US2150349A - Process and product relating to organic metal and metalloid containing complex compounds - Google Patents
Process and product relating to organic metal and metalloid containing complex compounds Download PDFInfo
- Publication number
- US2150349A US2150349A US73710A US7371036A US2150349A US 2150349 A US2150349 A US 2150349A US 73710 A US73710 A US 73710A US 7371036 A US7371036 A US 7371036A US 2150349 A US2150349 A US 2150349A
- Authority
- US
- United States
- Prior art keywords
- metal
- organic
- compound
- compounds
- acid
- 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
- 229910052751 metal Inorganic materials 0.000 title description 50
- 239000002184 metal Substances 0.000 title description 50
- 150000001875 compounds Chemical class 0.000 title description 40
- 229910052752 metalloid Inorganic materials 0.000 title description 21
- 150000002738 metalloids Chemical class 0.000 title description 19
- 238000000034 method Methods 0.000 title description 17
- 239000000376 reactant Substances 0.000 description 46
- 150000002894 organic compounds Chemical class 0.000 description 37
- 230000000737 periodic effect Effects 0.000 description 21
- 239000002253 acid Substances 0.000 description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- -1 alkaline earth metal carbonates Chemical class 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 14
- 229910044991 metal oxide Inorganic materials 0.000 description 13
- 150000004706 metal oxides Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- 229910000000 metal hydroxide Inorganic materials 0.000 description 12
- 150000004692 metal hydroxides Chemical class 0.000 description 12
- 150000002736 metal compounds Chemical class 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 5
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 5
- 229940112669 cuprous oxide Drugs 0.000 description 5
- 239000000446 fuel Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000002895 organic esters Chemical class 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001414 amino alcohols Chemical class 0.000 description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 150000003003 phosphines Chemical class 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 150000002737 metalloid compounds Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- UBJVUCKUDDKUJF-UHFFFAOYSA-N Diallyl sulfide Chemical compound C=CCSCC=C UBJVUCKUDDKUJF-UHFFFAOYSA-N 0.000 description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- RVIXKDRPFPUUOO-UHFFFAOYSA-N dimethylselenide Chemical compound C[Se]C RVIXKDRPFPUUOO-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WXEHBUMAEPOYKP-UHFFFAOYSA-N methylsulfanylethane Chemical compound CCSC WXEHBUMAEPOYKP-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000004986 phenylenediamines Chemical class 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- 239000002641 tar oil Substances 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 2
- HTDIUWINAKAPER-UHFFFAOYSA-N trimethylarsine Chemical compound C[As](C)C HTDIUWINAKAPER-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- PSKWBKFCLVNPMT-NSCUHMNNSA-N (e)-but-2-ene-1-thiol Chemical compound C\C=C\CS PSKWBKFCLVNPMT-NSCUHMNNSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- PCXJASANFWPUMO-UHFFFAOYSA-N 1-(methylamino)propan-1-ol Chemical compound CCC(O)NC PCXJASANFWPUMO-UHFFFAOYSA-N 0.000 description 1
- WAULAQAPARJWJJ-UHFFFAOYSA-N 1-butylselanylbutane Chemical compound CCCC[Se]CCCC WAULAQAPARJWJJ-UHFFFAOYSA-N 0.000 description 1
- GDZQGHGCKKWNAC-UHFFFAOYSA-N 1-phenyl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical group N1=CC=2C(O)=NC=NC=2N1C1=CC=CC=C1 GDZQGHGCKKWNAC-UHFFFAOYSA-N 0.000 description 1
- WIESVFXHPDMQMQ-UHFFFAOYSA-N 1-propylselanylpropane Chemical compound CCC[Se]CCC WIESVFXHPDMQMQ-UHFFFAOYSA-N 0.000 description 1
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- KSSWDYHDNFXVRM-UHFFFAOYSA-N 2-methyl-1-(2-methylprop-1-enylsulfanyl)prop-1-ene Chemical compound CC(C)=CSC=C(C)C KSSWDYHDNFXVRM-UHFFFAOYSA-N 0.000 description 1
- WVYSWPBECUHBMJ-UHFFFAOYSA-N 2-methylprop-1-en-1-ol Chemical compound CC(C)=CO WVYSWPBECUHBMJ-UHFFFAOYSA-N 0.000 description 1
- FIEMNCUPUKWJBC-UHFFFAOYSA-N 2-methylprop-1-ene-1-thiol Chemical compound CC(C)=CS FIEMNCUPUKWJBC-UHFFFAOYSA-N 0.000 description 1
- RNBCQLCYZIHPON-UHFFFAOYSA-N 3-(4-bromophenyl)-2-methylprop-2-enal Chemical compound O=CC(C)=CC1=CC=C(Br)C=C1 RNBCQLCYZIHPON-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- NPRJGJKFWAKWIF-UHFFFAOYSA-N C(C)SCC.C=CC Chemical compound C(C)SCC.C=CC NPRJGJKFWAKWIF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001446467 Mama Species 0.000 description 1
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 241000347389 Serranus cabrilla Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- KZNMRPQBBZBTSW-UHFFFAOYSA-N [Au]=O Chemical class [Au]=O KZNMRPQBBZBTSW-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 229910000074 antimony hydride Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical class CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical class CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
- PLLZRTNVEXYBNA-UHFFFAOYSA-L cadmium hydroxide Chemical compound [OH-].[OH-].[Cd+2] PLLZRTNVEXYBNA-UHFFFAOYSA-L 0.000 description 1
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 1
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- PUHAKHQMSBQAKT-UHFFFAOYSA-L copper;butanoate Chemical compound [Cu+2].CCCC([O-])=O.CCCC([O-])=O PUHAKHQMSBQAKT-UHFFFAOYSA-L 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- LZJJVTQGPPWQFS-UHFFFAOYSA-L copper;propanoate Chemical compound [Cu+2].CCC([O-])=O.CCC([O-])=O LZJJVTQGPPWQFS-UHFFFAOYSA-L 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- HWEQKSVYKBUIIK-UHFFFAOYSA-N cyclobuta-1,3-diene Chemical compound C1=CC=C1 HWEQKSVYKBUIIK-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- VZZJVOCVAZHETD-UHFFFAOYSA-N diethylphosphane Chemical compound CCPCC VZZJVOCVAZHETD-UHFFFAOYSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YMUZFVVKDBZHGP-UHFFFAOYSA-N dimethyl telluride Chemical compound C[Te]C YMUZFVVKDBZHGP-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZGOCSFDMWNGNIT-UHFFFAOYSA-N ethene ethylsulfanylethane Chemical compound C(C)SCC.C=C ZGOCSFDMWNGNIT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- ALCDAWARCQFJBA-UHFFFAOYSA-N ethylselanylethane Chemical compound CC[Se]CC ALCDAWARCQFJBA-UHFFFAOYSA-N 0.000 description 1
- ILXWFJOFKUNZJA-UHFFFAOYSA-N ethyltellanylethane Chemical compound CC[Te]CC ILXWFJOFKUNZJA-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910001922 gold oxide Inorganic materials 0.000 description 1
