US2446072A - Preparation of dialkenyl sulfides - Google Patents
Preparation of dialkenyl sulfides Download PDFInfo
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- US2446072A US2446072A US587831A US58783145A US2446072A US 2446072 A US2446072 A US 2446072A US 587831 A US587831 A US 587831A US 58783145 A US58783145 A US 58783145A US 2446072 A US2446072 A US 2446072A
- Authority
- US
- United States
- Prior art keywords
- zinc
- sulfides
- preparation
- dialkenyl
- olefin
- 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
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- 238000002360 preparation method Methods 0.000 title description 4
- 150000003568 thioethers Chemical class 0.000 title 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- 150000004763 sulfides Chemical class 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- -1 olefin sulfides Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- PGTXKIZLOWULDJ-UHFFFAOYSA-N [Mg].[Zn] Chemical compound [Mg].[Zn] PGTXKIZLOWULDJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000013040 rubber vulcanization Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- HRHOSXVNIFRFRK-UHFFFAOYSA-N 5-methyl-6-(5-methylnon-5-en-4-yldisulfanyl)non-4-ene Chemical compound CCCC=C(C)C(CCC)SSC(CCC)C(C)=CCCC HRHOSXVNIFRFRK-UHFFFAOYSA-N 0.000 description 1
- 241000331231 Amorphocerini gen. n. 1 DAD-2008 Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulphite Substances [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
Definitions
- invention relates to the method of preparing'sulfides of olefin'hydrocarbons, and to the resultingproducts;
- I it has been necessary to use as starting materials olefinic halides for the preparation of olefin sulfides, and in such cases theyields have beenpoor,
- An objectof this invention is to use the olefin hydrocarbons directly as a starting materlal with resulting good yields of the sulfides.
- reaction of olefins, with elemental sulfur, in the absence of zinc or similar metal in combination produces alkyl alkenyl polysulfides rather than dialkenyl sulfides.
- dialkenyl sulfide a monomeric compound consisting of sulfur bonded to two alkenyl groups. They subscribe tothe formula RSn-R where n is a whole number from 1 to 2, and R is an olefinic radical.
- I Alkenyl is used in the usual sense to refer to a monovalent I radical containing an ethylenic linkage.
- the chemicals are prepared by a method which consists in interacting any olefinic hydrocarbon containing from 3 to 12 prising the group with elemental sulfur, in the presence of zinc or similar metal in combination, and a nitrogencontaining compound which belongs totheclass of rubber vulcanization accelerators.
- the molecular proportion of the sulfur should be at least 1.5 atomic proportions for each molecular proportion of the olefin.
- the proportion of the nitrogen-containing accelerator need salt may be added as such or formed in situ, as
- reaction for preparing disulfide may be represented by the following equation:
- R is an aliphatic radical containing from 3 to 17 carbon atoms.
- olefins examples include propene, the butenes, the amenes,the hexenes, the heptenes, the catches, the nonenes, the decenes, the undecenes; and the dodecenes.
- W'here morethan one memher is referred to the intentionis to include each member of the class which contains a hydrogen atom attachedi'to the carbon atom which is alpha tothe double bond.v V 1 [Among the? sulfides may be mentioned 6,6'-dithiobis (5- methyl-4-nonene), and 6,6'-thlobis (5,- methylf-Fi-nonene) Z-butenyl monosulfide and d i-.
- the sulfides of this invention are clear liquids possessing a persistent garlic-like 'odor and may be used as insecticides, fumigants, and as intermediates in the preparation of dyes, pharmaceuticals, resins, etc.
- the reactive form of the zinc in the reaction appears to be the salt of the organic acids of the fatty acid series, such as zinc propionate, zinc stearate, etc., it is possible to substitute zinc oxide for a portion of the zinc salt only to such extent that the rate of the reaction is not impaired so that undesirable side reactions occur.
- the salt canbe formed in the reaction by introducing the proper amounts of the zinc oxide and of the acid.
- I 1 z-mercaptobenzothiazoleland other thiazylsulfides are exemplary of the so-called vulcanization acceleratorswhich are useful in promoting the reaction of sulfur with olefin according to my invention; others, called thiuram sulfides, such as I tetramethyl thiuram sulfide, tetramethyl thiuramdisulfide, and ureas such as ,diphenyh thiourea, and-amines, ,such as dibenzylamine; diphenylguanidine, and triamylamine, as well as other nitrogen-containing accelerators of rubber vulcanization can be used.
