SK6202000A3 - Method for producing aromatic nitro compounds - Google Patents

Method for producing aromatic nitro compounds Download PDF

Info

Publication number: SK6202000A3
Authority: SK; Slovakia
Prior art keywords: reaction; hno; weight; mixing; surfactants
Prior art date: 1997-11-03

Application number

SK620-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Bernd-Michael Konig

Johannes Duehr

Hans-Joachim Raatz

Manfred Kaczorowski

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1997-11-03

Filing date

1998-10-21

Publication date

2001-01-18

1998-03-02 Priority claimed from DE19808748A external-priority patent/DE19808748A1/de

1998-10-21 Application filed by Bayer Ag filed Critical Bayer Ag

2001-01-18 Publication of SK6202000A3 publication Critical patent/SK6202000A3/sk

Links

-1 aromatic nitro compounds Chemical class 0.000 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title description 2
239000002253 acid Substances 0.000 claims abstract description 61
238000006243 chemical reaction Methods 0.000 claims abstract description 50
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 47
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 44
229910017604 nitric acid Inorganic materials 0.000 claims abstract description 42
239000011541 reaction mixture Substances 0.000 claims abstract description 29
230000000802 nitrating effect Effects 0.000 claims abstract description 28
150000001491 aromatic compounds Chemical class 0.000 claims abstract description 22
235000011149 sulphuric acid Nutrition 0.000 claims abstract description 15
125000000129 anionic group Chemical group 0.000 claims abstract description 4
125000002091 cationic group Chemical group 0.000 claims abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 108
239000004094 surface-active agent Substances 0.000 claims description 48
238000000034 method Methods 0.000 claims description 47
238000002156 mixing Methods 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 28
239000000376 reactant Substances 0.000 claims description 23
ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical class CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 16
150000007513 acids Chemical class 0.000 claims description 13
238000003756 stirring Methods 0.000 claims description 12
150000005171 halobenzenes Chemical class 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
238000010790 dilution Methods 0.000 claims description 9
239000012895 dilution Substances 0.000 claims description 9
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 8
238000004821 distillation Methods 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
239000003093 cationic surfactant Substances 0.000 claims description 6
239000003945 anionic surfactant Substances 0.000 claims description 5
150000002989 phenols Chemical class 0.000 claims description 5
230000003068 static effect Effects 0.000 claims description 5
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
239000002736 nonionic surfactant Substances 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000002888 zwitterionic surfactant Substances 0.000 claims description 3
QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 claims description 2
150000004982 aromatic amines Chemical class 0.000 claims description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
238000007865 diluting Methods 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 2
235000011007 phosphoric acid Nutrition 0.000 abstract description 2
239000013543 active substance Substances 0.000 abstract 1
239000000203 mixture Substances 0.000 description 28
239000012071 phase Substances 0.000 description 28
238000006396 nitration reaction Methods 0.000 description 24
239000012074 organic phase Substances 0.000 description 15
239000006185 dispersion Substances 0.000 description 11
238000005191 phase separation Methods 0.000 description 9
239000002699 waste material Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
238000010924 continuous production Methods 0.000 description 7
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000012535 impurity Substances 0.000 description 5
VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 4
HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical compound CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 description 4
XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 4
PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 4
QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 4
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 4
238000010923 batch production Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
150000002894 organic compounds Chemical class 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
VMMLSJNPNVTYMN-UHFFFAOYSA-N dinitromethylbenzene Chemical class [O-][N+](=O)C([N+]([O-])=O)C1=CC=CC=C1 VMMLSJNPNVTYMN-UHFFFAOYSA-N 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000463 material Substances 0.000 description 3
238000005192 partition Methods 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
OGYMWUMPVDTUCW-UHFFFAOYSA-N 2,2-bis(2-ethylhexyl)-3-sulfobutanedioic acid Chemical compound CCCCC(CC)CC(C(O)=O)(C(C(O)=O)S(O)(=O)=O)CC(CC)CCCC OGYMWUMPVDTUCW-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000008051 alkyl sulfates Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000029087 digestion Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 1
QCVMOSGPTRRUQZ-UHFFFAOYSA-N 2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 QCVMOSGPTRRUQZ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
HOCHJWBNDOKTEV-UHFFFAOYSA-K [Na+].C(C)C(CC(C(C(=O)[O-])S(=O)(=O)[O-])(C(=O)[O-])CC(CCCC)CC)CCCC.[Na+].[Na+] Chemical compound [Na+].C(C)C(CC(C(C(=O)[O-])S(=O)(=O)[O-])(C(=O)[O-])CC(CCCC)CC)CCCC.[Na+].[Na+] HOCHJWBNDOKTEV-UHFFFAOYSA-K 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000004581 coalescence Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012430 organic reaction media Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
238000006557 surface reaction Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/02—Formation or introduction of functional groups containing nitrogen of nitro or nitroso groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK620-2000A 1997-11-03 1998-10-21 Method for producing aromatic nitro compounds SK6202000A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19748360		1997-11-03
DE19808748A DE19808748A1 (de)	1997-11-03	1998-03-02	Verfahren zur Herstellung aromatischer Nitroverbindungen
PCT/EP1998/006688 WO1999023061A1 (de)	1997-11-03	1998-10-21	Verfahren zur herstellung aromatischer nitroverbindungen

Publications (1)

Publication Number	Publication Date
SK6202000A3 true SK6202000A3 (en)	2001-01-18

Family

ID=26041268

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK620-2000A SK6202000A3 (en)	1997-11-03	1998-10-21	Method for producing aromatic nitro compounds

Country Status (16)

Country	Link
US (1)	US6242657B1 (id)
EP (1)	EP1028937A1 (id)
JP (1)	JP2001521920A (id)
CN (1)	CN1277601A (id)
AU (1)	AU741332B2 (id)
BR (1)	BR9814108A (id)
CA (1)	CA2308288A1 (id)
HU (1)	HUP0100200A3 (id)
ID (1)	ID24977A (id)
IL (1)	IL135402A0 (id)
MX (1)	MXPA00003884A (id)
NO (1)	NO20002247D0 (id)
PL (1)	PL340030A1 (id)
SK (1)	SK6202000A3 (id)
TW (1)	TW466223B (id)
WO (1)	WO1999023061A1 (id)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10047163A1 (de) *	2000-09-22	2002-04-11	Basf Ag	Verfahren zur Nitrierung aromatischer Kohlenwasserstoffe
DE10108979C1 (de) *	2001-02-23	2002-05-08	Bayer Ag	Kontinuierliches adiabatisches Verfahren zur Herstellung von Nitrochlorbenzol
DE10117207C1 (de) *	2001-04-06	2002-11-14	Bayer Ag	Kontinuierliches isothermes Verfahren zur Herstellung von Mononitrotoluolen in Gegenwart von Phosphorsäure
DE10205855A1 (de) *	2002-02-13	2003-08-21	Bayer Ag	Kontinuierliches adiabatisches Verfahren zur Nitrierung von Chlorbenzol
DE102008048713A1 (de) *	2008-09-24	2010-03-25	Bayer Materialscience Ag	Verfahren zur kontinuierlichen Herstellung von Nitrobenzol
WO2010051616A1 (en) *	2008-11-10	2010-05-14	Noram International Limited	Adiabatic process for making mononitrobenzene
US20110060464A1 (en) *	2009-09-09	2011-03-10	Akribio Corp.	Adiabatic control method for isothermal characteristics of reaction vessels
HU231038B1 (hu)	2015-06-12	2019-12-30	Noram International Ltd Regus Pembroke House	Eljárás nitráló eljárásból kapott nitrált aromás vegyületek tisztítására
DE102017110084C5 (de) *	2017-02-03	2026-02-26	Josef Meissner Gmbh & Co. Kg	Verwendungen von Nitroaromaten in der adiabatischen Nitrierung von Aromaten
FR3109580B1 (fr) *	2020-04-27	2023-03-10	Ipsomedic	Procédé de synthèse du paracétamol en continu
WO2023156832A1 (en) *	2022-02-16	2023-08-24	Vinati Organics Limited	A process for preparation of highly pure 4-(n-butyl) aniline
CN116283595A (zh) *	2023-03-20	2023-06-23	山东兴文工业技术研究院有限公司	一种采用微通道反应装置合成邻硝基甲苯的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3077502A (en)	1960-01-04	1963-02-12	Monsanto Chemicals	Process for the nitration of halobenzenes
US3076037A (en)	1960-02-05	1963-01-29	Monsanto Chemicals	Process for the nitration of halobenzenes
US3253045A (en)	1964-11-12	1966-05-24	Universal Oil Prod Co	Process for the preparation of p-nitrohalobenzenes
JPS50117737A (id)	1974-03-05	1975-09-16
US4392978A (en)	1979-12-26	1983-07-12	Allied Corporation	Selective aromatic nitration
JP3179930B2 (ja)	1993-04-09	2001-06-25	日産化学工業株式会社	芳香族ニトロ化合物の製造方法
DE4410417A1 (de) *	1994-02-14	1995-08-17	Bayer Ag	Verfahren zur adiabatischen Herstellung von Mononitrotoluolen
DE4411064A1 (de)	1994-03-30	1995-10-05	Bayer Ag	Verfahren zur adiabatischen Herstellung von Mononitrohalogenbenzolen

1998
- 1998-10-21 US US09/530,204 patent/US6242657B1/en not_active Expired - Fee Related
- 1998-10-21 CA CA002308288A patent/CA2308288A1/en not_active Abandoned
- 1998-10-21 PL PL98340030A patent/PL340030A1/xx not_active Application Discontinuation
- 1998-10-21 SK SK620-2000A patent/SK6202000A3/sk unknown
- 1998-10-21 ID IDW20000826A patent/ID24977A/id unknown
- 1998-10-21 HU HU0100200A patent/HUP0100200A3/hu unknown
- 1998-10-21 IL IL13540298A patent/IL135402A0/xx unknown
- 1998-10-21 BR BR9814108-2A patent/BR9814108A/pt not_active IP Right Cessation
- 1998-10-21 WO PCT/EP1998/006688 patent/WO1999023061A1/de not_active Ceased
- 1998-10-21 CN CN98810539A patent/CN1277601A/zh active Pending
- 1998-10-21 JP JP2000518938A patent/JP2001521920A/ja active Pending
- 1998-10-21 EP EP98952730A patent/EP1028937A1/de not_active Withdrawn
- 1998-10-21 AU AU10315/99A patent/AU741332B2/en not_active Ceased
- 1998-10-30 TW TW087118011A patent/TW466223B/zh active
2000
- 2000-04-19 MX MXPA00003884 patent/MXPA00003884A/es unknown
- 2000-04-28 NO NO20002247A patent/NO20002247D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HUP0100200A2 (hu)	2001-05-28
JP2001521920A (ja)	2001-11-13
ID24977A (id)	2000-08-31
WO1999023061A1 (de)	1999-05-14
NO20002247L (no)	2000-04-28
AU1031599A (en)	1999-05-24
US6242657B1 (en)	2001-06-05
IL135402A0 (en)	2001-05-20
NO20002247D0 (no)	2000-04-28
TW466223B (en)	2001-12-01
AU741332B2 (en)	2001-11-29
MXPA00003884A (id)	2001-01-01
BR9814108A (pt)	2000-10-03
CA2308288A1 (en)	1999-05-14
HUP0100200A3 (en)	2002-03-28
PL340030A1 (en)	2001-01-15
EP1028937A1 (de)	2000-08-23
CN1277601A (zh)	2000-12-20

Publication	Publication Date	Title
US7495136B2 (en)	2009-02-24	Process for the production of dinitrotoluene
SK6202000A3 (en)	2001-01-18	Method for producing aromatic nitro compounds
CN103562174B (zh)	2015-05-20	硝化产物的纯化方法和装置
KR100341038B1 (ko)	2002-12-05	모노니트로톨루엔의단열제조방법
CA3052335C (en)	2022-06-21	Process and plant for the adiabatic nitration of aromatic compounds
US5714647A (en)	1998-02-03	Process for the adiabatic preparation of mononitrohalogenobenzenes
CZ299615B6 (cs)	2008-09-24	Kontinuální adiabatický zpusob výroby nitrochlorbenzenu
US6583327B2 (en)	2003-06-24	Continuous isothermal process for preparing mononitrotoluenes
KR101277350B1 (ko)	2013-06-20	디니트로톨루엔 제조 방법
CZ20001627A3 (cs)	2000-08-16	Způsob přípravy aromatických nitrosloučenin
US6353142B1 (en)	2002-03-05	Process for the adiabatic preparation of 3,4-dichloronitrobenzene
DE19808748A1 (de)	1999-05-06	Verfahren zur Herstellung aromatischer Nitroverbindungen
WO2023223192A1 (en)	2023-11-23	A system and process of preparation of mono-nitro benzo trifluoride (nbtf)
CZ20021182A3 (cs)	2002-11-13	Kontinuální izotermní způsob výroby mononitritoluenů v přítomnosti kyseliny fosforečné
HK1032390A (en)	2001-07-20	Method for producing aromatic nitro compounds