DE2558729A1 - Neue mercaptocarbonsaeureester und verfahren zu deren herstellung - Google Patents
Neue mercaptocarbonsaeureester und verfahren zu deren herstellungInfo
- Publication number
- DE2558729A1 DE2558729A1 DE2558729A DE2558729A DE2558729A1 DE 2558729 A1 DE2558729 A1 DE 2558729A1 DE 2558729 A DE2558729 A DE 2558729A DE 2558729 A DE2558729 A DE 2558729A DE 2558729 A1 DE2558729 A1 DE 2558729A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carbon atoms
- alkyl
- group
- mercaptocarboxylic
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- UGEILJMYCXDBRH-UHFFFAOYSA-N sulfanyl hydrogen carbonate Chemical class OC(=O)OS UGEILJMYCXDBRH-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 20
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 18
- -1 Mercaptocarboxylic acid ester Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 17
- 150000002118 epoxides Chemical class 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000003549 soybean oil Substances 0.000 claims description 5
- 235000012424 soybean oil Nutrition 0.000 claims description 5
- 150000003568 thioethers Chemical class 0.000 claims description 5
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000005156 substituted alkylene group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 2
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000004597 plastic additive Substances 0.000 description 2
- 150000003151 propanoic acid esters Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GJEZBVHHZQAEDB-SYDPRGILSA-N (1s,5r)-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC[C@H]2O[C@H]21 GJEZBVHHZQAEDB-SYDPRGILSA-N 0.000 description 1
- JYPFIWQRWKQDKH-KTKRTIGZSA-N (z)-2-sulfanyloctadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCC(S)C(O)=O JYPFIWQRWKQDKH-KTKRTIGZSA-N 0.000 description 1
- FUJGFMYGMIFFKQ-UHFFFAOYSA-N 1-phenoxypropane-1,1-diol Chemical class CCC(O)(O)OC1=CC=CC=C1 FUJGFMYGMIFFKQ-UHFFFAOYSA-N 0.000 description 1
- OZAAEETZNZUQRX-UHFFFAOYSA-N 1-sulfanylnaphthalene-2-carboxylic acid Chemical compound C1=CC=CC2=C(S)C(C(=O)O)=CC=C21 OZAAEETZNZUQRX-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- KXSWSFNGQCBWQA-UHFFFAOYSA-N 1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene Chemical compound C1C2=CC=CC=C2CC2C1O2 KXSWSFNGQCBWQA-UHFFFAOYSA-N 0.000 description 1
- VGWMANKEPYEWNK-UHFFFAOYSA-N 2,2,3,3-tetraphenyloxirane Chemical compound C=1C=CC=CC=1C1(C=2C=CC=CC=2)OC1(C=1C=CC=CC=1)C1=CC=CC=C1 VGWMANKEPYEWNK-UHFFFAOYSA-N 0.000 description 1
- WISUILQECWFZCN-UHFFFAOYSA-N 2-(oxiran-2-ylmethylsulfanylmethyl)oxirane Chemical class C1OC1CSCC1CO1 WISUILQECWFZCN-UHFFFAOYSA-N 0.000 description 1
- BCJPEZMFAKOJPM-UHFFFAOYSA-N 2-ethyl-3-methyloxirane Chemical compound CCC1OC1C BCJPEZMFAKOJPM-UHFFFAOYSA-N 0.000 description 1
- CFPHMAVQAJGVPV-UHFFFAOYSA-N 2-sulfanylbutanoic acid Chemical compound CCC(S)C(O)=O CFPHMAVQAJGVPV-UHFFFAOYSA-N 0.000 description 1
- REFZTFPICLNNPM-UHFFFAOYSA-N 2-sulfanyldodecanoic acid Chemical compound CCCCCCCCCCC(S)C(O)=O REFZTFPICLNNPM-UHFFFAOYSA-N 0.000 description 1
- NTKCAHRZWRIYFH-UHFFFAOYSA-N 2-sulfanyloctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(S)C(O)=O NTKCAHRZWRIYFH-UHFFFAOYSA-N 0.000 description 1
