfate, sodium octyl benzene sulfonate, potassium decyl benzene sulfonate, sodium dioctyl sulfosuccinate, lithium diheptyl sulfoglutarate, potassium didecyl sulfosuberate, sodium dilauryl sulfosebacate, potassium diamyl sulfomaleate, sodium dimethyl sulfofumarate, sodium dibutyl sulfodimethyl succinate, potassium dilauryl sulfomethyl glutarate, sodium butyl sulfonate, potassium hexyl sul-- fonate, lithium octyl sulfonate, potassium decyl sulfonate, sodium dodecyl sulfonate, and the like. 7
Among the oil-soluble ceric alkyl sulfates which may be prepared according to the process of the present invention are those ceric alkyl sulfates in which the alkyl group contains between 4 and 20 carbon atoms and preferably between 8 and 12 carbon atoms. Included in .the group are ceric butyl sulfate, ceric amyl sulfate, ceric hexyl sulfate, ceric heptyl sulfate, ceric octyl sulfate, ceric nonyl sulfate, ceric decyl sulfate, ceric undecyl sulfate,
atent methyl sulfofumarate,
ice
ceric dodecyl sulfate, ceric tridecyl sulfate, ceric tetradecyl sulfate, ceric pentadecyl sulfate, ceric hexadecyl sulfate, ceric heptadecyl sulfate, ceric octadecyl sulfate, ceric nonadecyl sulfate, and ceric eicosyl sulfate. The alkyl groups in these ceric alkyl sulfates may be either a straight chain or a branch chain.
Among the oil-soluble ceric alkyl mono aromatic sulfonates which may be prepared according to the present invention are those in which the alkyl groups attached to the mono aromatic ring contain between 3 and 20 carbon atoms, and preferably between 8 and 12 carbon atoms. The mono aromatic grouping in said sulfonates may be phenyl, naphthyl, anthracyl, triphenylyl, perylyl, and the like. More specifically, these compounds include ceric butyl benzene sulfonate, ceric hexyl benzene sulfonate, ceric octyl benzene sulfonate, ceric nonyl benzene sulfonate, ceric decyl benzene sulfonate, ceric dodecyl benzene sulfonate, ceric octadecyl benzene sulfonate, ceric isopropyl naphthalene sulfonate, ceric heptyl naphthalene sulfonate, ceric tetradecyl naphthalene sulfonate, ceric heptadecyl naphthalene sulfonate, ceric eicosyl naphthalene sulfonate, and the like.
Among the oil-soluble ceric sulfonates of an aliphatic polycarboxylic acid dialkyl ester which may be prepared from the process of the present invention are those prepared from the sodium salts of a sulfonate of an aliphatic polycarboxylic acid dialkyl ester. These sodium salts and other alkali metal salts are shown in considerable detail in the US. Patent 2,028,091. The aliphatic dicarboxylic acids which may be used as starting materials include malonic, succinic, glutaric, sebacic, adipic, pimelic, suberic, azelaic, citric, tartaric, malic, maleic, fumaric, aconitic, itaconic, and the like. The diesters of these acids are prepared by reacting an aliphatic monohydric alcohol containing from 1 to 15 carbon atoms and preferably containing from 4 to 8 carbon atoms so as to form the dialkyl ester of said polycarboxylic acid. More specifically the following oil-soluble ceric salts may be prepared by the process of the present invention: ceric dihexyl sulfosuccinate, ceric dioctyl sulfosuccinate, ceric diheptyl sulfoglutarate, ceric didecyl sulfosubarate, ceric dilauryl sulfosebacate, ceric diamyl sulfomaleate, ceric diceric dibutyl sulfodimethyl succinate, ceric dilauryl sulfomethyl glutarate, ceric dipentadecyl sulfosuccinate, and the like.
Among the oil-soluble ceric aliphatic hydrocarbon sulfonates which may be prepared in keeping with the process of the present invention are those in which the aliphatic hydrocarbon contains between 4 and 20 carbon atoms and preferably those containing between 8 and 12 carbon atoms. More specifically, the oil-soluble ceric aliphatic hydrocarbon sulfonates of the present invention include ceric butyl sulfonate, ceric amyl sulfonate, ceric hexyl sulfonate, ceric octyl sulfonate, ceric decyl sulfonate, ceric dodecyl sulfonate, ceric tetradecyl sulfonate, ceric hexadecyl sulfonate, ceric octadecyl sulfonate, ceric eicosyl sulfonate, and the like.