- WDZVNNYQBQRJRX-UHFFFAOYSA-K gold(iii) hydroxide Chemical class O[Au](O)O WDZVNNYQBQRJRX-UHFFFAOYSA-K 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- WGXGAUQEMYSVJM-UHFFFAOYSA-N hexadecanenitrile Chemical compound CCCCCCCCCCCCCCCC#N WGXGAUQEMYSVJM-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- BPCWCZCOOFUXGQ-UHFFFAOYSA-N isocyanoethane Chemical compound CC[N+]#[C-] BPCWCZCOOFUXGQ-UHFFFAOYSA-N 0.000 description 1
- ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- LVBIMKHYBUACBU-CVBJKYQLSA-L nickel(2+);(z)-octadec-9-enoate Chemical compound [Ni+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LVBIMKHYBUACBU-CVBJKYQLSA-L 0.000 description 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical class [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical class CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NNOBHPBYUHDMQF-UHFFFAOYSA-N propylphosphine Chemical compound CCCP NNOBHPBYUHDMQF-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003498 tellurium compounds Chemical class 0.000 description 1
- 229910021515 thallium hydroxide Inorganic materials 0.000 description 1
- 229910003438 thallium oxide Inorganic materials 0.000 description 1
- QGYXCSSUHCHXHB-UHFFFAOYSA-M thallium(i) hydroxide Chemical compound [OH-].[Tl+] QGYXCSSUHCHXHB-UHFFFAOYSA-M 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BXJWDOYMROEHEN-UHFFFAOYSA-N tributylstibane Chemical compound CCCC[Sb](CCCC)CCCC BXJWDOYMROEHEN-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WWVNWQJKWKSDQM-UHFFFAOYSA-N triethylarsane Chemical compound CC[As](CC)CC WWVNWQJKWKSDQM-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- KKOFCVMVBJXDFP-UHFFFAOYSA-N triethylstibane Chemical compound CC[Sb](CC)CC KKOFCVMVBJXDFP-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- PORFVJURJXKREL-UHFFFAOYSA-N trimethylstibine Chemical compound C[Sb](C)C PORFVJURJXKREL-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5045—Complexes or chelates of phosphines with metallic compounds or metals
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/09—Complexes with metals
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
Definitions
- a valuable feature of the present invention is novel class of organic metal and metalloidconinherent in the simultaneous reaction of a mem- 5 taining complex compounds, which complex comber of one of the classes -01 compounds with at 5 pounds are adaptable to a wide variety of purleast one member selected from each of the other poses and which are particularly useful asmeans two classes.
- metals in a soluble form can be introthe invention,- the necessity of first preparing verbad into hydrocarbons and particularly hydroand isolating the organic metal compounds which carbon fractions, such as motor fuels, natural and it is desired to react with an organic metalloid in synthetic oils, lignite products, tar oils and the compound to obtain a metal and metalloid-conlike, for the purpose of improvingthese materials.
- taining complex organic compound of a prede- Three main groups or classes of compoundsare termined composition is obviated. This is a very contemplated as reactants in accordance with the advantageous feature of the invention for the process of the invention.
- the first class of reactants hereinafter desigtical yields and in some cases cannot be prepared nated as the metal compounds"
- the second class of reactants embraces organic inherent in the present invention are "clearly 25 compounds which possess one or a plurality of shown by the following example In the case that readily replaceable hydrogen atoms.
- organic metal compound ing are representative types of compounds concomplexes with an organic phosphine, for examtemplated as members of this class: the organic ple, it is not always possible, or on account of acids, the alcohols, the phenols, acid amides, amthe dangers and difliculties attendant thereon, 30 ines, nitriles, aminoalcohols, phosphines, mercap desirable to prepare such organic metal and met tans, thioethers, the cyclodiolefines, acetylene, alloid-containing complexes by first preparing the acetylene homologues, and the like.
- the third class of reactants embraces the oring it with the organic phosphine or otherorganic ganic compounds of the elements of the right metalloid compound.
- the desired 35 hand side of groups V and VI which have an organic metal compound maybe unavailable or atomic number not less than fifteen, and the orit may be so unstable as to preclude its economical ganic compounds of the element nitrogen. A preuse.
- 40 includes the alkyl, aryl, aralkyl and cycloaliphatic by a suitable selection of readily available react- 40 compounds, as well as the substitution products ants of theclasses herein described any desired, thereof, of the metalloid elements phosphorus, organic metal and metalloid-containing complex arsenic, antimony, sulphur, selenium, tellurium compound can be prepared economicallyin a andnitrogen and the organic esters of the acids of practical yield.
- the process of the invention comprises effecting class of metal oxides, metal hydroxides and metal the simultaneous reaction of a compound of the salts of weak acids, the following come into conclass consisting of metal oxides, metal hydroxsideration: the alkali metal oxides, the alkali metides and metal salts of weak acids with an oral hydroxides, the alkaline earth metal oxides,
- ganic compound containing one or a plurality of the alkaline earth metal hydroxides, aluminum 50 readily replaceable hydrogen atoms and with an hydroxides, aluminum oxide, cuprous oxide, cuprlc organic compound of an element of the right hand oxide, cupric hydroxide, cuprous hydroxide, silside of groups V and VI of the periodic table ver oxide, magnesium hydroxide, magnesium oxwhich has an atomic number not less than fifide, cadmium hydroxide, cadmium oxide, merteen, and the element nitrogen, whereby an orcuric hydroxide, mercuric oxide, mercurous ox 55 ide, thallium hydroxide, the thallium oxides, the zirconium oxides and hydroxides, the stannous and stannic oxides and hydroxides, the molyb-- platinum hydroxides.
- Suitable metalsalts of weak acids include the alkali metal and alkaline earth metal carbonates and bicarbonates, copper car-, bonate, magnesium carbonate, the metal borates, the metal tetraborates, the metal salts of the organic acids of which sodium formate, sodium acetate, copper formate, copper acetate, copper propionate, copper butyrate, lead acetate, nickel formate, nickel acetate, nickel oleate and the like are representative.
