CS237717B1 - Isolation method of 3-methyl-4-nitrophenole - Google Patents
Isolation method of 3-methyl-4-nitrophenole Download PDFInfo
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- CS237717B1 CS237717B1 CS832587A CS258783A CS237717B1 CS 237717 B1 CS237717 B1 CS 237717B1 CS 832587 A CS832587 A CS 832587A CS 258783 A CS258783 A CS 258783A CS 237717 B1 CS237717 B1 CS 237717B1
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- methyl
- nitrophenol
- sodium
- aqueous solution
- nitrophenolate
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- 238000002955 isolation Methods 0.000 title claims abstract description 5
- PIIZYNQECPTVEO-UHFFFAOYSA-N 4-nitro-m-cresol Chemical compound CC1=CC(O)=CC=C1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000012535 impurity Substances 0.000 claims abstract description 10
- DEQWBYKBSRNLCS-UHFFFAOYSA-M sodium;3-methyl-4-nitrophenolate Chemical compound [Na+].CC1=CC([O-])=CC=C1[N+]([O-])=O DEQWBYKBSRNLCS-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 7
- 239000011707 mineral Substances 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- 238000010979 pH adjustment Methods 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000013530 defoamer Substances 0.000 claims description 3
- 239000003849 aromatic solvent Chemical group 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 2
- 238000001556 precipitation Methods 0.000 abstract description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002518 antifoaming agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- -1 3-methyl-4-nitrophenyl Chemical group 0.000 description 5
- XGCZABZDVJOWTL-UHFFFAOYSA-N 3-methyl-4-nitrosophenol Chemical compound CC1=CC(O)=CC=C1N=O XGCZABZDVJOWTL-UHFFFAOYSA-N 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- DEQWBYKBSRNLCS-UHFFFAOYSA-N sodium 3-methyl-4-nitrophenol Chemical compound [Na+].CC1=CC(O)=CC=C1[N+]([O-])=O DEQWBYKBSRNLCS-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- UUZZMWZGAZGXSF-UHFFFAOYSA-N peroxynitric acid Chemical compound OON(=O)=O UUZZMWZGAZGXSF-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
Abstract
Spdsob izolácie 3-metyl-4-nitrofenolu z vodného roztoku 3-metyl-4-nitrofenolátu sodného obsahujúceho.ako nečistoty anorganické soli, organické zlúčeniny fosforu, síry a/alebo chlóru, zbytky aromatického rozpúšťadla. 3-metyl-4-nitrofenol sa získá z roztoku 3-metyl-4-nitrofenolátu sodného z výroby 0,0-dimetyl-0-(3-metyl-4-nitrofenyl)tiofosfátu, vyzrážaním s rainerálnou kyselinou na hodnotu pH 1 až 6. Vyzréžaný 3-metyl- -4-nitrofenol sa od nečistdt oddělí, napr. filtráciou. Na úpravu hodnoty pH sa použije minerálně kyselina obsahujúca ako nečistotu 3-metyl-4-nitrofenol. Úprava hodno$y pH sa výhodné robí v přítomnosti odpenovača. Spdsobu možno využit pri výrobě 3- -metyl-4-nitrofenolu, ktorý sa používá ako medziprodukt pri výrobě tnsekticídov.Method of isolation of 3-methyl-4-nitrophenol from an aqueous solution of 3-methyl-4-nitrophenolate sodium containing impurities as inorganic impurities phosphorus salts, organic compounds, sulfur and / or chlorine, aromatic residues solvent. 3-Methyl-4-nitrophenol is recovered from the solution Sodium 3-methyl-4-nitrophenolate 0,0-dimethyl-0- (3-methyl-4-nitrophenyl) thiophosphate, precipitation with rain acid to a pH of 1 to 6. The 4-nitrophenol is separated from the impurities, e.g. filtration. A pH adjustment is used mineral acid containing impurity 3-methyl-4-nitrophenol. Edit value The pH is preferably made in the presence of an antifoam. Spdsobu can be used in the production of 3- -methyl-4-nitrophenol to be used as an intermediate in the preparation of tectectides.
Description
Vynález sa týká izoléeie 3-metyl-4-nitrofenolu z vodného roztoku 3-metyl-4-nitrofenolátu sodného. 3-metyl-4-nitrofenol je používaný ako medziprodukt pre přípravu organofosfátových lnsektlcídov, najma 0,0-dimetyl-0-(3-metyl-4-nitrofenyl)tlofosfátu.The invention relates to the isolation of 3-methyl-4-nitrophenol from an aqueous solution of sodium 3-methyl-4-nitrophenol. 3-Methyl-4-nitrophenol is used as an intermediate for the preparation of organophosphate insecticides, in particular O, O-dimethyl-O- (3-methyl-4-nitrophenyl) thlophosphate.