- IMGGANUNCHXAQF-UHFFFAOYSA-N 2-sulfanylpentanoic acid Chemical compound CCCC(S)C(O)=O IMGGANUNCHXAQF-UHFFFAOYSA-N 0.000 description 1
- MTMDLUFMACHNQR-UHFFFAOYSA-N 3-methyl-2-sulfanylbutanoic acid Chemical compound CC(C)C(S)C(O)=O MTMDLUFMACHNQR-UHFFFAOYSA-N 0.000 description 1
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 1
- FLWILQBNWJWFOO-UHFFFAOYSA-N 3-sulfanylpentanedioic acid Chemical compound OC(=O)CC(S)CC(O)=O FLWILQBNWJWFOO-UHFFFAOYSA-N 0.000 description 1
- GCDFODQNNFXERB-UHFFFAOYSA-N 4,5-dimethyl-3-sulfanylhexanoic acid Chemical compound CC(C)C(C)C(S)CC(O)=O GCDFODQNNFXERB-UHFFFAOYSA-N 0.000 description 1
- HMKPBPAJTBLNLH-UHFFFAOYSA-N 4-hydroxy-3-sulfanylbutanoic acid Chemical compound OCC(S)CC(O)=O HMKPBPAJTBLNLH-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- DTRIDVOOPAQEEL-UHFFFAOYSA-N 4-sulfanylbutanoic acid Chemical compound OC(=O)CCCS DTRIDVOOPAQEEL-UHFFFAOYSA-N 0.000 description 1
- QXNCUGXEZGTWHK-UHFFFAOYSA-N 4-sulfanylhexanoic acid Chemical compound CCC(S)CCC(O)=O QXNCUGXEZGTWHK-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LXXNWCFBZHKFPT-UHFFFAOYSA-N Ethyl 2-mercaptopropionate Chemical compound CCOC(=O)C(C)S LXXNWCFBZHKFPT-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- MKYQPGPNVYRMHI-UHFFFAOYSA-N Triphenylethylene Chemical compound C=1C=CC=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 MKYQPGPNVYRMHI-UHFFFAOYSA-N 0.000 description 1
- 238000006853 Ziegler synthesis reaction Methods 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- VLFLYIUFLKXQMS-UHFFFAOYSA-M octadecanoate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CCCCCCCCCCCCCCCCCC([O-])=O VLFLYIUFLKXQMS-UHFFFAOYSA-M 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/226—Compounds with one or more Sn-S linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2558729A DE2558729A1 (de) | 1975-12-24 | 1975-12-24 | Neue mercaptocarbonsaeureester und verfahren zu deren herstellung |
| NL7614037A NL7614037A (nl) | 1975-12-24 | 1976-12-17 | Werkwijze voor het bereiden van nieuwe mercaptocarbonzuuresters. |
| CH1609976A CH623035A5 (en) | 1975-12-24 | 1976-12-21 | Process for the preparation of novel mercaptocarboxylic esters |
| LU76454A LU76454A1 (enExample) | 1975-12-24 | 1976-12-22 | |
| IT30756/76A IT1065676B (it) | 1975-12-24 | 1976-12-22 | Esteri di acidi mercaptocarbossilici e processo per la loro preparazione |
| AT951776A AT350039B (de) | 1975-12-24 | 1976-12-22 | Verahren zur herstellung neuer mercaptocarbon- saeureester |
| JP15436376A JPS5283328A (en) | 1975-12-24 | 1976-12-23 | New mercapto carboxylic ester and its method of manufacturing |
| CA268,650A CA1095073A (en) | 1975-12-24 | 1976-12-23 | Mercaptocarboxylic acid esters and process for their manufacture |
| DK581976A DK581976A (da) | 1975-12-24 | 1976-12-23 | Mercaptocarboxylsyreestere samt fremgangsmade til fremstilling deraf |
| BE173634A BE849858A (fr) | 1975-12-24 | 1976-12-24 | Esters d'acides thiol-carboxyliques et leur preparation |
| FR7639058A FR2336389A1 (fr) | 1975-12-24 | 1976-12-24 | Esters d'acides thiol-carboxyliques et leur preparation |
