DE1695116A1 - Lichtschutzmittel - Google Patents

Info

Publication number

DE1695116A1

DE1695116A1 DE19681695116 DE1695116A DE1695116A1 DE 1695116 A1 DE1695116 A1 DE 1695116A1 DE 19681695116 DE19681695116 DE 19681695116 DE 1695116 A DE1695116 A DE 1695116A DE 1695116 A1 DE1695116 A1 DE 1695116A1

Authority

DE

Germany

Prior art keywords

triazole

phenyl

hydroxy

methyl

formula

Prior art date

1967-02-07

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.)

Pending

Links

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• 239000004611 light stabiliser Substances 0.000 title claims description 30
• -1 p-hydroxyphenyl Chemical group 0.000 claims description 317
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 145
• 238000006243 chemical reaction Methods 0.000 claims description 54
• 238000000034 method Methods 0.000 claims description 53
• 150000001875 compounds Chemical class 0.000 claims description 44
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 238000002360 preparation method Methods 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 19
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 150000003852 triazoles Chemical group 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 230000002378 acidificating effect Effects 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 6
• 230000009471 action Effects 0.000 claims description 5
• 230000002829 reductive effect Effects 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 125000000383 tetramethylene group Chemical class [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
• 239000011368 organic material Substances 0.000 claims description 2
• BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 2
• 229920000620 organic polymer Polymers 0.000 claims 1
• 230000005855 radiation Effects 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 149
• 239000000243 solution Substances 0.000 description 133
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 118
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 81
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 78
• 239000000155 melt Substances 0.000 description 74
• 239000011541 reaction mixture Substances 0.000 description 65
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 63
• 229960000583 acetic acid Drugs 0.000 description 63
• 239000000203 mixture Substances 0.000 description 55
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 50
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 49
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
• 239000012362 glacial acetic acid Substances 0.000 description 39
• 125000004432 carbon atom Chemical group C* 0.000 description 34
• 238000002844 melting Methods 0.000 description 33
• 230000008018 melting Effects 0.000 description 33
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 32
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• 239000002244 precipitate Substances 0.000 description 29
• 239000006096 absorbing agent Substances 0.000 description 28
• 238000010992 reflux Methods 0.000 description 28
• 239000002253 acid Substances 0.000 description 27
• 238000001816 cooling Methods 0.000 description 26
• 229920000642 polymer Polymers 0.000 description 25
• 235000011054 acetic acid Nutrition 0.000 description 24
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 22
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• 238000003756 stirring Methods 0.000 description 20
• 125000003118 aryl group Chemical group 0.000 description 19
• 229910052801 chlorine Inorganic materials 0.000 description 19
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 18
• 239000000460 chlorine Substances 0.000 description 18
• 238000004519 manufacturing process Methods 0.000 description 18
• 239000012954 diazonium Substances 0.000 description 17
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
• 125000002252 acyl group Chemical group 0.000 description 15
• 239000013078 crystal Substances 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 150000002923 oximes Chemical class 0.000 description 15
• 150000003254 radicals Chemical class 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• 230000010933 acylation Effects 0.000 description 14
• 238000005917 acylation reaction Methods 0.000 description 14
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 14
• 238000006798 ring closing metathesis reaction Methods 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 13
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 12
• 238000002425 crystallisation Methods 0.000 description 12
• 230000008025 crystallization Effects 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 230000003647 oxidation Effects 0.000 description 12
• 238000007254 oxidation reaction Methods 0.000 description 12
• 239000001632 sodium acetate Substances 0.000 description 12
• 235000017281 sodium acetate Nutrition 0.000 description 12
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 11
• 230000008878 coupling Effects 0.000 description 11
• 238000010168 coupling process Methods 0.000 description 11
• 238000005859 coupling reaction Methods 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 10
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
• 238000001953 recrystallisation Methods 0.000 description 10
• 230000009467 reduction Effects 0.000 description 10
• 238000006722 reduction reaction Methods 0.000 description 10
• RPGLFLADGRRVLZ-UHFFFAOYSA-N 1-(furan-2-yl)-2-phenylethanone Chemical compound C=1C=COC=1C(=O)CC1=CC=CC=C1 RPGLFLADGRRVLZ-UHFFFAOYSA-N 0.000 description 9
• 239000007795 chemical reaction product Substances 0.000 description 9
• 150000001805 chlorine compounds Chemical class 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 9
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
• 150000007513 acids Chemical class 0.000 description 8
• 150000001298 alcohols Chemical class 0.000 description 8
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 8
• 150000001735 carboxylic acids Chemical class 0.000 description 8
• 239000000969 carrier Substances 0.000 description 8
• 239000012876 carrier material Substances 0.000 description 8