NajčastejSie sa 3-metyl-4-nitrofenol připravuje dvojstupňové nitrozéciou 3-metylfenolu a oxidáciou 3-metyl-4-nitrozofenolu kyselinou dusičnou. Pri natrácil s HNO^ vznikajú okrem želaného 3-metyl-4-nitrofenolu aj ňalšie izoméry znižujúce výtažok. Známa je příprava 3-metyl-4-nitrofenolu reakciou metytoluidínu s dusitanem sodným v přítomnosti kyseliny sírovej.Most commonly, 3-methyl-4-nitrophenol is prepared by two-step nitrosation of 3-methylphenol and oxidation of 3-methyl-4-nitrosophenol with nitric acid. In addition to the desired 3-methyl-4-nitrophenol, also other isomers are reduced in yield with HNO4. It is known to prepare 3-methyl-4-nitrophenol by reacting methyl toluidine with sodium nitrite in the presence of sulfuric acid.
fiale j sa 3-metyl-4-nltrofenol připravuje nitrozéciou 3-aetylfenolu s kyselinou dusitou a následnou oxidáciou 3-aetyl-4-nitrózofenolu na 3-metyl-4-nitrofenol v prostředí kyseliny sírovej (Bridge Morgan, J. Am. Chem. Soc. 20 766) (1898), v prostředí koncentrované j kyseliny sírovej (US pat. 1 502 849).3-Methyl-4-nitrophenol is prepared by nitrosating 3-methylphenol with nitrous acid followed by oxidation of 3-methyl-4-nitrosophenol to 3-methyl-4-nitrophenol in sulfuric acid (Bridge Morgan, J. Am. Chem. Soc., 20,766) (1898), in concentrated sulfuric acid (US Pat. 1,502,849).
Oxidécia 3-metyl-4-nitrózofenolu sa uskutečňuje kyselinou dusičnou (Koelsch, J. Am. Chem. Soc. 66. 2019 (1944)), čs. pat. 146 179 a čs. AO 149 726). Oxidácla 3-metyl-4-nitrózofenolu peroxidom vodíka v alkalickom prostředí je popísaná v Travagli, Chem.Oxidation of 3-methyl-4-nitrosophenol is carried out with nitric acid (Koelsch, J. Am. Chem. Soc. 66, 2019 (1944)), no. pat. 146 179 and MS. AO 149,726). The oxidation of 3-methyl-4-nitrosophenol with hydrogen peroxide in an alkaline medium is described in Travagli, Chem.
Abstr. & 7594 e (1951).Abstr. &Amp; 7594 e (1951).
Vo vyššie uvedených literárnych odkazoch sa nespomína izolácia 3-metyl-4-nitrofenolu z odpadných vOd vznikajúcich pri výrobě 0,0-dimetyl-0-(3-metyl-4-nitrofenyl)tiořosfátu. 'The above references do not mention the isolation of 3-methyl-4-nitrophenol from the waste water resulting from the production of O, O-dimethyl-O- (3-methyl-4-nitrophenyl) thiophosphate. '
Vyššie uvedená nedostatky sú odstránené podTa vynálezu spOsobom izolácia 3-metyl-4-nitrofenolu, z vodného roztoku 3-metyl-4-nitrofenolátu sodného obsahujúeeho nečistoty ako anorganická soli, organická zlúčeniny fosforu, siry a/alebo chlóru, zbytky aromatických rozpúštadiel z výroby 0,0-diaetyl-0-(3-metyl-4-nitrofenyl)tiofo8fátu. Z vodného roztoku 3-metyl-4-nitrofenolátu sodného sa vyzráža 3-metyl-4-nitrofenol úpravou hodnoty pH na 1 až 6. Vyzrážaný 3-metyl-4-nitrofenol sa od rozpuštěných nečistot oddělí napr. filtráclou alebo odstřelováním.The above drawbacks are overcome by the process of isolating 3-methyl-4-nitrophenol from an aqueous solution of sodium 3-methyl-4-nitrophenol containing impurities such as inorganic salts, organic phosphorus, sulfur and / or chlorine compounds, aromatic solvent residues from production 0. 0 diaetyl-0- (3-methyl-4-nitrophenyl) tiofo8fátu. Sodium 3-methyl-4-nitrophenol is precipitated from the aqueous solution of 3-methyl-4-nitrophenol by adjusting the pH to 1 to 6. The precipitated 3-methyl-4-nitrophenol is separated from the dissolved impurities e.g. by filtration or blasting.
