TW491872B - Block oligomers containing l-hydrocarbyloxy-2,2,6,6-tetramethyl-4- piperidyl groups as stabilizers for lower polyolefin - Google Patents

Info

Publication number

TW491872B

TW491872B TW087107195A TW87107195A TW491872B TW 491872 B TW491872 B TW 491872B TW 087107195 A TW087107195 A TW 087107195A TW 87107195 A TW87107195 A TW 87107195A TW 491872 B TW491872 B TW 491872B

Authority

TW

Taiwan

Prior art keywords

formula

compound

tert

cns

group

Prior art date

1997-05-27

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• 229920000098 polyolefin Polymers 0.000 title claims description 16
• 239000003381 stabilizer Substances 0.000 title abstract description 10
• 150000001875 compounds Chemical class 0.000 claims abstract description 125
• 230000003647 oxidation Effects 0.000 claims abstract description 9
• 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
• -1 polyethylene Polymers 0.000 claims description 194
• 239000000203 mixture Substances 0.000 claims description 102
• 238000011049 filling Methods 0.000 claims description 68
• 238000006243 chemical reaction Methods 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 21
• 239000004743 Polypropylene Substances 0.000 claims description 20
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• 229920001155 polypropylene Polymers 0.000 claims description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 239000004698 Polyethylene Substances 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
• 150000007529 inorganic bases Chemical class 0.000 claims description 10
• 239000003960 organic solvent Substances 0.000 claims description 9
• 229920000573 polyethylene Polymers 0.000 claims description 8
• 230000015556 catabolic process Effects 0.000 claims description 6
• 238000006731 degradation reaction Methods 0.000 claims description 6
• 239000006185 dispersion Substances 0.000 claims description 4
• 230000000087 stabilizing effect Effects 0.000 claims description 4
• 229910052702 rhenium Inorganic materials 0.000 claims description 2
• WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
• 239000013589 supplement Substances 0.000 claims description 2
• PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
• 230000009286 beneficial effect Effects 0.000 claims 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
• 150000004291 polyenes Chemical class 0.000 claims 1
• 229920002098 polyfluorene Polymers 0.000 claims 1
• 239000001257 hydrogen Substances 0.000 abstract description 19
• 229910052739 hydrogen Inorganic materials 0.000 abstract description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 9
• 229920001059 synthetic polymer Polymers 0.000 abstract description 5
• 239000004611 light stabiliser Substances 0.000 abstract description 3
• 239000012760 heat stabilizer Substances 0.000 abstract 1
• 239000011368 organic material Substances 0.000 abstract 1
• 230000000306 recurrent effect Effects 0.000 abstract 1
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 43
• 229920001577 copolymer Polymers 0.000 description 39
• 229910052757 nitrogen Inorganic materials 0.000 description 38
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 229920000642 polymer Polymers 0.000 description 26
• 230000002079 cooperative effect Effects 0.000 description 24
• 239000000126 substance Substances 0.000 description 24
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• 238000002360 preparation method Methods 0.000 description 18
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
• 150000001412 amines Chemical class 0.000 description 16
• 239000000047 product Substances 0.000 description 16
• 239000008096 xylene Substances 0.000 description 15
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
• 239000005977 Ethylene Substances 0.000 description 14
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
• 239000002585 base Substances 0.000 description 14
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 14
• 229920001684 low density polyethylene Polymers 0.000 description 14
• 239000004702 low-density polyethylene Substances 0.000 description 14
• 229920000768 polyamine Polymers 0.000 description 13
• 239000000243 solution Substances 0.000 description 13
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 150000002148 esters Chemical class 0.000 description 12
• 239000007858 starting material Substances 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 11
• 229910052751 metal Inorganic materials 0.000 description 11
• 239000002184 metal Substances 0.000 description 11
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 10
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 10
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
• 150000002431 hydrogen Chemical class 0.000 description 10
• 239000005062 Polybutadiene Substances 0.000 description 9
• 239000000654 additive Substances 0.000 description 9
• 125000003545 alkoxy group Chemical group 0.000 description 9
• 238000004458 analytical method Methods 0.000 description 9
• 229920002857 polybutadiene Polymers 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
• 239000007983 Tris buffer Substances 0.000 description 8
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 8
• 238000009826 distribution Methods 0.000 description 8
• 150000002430 hydrocarbons Chemical group 0.000 description 8
• 239000011572 manganese Substances 0.000 description 8
• 230000007246 mechanism Effects 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 125000003342 alkenyl group Chemical group 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• 239000000835 fiber Substances 0.000 description 7
• 238000005227 gel permeation chromatography Methods 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 230000008018 melting Effects 0.000 description 7
• 229960003742 phenol Drugs 0.000 description 7
• 239000004417 polycarbonate Substances 0.000 description 7
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 7
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 150000001993 dienes Chemical class 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• 238000006116 polymerization reaction Methods 0.000 description 6
• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
• 239000004721 Polyphenylene oxide Substances 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 125000006309 butyl amino group Chemical group 0.000 description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 235000019198 oils Nutrition 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• 229920000728 polyester Polymers 0.000 description 5
• 125000004076 pyridyl group Chemical group 0.000 description 5
• 150000005846 sugar alcohols Polymers 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
• 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 4
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
• 239000004925 Acrylic resin Substances 0.000 description 4
• 229920000178 Acrylic resin Polymers 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• 239000004215 Carbon black (E152) Substances 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
• 229920000877 Melamine resin Polymers 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
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• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 230000008859 change Effects 0.000 description 4
• 239000012141 concentrate Substances 0.000 description 4
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• 125000002993 cycloalkylene group Chemical group 0.000 description 4
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
• 229920001971 elastomer Polymers 0.000 description 4
• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
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• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical class OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
• 239000002245 particle Substances 0.000 description 4
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• 150000003254 radicals Chemical class 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 238000009987 spinning Methods 0.000 description 4
• 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
• CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
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• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
• BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
• MUNGMRPYTCHBFX-UHFFFAOYSA-N 1,5-diphenylpentane-1,3,5-trione Chemical compound C=1C=CC=CC=1C(=O)CC(=O)CC(=O)C1=CC=CC=C1 MUNGMRPYTCHBFX-UHFFFAOYSA-N 0.000 description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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• 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 description 3
• 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 3
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• 239000004952 Polyamide Substances 0.000 description 3
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• 229910052783 alkali metal Inorganic materials 0.000 description 3
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• 239000003963 antioxidant agent Substances 0.000 description 3
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• 239000008346 aqueous phase Substances 0.000 description 3
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• 239000012964 benzotriazole Substances 0.000 description 3
• FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
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• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
• 239000008116 calcium stearate Substances 0.000 description 3
• 235000013539 calcium stearate Nutrition 0.000 description 3
• 150000001991 dicarboxylic acids Chemical class 0.000 description 3
• 229940035422 diphenylamine Drugs 0.000 description 3
• 238000004821 distillation Methods 0.000 description 3
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
• 238000001125 extrusion Methods 0.000 description 3
• 238000005984 hydrogenation reaction Methods 0.000 description 3
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• 239000003607 modifier Substances 0.000 description 3
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 3
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
• 239000001301 oxygen Substances 0.000 description 3
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