- the particular metal salt is selected with respectto the compound containing a readily replaceable hydrogen atom so that the compound in which the hydrogen atom is to be replaced by a metal atom has a stronger acid character than the weak acid from which the metal salt has been prepared.
- the following compounds are representative organic-compounds which contain at least one readily replaceable hydrogen atom: the organic monobasic and polybasic-acids of saturated and unsaturated character as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, the valeric acids and homologues and suitable substitution products of these aliphatic acids, benzoic acid, cinnamic acid, maleic acid, malonic acid,
- oxalic acid lactic acid, succinic acid, the higherunsaturated acids as oleic, palmitic and the like; the saturated and unsaturated alcohols of monohydric as well as polyhydric character as methyl alcohol, ethyl alcohol, the propyl alcohols, primary butyl alcohol, secondary butyl alcohol, tertiary butyl alcohol, the amyl alcohols and the like, ethylene glycol, propylene glycol, the butylene glycols, the amylene glycols, diethylene glycol, dipropylene glycol, the dibutylene glycols, triethylene glycol, tripropylene glycol, glycerol, diglycerol, p-methyl glycerol, di-p-methyl glycerol, erythritol and the'like and their homologues, analogues and suitable substitution products.
- the saturated and unsaturated alcohols of monohydric as well as polyhydric character as methyl alcohol, ethyl
- the unsaturated alcohols as allyl alcohol, crotyl'alcohol, isobutenol, cinnamyl alcohol, propargyl alcohol and the like are also suitable.
- Suitable phenolic bodies include phenol, the cresols, hydroquinone, pyrogallol, the naphthols, the xylenols and the like.
- Representative acid amides are formamide, ethanamide, propanamide, the butanamides, etc., and their homologues and analogues.
- the amines of primary, secondary and mixed character are suitable, the following being representative members: methyl amine, dimethyl amine, ethyl amine, diethyl amine, methyl ethyl amine, the propyl monoamines, the propyl-diamines, analine, phenylene diamine, ethylene diamine, and the like and their homologues and suitable substitution products.
- nitriles are represented by the following aliphatic, aromatic and aralkyl compounds: aceto-nitrile, propionitrile, butyro-nitrile, valeromitrile, palmitonitrile, methyl isocyanide, ethyl isocyanide, benzonitrile, benzyl cyanide and the like.
- Suitable amino-alcohols include the mono-, diand trimethanolamines, monoethanolamine, triethanolamine, diethanolamine, the monoand polypropanol amines, methyl amino-propanol and the like and their homologues, analogues and suitable substitution products.
- Suitable phosphines include "methyl phosphine, dimethyl phosphine, ethyl phosphine, diethyl phosphine, propyl phosphine, butyl phosphine, phenyl phosphine, benzyl 'phosphine and the like.
- Suitable mercaptans include the saturated and unsaturated alkyl and aralkyl mercaptans and the aromatic and other cyclic mercaptans as methyl mercaptan, ethyl mercaptan, the propyl mercaptans, allyl mercap tan, crotyl mercaptan, isobutenyl mercaptan, the
- Suitable hydrocarbons whichcontain readily replaceable hydrogen atoms include, among others, the alkadienes, as butadiene, pentadiene, hexadiene, etc., and particularly the cycloalkadienes as cyclobutadiene, cyclopentadiene, cyclohexadiene, cycloheptadiene and the like and compounds containing an acetylenic linkage as acetylene and its homologues as methyl acetylene and the like and other suitable hydrocarbons containing readily replaceable hydrogen atoms.
- Suitable substituted and non-substituted alkyl, aralkyl, aryl and cycloaliphatic compounds of the elements of the right hand side of groups V and VI of the periodic table which have an atomic number not less than 15, and the element nitrogen and the esters of acids of these compounds are pyridine, ethyl amine, ethyl diamine, ethyl triamine, the methyl, propyl, butyl and the higher amines, the mixed amines as ethyl propyl amine, aniline, ethylene diamine, phenylene diamine, ethanolamine, diethanolamine, triethanolamine, propanolamine, aminoacetic acid, aminobutyric acid, ethyl carbylamine, propyl carbylamine, phenyl carbylamine, aceto-nitrile, propio-nitrile, butyro-nitrile, trimethyl phosphine, triethyl phosphine, trip
- the reaction may be effected with any suitable proportion of the reactants depending upon the particular operation and the particular complex compound desired. In some cases it is desirable to exe'cute the invention with the reactants present in the reaction mixture in equivalent amounts or with the other reactants in excess of the metal oxide, metal hydroxide or metal saltof a weak acid so as to facilitate conversion of the latter.
- the reaction is preferably effected in a reaction vessel equipped with suitable heating and cooling means and means for agitating the reaction mixture as by shaking or mechanical stirring.
- the reactants may be introduced into the reaction vessel in any desirable manner and order provided that the reactants are present in the reaction mixture at sucha time and in such amounts that simultaneous reaction of the three classes of reactants occurs.
- the reaction may be effected at any desired temperature and pres- About 13.5 gm. of tri-n-propyl phosphite were heated with about 3.0 gm. of nickel hydroxide and about 3.9 gm. of formaniline in a nitrogen atmosphere at a temperature of about 170 C. to 180 C. for about 3 hours.
- organic metalloid compound of the class consisting of the hydrocarbon and substituted hydrocarbon compounds of the elements'of the right hand side of groups V and VI of the periodic table which have an atomic number not less than 15, and the element nitrogen, and the organic esters of acids of these elements, the resulting organic metal and metalloid-containing complex compounds are novel.
- the members of this novel class of organic metal and metalloid-containing complex compounds may be represented by the general for-' mula (MR) .arZ, wherein (MR) represents the compound of a. metal with an organic compound of the class consisting of alcohols, acid amides, amines, nitriles, aminoalcohols, phosphines, mercaptans, alkadienes, cycloalkadienes, acetylene and acetylene homologues, and Z represents an organic metalloid compound of the class consisting of the hydrocarbon and substituted hydrocarbon compounds of,-and the organic esters of acids of, the elements of the right hand side of groups V and VI of the periodic table which have an atomic number not less than 15, and the element nitrogen, :1; representing an integer not usually greater than 2.
- MR represents the compound of a. metal with an organic compound of the class consisting of alcohols, acid amides, amines, nitriles, aminoalcohols, phosphines
- a valuable subgroup of novel organic'metal and metalloid-containing complex compounds embraces the double compounds of metal salts of organic acids and phenolic compounds with substituted or non-substituted alkyl, aralkyl, aryl and cycloaliphatic compounds of phosphorus, arsenic, antimony, sulphur, selenium and tellurium or with organic esters of acids of these elements.