| GB54128/76A GB1566310A (en) | 1975-12-24 | 1976-12-24 | Mercaptocarboxylic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2558729A DE2558729A1 (de) | 1975-12-24 | 1975-12-24 | Neue mercaptocarbonsaeureester und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2558729A1 true DE2558729A1 (de) | 1977-07-14 |
Family
ID=5965665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2558729A Withdrawn DE2558729A1 (de) | 1975-12-24 | 1975-12-24 | Neue mercaptocarbonsaeureester und verfahren zu deren herstellung |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5283328A (enExample) |
| AT (1) | AT350039B (enExample) |
| BE (1) | BE849858A (enExample) |
| CA (1) | CA1095073A (enExample) |
| CH (1) | CH623035A5 (enExample) |
| DE (1) | DE2558729A1 (enExample) |
| DK (1) | DK581976A (enExample) |
| FR (1) | FR2336389A1 (enExample) |
| GB (1) | GB1566310A (enExample) |
| IT (1) | IT1065676B (enExample) |
| LU (1) | LU76454A1 (enExample) |
| NL (1) | NL7614037A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4122064A (en) * | 1975-12-30 | 1978-10-24 | Hoechst Aktiengesellschaft | Novel organo-tin compounds and their use as stabilizers |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2933388C2 (de) * | 1979-08-17 | 1987-03-12 | Henkel KGaA, 4000 Düsseldorf | Verwendung schwefelhaltiger Hydroxicarbonsäuren als Korrosionsinhibitoren |
| AU614636B2 (en) * | 1988-07-21 | 1991-09-05 | Ciba Specialty Chemicals Holding Inc. | Corrosion inhibition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1236925A (en) * | 1967-09-27 | 1971-06-23 | Ici Ltd | Stabilisers for polymeric compositions |
| GB1233036A (enExample) * | 1968-11-22 | 1971-05-26 | ||
| GB1349913A (en) * | 1970-10-02 | 1974-04-10 | Interstab Ltd | Stabilisers for vinyl chloride resins |
-
1975
- 1975-12-24 DE DE2558729A patent/DE2558729A1/de not_active Withdrawn
-
1976
- 1976-12-17 NL NL7614037A patent/NL7614037A/xx not_active Application Discontinuation
- 1976-12-21 CH CH1609976A patent/CH623035A5/de not_active IP Right Cessation
- 1976-12-22 AT AT951776A patent/AT350039B/de not_active IP Right Cessation
- 1976-12-22 LU LU76454A patent/LU76454A1/xx unknown
- 1976-12-22 IT IT30756/76A patent/IT1065676B/it active
- 1976-12-23 JP JP15436376A patent/JPS5283328A/ja active Pending
- 1976-12-23 DK DK581976A patent/DK581976A/da unknown
- 1976-12-23 CA CA268,650A patent/CA1095073A/en not_active Expired
- 1976-12-24 FR FR7639058A patent/FR2336389A1/fr active Granted
- 1976-12-24 GB GB54128/76A patent/GB1566310A/en not_active Expired
- 1976-12-24 BE BE173634A patent/BE849858A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4122064A (en) * | 1975-12-30 | 1978-10-24 | Hoechst Aktiengesellschaft | Novel organo-tin compounds and their use as stabilizers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1566310A (en) | 1980-04-30 |
| FR2336389B1 (enExample) | 1980-06-06 |
| BE849858A (fr) | 1977-06-24 |
| DK581976A (da) | 1977-06-25 |
| ATA951776A (de) | 1978-10-15 |
| CA1095073A (en) | 1981-02-03 |
| NL7614037A (nl) | 1977-06-28 |
| AT350039B (de) | 1979-05-10 |
| CH623035A5 (en) | 1981-05-15 |
| FR2336389A1 (fr) | 1977-07-22 |
| IT1065676B (it) | 1985-03-04 |
| LU76454A1 (enExample) | 1977-07-05 |
| JPS5283328A (en) | 1977-07-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |