CH378334A - Verfahren zur Herstellung von tetrameren Halogencyanen - Google Patents

Verfahren zur Herstellung von tetrameren Halogencyanen

Info

Publication number: CH378334A
Authority: CH; Switzerland
Prior art keywords: cyanogen; tetrameric; chloride; polymerization; parts
Prior art date: 1960-01-19

Application number

CH53260A

Other languages

German (de)

English (en)

Inventor

Riethmann Jean

Hans Dr Wegmueller

Original Assignee

Geigy Ag J R

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.)

1960-01-19

Filing date

1960-01-19

Publication date

1964-06-15

1960-01-19 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1960-01-19 Priority to CH53260A priority Critical patent/CH378334A/de

1961-01-18 Priority to ES0264106A priority patent/ES264106A1/es

1961-01-18 Priority to BE599211A priority patent/BE599211A/fr

1964-06-15 Publication of CH378334A publication Critical patent/CH378334A/de

Links

-1 cyanogen halides Chemical class 0.000 title claims description 17
JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 title claims description 16
238000000034 method Methods 0.000 title claims description 13
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
238000006116 polymerization reaction Methods 0.000 claims description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 6
235000014113 dietary fatty acids Nutrition 0.000 claims description 6
239000000194 fatty acid Substances 0.000 claims description 6
229930195729 fatty acid Natural products 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
150000004665 fatty acids Chemical class 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000000975 dye Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000005313 fatty acid group Chemical group 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
MCLXKFUCPVGZEN-UHFFFAOYSA-N 4,6-dichloro-1,3,5-triazin-2-amine Chemical compound NC1=NC(Cl)=NC(Cl)=N1 MCLXKFUCPVGZEN-UHFFFAOYSA-N 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical class [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910001513 alkali metal bromide Inorganic materials 0.000 description 1
229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000101 thioether group Chemical group 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH53260A 1960-01-19 1960-01-19 Verfahren zur Herstellung von tetrameren Halogencyanen CH378334A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH53260A CH378334A (de)	1960-01-19	1960-01-19	Verfahren zur Herstellung von tetrameren Halogencyanen
ES0264106A ES264106A1 (es)	1960-01-19	1961-01-18	Procedimiento para la preparacion de haluros de cianogeno tetrameros
BE599211A BE599211A (fr)	1960-01-19	1961-01-18	Nouveaux halogénures de cyanogène tétramères et leur préparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH53260A CH378334A (de)	1960-01-19	1960-01-19	Verfahren zur Herstellung von tetrameren Halogencyanen

Publications (1)

Publication Number	Publication Date
CH378334A true CH378334A (de)	1964-06-15

Family

ID=4189159

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH53260A CH378334A (de)	1960-01-19	1960-01-19	Verfahren zur Herstellung von tetrameren Halogencyanen

Country Status (3)

Country	Link
BE (1)	BE599211A (fr)
CH (1)	CH378334A (fr)
ES (1)	ES264106A1 (fr)

1960
- 1960-01-19 CH CH53260A patent/CH378334A/de unknown
1961
- 1961-01-18 BE BE599211A patent/BE599211A/fr unknown
- 1961-01-18 ES ES0264106A patent/ES264106A1/es not_active Expired

Also Published As

Publication number	Publication date
ES264106A1 (es)	1961-07-16
BE599211A (fr)	1961-07-18

Publication	Publication Date	Title
DE1620392A1 (de)	1970-04-02	Verfahren zur Herstellung von aromatischen Polynitrilsulfiten und Polyisocyanaten
DE2360709A1 (de)	1975-06-12	S-triazin-vorpolymerisaten
DE2654939A1 (de)	1977-06-16	Verfahren zur herstellung von aromatischen urethanen
DE2837341A1 (de)	1980-03-20	Verfahren zur herstellung von organischen mono- und polyisocyanaten durch thermische spaltung der hydrochloride trisubstituierter harnstoffe
DE1593865C3 (de)	1975-07-10	Verfahren zur Isolierung von 4,4'-Diaminodiphenylmethan aus Polyphenylmethylenpolyamingemischen
DE1493194A1 (de)	1969-04-03	Kernfluorierte aromatische Verbindungen und Verfahren zu deren Herstellung
DE3025999A1 (de)	1981-01-29	Verfahren zur herstellung von polymethylen-polyphenyl-polycarbamaten
CH378334A (de)	1964-06-15	Verfahren zur Herstellung von tetrameren Halogencyanen
DE2156761B2 (fr)	1974-05-22
DE2025891C3 (de)	1982-03-18	Verfahren zur Herstellung von Tris-(3,5-dialkyl-4-hydroxy-benzyl)-isocyanuraten
DE1900133B2 (de)	1978-02-02	Verfahren zur herstellung von 2- (morpholinothio)-benzothiazol
DE1132559B (de)	1962-07-05	Verfahren zur Herstellung von tetrameren Halogencyanen
DE2633204C3 (de)	1981-06-19	Verfahren zur Herstellung von Benzylnatrium oder Chlorbenzylnatrium
US3137694A (en)	1964-06-16	Method for isolating tetrameric cyanogen halide from its reaction mixture
DE2937028A1 (de)	1981-04-09	1-monohalogenierte isocyanate und verfahren zur herstellung von gemischen von 1-monohalogenierten isocyanaten und 1,2-ungesaettigten isocyanaten
DE69117137T2 (de)	1996-08-22	2-Chlorpropionaldehyd-Trimer und Verfahren zur Herstellung davon
DE1232133B (de)	1967-01-12	Verfahren zur Herstellung von Isocyanat-kohlensaeureestern
DE1670296A1 (de)	1971-01-28	Verfahren zur Herstellung von substituierten Phosphiniminen und entsprechenden Amidophosphoniumhalogeniden
DE68910733T2 (de)	1994-03-10	Perfluordiaziridine und Verfahren zu ihrer Herstellung.
EP0037481B1 (fr)	1983-06-29	Procédé de préparation du chlorure de 1-monochloroéthyl-carbamoyle
DE2038526A1 (de)	1971-02-25	Verfahren zur Herstellung von organischen Isocyanaten
AT231469B (de)	1964-01-27	Verfahren zur Herstellung neuer Organophosphorverbindungen
DE2456544C3 (de)	1977-11-24	Verfahren zur Herstellung von Diaminomaleinsäurenitril
DD298779A5 (de)	1992-03-12	Verfahren zur herstellung von carbomaten und zwischenprodukten in diesem verfahren
AT214425B (de)	1961-04-10	Verfahren zur Herstellung von N-substituierten Malonimiden und deren Polymeren