SK84595A3 - Catalytic oxidation process - Google Patents

Catalytic oxidation process Download PDF

Info

Publication number: SK84595A3
Authority: SK; Slovakia
Prior art keywords: mercaptan; oxygen; oxidized; salt; dithiocarbamic acid
Prior art date: 1992-12-30

Application number

SK845-95A

Other languages

English (en)

Slovak (sk)

Inventor

Denis O Comeyne

Eric J Meerbergen

Dennis P Riley

David J Sikora

Gilbert F J Strackx

Mary J T Young

Original Assignee

Monsanto Co

Priority date (The priority date 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 date listed.)

1992-12-30

Filing date

1993-12-03

Publication date

1995-12-06

1993-12-03 Application filed by Monsanto Co filed Critical Monsanto Co

1995-12-06 Publication of SK84595A3 publication Critical patent/SK84595A3/sk

Links

230000003647 oxidation Effects 0.000 title claims abstract description 14
238000007254 oxidation reaction Methods 0.000 title claims abstract description 14
230000003197 catalytic effect Effects 0.000 title claims abstract description 6
238000000034 method Methods 0.000 title claims description 52
230000008569 process Effects 0.000 title claims description 23
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 52
239000003054 catalyst Substances 0.000 claims abstract description 43
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 30
229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
239000001301 oxygen Substances 0.000 claims abstract description 30
150000003573 thiols Chemical class 0.000 claims abstract description 17
229910052799 carbon Inorganic materials 0.000 claims abstract description 13
-1 thiol salts Chemical class 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
239000002253 acid Substances 0.000 claims abstract description 4
150000007513 acids Chemical class 0.000 claims abstract description 3
150000004696 coordination complex Chemical class 0.000 claims abstract description 3
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 31
238000006243 chemical reaction Methods 0.000 claims description 30
150000001412 amines Chemical class 0.000 claims description 13
239000002184 metal Substances 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 11
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
150000003335 secondary amines Chemical class 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 6
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 5
HKAVADYDPYUPRD-UHFFFAOYSA-N 1h-pyrazine-2-thione Chemical compound SC1=CN=CC=N1 HKAVADYDPYUPRD-UHFFFAOYSA-N 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 4
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 claims description 4
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims description 4
CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 claims description 3
239000011261 inert gas Substances 0.000 claims description 3
239000012429 reaction media Substances 0.000 claims description 3
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 2
MGAXHFMCFLLMNG-UHFFFAOYSA-N 1h-pyrimidine-6-thione Chemical compound SC1=CC=NC=N1 MGAXHFMCFLLMNG-UHFFFAOYSA-N 0.000 claims description 2
KXZSVYHFYHTNBI-UHFFFAOYSA-N 1h-quinoline-2-thione Chemical compound C1=CC=CC2=NC(S)=CC=C21 KXZSVYHFYHTNBI-UHFFFAOYSA-N 0.000 claims description 2
OJOPTXKXKPMMGC-UHFFFAOYSA-N 4-methyl-1h-quinoline-2-thione Chemical compound C1=CC=C2C(C)=CC(S)=NC2=C1 OJOPTXKXKPMMGC-UHFFFAOYSA-N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 claims description 2
229940043279 diisopropylamine Drugs 0.000 claims description 2
MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 claims description 2
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 claims description 2
239000003586 protic polar solvent Substances 0.000 claims description 2
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims description 2
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 claims description 2
239000000463 material Substances 0.000 claims 4
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
SZRLKIKBPASKQH-UHFFFAOYSA-N dibutyldithiocarbamic acid Chemical compound CCCCN(C(S)=S)CCCC SZRLKIKBPASKQH-UHFFFAOYSA-N 0.000 claims 1
150000002926 oxygen Chemical class 0.000 claims 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
239000000203 mixture Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
238000002360 preparation method Methods 0.000 description 15
IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 9
102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 8
101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 8
AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 4
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 4
230000036284 oxygen consumption Effects 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
IKJXJJQDWMQZQQ-UHFFFAOYSA-N 2-methyl-n-pyridin-2-ylsulfanylpropan-2-amine Chemical compound CC(C)(C)NSC1=CC=CC=N1 IKJXJJQDWMQZQQ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 3
VIHMZNMSEVOOPY-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)propan-2-amine Chemical compound C1=CC=C2SC(SNC(C)C)=NC2=C1 VIHMZNMSEVOOPY-UHFFFAOYSA-N 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
ODHAQPXNQDBHSH-UHFFFAOYSA-N Dicyclohexyl disulfide Chemical compound C1CCCCC1SSC1CCCCC1 ODHAQPXNQDBHSH-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000197 pyrolysis Methods 0.000 description 2
238000005070 sampling Methods 0.000 description 2
QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
YUMISYNFFDGTRK-UHFFFAOYSA-N 2-methyl-n-(1,3-thiazol-2-ylsulfanyl)propan-2-amine Chemical compound CC(C)(C)NSC1=NC=CS1 YUMISYNFFDGTRK-UHFFFAOYSA-N 0.000 description 1
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
FEUISMYEFPANSS-UHFFFAOYSA-N 2-methylcyclohexan-1-amine Chemical compound CC1CCCCC1N FEUISMYEFPANSS-UHFFFAOYSA-N 0.000 description 1
QRYFCNPYGUORTK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yldisulfanyl)morpholine Chemical compound C1COCCN1SSC1=NC2=CC=CC=C2S1 QRYFCNPYGUORTK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
240000007049 Juglans regia Species 0.000 description 1
235000009496 Juglans regia Nutrition 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
150000001785 cerium compounds Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
BLEBFDYUDVZRFG-UHFFFAOYSA-N dichloromethane;propan-2-ol Chemical compound ClCCl.CC(C)O BLEBFDYUDVZRFG-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical class OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 1
239000003345 natural gas Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000033116 oxidation-reduction process Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000003415 peat Substances 0.000 description 1
IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
238000004448 titration Methods 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/30—Dithiocarbamic acids; Derivatives thereof having sulfur atoms of dithiocarbamic groups bound to other sulfur atoms
- C07C333/32—Thiuramsulfides; Thiurampolysulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/78—Sulfur atoms attached to a second hetero atom to a second sulphur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK845-95A 1992-12-30 1993-12-03 Catalytic oxidation process SK84595A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US99871392A	1992-12-30	1992-12-30
PCT/US1993/011740 WO1994015927A1 (en)	1992-12-30	1993-12-03	Catalytic oxidation process

Publications (1)

Publication Number	Publication Date
SK84595A3 true SK84595A3 (en)	1995-12-06

Family

ID=25545498

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK845-95A SK84595A3 (en)	1992-12-30	1993-12-03	Catalytic oxidation process

Country Status (17)

Country	Link
EP (1)	EP0677045B1 (de)
JP (1)	JPH08505618A (de)
KR (1)	KR0160588B1 (de)
CN (1)	CN1041924C (de)
AT (1)	ATE176667T1 (de)
AU (1)	AU674558B2 (de)
BR (1)	BR9307799A (de)
CA (1)	CA2150388A1 (de)
CZ (1)	CZ154995A3 (de)
DE (1)	DE69323500T2 (de)
ES (1)	ES2128548T3 (de)
GE (1)	GEP19991598B (de)
HU (1)	HUT72002A (de)
MX (1)	MX9400063A (de)
RU (1)	RU2104275C1 (de)
SK (1)	SK84595A3 (de)
WO (1)	WO1994015927A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE147072T1 (de) *	1992-06-05	1997-01-15	Monsanto Co	4-pyrimidin sulfenamide und ihre verwendung in kautschuk
CN101139338B (zh) *	2007-07-09	2013-10-23	青岛科技大学	基于2-硫醇苯并噻唑铵盐的氧气法制备2,2＇-二硫代二苯并噻唑
CN103554055B (zh) *	2013-10-29	2015-06-17	西南化工研究设计院有限公司	一种n-氧二乙撑-2-苯并噻唑次磺酰胺的绿色制备工艺
CN107638877B (zh) *	2017-09-28	2020-07-14	晋城天成化工有限公司	二硫化四甲基秋兰姆的合成方法
CN108101864B (zh) *	2017-12-20	2021-08-10	蔚林新材料科技股份有限公司	N-叔丁基-2-苯并噻唑次磺酰胺的制备方法
CN116102520B (zh) *	2022-12-19	2024-06-07	山东尚舜化工有限公司	一种氧气氧化法合成促进剂mbts（dm）的方法
CN115999495B (zh) *	2023-03-24	2023-06-27	东营巨宝工贸有限公司	一种应用于氧气氧化法生产硫化促进剂的反应釜

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US3654297A (en) *	1969-02-10	1972-04-04	American Cyanamid Co	Process for oxidizing 2-mercaptobenzothiazole
US3737431A (en) *	1970-02-24	1973-06-05	Monsanto Co	Preparation of sulfenamides by catalytic oxidation
US4182873A (en) *	1972-10-04	1980-01-08	Rhone-Poulenc S.A.	Process for the preparation of thiazolesulphenamides
DE2944225A1 (de) *	1979-11-02	1981-05-07	Akzo Gmbh, 5600 Wuppertal	Verfahren zur herstellung von dithiazoldisulfiden
ES8200357A1 (es) *	1979-11-23	1981-11-16	Monsanto Europe Sa	Un proceso para la produccion de sulfenamidas
DE3205555A1 (de) *	1982-02-17	1983-08-25	Akzo Gmbh, 5600 Wuppertal	Verfahren zur herstellung von dithiazoldisulfiden
DE3325724A1 (de) *	1983-07-16	1985-01-24	Akzo Gmbh, 5600 Wuppertal	Verfahren zur herstellung von thiazolyl-2-sulfenamiden
DE4032680A1 (de) *	1990-10-15	1992-04-16	Akzo Gmbh	Verfahren zur herstellung von 2-aminodithiothiazolen und 2-aminotrithiothiazolen

1993
- 1993-12-03 ES ES94903426T patent/ES2128548T3/es not_active Expired - Lifetime
- 1993-12-03 RU RU95113603A patent/RU2104275C1/ru active
- 1993-12-03 WO PCT/US1993/011740 patent/WO1994015927A1/en not_active Ceased
- 1993-12-03 CA CA002150388A patent/CA2150388A1/en not_active Abandoned
- 1993-12-03 KR KR1019950702658A patent/KR0160588B1/ko not_active Expired - Fee Related
- 1993-12-03 GE GEAP19932774A patent/GEP19991598B/en unknown
- 1993-12-03 AT AT94903426T patent/ATE176667T1/de not_active IP Right Cessation
- 1993-12-03 HU HU9501952A patent/HUT72002A/hu unknown
- 1993-12-03 AU AU57379/94A patent/AU674558B2/en not_active Ceased
- 1993-12-03 BR BR9307799A patent/BR9307799A/pt not_active IP Right Cessation
- 1993-12-03 CZ CZ951549A patent/CZ154995A3/cs unknown
- 1993-12-03 SK SK845-95A patent/SK84595A3/sk unknown
- 1993-12-03 DE DE69323500T patent/DE69323500T2/de not_active Expired - Fee Related
- 1993-12-03 JP JP6515989A patent/JPH08505618A/ja active Pending
- 1993-12-03 EP EP94903426A patent/EP0677045B1/de not_active Expired - Lifetime
- 1993-12-29 CN CN93121511A patent/CN1041924C/zh not_active Expired - Fee Related
1994
- 1994-01-03 MX MX9400063A patent/MX9400063A/es unknown

Also Published As

Publication number	Publication date
HU9501952D0 (en)	1995-09-28
CZ154995A3 (en)	1995-12-13
HUT72002A (en)	1996-03-28
DE69323500D1 (de)	1999-03-25
AU674558B2 (en)	1997-01-02
RU95113603A (ru)	1997-06-10
CA2150388A1 (en)	1994-07-21
WO1994015927A1 (en)	1994-07-21
DE69323500T2 (de)	1999-09-16
GEP19991598B (en)	1999-04-29
JPH08505618A (ja)	1996-06-18
RU2104275C1 (ru)	1998-02-10
KR960700234A (ko)	1996-01-19
BR9307799A (pt)	1995-11-14
KR0160588B1 (ko)	1998-12-01
EP0677045B1 (de)	1999-02-10
MX9400063A (es)	1994-07-29
EP0677045A1 (de)	1995-10-18
ATE176667T1 (de)	1999-02-15
ES2128548T3 (es)	1999-05-16
CN1041924C (zh)	1999-02-03
CN1096024A (zh)	1994-12-07
AU5737994A (en)	1994-08-15

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Blank et al.	1977	Synthesis and hypoglycemic activity of 4-substituted 3-mercaptopicolinic acids