- thiuram sulfides such as I tetramethyl thiuram sulfide, tetramethyl thiuramdisulfide, and ureas such as ,diphenyh thiourea
- -amines such as dibenzylamine; diphenylgu
- n is an integer from 1 to 2; which comprises reacting;- at aggt'emperature in the-range frd'mabout 90-"'. to about"'180 C., 2 molecular proportions of an olefinic hydrocarbon containing from 3 to 12 carbon atoms and conwith atleast ljatomic proportions of elemental suljurfln the presence of at least 1 molecular proportionof a metal salt of a saturated fatty acid a; haying irom 3 to 18 carbon atoms, the metal thereof being selected fgrom the magnesium-zinc ami y f me 1 or hem-rio icttablaa ndr cat lystasmmt uheffcctivaamountr ta rcr.
- Butene-2 is reacted withsulfur in a manneranalogous to that of Examples Land 2' above and ithlat ea t 15 t m c l r p rtlon y.oil emental ilv lurr .tha resanccofat1east..1-, 1ac1 1arPm; p rtio f. am a t 1a a rat dl atty. acid ing m 8 1I'p n.. tQ n; e, mt@1.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented July 27, 1948 .UNi-TED- STATES PATENT? OFFICE PREPARATION OF nmtnnurt'sptrmns Robert T. Armstrong, Johnson City Tenn; as-
signor to United States Rubber Company, New I I York, N. Y., acorporation of New Jersey V I I No Drawing. Application April 11, 1945,
- Serial No. 587,831
4 Claims. (01. 260-608) invention relates to the method of preparing'sulfides of olefin'hydrocarbons, and to the resultingproducts; I Heretofore it has been necessary to use as starting materials olefinic halides for the preparation of olefin sulfides, and in such cases theyields have beenpoor, An objectof this invention is to use the olefin hydrocarbons directly as a starting materlal with resulting good yields of the sulfides. Further, it has been found that the reaction of olefins, with elemental sulfur, in the absence of zinc or similar metal in combination, produces alkyl alkenyl polysulfides rather than dialkenyl sulfides. By a dialkenyl sulfide is meant a monomeric compound consisting of sulfur bonded to two alkenyl groups. They subscribe tothe formula RSn-R where n is a whole number from 1 to 2, and R is an olefinic radical. I Alkenyl is used in the usual sense to refer to a monovalent I radical containing an ethylenic linkage.
The chemicals are prepared by a method which consists in interacting any olefinic hydrocarbon containing from 3 to 12 prising the group with elemental sulfur, in the presence of zinc or similar metal in combination, and a nitrogencontaining compound which belongs totheclass of rubber vulcanization accelerators.
There should be present at least one molecular proportion of zinc or similar metal in combination for each two molecular proportions of the olefin;
an excesstends to minimize undesirable side reactions. The molecular proportion of the sulfur should be at least 1.5 atomic proportions for each molecular proportion of the olefin. The proportion of the nitrogen-containing accelerator need salt may be added as such or formed in situ, as
where zinc oxide is added with the fatty acid. The reaction for preparing disulfide may be represented by the following equation:
R is an aliphatic radical containing from 3 to 17 carbon atoms.
carbon atoms and comtion,
Examples of olefins are propene, the butenes, the amenes,the hexenes, the heptenes, the catches, the nonenes, the decenes, the undecenes; and the dodecenes. W'here morethan one memher is referred to the intentionis to include each member of the class which contains a hydrogen atom attachedi'to the carbon atom which is alpha tothe double bond.v V 1 [Among the? sulfides may be mentioned 6,6'-dithiobis (5- methyl-4-nonene), and 6,6'-thlobis (5,- methylf-Fi-nonene) Z-butenyl monosulfide and d i-. sulfide, and 2-methyl2-butenyl monosulfideand disulfide. f I Q The sulfides of this invention are clear liquids possessing a persistent garlic-like 'odor and may be used as insecticides, fumigants, and as intermediates in the preparation of dyes, pharmaceuticals, resins, etc. Although the reactive form of the zinc in the reaction appears to be the salt of the organic acids of the fatty acid series, such as zinc propionate, zinc stearate, etc., it is possible to substitute zinc oxide for a portion of the zinc salt only to such extent that the rate of the reaction is not impaired so that undesirable side reactions occur. Also, the salt canbe formed in the reaction by introducing the proper amounts of the zinc oxide and of the acid. I a I In place of zinc, othermembers Of the so-called magnesium-zinc family of elements (see page344 of Mellors Modern Inorganic Chemistry," published by Longman, Green &Company, 1922), which family includes besides zinc, cadmium, magnesium, and mercury-may be used in place of the corresponding zinc compounds. I 1 z-mercaptobenzothiazoleland other thiazylsulfides are exemplary of the so-called vulcanization acceleratorswhich are useful in promoting the reaction of sulfur with olefin according to my invention; others, called thiuram sulfides, such as I tetramethyl thiuram sulfide, tetramethyl thiuramdisulfide, and ureas such as ,diphenyh thiourea, and-amines, ,such as dibenzylamine; diphenylguanidine, and triamylamine, as well as other nitrogen-containing accelerators of rubber vulcanization can be used.