In the practice of the process of the present invention, the inorganic ceric salt is introduced into the reaction sphere with an alkali metal salt of an alkyl sulfate or an alkyl mono aromatic sulfonate or a sulfonate of an aliphatic polycarboxylic acid dialkyl ester or an aliphatic hydrocarbon sulfonate in an aqueous medium. The temperature of the reaction may be controlled between about 0 C. and 40 C. and preferably between 20 and 25 C .The pH of the system should be adjusted to 3.5 or below and preferably between about 1 and 2. The system will be rendered acidic by the use of an acid material and preferably an inorganic acid material such as nitric acid,
perchloric acid, and the like. In order to insure substanmono aromatic sulfonates or the sulfonates of an aliphatic polycarboxylic acid dialkyl ester or the aliphatic hydrocarbon sulfonates, agitation is preferred as contrasted with quiescence in the course of reaction. For satisfactory yields, one should use at least 1 mol Ofthe alkali metal sulfate or sulfonate per mol of the eerie inorganic salt and as much as 4 mols of the alkali metal sulfate or sulfonate per mol of the ceric inorganic salt. Larger quantities of the alkali metal sulfate or sulfonate may be used such as 5 mols or even 6 but no appreciable advantage is to be gained. It is preferred that the mol ratio of the alkali metal sulfates or sulfonates per mol of ceric inorganic salt be controlled between about 1.521 and 2:1, respectively.
The novel oil-soluble ceric salts'of the present invention will find utility in the polymerization of polymerizable monomeric compounds such as styrene, acrylonitrile, vinyl acetate, acrylamide, and the like, and particularly in a system in which a grafting mechanism is being carried out with a polymeric organic reducing agent such as when an aqueous emulsion system is utilized.
In order that the concept of the present invention may be more completely understood, the following examples are set forth in which all parts are parts by weight unless otherwise indicated. These examples are set forth primarily for the purpose of illustration and any specific enumeration of detail contained therein should not be interpreted as a limitation on the case except as is indicated in the appended claims. a 7
Example 1 Into a suitable reaction vessel equipped with a mechanical stirrer, there is introduced a solution of 11 parts of ceric ammonium nitrate in 100 parts of water at room temperature. With constant stirring, there is added thereto a solution of 15.4-parts of sodium dihexyl sulfosuccinate in 100 parts of water. The stirring is continued even after the addition is completed and is stopped only when all of the precipitate has come out of the blended solutions. The precipitate is separated from the water by a simple filtration producing a yield of 14 parts of ceric dihexyl sulfosuccinate. 7
Example 2 parts of a 0.1 molar solution of nitric acid at 15 C.
The resulting yellow precipitate, after separation by filtra: tion and drying in vacuo at C., weighed 12.6 parts and was identified as ceric diamyl sulfosuccinate.
Example 3 11 parts of ceric ammonium nitrate are dissolved in 100 parts of a 0.1 molar solution of nitric acid at 25 C. To this solution there is added, with rapid stirring,
a solution of 13.8 parts of sodium dodecyl benzene sulfonate in 100 parts of water. The yellow precipitate which formed was separated by filtration and dried in vacuo at 45 C. The yield was 4.8 parts and was identified as ceric dodecyl benzene sulfonate. The ceric salt thus produced was soluble in' ethyl acetate, benzene and chloroform. v 7
Example 4 y seesh eri e and mete 1. m re.
fate and was soluble in benzene, methyl acrylate, meth- 11 parts of ceric ammonium nitrate are dissolved in parts of 0.1 N nitric acid at 20 C. To this is added with rapid stirring a solution of 8.7 parts of sodium octane sulfonate in 100 parts ofwater. The yellow precipitate is separated by filtration, washed with water, then dried in vacuo at 4045 C. The yield is 5.7 parts.
The term oil soluble is one frequently used in the art and signifies solubility in an organic solvent, which sol: vent is itself not miscible with water. A plurality of these solvents have been recited hereinabove and a substantial plurality of said solvents are well known in the art.
Further delineation is deemed to be unnecessary.
We claim:
1. An oil-soluble ceric salt selected from the group consisting of (1) a ceric alkyl sulfate, (2) a ceric alkyl arene sulfonate, (3) a ceric sulfonate of an unsubstituted aliphatic polycarboxylic acid dialkyl ester and (4) a ceric aliphatic hydrocarbon sulfonate.
2, An oil-soluble ceric alkyl sulfate.
3.'An oil-soluble ceric alkyl arene sulfonate.
4,. An oil-soluble ceric sulfonate of an unsubstituted aliphatic polycarboxylic acid dialkyl ester. 5. An oil-soluble ceric aliphatic hydrocarbon sulfonate.
6. Ceric dihexyl sulfosuccinate. '7. Ceric diamyl sulfosuccinate.
8. Ceric dodecyl benzene sultonate.
9. Ceric dodecyl sulfate.
10. ,Ceric dodecyl sulfonate.