- novel organic metal and metalloid-containing complex compounds embraces the, double compounds of inorganic metal salts, exclusive of the metal halides, with substituted or non-substituted alkyl, aralkyl, aryl and cycloaliphat ic compounds of phosphorus, arsenic, antimony, sulphur, selenium and tellurium or with organic esters of acids of these elements.
- the organic metal and metalloid-containing complex compounds are useful for a wide variety of purposes. They are of particular value as means of introducing metals in a soluble and ac tive form into hydrocarbons and hydrocarbon mixtures, particularly motor fuels and lubricating oil compositions for the purpose of enhancing the value of such hydrocarbon materials and making them more suitable for special purposes.
- organic complex compounds which are prepared in accordance with the process of the invention are readily soluble to a considerable extent in a wide variety of organic solvents. They are even readily soluble in the non-polar and slightly polar solvents such as tar oil products (benzol and its homologues), petroleum fractions as kerosene, gasoline, gasoil, lubricating oils and the like, hydrogenation products of olefine polymers, coal, tar, mineral oils, shale oils, etc., cracking products of tars, waxes, mineral oils, animal oils, vegetable oils and the like carbonaceous materials.
- non-polar and slightly polar solvents such as tar oil products (benzol and its homologues), petroleum fractions as kerosene, gasoline, gasoil, lubricating oils and the like, hydrogenation products of olefine polymers, coal, tar, mineral oils, shale oils, etc., cracking products of tars, waxes, mineral oils, animal oils, vegetable oils and the like carbonaceous
- the organic metal and metalloid-containing complex compounds may be dissolved in the required amount in a hydrocarbon material, or suspended in such a hydrocarbon material, to improve it in some desired respect.
- the organic metal complex compounds also act as anti-oxidants, and when added to lubricating oils and greases render them suitable as extreme pressure lubricants.
- VI of the periodic table which has an atomicity greater than one and an atomic number not eater than 52
- the third reactant being an organic compound of an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
- a process for the production of useful metal and metalloid-containing complex organic compounds which comprises bringing together and simultaneously reacting, in the liquid phase and in the presence ofa substantially inertnormally liquid diluent material, at least three different reactants, one reactantbeing a metal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52, and the third reactant being an organic compound of an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
- a process for the production of useful metal and metalloid-containing complex organiccompounds which comprises bringing together and simultaneously reacting at least three different reactants, one reactant being a metal oxide, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52, and the third reactant being an organic compound of an acidforming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
- a process for the production of a useful copper and metalloid-containing complex organic compound which comprises bringing together and simultaneously reacting at least three different reactants, one reactant being a copper oxide, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greaterthan 52, and the third re actant being an organic compound of an acidforming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
- a process for the production of useful metal and metaJloid-containing complex organic com-' pounds which comprises bringing togetherand simultaneously reacting at least three different reactants, one reactant being a metal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic hydroxy compound but devoid of any acidforming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not reater than 52, and the third reactant being an organic compound of an acid-forming multivalent element of groups V and VI of the'periodic table which has an atomicity greater than one and an atomic number not greater than 52.
- a process for the production of useful metal and metalloid-containingcomplex organic compounds which comprisesbringing together and simultaneously reacting at leastthree different reactants, one reactant being a metal compound of the class consisting of the metal oxides and metalhydroxides; another reactant being an organic compound containing a readily'replaceable hydrogen atom but devoid of any acid-forming multivalent elementof groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52,. and the third reactant being an organic compoundof the class consisting of the alkyl, aralkyl and aryl compounds of acid-forming multivalent elements of groups Vand VI of the periodic table whichhave an atomicitygreater than one and an atomic number not greater than 52.
- a process for the production of useful metal and metalloid-containing complex organic compounds which comprises bringing together and simultaneously reacting at least three different reactants, one reactant being a metal, compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52, and the third reactant being an alkyl compound of an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
- a process for the production of useful metal and metalloid-containing complex organic compounds which comprises bringing together and simultaneously reacting at least three diiierent reactants, one reactant being a metal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom, and the third reactant being an alkyl ester of an inorganic acid of an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
- a process for the production of useful metal and metalloid-containing complex organic compound which comprises bringing together and simultaneously reacting at least three different reactants, one reactant being a metal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of phosphorus, and the third reactant being an organic compound of phosphorus.
- a process for the production of cuprobutyrate-diethyl sulphide'of the formula CuOOCCsHv. (Col-I) 23 which comprises reacting cuprous oxide simultaneously with butyric acid and with diethyl sulphide, the reaction being elfected in the liquid phase in a substantially inert non-oxidizing atmosphere.
- the metal and metalloid-containinglcomr plex organic compounds of the general .formula (MR) .xZ the group MR representing the metal salt of an organic acid, Z representing'an organic compound of an acid-forming multivalent elesenting an integer not greater than two, the compound Z being bound to the group MR to form a metal-containing complex organic compound.
- the complex compound cuprob utyratediethyl sulphide of the formula 14.