Hodnota pH vodného roztoku 3-metyl-4-nitrofenolétu sodného sa výhodné upraví s minerálnou kyselinou.The pH of the aqueous solution of sodium 3-methyl-4-nitrophenoleate is preferably adjusted with a mineral acid.
Výhodné je možná použit na úpravu hodnoty pH minerálnu kyselinu, ktorá obsahuje ako nečistotu 3-metyl-4-nitrofenol.Advantageously, a mineral acid containing 3-methyl-4-nitrophenol as impurity may be used to adjust the pH.
Úprava hodnoty pH vodného roztoku sa výhodné robí v přítomnosti odpeňovača. Rozruší sa pěna, ktorá vzniká pri reakcil uhličitanev, napr. NagCO^, KgCO^s mlnerálnou kyselinou.The pH adjustment of the aqueous solution is preferably done in the presence of a defoamer. The foam formed by the carbonate reagent, e.g. NagCO3, KgCO3 with mineral acid.
Postupom podl'a vynálezu sa získá 3-metyl-4-nitrofenol z odpadných v6d. Postup možno výhodné využit v tých případech, kde nie je možná získat kvalitný 3-metyl-4-nitrofenolát sodný kryštalizáciou. Jedná sa predovšetkým o vodné roztoky, v kterých koncentrácia 3-metyl-4-nitrofenolátu sodného je pod 2 % hmot., alebo o roztoky s vysokou koncentráciou minerálnych solí, pričom kryštalizáciou získaný 3-metyl-4-nitrofenolát sodný by bol nimi znečistěný. Postupom podl*a vynálezu sa zníži obsah derivátov fenolu v odpadných vodách. Získaný 3-metyl-4-nitrofenol je dobrej kvality a najde použitie napr. pri výrobě 0,0-dimetyl-0-(3-metyl~4-nitrof enyl/tiof osfátu.The process according to the invention yields 3-methyl-4-nitrophenol from waste water. The process can be advantageously used in those cases where it is not possible to obtain high-quality sodium 3-methyl-4-nitrophenolate by crystallization. These are in particular aqueous solutions in which the concentration of sodium 3-methyl-4-nitrophenolate is below 2% by weight, or solutions with a high concentration of mineral salts, the sodium 3-methyl-4-nitrophenolate obtained by crystallization being contaminated by them. The process according to the invention reduces the content of phenol derivatives in waste water. The obtained 3-methyl-4-nitrophenol is of good quality and finds use e.g. in the preparation of O, O-dimethyl-O- (3-methyl-4-nitrophenyl / thiophosphate).
PřikladlEXAMPLE
Do trojhrdlej banky opatrenej miešadlom, teplomerom a deliacim lievikom sa dalo 500 ml toluénu, 75 g 76,2 % hmot. 3-metyl-4-nitrofenolétu sodného a 10 g KgCOj. Zmes sa vyhriala do mierneho varu. Deliacim liévikom sa k reakčnej zmesi dávkovalo 180 mlA three-necked flask equipped with a stirrer, a thermometer and a separatory funnel was charged with 500 ml of toluene, 75 g of 76.2 wt. Sodium 3-methyl-4-nitrophenoleate and 10 g of KgCO3. The mixture was heated to gentle boiling. 180 ml was added to the reaction mixture by separatory funnel
30,5 % hmot. toluénového roztoku 0,0-dimetylchlortiofosfétu. Reakčná zmes sa udržiavala pri miernom vare 6 hodin.30.5 wt. toluene solution of O, O-dimethylchlorotriophosphate. The reaction mixture was kept under gentle boiling for 6 hours.
Po ukončení reakcie sa k reakčnej zmesi přidalo 200 ml 80 °C vody na rozpustenie' krystalických solí. Toluénová vrstva sa oddělila od.vodnej. Vodná vrstva obsahovala 11,3 g 3-metyl-4-nitrofenolátu sodného, 0,06 % hmot. organicky viazaného fosforu a 0,05 16 hmot. organicky viazanej síry.After completion of the reaction, 200 mL of 80 ° C water was added to the reaction mixture to dissolve the crystalline salts. The toluene layer was separated from the aqueous. The aqueous layer contained 11.3 g of sodium 3-methyl-4-nitrophenolate, 0.06 wt. % organically bound phosphorus and 0.05 16 wt. organically bound sulfur.
