TWI574952B - Preparation of sulfur - containing epoxy compounds - Google Patents
Preparation of sulfur - containing epoxy compounds Download PDFInfo
- Publication number
- TWI574952B TWI574952B TW102112489A TW102112489A TWI574952B TW I574952 B TWI574952 B TW I574952B TW 102112489 A TW102112489 A TW 102112489A TW 102112489 A TW102112489 A TW 102112489A TW I574952 B TWI574952 B TW I574952B
- Authority
- TW
- Taiwan
- Prior art keywords
- sulfur
- compound
- containing epoxy
- integer
- bis
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 89
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 61
- 229910052717 sulfur Inorganic materials 0.000 title claims description 61
- 239000011593 sulfur Substances 0.000 title claims description 60
- 239000004593 Epoxy Substances 0.000 title claims description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 108
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 92
- 238000006243 chemical reaction Methods 0.000 claims description 53
- -1 haloalcohol compound Chemical class 0.000 claims description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 35
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 150000007514 bases Chemical class 0.000 claims description 16
- 239000012046 mixed solvent Substances 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 9
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 8
- 239000000920 calcium hydroxide Substances 0.000 claims description 8
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- SVEHZCKYZJXGCW-UHFFFAOYSA-N 1-chloro-3-(3-chloro-2-hydroxypropyl)sulfanylpropan-2-ol Chemical compound ClCC(O)CSCC(O)CCl SVEHZCKYZJXGCW-UHFFFAOYSA-N 0.000 description 11
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- WISUILQECWFZCN-UHFFFAOYSA-N 2-(oxiran-2-ylmethylsulfanylmethyl)oxirane Chemical compound C1OC1CSCC1CO1 WISUILQECWFZCN-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000008282 halocarbons Chemical class 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 229920006295 polythiol Polymers 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 4
- 239000000347 magnesium hydroxide Substances 0.000 description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- FLRNMYGRTLNEOW-UHFFFAOYSA-N 1-chloro-3-[(3-chloro-2-hydroxypropyl)disulfanyl]propan-2-ol Chemical compound ClCC(O)CSSCC(O)CCl FLRNMYGRTLNEOW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000002366 halogen compounds Chemical class 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 3
- 239000001095 magnesium carbonate Substances 0.000 description 3
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- SZPVNHKZNBIEBT-UHFFFAOYSA-N 1,3-di(undecyl)benzene Chemical compound CCCCCCCCCCCC1=CC=CC(CCCCCCCCCCC)=C1 SZPVNHKZNBIEBT-UHFFFAOYSA-N 0.000 description 2
- ZXACHZITICPUKS-UHFFFAOYSA-N 2-[(oxiran-2-ylmethyldisulfanyl)methyl]oxirane Chemical compound C1OC1CSSCC1CO1 ZXACHZITICPUKS-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- QEUCBMQFJDGQFC-UHFFFAOYSA-N CCCCCCCCCCCC1CCCC(C1)CCCCCCCCCCC Chemical compound CCCCCCCCCCCC1CCCC(C1)CCCCCCCCCCC QEUCBMQFJDGQFC-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical class ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- HYXPQIIYXQBMSW-UHFFFAOYSA-N 1,4-di(undecyl)cyclohexane Chemical compound C(CCCCCCCCC)CC1CCC(CC1)CCCCCCCCCCC HYXPQIIYXQBMSW-UHFFFAOYSA-N 0.000 description 1
