DE137956C - - Google Patents

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Publication number

DE137956C

DE137956C DENDAT137956D DE137956DA DE137956C DE 137956 C DE137956 C DE 137956C DE NDAT137956 D DENDAT137956 D DE NDAT137956D DE 137956D A DE137956D A DE 137956DA DE 137956 C DE137956 C DE 137956C

Authority

DE

Germany

Prior art keywords

methyl ether

nitro

sulfuric acid

methyl

ether

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.)

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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 7
• XVBAPYDWAVGVGW-UHFFFAOYSA-N 2-chloro-1-methoxy-3-nitrobenzene Chemical compound COC1=CC=CC([N+]([O-])=O)=C1Cl XVBAPYDWAVGVGW-UHFFFAOYSA-N 0.000 claims description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
• RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 claims description 2
• 150000001875 compounds Chemical class 0.000 claims description 2
• 238000000034 method Methods 0.000 claims description 2
• 239000003513 alkali Substances 0.000 claims 1
• 239000002585 base Substances 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 238000002844 melting Methods 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• -1 nitro-acetyl compound Chemical class 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 235000011121 sodium hydroxide Nutrition 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 description 1
• DWZHBDDEQQAESG-UHFFFAOYSA-N 2-(chloromethoxy)aniline Chemical compound NC1=CC=CC=C1OCCl DWZHBDDEQQAESG-UHFFFAOYSA-N 0.000 description 1
• CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 description 1
• XWPDPFLBSAPRCO-UHFFFAOYSA-N 4-(chloromethoxy)aniline Chemical compound NC1=CC=C(OCCl)C=C1 XWPDPFLBSAPRCO-UHFFFAOYSA-N 0.000 description 1
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 230000021736 acetylation Effects 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 150000008049 diazo compounds Chemical class 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 238000004043 dyeing Methods 0.000 description 1
• LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 238000006396 nitration reaction Methods 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
• RGHXWDVNBYKJQH-UHFFFAOYSA-N nitroacetic acid Chemical class OC(=O)C[N+]([O-])=O RGHXWDVNBYKJQH-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1