; The re action takes place slowly at room tem-, perature and increases in rate with increasing temperature. The maximum temperature is lim ited only by theteinperature at which thermal decomposition of the products occurs. Eflicient temperatures are in the range from to 180 C. The following xarnples illustrate theinventhe parts being by Weight.
azole, 56 parts of zinc propionate, and 106 parts of zinc oxide is heated for 24 hours at C. The
ing the residue with an acetone-water solution of-- sodium sulfite. The high-boiling;prcdllctdsi.dis; 1
tilled in a molecular still, and is found to consist mainly of a mixture of the.=-dialken-yl ,-disulfides 1 formed by substitution of sulfur at ana-ngethy lene group of the olefin, together with a" small** amount of monosulfide. l v
Analyses Calc. for CzqHaS; s, 10.3;
ExAMrLn: 2 n v A mixture pa ts of trimerihr ethyi '1 90 par so u iu z fidrafisoizim oxi e 85.1w; i. ia lei nate and. zrarts of ZflI QIQ PP bSQWZQT thla ple hsat dat 3. Ci for, 1 1 101 he product, purified as in Example 'labove, is f oun d 9 1 on ist, o nrloximate g e ua .v par f h allsqnyl .mon s lfld and islllvfide which are, hen e ar ed br act smal. di illat on l rider cuum Analyses.-
an olefinic radical, and n is an integer from 1 to 2; which comprises reacting;- at aggt'emperature in the-range frd'mabout 90-"'. to about"'180 C., 2 molecular proportions of an olefinic hydrocarbon containing from 3 to 12 carbon atoms and conwith atleast ljatomic proportions of elemental suljurfln the presence of at least 1 molecular proportionof a metal salt of a saturated fatty acid a; haying irom 3 to 18 carbon atoms, the metal thereof being selected fgrom the magnesium-zinc ami y f me 1 or hem-rio icttablaa ndr cat lystasmmt uheffcctivaamountr ta rcr. gen-containing compound recognizedag; ulcani ati no cc l a rfor: uhban I 3-; A1 me o pre ri g; ial en ll sulfides sub c bin t t for la, Rh us- R an 1efin ad aL and n E an r tcs q rom "1 m w ch mpr s rea t ve z'molec lannmm ionsm anc sfin c hy roca bon; on inin f:
3 t 2 arbonsa om an c t ningltha tructure wi hlatfl eastiiaato ic p o ort ons ,dfvl'e emental ul ur, n th pre ence of .at ast. molecu arln tfla B1B. inlzo" 3 07; Began; r -g g Monosulfide from trimethylethylene: V v
Found Q .fio fifl/fignlmnn 1.497; 0.892. 70.5 1' 1111' 1 18:4 Calc,fo r QmHisS m. 70,6 10.6- 18. 8 Disulfide from t irpethylethylene taco/1mm o. 975 59. 9 9. 4 a1. 7 t 1 594 8.9 31. 7
EXAMPLE:
Butene-2 is reacted withsulfur in a manneranalogous to that of Examples Land 2' above and ithlat ea t 15 t m c l r p rtlon y.oil emental ilv lurr .tha resanccofat1east..1-, 1ac1 1arPm; p rtio f. am a t 1a a rat dl atty. acid ing m 8 1I'p n.. tQ n; e, mt@1.
canization acceleratorfog lrubber.
2. A method of preparing dialkenyl sulfides subscribing tot-then formulalR-asn-rR- where..R,=is
yields a mixture of-the 2-butenylmonoand gdi portion of zinc salt of a saturated fatty acid having from 3 to 18 carbon atomsand as catalysta smallnbut efiective amount of a nitrogen-containing. v compound:::recog1 nized 1 as -a. vulcanization accelerator-i fonrubber. I 4. A method of -preparing dialkenyl sul'fides subscribingcto thaformula *where-R is an olefinic radical, and w isanintegerfrom-1 2 ,1 which (comprises reacting 2--molecular propor tionsof an olefin ic hydrocarboncontaining-from 32to.12 carbonatoms and containing the structure v C=( C m lca izat mo t ubb rt th 1 1- ROBERT ARMSTBQNG REFERENCES 01111511;
T ,I JlQW rsl-m ier nm v. 1.: ozf'reeordim the file of this patent-;:; 3
N TED :ST ES. PAT NTS Number Name Date 2,329,486 Rummelsburg Sept. 14, 1943 2,338,829 Werntz Jan. 11, 1945
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US587831A US2446072A (en) | 1945-04-11 | 1945-04-11 | Preparation of dialkenyl sulfides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US587831A US2446072A (en) | 1945-04-11 | 1945-04-11 | Preparation of dialkenyl sulfides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2446072A true US2446072A (en) | 1948-07-27 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US587831A Expired - Lifetime US2446072A (en) | 1945-04-11 | 1945-04-11 | Preparation of dialkenyl sulfides |
Country Status (1)
| Country | Link |
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| US (1) | US2446072A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2748144A (en) * | 1951-01-22 | 1956-05-29 | Exxon Research Engineering Co | Process for preparing aryl thiophenes |
| US4643994A (en) * | 1984-12-17 | 1987-02-17 | The Research Foundation Of State University Of New York | Novel organic trithio oxides and method for the preparation thereof |
| US4665088A (en) * | 1984-11-14 | 1987-05-12 | The Research Foundation Of State University Of New York | (E-Z)-4,5,9-trithiadodeca-1,6,11-triene 9-oxides |
| US20030077264A1 (en) * | 2001-09-20 | 2003-04-24 | Goodrich Laura L. | Antimicrobial blood treatment using allicin and related compounds |
| JP2008538199A (en) * | 2005-01-26 | 2008-10-16 | メリアル リミテッド | Substituted thioethers as pesticides. |
| US20100152072A1 (en) * | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
| US20100152074A1 (en) * | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
| US20100152073A1 (en) * | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
| WO2017079017A1 (en) | 2015-11-06 | 2017-05-11 | The Lubrizol Corporation | Low viscosity gear lubricants |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2329486A (en) * | 1941-05-31 | 1943-09-14 | Hercules Powder Co Ltd | Terpene derivatives |
| US2338829A (en) * | 1941-05-06 | 1944-01-11 | Du Pont | Chemical process and product |
-
1945
- 1945-04-11 US US587831A patent/US2446072A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2338829A (en) * | 1941-05-06 | 1944-01-11 | Du Pont | Chemical process and product |
| US2329486A (en) * | 1941-05-31 | 1943-09-14 | Hercules Powder Co Ltd | Terpene derivatives |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2748144A (en) * | 1951-01-22 | 1956-05-29 | Exxon Research Engineering Co | Process for preparing aryl thiophenes |
| US4665088A (en) * | 1984-11-14 | 1987-05-12 | The Research Foundation Of State University Of New York | (E-Z)-4,5,9-trithiadodeca-1,6,11-triene 9-oxides |
| US4643994A (en) * | 1984-12-17 | 1987-02-17 | The Research Foundation Of State University Of New York | Novel organic trithio oxides and method for the preparation thereof |
| US20030077264A1 (en) * | 2001-09-20 | 2003-04-24 | Goodrich Laura L. | Antimicrobial blood treatment using allicin and related compounds |
| JP2008538199A (en) * | 2005-01-26 | 2008-10-16 | メリアル リミテッド | Substituted thioethers as pesticides. |
| US20100152074A1 (en) * | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
| US20100152072A1 (en) * | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
| US20100152073A1 (en) * | 2008-12-17 | 2010-06-17 | Chevron Oronite Company Llc | Lubricating oil compositions |
| EP2829596A1 (en) | 2008-12-17 | 2015-01-28 | Chevron Oronite Company LLC | Lubricating oil compositions |
| US9193931B2 (en) | 2008-12-17 | 2015-11-24 | Chevron Oronite Company Llc | Lubricating oil compositions |
| US9303229B2 (en) | 2008-12-17 | 2016-04-05 | Chevron U.S.A. Inc. | Lubricating oil composition |
| US9523061B2 (en) | 2008-12-17 | 2016-12-20 | Chevron Oronite Company Llc | Lubricating oil compositons |
| WO2017079017A1 (en) | 2015-11-06 | 2017-05-11 | The Lubrizol Corporation | Low viscosity gear lubricants |
| EP3786264A1 (en) | 2015-11-06 | 2021-03-03 | The Lubrizol Corporation | Low vicosity gear lubricants |
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