11, A method for preparing an .oil-soluble ceric salt which comprises reacting an inorganic ceric salt selected from the group consisting of ceric nitrate, ceric ammonium nitrate and ceric perchlorate with an alkali metal salt of a material selected from the group consisting of (1) an alkyl sulfate, (2) an alkyl arene sulfonate, (3) a sulfonate of an unsubstituted aliphatic polycarboxylic acid dialkyl ester and (4) an aliphatic hydrocarbon sulfonate. g
12. A method for preparing an oil-soluble ceric comprising reacting an inorganic ceric salt selected from the group consisting of ceric nitrate, ceric ammonium comprising reactlng an inorganic ceric salt selected from the group consisting of'ceric nitrate, ceric ammonium nitrate and ceric perchlorate with an alkali metal salt of an alkyl arene sulfonate.
14. A method for preparing an oil-soluble ceric salt comprising reacting an inorganic ceric salt selected from the group consisting of ceric nitrate, ceric ammonium nitrate and ceric perchlorate with an alkali metal salt of a sulfonate of an unsubstituted aliphaticpolycarboxylic acid dialkyl ester.
15. A method for preparing an oil-soluble ceric salt comprising reacting an inorganic ceric salt selected from the group consisting of ceric nitrate, ceric ammonium nitrate and ceric perchlorate with an alkali metal salt of an aliphati hydrocarbon .sulfonate. V
16. A method comprising reacting ceric ammonium nitrate with sodium dihexyl sulfosuccinate. V f
17. A process comprising reacting, ceric ammonium nitrate with sodium diamyl sulfosuccinate. H ,1 "f
18. A process comprising reacting cetjic ammonium nitrate with sodium dodecyl benzene sulfona'te. i
19. A process comprising reacting ceric ammonium nitrate with sodium dodecyl sulfate.
.20. A process comprising reacting ceric ammonium nitrate with'sodium dodecyl'sulfonate.
2,485,535 Park 2 :5 4;50 H wa d.
nitrate and ceric perchlorate with an alkali metal salt of
Claims (2)
1. AN OIL-SOLUBLE CERIC SALT SELECTED FROM THE GROUP CONSISTING OF (1) A CERIC ALKYL SULFATE, (2) A CERIC ALKYL ARENE SULFONATE, (3) A CERIC SULFONATE OF AN UNSUBSTITUTED ALIPHATIC POLYCARBOXYLIC ACID DIALKYL ESTER AND (4) A CERIC ALIPHATIC HYDROCARBON SULFONATE.
11. A METHOD FOR PREPARING AN OIL-SOLUBLE CERIC SALT WHICH COMPRISES REACTING AN INORGANIC CERIC SALT SELECTED FROM THE GROUP CONSISTING OF CERIC NITRATE, CERIC AMMONIUM NITRATE AND CERIC PERCHLORATE WITH AN ALKALI METAL SALT OF A MATERIAL SELECTED FROM THE GROUP CONSISTING OF (1) AN ALKYL SULFATE, (2) AN ALKYL ARENE SULFONATE, (3) A SULFONATE OFF AN UNSUBSTITUTED ALIPHATIC POLYCARBOXYLIC ACID DIALKYL ESTER AND (4) AN ALIPHATIC HYDROCARBON SULFONATE.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3157682A (en) * | 1960-11-04 | 1964-11-17 | Exxon Research Engineering Co | Oil-soluble liquid chelate compounds and their preparation |
EP0134161A1 (en) * | 1983-08-09 | 1985-03-13 | Rhone-Poulenc Chimie | Process for the preparation of cerium alcoholates |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2485535A (en) * | 1946-12-12 | 1949-10-18 | Monsanto Chemicals | Ceric sulfate catalyzed emulsion polymerization of styrene |
US2594560A (en) * | 1950-04-27 | 1952-04-29 | Du Pont | Low-temperature polymerization of ethylenic compounds using as initiators compositions comprising sodium azide and an oxidant |
-
1958
- 1958-06-03 US US379458A patent/US2922801A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2485535A (en) * | 1946-12-12 | 1949-10-18 | Monsanto Chemicals | Ceric sulfate catalyzed emulsion polymerization of styrene |
US2594560A (en) * | 1950-04-27 | 1952-04-29 | Du Pont | Low-temperature polymerization of ethylenic compounds using as initiators compositions comprising sodium azide and an oxidant |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3157682A (en) * | 1960-11-04 | 1964-11-17 | Exxon Research Engineering Co | Oil-soluble liquid chelate compounds and their preparation |
EP0134161A1 (en) * | 1983-08-09 | 1985-03-13 | Rhone-Poulenc Chimie | Process for the preparation of cerium alcoholates |
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