DD233123A5 - Verfahren zur herstellung von n-isopropyl-alpha-chlor-acetanilid - Google Patents

Verfahren zur herstellung von n-isopropyl-alpha-chlor-acetanilid Download PDF

Info

Publication number: DD233123A5
Authority: DD; German Democratic Republic
Prior art keywords: isopropyl; temperature; acetanilide; acylation; chloro
Prior art date: 1983-11-17

Application number

DD26948484A

Other languages

German (de)

English (en)

Inventor

Gyoergy Huszak

Jenoe Pelyva

Antal Kovacs

Arpad Erdelyi

Elemer Toemoerdi

Gyula Pamuk

Laszlo Lendvai

Original Assignee

Nitrokemia Ipartelepek,Hu

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.)

1983-11-17

Filing date

1984-11-14

Publication date

1986-02-19

1984-11-14 Application filed by Nitrokemia Ipartelepek,Hu filed Critical Nitrokemia Ipartelepek,Hu

1986-02-19 Publication of DD233123A5 publication Critical patent/DD233123A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 29
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 title description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 23
230000010933 acylation Effects 0.000 claims abstract description 10
238000005917 acylation reaction Methods 0.000 claims abstract description 10
FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical class CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims abstract description 8
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
239000011541 reaction mixture Substances 0.000 claims abstract description 7
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 6
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 6
238000000354 decomposition reaction Methods 0.000 claims abstract description 5
BKUFESVLWSPJHJ-UHFFFAOYSA-N n-propan-2-ylaniline;hydrochloride Chemical group Cl.CC(C)NC1=CC=CC=C1 BKUFESVLWSPJHJ-UHFFFAOYSA-N 0.000 claims abstract description 5
150000001412 amines Chemical class 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 15
239000004480 active ingredient Substances 0.000 abstract description 2
230000002363 herbicidal effect Effects 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000002253 acid Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
-1 N-substituted acetanilides Chemical class 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
241000380130 Ehrharta erecta Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical class Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002585 base Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
150000003839 salts Chemical group 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Jib Cranes (AREA)

DD26948484A 1983-11-17 1984-11-14 Verfahren zur herstellung von n-isopropyl-alpha-chlor-acetanilid DD233123A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU395083A HU190744B (en)	1983-11-17	1983-11-17	Improved process for production of n-izoprophyl-alphachlor-acetanilid

Publications (1)

Publication Number	Publication Date
DD233123A5 true DD233123A5 (de)	1986-02-19

Family

ID=10966195

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD26948484A DD233123A5 (de)	1983-11-17	1984-11-14	Verfahren zur herstellung von n-isopropyl-alpha-chlor-acetanilid

Country Status (6)

Country	Link
BG (1)	BG43186A3 (cs)
CS (1)	CS255865B2 (cs)
DD (1)	DD233123A5 (cs)
HU (1)	HU190744B (cs)
PL (1)	PL143144B1 (cs)
RO (1)	RO90919B (cs)

1983
- 1983-11-17 HU HU395083A patent/HU190744B/hu unknown
1984
- 1984-11-12 PL PL25041184A patent/PL143144B1/pl unknown
- 1984-11-14 BG BG067522A patent/BG43186A3/xx unknown
- 1984-11-14 DD DD26948484A patent/DD233123A5/de unknown
- 1984-11-16 RO RO116307A patent/RO90919B/ro unknown
- 1984-11-16 CS CS848761A patent/CS255865B2/cs unknown

Also Published As

Publication number	Publication date
PL143144B1 (en)	1988-01-30
CS876184A2 (en)	1987-08-13
CS255865B2 (en)	1988-03-15
RO90919A (ro)	1987-02-27
BG43186A3 (en)	1988-04-15
RO90919B (ro)	1987-02-27
HU190744B (en)	1986-10-28
PL250411A1 (en)	1986-05-20

Publication	Publication Date	Title
DE2850680A1 (de)	1979-05-31	Verfahren zur herstellung von nitrodiarylamin
DE2803651C2 (cs)	1988-10-20
US3941783A (en)	1976-03-02	Process for the production of N,N-disubstituted carboxylic amides
DE69826845T2 (de)	2006-03-09	Verfahren zur herstellung von arylsulfonylchlorid
DE3131096C2 (cs)	1990-06-28
DD233123A5 (de)	1986-02-19	Verfahren zur herstellung von n-isopropyl-alpha-chlor-acetanilid
DE1795344B2 (de)	1976-05-06	Verfahren zur herstellung von 3-aminoisothiazolen
DE69922999T2 (de)	2005-05-19	Verfahren zur herstellung von polyhalogenierten para-trifluoroanilinen
US2370015A (en)	1945-02-20	Derivatives of tertiary amino aliphatic acids
EP0091044B1 (de)	1986-06-18	Verfahren zur Herstellung von 4-Hydroxy-3-(heterocyclocarbamoyl)-2H-1,2-benzothiazin-1,1-dioxiden
DE2737481A1 (de)	1978-03-02	Verfahren zur herstellung von 2-alkyl- oder 2-cycloalkyl-4-methyl-6-hydroxypyrimidinen
CH460773A (de)	1968-08-15	Verfahren zur Herstellung von substituierten 3-(3-Hydroxyphenyl)-1-phenacyl-piperidinen
DE2756865A1 (de)	1978-06-29	Verfahren zur herstellung von 2-chlor-4,6-bis-alkylamino-s-triazinen
DE3221874C2 (cs)	1988-03-31
AT211821B (de)	1960-11-10	Verfahren zur Herstellung Alkylaminoacetaryliden
AT323123B (de)	1975-06-25	Verfahren zur herstellung von n,n-disubstituierten charbonsäureamiden
AT204564B (de)	1959-07-25	Verfahren zur Herstellung von neuen stickstoffhaltigen organischen Phosphorverbindungen
AT371445B (de)	1983-06-27	Verfahren zur herstellung von neuen cis-4a-phenyl-isochinolinderivaten und ihren saeureadditionssalzen
AT250359B (de)	1966-11-10	Verfahren zur Herstellung neuer Diphenylsulfide
AT220151B (de)	1962-03-12	Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazin-Derivaten
AT221520B (de)	1962-06-12	Verfahren zur Herstellung von neuen N,N'-tetrasubstituierten 3-Amino-2-azaprop-2-en-1-ylidenammoniumhalogeniden
AT361473B (de)	1981-03-10	Verfahren zur herstellung von neuen thiazoli- dinderivaten und von deren saeureadditionssalzen
AT221508B (de)	1962-06-12	Verfahren zur Herstellung von neuen Aniliden und deren Salzen
AT338793B (de)	1977-09-12	Verfahren zur herstellung von neuen benzazocinderivaten
DE1620242A1 (de)	1970-06-04	Verfahren zur Herstellung neuer Diphenylsulfid-Derivate