- the metal and metalloid-containing com- plex organic compound of the general formula (MR) .rZ, the group MR representing an organic compound devoid of phosphorus and wherein a readily replaceable hydrogen atom has been replaced by a metal radical, X representing an integer not greater than two and Z representing i
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Description
mama Mar. 14, 1939 2,150,349
UNITED, STATES PATENT oFFrcs PROCESS AND PRODUCT RELATING TO ORGANIC LIETAL AND MIETALLOID' CON- TAININ G COIHPLEX COBIPOUNDS Adrianus Johannesvan Peski and Johannes Andreas, van Melsen, Amsterdam, Netherlands, assignors to Shell Development Company, San Francisco, Calif., a corporation of Delaware No Drawing. Application April I0, 1936, Serial No. 73,710. In the Netherlands April 11, 1935 I Claims. (Cl. 260438) This invention relates to the production of valgarlic metal and metalloid-containing complex uable organic metal and metalloid-containlng compound is formed. complex compounds, and it further relates to a A valuable feature of the present invention is novel class of organic metal and metalloidconinherent in the simultaneous reaction of a mem- 5 taining complex compounds, which complex comber of one of the classes -01 compounds with at 5 pounds are adaptable to a wide variety of purleast one member selected from each of the other poses and which are particularly useful asmeans two classes. In accordance with the process of whereby metals in a soluble form can be introthe invention,- the necessity of first preparing duced into hydrocarbons and particularly hydroand isolating the organic metal compounds which carbon fractions, such as motor fuels, natural and it is desired to react with an organic metalloid in synthetic oils, lignite products, tar oils and the compound to obtain a metal and metalloid-conlike, for the purpose of improvingthese materials. taining complex organic compound of a prede- Three main groups or classes of compoundsare termined composition, is obviated. This is a very contemplated as reactants in accordance with the advantageous feature of the invention for the process of the invention. In apreferred embodireason that manyof the organic metal com- 15 ment of the invention one or more members sepounds, such as those which might be prepared lected from each of the classes of reactants hereby reacting a metal oxide, metal hydroxide or inafter described is caused to react simultanea metal saltof a weak acid with an organic comously with one or more members selected from pound containing a readily replaceable hydrogen each of the other two classes of reactants. atom, are extremely diflicult to prepare in prac- 0 The first class of reactants, hereinafter desigtical yields and in some cases cannot be prepared nated as the metal compounds", embraces the at all, in still other cases the organic metal commetal oxides, metal hydroxides and metal salts pounds may be so unstable as to render their use of weak acids. impractical and even dangerous. The advantages l The second class of reactants embraces organic inherent in the present invention are "clearly 25 compounds which possess one or a plurality of shown by the following example In the case that readily replaceable hydrogen atoms. The followit is desired to prepare, organic metal compound ing are representative types of compounds concomplexes with an organic phosphine, for examtemplated as members of this class: the organic ple, it is not always possible, or on account of acids, the alcohols, the phenols, acid amides, amthe dangers and difliculties attendant thereon, 30 ines, nitriles, aminoalcohols, phosphines, mercap desirable to prepare such organic metal and met tans, thioethers, the cyclodiolefines, acetylene, alloid-containing complexes by first preparing the acetylene homologues, and the like. organic metal compound and subsequently react- The third class of reactants embraces the oring it with the organic phosphine or otherorganic ganic compounds of the elements of the right metalloid compound. In many cases, the desired 35 hand side of groups V and VI which have an organic metal compound maybe unavailable or atomic number not less than fifteen, and the orit may be so unstable as to preclude its economical ganic compounds of the element nitrogen. A preuse. In accordance with the process of the presferred'subgroup of the compounds 01 this class entinvention these dlmculties are obviated and 40 includes the alkyl, aryl, aralkyl and cycloaliphatic by a suitable selection of readily available react- 40 compounds, as well as the substitution products ants of theclasses herein described any desired, thereof, of the metalloid elements phosphorus, organic metal and metalloid-containing complex arsenic, antimony, sulphur, selenium, tellurium compound can be prepared economicallyin a andnitrogen and the organic esters of the acids of practical yield.
5 these metalloid elements. As preferably employed specific members of the The process of the invention comprises effecting class of metal oxides, metal hydroxides and metal the simultaneous reaction of a compound of the salts of weak acids, the following come into conclass consisting of metal oxides, metal hydroxsideration: the alkali metal oxides, the alkali metides and metal salts of weak acids with an oral hydroxides, the alkaline earth metal oxides,
ganic compound containing one or a plurality of the alkaline earth metal hydroxides, aluminum 50 readily replaceable hydrogen atoms and with an hydroxides, aluminum oxide, cuprous oxide, cuprlc organic compound of an element of the right hand oxide, cupric hydroxide, cuprous hydroxide, silside of groups V and VI of the periodic table ver oxide, magnesium hydroxide, magnesium oxwhich has an atomic number not less than fifide, cadmium hydroxide, cadmium oxide, merteen, and the element nitrogen, whereby an orcuric hydroxide, mercuric oxide, mercurous ox 55 ide, thallium hydroxide, the thallium oxides, the zirconium oxides and hydroxides, the stannous and stannic oxides and hydroxides, the molyb-- platinum hydroxides. the platinum oxides, palladium hydroxide, the gold hydroxides, the gold oxides, and the like. Suitable metalsalts of weak acids include the alkali metal and alkaline earth metal carbonates and bicarbonates, copper car-, bonate, magnesium carbonate, the metal borates, the metal tetraborates, the metal salts of the organic acids of which sodium formate, sodium acetate, copper formate, copper acetate, copper propionate, copper butyrate, lead acetate, nickel formate, nickel acetate, nickel oleate and the like are representative.
Preferably, when metal salts of weak acids are used in the execution of the invention, the particular metal salt is selected with respectto the compound containing a readily replaceable hydrogen atom so that the compound in which the hydrogen atom is to be replaced by a metal atom has a stronger acid character than the weak acid from which the metal salt has been prepared.
The following compounds are representative organic-compounds which contain at least one readily replaceable hydrogen atom: the organic monobasic and polybasic-acids of saturated and unsaturated character as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, the valeric acids and homologues and suitable substitution products of these aliphatic acids, benzoic acid, cinnamic acid, maleic acid, malonic acid,
oxalic acid, lactic acid, succinic acid, the higherunsaturated acids as oleic, palmitic and the like; the saturated and unsaturated alcohols of monohydric as well as polyhydric character as methyl alcohol, ethyl alcohol, the propyl alcohols, primary butyl alcohol, secondary butyl alcohol, tertiary butyl alcohol, the amyl alcohols and the like, ethylene glycol, propylene glycol, the butylene glycols, the amylene glycols, diethylene glycol, dipropylene glycol, the dibutylene glycols, triethylene glycol, tripropylene glycol, glycerol, diglycerol, p-methyl glycerol, di-p-methyl glycerol, erythritol and the'like and their homologues, analogues and suitable substitution products. The unsaturated alcohols as allyl alcohol, crotyl'alcohol, isobutenol, cinnamyl alcohol, propargyl alcohol and the like are also suitable. Suitable phenolic bodies include phenol, the cresols, hydroquinone, pyrogallol, the naphthols, the xylenols and the like. Representative acid amides are formamide, ethanamide, propanamide, the butanamides, etc., and their homologues and analogues. The amines of primary, secondary and mixed character are suitable, the following being representative members: methyl amine, dimethyl amine, ethyl amine, diethyl amine, methyl ethyl amine, the propyl monoamines, the propyl-diamines, analine, phenylene diamine, ethylene diamine, and the like and their homologues and suitable substitution products. The nitriles are represented by the following aliphatic, aromatic and aralkyl compounds: aceto-nitrile, propionitrile, butyro-nitrile, valeromitrile, palmitonitrile, methyl isocyanide, ethyl isocyanide, benzonitrile, benzyl cyanide and the like. Suitable amino-alcohols include the mono-, diand trimethanolamines, monoethanolamine, triethanolamine, diethanolamine, the monoand polypropanol amines, methyl amino-propanol and the like and their homologues, analogues and suitable substitution products. Suitable phosphines include "methyl phosphine, dimethyl phosphine, ethyl phosphine, diethyl phosphine, propyl phosphine, butyl phosphine, phenyl phosphine, benzyl 'phosphine and the like. Suitable mercaptans include the saturated and unsaturated alkyl and aralkyl mercaptans and the aromatic and other cyclic mercaptans as methyl mercaptan, ethyl mercaptan, the propyl mercaptans, allyl mercap tan, crotyl mercaptan, isobutenyl mercaptan, the
butyl mercaptans, benzyl mercaptan,-phenyl mercaptan and the like and their homologues. Suitable hydrocarbons whichcontain readily replaceable hydrogen atoms include, among others, the alkadienes, as butadiene, pentadiene, hexadiene, etc., and particularly the cycloalkadienes as cyclobutadiene, cyclopentadiene, cyclohexadiene, cycloheptadiene and the like and compounds containing an acetylenic linkage as acetylene and its homologues as methyl acetylene and the like and other suitable hydrocarbons containing readily replaceable hydrogen atoms.