Příklad 2Example 2
Postupovalo sa podl’a příkladu 1 s tým rozdielom, že miesto vody sa k reakčnej zmesi přidala vodná vrstva z predcházajúceho pokusu. Postup sa opakoval šest krát. Získal ss vodný roztok, ktorý obsahoval 54,2. g 3-metyl-4-nitrofenolu. Roztok sa ochladil na 10 °C, pričom vykrystalizoval 3-metyl-4-nitrofenolét sodný, ktorý sa odfiltroval.The procedure of Example 1 was followed except that an aqueous layer from the previous experiment was added to the reaction mixture instead of water. The procedure was repeated six times. An aqueous solution was obtained which contained 54.2. g of 3-methyl-4-nitrophenol. The solution was cooled to 10 ° C, crystallizing sodium 3-methyl-4-nitrophenoletol, which was filtered off.
Matečný lúh obsahoval 2,6 % hmot. 3-metyl-4-nitrofenolátu sodného. Z roztoku sa vyzrážal 3-metyl-4-nitrofenol přidáním kyseliny chlorovodíkovéj 10 16 hmot., pričom hodnota pH vodnéj vrstvy bola 3,1. Vyzrážaný 3-metyl-4-nitrofenol sa odfiltroval. Získalo 88 7,9 g 51,6 16 hmot. 3-metyl-4-nitrofenolu. Filtrát obsahoval 0,05 16 hmot. organicky viazaného fosforu a 0,05 16 hmot. organicky viazanej síry.The mother liquor contained 2.6 wt. Sodium 3-methyl-4-nitrophenolate. 3-Methyl-4-nitrophenol precipitated from the solution by the addition of hydrochloric acid 10 16%, the pH of the aqueous layer being 3.1. The precipitated 3-methyl-4-nitrophenol was filtered off. 88 7.9 g 51.6 16 wt. 3-methyl-4-nitrophenol. The filtrate contained 0.05 16 wt. % organically bound phosphorus and 0.05 16 wt. organically bound sulfur.
Příklad 3Example 3
Postupovalo sa podlá příkladu 2 s tým rozdielom, že sa roztok nenechal ochladit na 10 °C, ale pri teplete 70 °C sa z roztoku vyzrážal 3-metyl-4-nitrofenol úpravou hodnoty pH na 4,6 s 10,3 16 hmot. HgSO. obsahujúcou 1 480 mg/1 3-metyl-4-nitrofenolu. Potom sa roztok nechal ochladit na 10 °G a vyzrážaný 3-metyl-4-nitrofenol sa odfiltroval. Získalo sa 8,1 g 51,4 56 hmot. 3-metyl-4-nitrofenolu.The procedure of Example 2 was followed except that the solution was not allowed to cool to 10 ° C, but at 70 ° C, 3-methyl-4-nitrophenol precipitated out of solution by adjusting the pH to 4.6 with 10.3 16 wt. HgSO. containing 1480 mg / L of 3-methyl-4-nitrophenol. Then the solution was allowed to cool to 10 ° C and the precipitated 3-methyl-4-nitrophenol was filtered off. 8.1 g 51.4 56 wt. 3-methyl-4-nitrophenol.
Příklad 4Example 4
Postupovalo sa podlá příkladu 3, iba penenie spdsobené rozkladom uhličitanov kyselinou sírovou sa znížilo prídavkom 0,01 g odpeňovača na báze polydimetylsiloxanu (Lukosan S). Hodnota pH po zrážaní bola 1,4. Vyzrážaný 3-metyl-4-nitrofenol sa zo suspenzie odfiltroval. Získalo sa 8,0 g 52,3 16 hmot. 3-metyl-4-nitrofenolu. Získaný 3-metyl-4-nitrofenol mel Čistotu 99,6 % hmot.Following the procedure of Example 3, only the foaming caused by the decomposition of the carbonates with sulfuric acid was reduced by the addition of 0.01 g of a polydimethylsiloxane-based defoamer (Lukosan S). The pH after precipitation was 1.4. The precipitated 3-methyl-4-nitrophenol was filtered from the suspension. 8.0 g 52.3 16 wt. 3-methyl-4-nitrophenol. The 3-methyl-4-nitrophenol obtained had a purity of 99.6% by weight.
Vynález možno využit pri výrobě 3-metyl-4-nitrofenolu, pričom sa využije vodný roztok 3-metyl-4-nitrofenolátu sodného odpadajúci pri výrobě 0,0-dimetyl-0-(3-metyl-4-nitrofenyl)tiofosfátu.The invention can be used in the preparation of 3-methyl-4-nitrophenol by using an aqueous solution of sodium 3-methyl-4-nitrophenol which is lost in the production of O, O-dimethyl-O- (3-methyl-4-nitrophenyl) thiophosphate.
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