- JFLJVRLBIZHFSU-UHFFFAOYSA-N 1,4-dithiane-2,5-dithiol Chemical compound SC1CSC(S)CS1 JFLJVRLBIZHFSU-UHFFFAOYSA-N 0.000 description 1
- XUDTWQTVXHPHBQ-UHFFFAOYSA-N 13-chlorotridecan-3-ol Chemical compound ClCCCCCCCCCCC(CC)O XUDTWQTVXHPHBQ-UHFFFAOYSA-N 0.000 description 1
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 1
- RWIUFGUSXTVQNV-UHFFFAOYSA-N 2-[[5-(oxiran-2-ylmethylsulfanylmethyl)-1,4-dithian-2-yl]methylsulfanylmethyl]oxirane Chemical compound C1OC1CSCC(SC1)CSC1CSCC1CO1 RWIUFGUSXTVQNV-UHFFFAOYSA-N 0.000 description 1
- NKTXJFKBFZWDLD-UHFFFAOYSA-N 3-methyl-3h-dithiole Chemical compound CC1SSC=C1 NKTXJFKBFZWDLD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NDBCPUURYCQHCX-UHFFFAOYSA-N C(CCCCCCCCC)CC1SCC(SC1)CCCCCCCCCCC Chemical compound C(CCCCCCCCC)CC1SCC(SC1)CCCCCCCCCCC NDBCPUURYCQHCX-UHFFFAOYSA-N 0.000 description 1
- HZTYJZRJMAQQKS-UHFFFAOYSA-N CO.ClCC(CSSCC(CCl)O)O Chemical compound CO.ClCC(CSSCC(CCl)O)O HZTYJZRJMAQQKS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000694440 Colpidium aqueous Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal 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
- 230000004075 alteration Effects 0.000 description 1
- ZWOASCVFHSYHOB-UHFFFAOYSA-N benzene-1,3-dithiol Chemical compound SC1=CC=CC(S)=C1 ZWOASCVFHSYHOB-UHFFFAOYSA-N 0.000 description 1
- WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- UMSNERSLSHPBNT-UHFFFAOYSA-N cyclohexane-1,3-dithiol Chemical compound SC1CCCC(S)C1 UMSNERSLSHPBNT-UHFFFAOYSA-N 0.000 description 1
- QQKBIYRSRXCROF-UHFFFAOYSA-N cyclohexane-1,4-dithiol Chemical compound SC1CCC(S)CC1 QQKBIYRSRXCROF-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- UGQWDFALGKAXTL-UHFFFAOYSA-M tetraoctylazanium;acetate Chemical compound CC([O-])=O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC UGQWDFALGKAXTL-UHFFFAOYSA-M 0.000 description 1
- SNNIPOQLGBPXPS-UHFFFAOYSA-M tetraoctylazanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC SNNIPOQLGBPXPS-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012093196 | 2012-04-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201345901A TW201345901A (zh) | 2013-11-16 |
| TWI574952B true TWI574952B (zh) | 2017-03-21 |
Family
ID=49383447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102112489A TWI574952B (zh) | 2012-04-16 | 2013-04-09 | Preparation of sulfur - containing epoxy compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9242947B2 (enExample) |
| EP (1) | EP2840082B1 (enExample) |
| JP (1) | JP5743025B2 (enExample) |
| KR (1) | KR101562636B1 (enExample) |
| CN (1) | CN104245684B (enExample) |
| BR (1) | BR112014021938B1 (enExample) |
| IN (1) | IN2014DN09394A (enExample) |
| TW (1) | TWI574952B (enExample) |
| WO (1) | WO2013157490A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015137402A1 (ja) | 2014-03-11 | 2015-09-17 | 三井化学株式会社 | 光学材料用エピスルフィド化合物の製造方法、エピスルフィド含有組成物、および該組成物を含む光学材料用重合性組成物 |
| JP6187722B2 (ja) * | 2015-03-24 | 2017-08-30 | 三菱瓦斯化学株式会社 | 新規な硫黄化合物及びそれを含む光学材料用組成物 |
| CN107250125B (zh) * | 2015-03-31 | 2018-07-13 | 三菱瓦斯化学株式会社 | 新型的环硫化合物及包含其的光学材料用组合物 |
| EP3228652B1 (en) * | 2015-03-31 | 2018-08-29 | Mitsubishi Gas Chemical Company, Inc. | Episulfide compound and optical material composition including the same |
| EP3431466B1 (en) * | 2016-03-18 | 2020-08-26 | Mitsui Chemicals, Inc. | Method for producing (poly)sulfide compound, and method for producing episulfide compound |
| CN106397370B (zh) * | 2016-08-30 | 2018-08-17 | 黄河三角洲京博化工研究院有限公司 | 一种生产高品质环氧化合物的方法 |