Examples of suitable substituted and non-substituted alkyl, aralkyl, aryl and cycloaliphatic compounds of the elements of the right hand side of groups V and VI of the periodic table which have an atomic number not less than 15, and the element nitrogen and the esters of acids of these compounds, are pyridine, ethyl amine, ethyl diamine, ethyl triamine, the methyl, propyl, butyl and the higher amines, the mixed amines as ethyl propyl amine, aniline, ethylene diamine, phenylene diamine, ethanolamine, diethanolamine, triethanolamine, propanolamine, aminoacetic acid, aminobutyric acid, ethyl carbylamine, propyl carbylamine, phenyl carbylamine, aceto-nitrile, propio-nitrile, butyro-nitrile, trimethyl phosphine, triethyl phosphine, tripropyl phosphine, tributyl phosphine, tribenzyl phosphine, triphenyl phosphine, trimethyl phosphite, triethyl phosphite, tripropyl phosphite, tributyl phosphite, trimethyl stibine, triethyl stibine, tripropyl stibine, tributyl stibine, methyl ethyl sulphide, dimethyl sulphide, diethyl sulphide, dipropyl sulphide, dibutyl sulphide, S-ethyl thioglycollic acid ethyl ester, ethylene diethyl sulphide, propylene diethyl sulphide, diethyl disulphide, dimethyl selenium, diethyl selenium, dipropyl selenium, dibutyl selenium, allyl sulphide, isobutenyl sulphide, dimethyl tellurium, trimethyl arsine, triethylarsine, bismuth trimethyl, diethyl tellurium and the like and their homologues, analogues and suitable substitution products.
The reaction may be effected with any suitable proportion of the reactants depending upon the particular operation and the particular complex compound desired. In some cases it is desirable to exe'cute the invention with the reactants present in the reaction mixture in equivalent amounts or with the other reactants in excess of the metal oxide, metal hydroxide or metal saltof a weak acid so as to facilitate conversion of the latter.
The reaction is preferably effected in a reaction vessel equipped with suitable heating and cooling means and means for agitating the reaction mixture as by shaking or mechanical stirring. The reactants may be introduced into the reaction vessel in any desirable manner and order provided that the reactants are present in the reaction mixture at sucha time and in such amounts that simultaneous reaction of the three classes of reactants occurs. The reaction may be effected at any desired temperature and pres- About 13.5 gm. of tri-n-propyl phosphite were heated with about 3.0 gm. of nickel hydroxide and about 3.9 gm. of formaniline in a nitrogen atmosphere at a temperature of about 170 C. to 180 C. for about 3 hours. At the end of this time the mixture was added to 1 liter of a benzine substantially free of aromatic hydrocarbons and the mixture shaken for about 12 hours. The mixture was then filtered and the filtrate analyzed. It contained more than 0.2% of Ni, boundv in a double :compound of the formula nicumiomaz (CaH'zO) 3? EXAMPLE VI Preparation of cupro-cyclopentadiene-tri-normal prom/l phosphzne (CuC'5H5.2(C3H7) 3P) A mixture consisting of about 29 gm. of tri-npropyl phosphine, about 6.5 gm. of cuprous oxide, about 6.0 gm. of cyclopentadiene and about 20 c. c. of benzol was charged to a suitable reaction vessel, put under a nitrogen atmosphere, and heated to the boiling temperature of the mixture for about 2 hours. A clearly perceptible reaction took place, as indicated by water formation and the gradual consumption of the solid cuprous oxide. At the end of two hours of treatment the mixture was cooled and'filtered. About 2.5 gm. of unreacted cuprous oxide were filtered from the mixture. The filtrate was evaporated to remove the lower boiling constituents. The residue, about 34.4 gm. being obtained, was found to have the formula CuC5Hs.2(C3H7)3P. This complex organic metal compound is readily soluble in benzine fractions, particularly in those fractions substantially free of aromatics.
Other representative examples of valuable organic metal and metalloid complex compounds, which may be readily prepared in good yield in accordance with the process of our invention, are
the following:
Cupro-acetateethylene diamine cuoocomolnlmm Cupro-urea-triethyl phospliine CuNHC ON Hz.(C:Hs)aP Dicupro-urea-triethyl phosphine Cu2NCONH2-(C2H5)3P stg n cresolate-triethyl phosphite Sn (0C5H5CH3).(C,H;O);P Ferri-phcnolatetriethyl phosphite F6(OCuH5)3-(C:H5O)3P When a compound of the class consisting of metaloxides, metal hydroxides and salts of weak acids is simultaneously reacted with a compound of the class consisting of alcohols, acid amides,
amines, nitriles, aminoalcohols, phosphines, mercaptans, alkadienes, cycloalkadienes, acetylene and acetylene homologues and with an organic metalloid compound of the class consisting of the hydrocarbon and substituted hydrocarbon compounds of the elements'of the right hand side of groups V and VI of the periodic table which have an atomic number not less than 15, and the element nitrogen, and the organic esters of acids of these elements, the resulting organic metal and metalloid-containing complex compounds are novel.
The members of this novel class of organic metal and metalloid-containing complex compounds may be represented by the general for-' mula (MR) .arZ, wherein (MR) represents the compound of a. metal with an organic compound of the class consisting of alcohols, acid amides, amines, nitriles, aminoalcohols, phosphines, mercaptans, alkadienes, cycloalkadienes, acetylene and acetylene homologues, and Z represents an organic metalloid compound of the class consisting of the hydrocarbon and substituted hydrocarbon compounds of,-and the organic esters of acids of, the elements of the right hand side of groups V and VI of the periodic table which have an atomic number not less than 15, and the element nitrogen, :1; representing an integer not usually greater than 2.
