JPS5822102B2 - ジニトロアニリン類の精製法 - Google Patents

ジニトロアニリン類の精製法

Info

Publication number: JPS5822102B2
Authority: JP; Japan
Prior art keywords: hydrogen chloride; nitrosamines; chloride gas; trifluralin; minutes
Prior art date: 1977-07-18
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.): Expired

Application number

JP53088257A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5422329A (en

Inventor

ウイリアム・ナザニエル・キヤノン

キヤスリーン・ローズ・ボグラー

リチヤード・フランク・アイゼンバー

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

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.)

1977-07-18

Filing date

1978-07-18

Publication date

1983-05-06

1978-07-18 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1979-02-20 Publication of JPS5422329A publication Critical patent/JPS5422329A/ja

1983-05-06 Publication of JPS5822102B2 publication Critical patent/JPS5822102B2/ja

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 25
CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 title claims description 22
238000000746 purification Methods 0.000 title description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 115
150000004005 nitrosamines Chemical class 0.000 claims abstract description 44
LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 claims abstract description 16
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 60
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 60
239000007789 gas Substances 0.000 claims description 56
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 7
239000012535 impurity Substances 0.000 claims description 7
239000007791 liquid phase Substances 0.000 claims description 6
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000003849 aromatic solvent Substances 0.000 claims 1
230000003247 decreasing effect Effects 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
150000003138 primary alcohols Chemical class 0.000 claims 1
239000004009 herbicide Substances 0.000 abstract description 3
XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 48
239000000523 sample Substances 0.000 description 34
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
-1 nitrone amine Chemical class 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 16
229910000029 sodium carbonate Inorganic materials 0.000 description 12
239000012044 organic layer Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
239000010410 layer Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
OFDYMSKSGFSLLM-UHFFFAOYSA-N Dinitramine Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O OFDYMSKSGFSLLM-UHFFFAOYSA-N 0.000 description 3
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
XTKDYPFKEUCACS-UHFFFAOYSA-N 1,3,6-trihydroxy-2,5-dimethoxy-10-methylacridin-9-one Chemical compound OC1=CC=C2C(=O)C3=C(O)C(OC)=C(O)C=C3N(C)C2=C1OC XTKDYPFKEUCACS-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
YLKFDHTUAUWZPQ-UHFFFAOYSA-N N-Nitrosodi-n-propylamine Chemical compound CCCN(N=O)CCC YLKFDHTUAUWZPQ-UHFFFAOYSA-N 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
MMFBQHXDINNBMW-UHFFFAOYSA-N n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=CC=C1 MMFBQHXDINNBMW-UHFFFAOYSA-N 0.000 description 2
125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
PTFJIKYUEPWBMS-UHFFFAOYSA-N Ethalfluralin Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PTFJIKYUEPWBMS-UHFFFAOYSA-N 0.000 description 1
MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
150000004008 N-nitroso compounds Chemical class 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
239000004157 Nitrosyl chloride Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000005587 Oryzalin Substances 0.000 description 1
ITVQAKZNYJEWKS-UHFFFAOYSA-N Profluralin Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CCC)CC1CC1 ITVQAKZNYJEWKS-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
231100000315 carcinogenic Toxicity 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000013068 control sample Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
QBTUBLBTJXFCCB-UHFFFAOYSA-N n-pentan-3-ylaniline Chemical compound CCC(CC)NC1=CC=CC=C1 QBTUBLBTJXFCCB-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000002832 nitroso derivatives Chemical class 0.000 description 1
VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
235000019392 nitrosyl chloride Nutrition 0.000 description 1
UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000012264 purified product Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical group 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP53088257A 1977-07-18 1978-07-18 ジニトロアニリン類の精製法 Expired JPS5822102B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81655877A	1977-07-18	1977-07-18
US87883478A	1978-02-17	1978-02-17

Publications (2)

Publication Number	Publication Date
JPS5422329A JPS5422329A (en)	1979-02-20
JPS5822102B2 true JPS5822102B2 (ja)	1983-05-06

Family

ID=27124088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP53088257A Expired JPS5822102B2 (ja)	1977-07-18	1978-07-18	ジニトロアニリン類の精製法

Country Status (21)

Country	Link
JP (1)	JPS5822102B2 (fr)
AR (1)	AR221846A1 (fr)
AU (1)	AU516698B2 (fr)
BG (1)	BG34182A3 (fr)
BR (1)	BR7804599A (fr)
CA (1)	CA1081256A (fr)
CS (1)	CS203196B2 (fr)
DD (1)	DD137222A5 (fr)
DE (1)	DE2831119C2 (fr)
DK (1)	DK152113C (fr)
ES (1)	ES471821A1 (fr)
FR (1)	FR2398044A1 (fr)
GB (1)	GB1599930A (fr)
HU (1)	HU182483B (fr)
IE (1)	IE47127B1 (fr)
IL (1)	IL55142A (fr)
IT (1)	IT1097822B (fr)
MX (1)	MX5203E (fr)
NL (1)	NL189911C (fr)
PL (1)	PL119759B1 (fr)
RO (1)	RO75656A (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3061492D1 (en) *	1979-05-21	1983-02-03	Hoechst Ag	Process for the removal of nitrozation agents from nitrated aromatic compounds
DE2926947C2 (de) *	1979-07-04	1982-03-18	Hoechst Ag, 6000 Frankfurt	Verfahren zur Entfernung von Nitrosierungsmittel (n) aus nitrierten aromatischen Verbindungen
DE3345157A1 (de) *	1983-12-14	1985-06-27	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von nitrosaminfreien n,n-disubstituierten nitroaromatischen aminen und deren stabilisierung gegen nitrosaminbildung
IT1195822B (it) *	1986-08-12	1988-10-27	I Pi Ci Spa	Procedimento per la purificazione della trifluralina
IT1293450B1 (it) *	1997-07-14	1999-03-01	Finchimica Srl	Procedimento per la purificazione di dinitroaniline.
CA2973331C (fr)	2015-01-07	2019-10-22	Mitsubishi Hitachi Power Systems, Ltd.	Procede et dispositif pour traiter un compose nitrose
CN109320424B (zh) *	2017-07-31	2021-12-21	江苏永安化工有限公司	一种二甲戊灵的纯化方法
CN116735760B (zh) *	2023-08-16	2024-02-09	山东道可化学有限公司	一种氟乐灵中n,n-二丙基亚硝胺的检测方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4134917A (en) *	1977-04-25	1979-01-16	American Cyanamid Company	Method for the denitrosation of organic nitrosamines

1976
- 1976-07-14 RO RO7694675A patent/RO75656A/fr unknown
1978
- 1978-05-31 GB GB25279/78A patent/GB1599930A/en not_active Expired
- 1978-07-14 AU AU38058/78A patent/AU516698B2/en not_active Expired
- 1978-07-14 CS CS784725A patent/CS203196B2/cs unknown
- 1978-07-14 DE DE2831119A patent/DE2831119C2/de not_active Expired
- 1978-07-14 IL IL55142A patent/IL55142A/xx unknown
- 1978-07-14 NL NLAANVRAGE7807576,A patent/NL189911C/xx not_active IP Right Cessation
- 1978-07-14 CA CA307,403A patent/CA1081256A/fr not_active Expired
- 1978-07-14 BG BG040406A patent/BG34182A3/xx unknown
- 1978-07-14 IT IT25724/78A patent/IT1097822B/it active
- 1978-07-14 HU HU78EI798A patent/HU182483B/hu unknown
- 1978-07-17 DK DK319378A patent/DK152113C/da not_active IP Right Cessation
- 1978-07-17 ES ES471821A patent/ES471821A1/es not_active Expired
- 1978-07-17 MX MX787265U patent/MX5203E/es unknown
- 1978-07-17 BR BR7804599A patent/BR7804599A/pt unknown
- 1978-07-17 IE IE1430/78A patent/IE47127B1/en not_active IP Right Cessation
- 1978-07-17 FR FR7821173A patent/FR2398044A1/fr active Granted
- 1978-07-18 DD DD78206786A patent/DD137222A5/xx not_active IP Right Cessation
- 1978-07-18 AR AR272995A patent/AR221846A1/es active
- 1978-07-18 JP JP53088257A patent/JPS5822102B2/ja not_active Expired
- 1978-07-18 PL PL1978208500A patent/PL119759B1/pl unknown

Also Published As

Publication number	Publication date
DD137222A5 (de)	1979-08-22
GB1599930A (en)	1981-10-07
HU182483B (en)	1984-01-30
PL208500A1 (pl)	1979-07-02
IL55142A0 (en)	1978-09-29
DK152113C (da)	1988-06-20
CA1081256A (fr)	1980-07-08
PL119759B1 (en)	1982-01-30
IT1097822B (it)	1985-08-31
CS203196B2 (en)	1981-02-27
IE781430L (en)	1979-01-18
BR7804599A (pt)	1979-03-20
NL7807576A (nl)	1979-01-22
DK152113B (da)	1988-02-01
FR2398044B1 (fr)	1980-10-31
NL189911C (nl)	1993-09-01
BG34182A3 (en)	1983-07-15
IE47127B1 (en)	1983-12-28
JPS5422329A (en)	1979-02-20
IL55142A (en)	1981-06-29
AR221846A1 (es)	1981-03-31
IT7825724A0 (it)	1978-07-14
MX5203E (es)	1983-04-25
ES471821A1 (es)	1979-10-01
AU3805878A (en)	1980-01-17
DE2831119A1 (de)	1979-02-08
AU516698B2 (en)	1981-06-18
RO75656A (fr)	1981-04-20
FR2398044A1 (fr)	1979-02-16
DE2831119C2 (de)	1983-05-26
DK319378A (da)	1979-01-19
NL189911B (nl)	1993-04-01

Publication	Publication Date	Title
US9284255B2 (en)	2016-03-15	Method for producing nitrobenzene by adiabatic nitriding
CA1062729A (fr)	1979-09-18	Purification de la dinitroaniline a l'aide d'halogenures d'un acide inorganique
JPS5822102B2 (ja)	1983-05-06	ジニトロアニリン類の精製法
Nielsen et al.	1979	Synthetic routes to aminodinitrotoluenes
US4226789A (en)	1980-10-07	Removal of nitrosamines from denitroanilines by treatment with HCl
US9771291B2 (en)	2017-09-26	Process for working up waste water from nitrobenzene preparation
JPS5822101B2 (ja)	1983-05-06	ジニトロアニリン類の精製方法
PL118036B1 (en)	1981-09-30	Method of reduction of nitrosating agents concentration in 1-chloro-2,6-dinitro-4-/trifluoromethyl/benzene v 1-khloro-2,6-dinitro-4/triftorometilo/benzole
US9771290B2 (en)	2017-09-26	Process for working up waste water from nitrobenzene preparation
US4127610A (en)	1978-11-28	Dinitroaniline purification with bromine and chlorine
CA2469858A1 (fr)	2003-06-19	Diamantoides superieurs fonctionnalises
KR820000427B1 (ko)	1982-04-01	디니트로아닐린 정제법
JP2005534659A (ja)	2005-11-17	１，３，５−トリアミノベンゼンの調製とそれを高純度のフロログルシノ−ルに加水分解する方法
EP0644178B1 (fr)	1997-04-02	Procédé de purification d'éthalfluralin
JP2793281B2 (ja)	1998-09-03	アミン酸化物の製造法
US3499931A (en)	1970-03-10	Process for the separation of a mixture of primary alkanolamines and secondary alkanolamines
KR820000056B1 (ko)	1982-02-06	브롬과 염소로서 디니트로 아닐린을 정제하는 방법
Parker et al.	1963	N-Pantoyl-(substituted-phenyl) alkylamines, Inhibitory Analogs of Pantothenic Acid1, 2
JPH0217198A (ja)	1990-01-22	２’−デオキシ−β−シチジン誘導体およびその塩の製造法
CN117049967A (zh)	2023-11-14	2,6-二硝基-3,4-二甲基苯酚衍生物的制备方法及活性应用
KR820000052B1 (ko)	1982-02-06	무기산 할라이드로 디니트로 아닐린을 정제하는 방법
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