| CN112218854A (zh) * | 2018-06-29 | 2021-01-12 | 三菱瓦斯化学株式会社 | 多官能含硫环氧化合物的制造方法 |
| CN110156748A (zh) * | 2019-06-18 | 2019-08-23 | 江苏可奥熙光学材料科技有限公司 | 一种高折光率镜片单体的制备方法 |
| CN111646957B (zh) * | 2020-06-17 | 2023-06-09 | 益丰新材料股份有限公司 | 一种环氧化合物的制备方法 |
| CN112300098B (zh) * | 2020-10-29 | 2023-01-31 | 杭州光粒科技有限公司 | 光致聚合物组合物、环硫/环氧书写单体与光栅 |
| KR102600309B1 (ko) * | 2020-11-23 | 2023-11-08 | 대구가톨릭대학교산학협력단 | 염 화합물, 이의 제조방법 및 이를 포함한 알킬화제 |
| CN113461642B (zh) * | 2021-06-21 | 2023-03-10 | 西安瑞联新材料股份有限公司 | 一种2,2’-[硫代双(亚甲基)]双环氧乙烷的制备方法 |
| KR102881600B1 (ko) * | 2021-08-25 | 2025-11-11 | 동우 화인켐 주식회사 | 감광성 수지 조성물, 이를 이용한 돌출형 패턴 및 화상표시장치 |
| CN115974736A (zh) * | 2022-12-27 | 2023-04-18 | 益丰新材料股份有限公司 | 一种连续合成二(3-氯-2-羟丙基)硫化物的方法 |
| CN117105885A (zh) * | 2023-07-28 | 2023-11-24 | 益丰新材料股份有限公司 | 一种利用连续流反应器制备高品质含硫环氧化合物的方法 |
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| US3673260A (en) * | 1968-05-21 | 1972-06-27 | Aquitaine Petrole | Halogenated thioethers and method of preparations |
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| FR1578068A (enExample) * | 1968-05-21 | 1969-08-14 | ||
| US5807975A (en) | 1995-08-16 | 1998-09-15 | Mitsubishi Gas Chemical Company,Inc. | Alkyl sulfide type episulfide compound |
| JP3491660B2 (ja) | 1995-08-16 | 2004-01-26 | 三菱瓦斯化学株式会社 | 新規な直鎖アルキルスルフィド型エピスルフィド化合物 |
| JP3864998B2 (ja) | 1995-09-08 | 2007-01-10 | 三菱瓦斯化学株式会社 | 新規な分岐アルキルスルフィド型エピスルフィド化合物 |
| JPH09255781A (ja) | 1996-01-17 | 1997-09-30 | Mitsubishi Gas Chem Co Inc | 新規なエピスルフィド化合物 |
| US5945504A (en) | 1996-01-17 | 1999-08-31 | Mitsubishi Gas Chemical Company, Inc. | Episulfide compound |
| US6204311B1 (en) | 1998-03-13 | 2001-03-20 | Mitsui Chemicals, Inc. | Polymerizable composition |
| JP3315090B2 (ja) | 1998-03-13 | 2002-08-19 | 三井化学株式会社 | 重合性組成物 |
| JP4069342B2 (ja) | 1998-11-16 | 2008-04-02 | 三菱瓦斯化学株式会社 | ハロヒドリン化合物の製造方法 |
| JP2003048883A (ja) | 2001-05-29 | 2003-02-21 | Mitsubishi Gas Chem Co Inc | エピスルフィド化合物の製造方法 |
| JP4477393B2 (ja) * | 2004-03-26 | 2010-06-09 | 三井化学株式会社 | エピスルフィド化合物の安定剤 |
| JP5606112B2 (ja) * | 2010-03-18 | 2014-10-15 | 住友精化株式会社 | 新規ジアリールスルホン化合物、及びその製造方法 |
| TWI555725B (zh) * | 2010-03-18 | 2016-11-01 | 住友精化股份有限公司 | 新穎二芳基碸化合物及其製造方法 |
| JP2013142073A (ja) * | 2012-01-11 | 2013-07-22 | Mitsubishi Gas Chemical Co Inc | 含硫エポキシ化合物及びその製造方法 |
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- 2013-04-12 CN CN201380020112.7A patent/CN104245684B/zh active Active
- 2013-04-12 KR KR1020147021692A patent/KR101562636B1/ko active Active
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| US3673260A (en) * | 1968-05-21 | 1972-06-27 | Aquitaine Petrole | Halogenated thioethers and method of preparations |
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Also Published As
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| EP2840082A4 (en) | 2015-07-15 |
| US20140371475A1 (en) | 2014-12-18 |
| TW201345901A (zh) | 2013-11-16 |
| WO2013157490A1 (ja) | 2013-10-24 |
| IN2014DN09394A (enExample) | 2015-07-17 |
| JPWO2013157490A1 (ja) | 2015-12-21 |
| KR20150008375A (ko) | 2015-01-22 |
| EP2840082A1 (en) | 2015-02-25 |
| CN104245684A (zh) | 2014-12-24 |
| EP2840082B1 (en) | 2017-02-01 |
| KR101562636B1 (ko) | 2015-10-23 |
| BR112014021938A8 (pt) | 2019-08-27 |
| CN104245684B (zh) | 2016-01-06 |
| JP5743025B2 (ja) | 2015-07-01 |
| BR112014021938B1 (pt) | 2019-09-24 |
| US9242947B2 (en) | 2016-01-26 |
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