A valuable subgroup of novel organic'metal and metalloid-containing complex compounds embraces the double compounds of metal salts of organic acids and phenolic compounds with substituted or non-substituted alkyl, aralkyl, aryl and cycloaliphatic compounds of phosphorus, arsenic, antimony, sulphur, selenium and tellurium or with organic esters of acids of these elements.
Another subgroup of novel organic metal and metalloid-containing complex compounds embraces the, double compounds of inorganic metal salts, exclusive of the metal halides, with substituted or non-substituted alkyl, aralkyl, aryl and cycloaliphat ic compounds of phosphorus, arsenic, antimony, sulphur, selenium and tellurium or with organic esters of acids of these elements.
The organic metal and metalloid-containing complex compounds are useful for a wide variety of purposes. They are of particular value as means of introducing metals in a soluble and ac tive form into hydrocarbons and hydrocarbon mixtures, particularly motor fuels and lubricating oil compositions for the purpose of enhancing the value of such hydrocarbon materials and making them more suitable for special purposes.
The great majority of the organic complex compounds which are prepared in accordance with the process of the invention are readily soluble to a considerable extent in a wide variety of organic solvents. They are even readily soluble in the non-polar and slightly polar solvents such as tar oil products (benzol and its homologues), petroleum fractions as kerosene, gasoline, gasoil, lubricating oils and the like, hydrogenation products of olefine polymers, coal, tar, mineral oils, shale oils, etc., cracking products of tars, waxes, mineral oils, animal oils, vegetable oils and the like carbonaceous materials. Consequently, the organic metal and metalloid-containing complex compounds may be dissolved in the required amount in a hydrocarbon material, or suspended in such a hydrocarbon material, to improve it in some desired respect. Many of the organic metal complex compounds when added to motor fuels as gasoline, iso-octane, etc., improve the anti-knock properties of the fuels or fuel mixtures. The organic metal complex compounds also act as anti-oxidants, and when added to lubricating oils and greases render them suitable as extreme pressure lubricants.
While we have in the foregoing described in some detail the preferred embodiment of our invention and some variants thereof, it will be understood that this is only for the purpose of making the invention more clear and that the same is not to be regarded as limited to the details of operation described nor is it dependent upon the soundness or accuracy of the theories which we have advanced as to the advantageous results attained. On the other hand, the invention is to be regarded as limited only by the terms and metalloid-containing complex organic compounds which comprises bringing together and simultaneously reacting at least three difierent reactants, one reactant being ametal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acidforming multivalent element of groups V and. VI of the periodic table which has an atomicity greater than one and an atomic number not eater than 52, and the third reactant being an organic compound of an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
2. A process for the production of useful metal and metalloid-containing complex organic compounds which comprises bringing together and simultaneously reacting, in the liquid phase and in the presence ofa substantially inertnormally liquid diluent material, at least three different reactants, one reactantbeing a metal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52, and the third reactant being an organic compound of an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
3. A process for the production of useful metal and metalloid-containing complex organiccompounds which comprises bringing together and simultaneously reacting at least three different reactants, one reactant being a metal oxide, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52, and the third reactant being an organic compound of an acidforming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
4. A process for the production of a useful copper and metalloid-containing complex organic compound which comprises bringing together and simultaneously reacting at least three different reactants, one reactant being a copper oxide, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greaterthan 52, and the third re actant being an organic compound of an acidforming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
5. A process for the production of useful metal and metaJloid-containing complex organic com-' pounds which comprises bringing togetherand simultaneously reacting at least three different reactants, one reactant being a metal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic hydroxy compound but devoid of any acidforming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not reater than 52, and the third reactant being an organic compound of an acid-forming multivalent element of groups V and VI of the'periodic table which has an atomicity greater than one and an atomic number not greater than 52.
6. A process for the production of useful metal and metalloid-containingcomplex organic compounds which comprisesbringing together and simultaneously reacting at leastthree different reactants, one reactant being a metal compound of the class consisting of the metal oxides and metalhydroxides; another reactant being an organic compound containing a readily'replaceable hydrogen atom but devoid of any acid-forming multivalent elementof groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52,. and the third reactant being an organic compoundof the class consisting of the alkyl, aralkyl and aryl compounds of acid-forming multivalent elements of groups Vand VI of the periodic table whichhave an atomicitygreater than one and an atomic number not greater than 52. I
7. A process for the production of useful metal and metalloid-containing complex organic compounds which comprises bringing together and simultaneously reacting at least three different reactants, one reactant being a metal, compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of any acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52, and the third reactant being an alkyl compound of an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
8. A process for the production of useful metal and metalloid-containing complex organic compounds which comprises bringing together and simultaneously reacting at least three diiierent reactants, one reactant being a metal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom, and the third reactant being an alkyl ester of an inorganic acid of an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52.
9. A process for the production of useful metal and metalloid-containing complex organic compound which comprises bringing together and simultaneously reacting at least three different reactants, one reactant being a metal compound of the class consisting of the metal oxides and metal hydroxides, another reactant being an organic compound containing a readily replaceable hydrogen atom but devoid of phosphorus, and the third reactant being an organic compound of phosphorus.
10. A process for the production of cuprobutyrate-diethyl sulphide'of the formula CuOOCCsHv. (Col-I) 23 which comprises reacting cuprous oxide simultaneously with butyric acid and with diethyl sulphide, the reaction being elfected in the liquid phase in a substantially inert non-oxidizing atmosphere.
11. The metal and metalloid-contaim'ng coinplex organic compounds of the generaliormula (MR) .acZ, the group MR representing an organic compound wherein a readily replaceable hydrogen atom has been replaced by a metal radical, Z representing an organic compound of anacidforming multivalent element of groups V and VI of the periodic table whichihas an atomicity greater than one and an atomic number. not greater than 52, and :1: representing an integer not greater than two, the compound Z, being bound to the group MR to form a metal-containing complex organic compound. 7'
12. The metal and metalloid-containinglcomr plex organic compounds of the general .formula (MR) .xZ, the group MR representing the metal salt of an organic acid, Z representing'an organic compound of an acid-forming multivalent elesenting an integer not greater than two, the compound Z being bound to the group MR to form a metal-containing complex organic compound.