• 229910052736 halogen Inorganic materials 0.000 description 8
• 150000002367 halogens Chemical class 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 235000010288 sodium nitrite Nutrition 0.000 description 8
• 239000000758 substrate Substances 0.000 description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
• 125000004442 acylamino group Chemical group 0.000 description 7
• 150000008064 anhydrides Chemical class 0.000 description 7
• 239000003963 antioxidant agent Substances 0.000 description 7
• 230000005540 biological transmission Effects 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 238000000354 decomposition reaction Methods 0.000 description 7
• NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 7
• 238000005984 hydrogenation reaction Methods 0.000 description 7
• 150000002576 ketones Chemical class 0.000 description 7
• 239000000178 monomer Substances 0.000 description 7
• 229920003023 plastic Polymers 0.000 description 7
• 239000004033 plastic Substances 0.000 description 7
• 229920000728 polyester Polymers 0.000 description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
• 238000007127 saponification reaction Methods 0.000 description 7
• 238000001256 steam distillation Methods 0.000 description 7
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
• OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 6
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 238000009835 boiling Methods 0.000 description 6
• 150000003857 carboxamides Chemical class 0.000 description 6
• 229920001577 copolymer Polymers 0.000 description 6
• 230000032050 esterification Effects 0.000 description 6
• 238000005886 esterification reaction Methods 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 150000002429 hydrazines Chemical class 0.000 description 6
• 239000005457 ice water Substances 0.000 description 6
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
• 230000004048 modification Effects 0.000 description 6
• 238000012986 modification Methods 0.000 description 6
• 125000004430 oxygen atom Chemical group O* 0.000 description 6
• QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 6
• 229920001225 polyester resin Polymers 0.000 description 6
• 239000004645 polyester resin Substances 0.000 description 6
• 238000000859 sublimation Methods 0.000 description 6
• 230000008022 sublimation Effects 0.000 description 6
• 125000000542 sulfonic acid group Chemical group 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 5
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
• 239000007868 Raney catalyst Substances 0.000 description 5
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
• 229910000564 Raney nickel Inorganic materials 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 230000029936 alkylation Effects 0.000 description 5
• 238000005804 alkylation reaction Methods 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• 150000001728 carbonyl compounds Chemical class 0.000 description 5
• 238000009833 condensation Methods 0.000 description 5
• 230000005494 condensation Effects 0.000 description 5
• ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 150000002430 hydrocarbons Chemical group 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
• 125000002560 nitrile group Chemical group 0.000 description 5
• 150000002989 phenols Chemical class 0.000 description 5
• 239000012286 potassium permanganate Substances 0.000 description 5
• 239000011241 protective layer Substances 0.000 description 5
• 150000003839 salts Chemical class 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 229920002554 vinyl polymer Polymers 0.000 description 5
• 239000001993 wax Substances 0.000 description 5
• 238000004383 yellowing Methods 0.000 description 5
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
• KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 4
• ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
• 238000005727 Friedel-Crafts reaction Methods 0.000 description 4
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
• 239000004698 Polyethylene Substances 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• 239000012346 acetyl chloride Substances 0.000 description 4
• 239000000654 additive Substances 0.000 description 4
• 125000003710 aryl alkyl group Chemical group 0.000 description 4
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 229920002678 cellulose Polymers 0.000 description 4
• 229910000365 copper sulfate Inorganic materials 0.000 description 4
• 125000000753 cycloalkyl group Chemical group 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 150000002170 ethers Chemical class 0.000 description 4
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
• 239000013067 intermediate product Substances 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 229910052751 metal Inorganic materials 0.000 description 4
• 239000002184 metal Substances 0.000 description 4
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
• REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 4
• 239000007800 oxidant agent Substances 0.000 description 4
• 230000001590 oxidative effect Effects 0.000 description 4
• 229940067157 phenylhydrazine Drugs 0.000 description 4
• 229910052698 phosphorus Inorganic materials 0.000 description 4
• 229920000573 polyethylene Polymers 0.000 description 4
• 229910052938 sodium sulfate Inorganic materials 0.000 description 4
• 235000011152 sodium sulphate Nutrition 0.000 description 4
• 238000001179 sorption measurement Methods 0.000 description 4
• 125000003944 tolyl group Chemical group 0.000 description 4
• ZZOJDCWBIOFSAI-UHFFFAOYSA-N (2-methoxy-5-methylphenyl)hydrazine Chemical compound COC1=CC=C(C)C=C1NN ZZOJDCWBIOFSAI-UHFFFAOYSA-N 0.000 description 3
• RBLBZXMXQHOMHZ-UHFFFAOYSA-N (2-methoxy-5-phenylphenyl)hydrazine Chemical compound C1=C(NN)C(OC)=CC=C1C1=CC=CC=C1 RBLBZXMXQHOMHZ-UHFFFAOYSA-N 0.000 description 3
• FGODPVCKFLEVFG-UHFFFAOYSA-N (2-methoxyphenyl)hydrazine Chemical compound COC1=CC=CC=C1NN FGODPVCKFLEVFG-UHFFFAOYSA-N 0.000 description 3
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