13. The complex compound: cuprob utyratediethyl sulphide of the formula 14. The copper-containing complex organic compound of the general formula (l\/IR).:|:Z, wherein MR represents the copper salt of a carboxylic acid, n: represents an integer not greater than two, and Z represents an alkyl compound of "an acid-forming multivalent element of groups V and VI of the periodic table which has an atomicity greater than one and an atomic number not greater than 52, Z being bound to MR to form a copper-containing complex organic compound.
v 15. The metal and metalloid-containing com-= plex organic compound of the general formula (MR) .rZ, the group MR representing an organic compound devoid of phosphorus and wherein a readily replaceable hydrogen atom has been replaced by a metal radical, X representing an integer not greater than two and Z representing i
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Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2474869A (en) * | 1946-02-07 | 1949-07-05 | Koppers Co Inc | Mercury acetylide-silver nitrate complex and process of making same |
US2483440A (en) * | 1946-02-07 | 1949-10-04 | Koppers Co Inc | Silver acetylide compound and process of making same |
US2630419A (en) * | 1949-09-10 | 1953-03-03 | Union Carbide & Carbon Corp | Polyester resins modified with complex metal-phenol-nitrogen compounds |
US2838554A (en) * | 1954-04-15 | 1958-06-10 | Metal & Thermit Corp | Process for making organotin maleates |
US2938828A (en) * | 1956-03-29 | 1960-05-31 | Shell Oil Co | Oil-soluble fungicides |
US3006742A (en) * | 1957-11-26 | 1961-10-31 | Ethyl Corp | Fuel compositions |
US3010902A (en) * | 1956-07-04 | 1961-11-28 | Alpha Molykote Corp | Organic sulfur-molybdenum blue composition and a lubricating oil containing same |
US3116126A (en) * | 1960-09-30 | 1963-12-31 | California Research Corp | Antiknock gasoline |
US3130017A (en) * | 1952-07-05 | 1964-04-21 | Ethyl Corp | Antiknock fuel |
US3155620A (en) * | 1962-10-08 | 1964-11-03 | Ethyl Corp | Fuel compositions |
US3181938A (en) * | 1959-07-13 | 1965-05-04 | Texaco Inc | Motor fuel containing octane appreciator |
US3345392A (en) * | 1964-03-24 | 1967-10-03 | American Cyanamid Co | Organophosphorus-copper complex compounds |
US4070405A (en) * | 1975-07-19 | 1978-01-24 | Bayer Aktiengesellschaft | Process for working up liquid copper-containing catalyst waste from isomerization reactions of dichlorobutene |
US4201719A (en) * | 1977-10-21 | 1980-05-06 | Gte Sylvania Incorporated | Precious metal nitrogenous organo reaction products |
US4208341A (en) * | 1979-01-08 | 1980-06-17 | Allied Chemical Corporation | Copper (II) reagent and preparation thereof |
US4336148A (en) * | 1977-09-07 | 1982-06-22 | Ciba-Geigy Corporation | Complex compound, process for their preparation, and their use |
US4425278A (en) | 1977-09-07 | 1984-01-10 | Ciba-Geigy Corporation | Complex compounds, process for their preparation, and their use |
US4494961A (en) * | 1983-06-14 | 1985-01-22 | Mobil Oil Corporation | Increasing the cetane number of diesel fuel by partial oxidation _ |
US5021598A (en) * | 1989-07-24 | 1991-06-04 | Mooney Chemicals, Inc. | Process for making bismuth carboxylates |
US20090181592A1 (en) * | 2008-01-11 | 2009-07-16 | Fiber Innovation Technology, Inc. | Metal-coated fiber |
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1936
- 1936-04-10 US US73710A patent/US2150349A/en not_active Expired - Lifetime
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
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US2483440A (en) * | 1946-02-07 | 1949-10-04 | Koppers Co Inc | Silver acetylide compound and process of making same |
US2474869A (en) * | 1946-02-07 | 1949-07-05 | Koppers Co Inc | Mercury acetylide-silver nitrate complex and process of making same |
US2630419A (en) * | 1949-09-10 | 1953-03-03 | Union Carbide & Carbon Corp | Polyester resins modified with complex metal-phenol-nitrogen compounds |
US3130017A (en) * | 1952-07-05 | 1964-04-21 | Ethyl Corp | Antiknock fuel |
US2838554A (en) * | 1954-04-15 | 1958-06-10 | Metal & Thermit Corp | Process for making organotin maleates |
US2938828A (en) * | 1956-03-29 | 1960-05-31 | Shell Oil Co | Oil-soluble fungicides |
US3010902A (en) * | 1956-07-04 | 1961-11-28 | Alpha Molykote Corp | Organic sulfur-molybdenum blue composition and a lubricating oil containing same |
US3006742A (en) * | 1957-11-26 | 1961-10-31 | Ethyl Corp | Fuel compositions |
US3181938A (en) * | 1959-07-13 | 1965-05-04 | Texaco Inc | Motor fuel containing octane appreciator |
US3116126A (en) * | 1960-09-30 | 1963-12-31 | California Research Corp | Antiknock gasoline |
US3155620A (en) * | 1962-10-08 | 1964-11-03 | Ethyl Corp | Fuel compositions |
US3345392A (en) * | 1964-03-24 | 1967-10-03 | American Cyanamid Co | Organophosphorus-copper complex compounds |
US4070405A (en) * | 1975-07-19 | 1978-01-24 | Bayer Aktiengesellschaft | Process for working up liquid copper-containing catalyst waste from isomerization reactions of dichlorobutene |
US4336148A (en) * | 1977-09-07 | 1982-06-22 | Ciba-Geigy Corporation | Complex compound, process for their preparation, and their use |
US4425278A (en) | 1977-09-07 | 1984-01-10 | Ciba-Geigy Corporation | Complex compounds, process for their preparation, and their use |
US4201719A (en) * | 1977-10-21 | 1980-05-06 | Gte Sylvania Incorporated | Precious metal nitrogenous organo reaction products |
US4208341A (en) * | 1979-01-08 | 1980-06-17 | Allied Chemical Corporation | Copper (II) reagent and preparation thereof |
US4494961A (en) * | 1983-06-14 | 1985-01-22 | Mobil Oil Corporation | Increasing the cetane number of diesel fuel by partial oxidation _ |
US5021598A (en) * | 1989-07-24 | 1991-06-04 | Mooney Chemicals, Inc. | Process for making bismuth carboxylates |
US20090181592A1 (en) * | 2008-01-11 | 2009-07-16 | Fiber Innovation Technology, Inc. | Metal-coated fiber |
US8007904B2 (en) | 2008-01-11 | 2011-08-30 | Fiber Innovation Technology, Inc. | Metal-coated fiber |
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