CH431499A - Verfahren zur Herstellung perchlorierter Arylisocyanate - Google Patents

Verfahren zur Herstellung perchlorierter Arylisocyanate

Info

Publication number: CH431499A
Authority: CH; Switzerland
Prior art keywords: isocyanates; chlorination; chlorinated; stage; temperature
Prior art date: 1962-05-10

Application number

CH506363A

Other languages

German (de)

English (en)

Inventor

Hans Dr Holtschmidt

Otto Prof Dr Dr H C Dr E Bayer

Eberhard Dr Degener

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.)

1962-05-10

Filing date

1963-04-23

Publication date

1967-03-15

1963-04-23 Application filed by Bayer Ag filed Critical Bayer Ag

1967-03-15 Publication of CH431499A publication Critical patent/CH431499A/de

Links

239000012948 isocyanate Substances 0.000 title claims description 22
238000000034 method Methods 0.000 title claims description 21
-1 perchlorinated aryl isocyanates Chemical class 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 4
238000005660 chlorination reaction Methods 0.000 claims description 21
229910052751 metal Inorganic materials 0.000 claims description 12
239000002184 metal Substances 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
150000002513 isocyanates Chemical class 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
229910021576 Iron(III) bromide Inorganic materials 0.000 claims description 2
229910003074 TiCl4 Inorganic materials 0.000 claims description 2
FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims description 2
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
229910052959 stibnite Inorganic materials 0.000 claims description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 claims description 2
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
239000000969 carrier Substances 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
125000005521 carbonamide group Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
XYUCULXRVSQDCG-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-isocyanatobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(N=C=O)C(Cl)=C1Cl XYUCULXRVSQDCG-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
WPYQZMMKVPVYSK-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3,6-diisocyanatobenzene Chemical compound ClC1=C(Cl)C(N=C=O)=C(Cl)C(Cl)=C1N=C=O WPYQZMMKVPVYSK-UHFFFAOYSA-N 0.000 description 1
MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
JASTZOAHAWBRLM-UHFFFAOYSA-N 1-(3-isocyanatophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(N=C=O)=C1 JASTZOAHAWBRLM-UHFFFAOYSA-N 0.000 description 1
KHCZSJXTDDHLGJ-UHFFFAOYSA-N 2,3,4,5,6-pentachloroaniline Chemical compound NC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl KHCZSJXTDDHLGJ-UHFFFAOYSA-N 0.000 description 1
OLBJNSPBWLCTOT-UHFFFAOYSA-N 2,4-dichloro-1-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C(Cl)=C1 OLBJNSPBWLCTOT-UHFFFAOYSA-N 0.000 description 1
AKKHQNDBSBENFW-UHFFFAOYSA-N 2,4-diisocyanato-1-(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(N=C=O)C=C1N=C=O AKKHQNDBSBENFW-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/16—Preparation of derivatives of isocyanic acid by reactions not involving the formation of isocyanate groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH506363A 1962-05-10 1963-04-23 Verfahren zur Herstellung perchlorierter Arylisocyanate CH431499A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF36762A DE1157601B (de)	1962-05-10	1962-05-10	Verfahren zur Herstellung perchlorierter Arylisocyanate

Publications (1)

Publication Number	Publication Date
CH431499A true CH431499A (de)	1967-03-15

Family

ID=7096591

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH506363A CH431499A (de)	1962-05-10	1963-04-23	Verfahren zur Herstellung perchlorierter Arylisocyanate

Country Status (6)

Country	Link
AT (1)	AT237608B (fr)
BE (1)	BE632073A (fr)
CH (1)	CH431499A (fr)
DE (1)	DE1157601B (fr)
FR (1)	FR1356627A (fr)
GB (1)	GB989313A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101778877B (zh)	2007-07-23	2013-01-02	陶氏环球技术公司	在使用温度范围内g-模量基本一致的两部分聚氨酯可固化组合物
WO2015100128A1 (fr)	2013-12-23	2015-07-02	Dow Global Technologies Llc	Adhésif contenant un prépolymère polyol polyuréthanne de type copolymère à teneur élevée en solides

1962
- 1962-05-10 DE DEF36762A patent/DE1157601B/de active Pending
1963
- 1963-04-23 CH CH506363A patent/CH431499A/de unknown
- 1963-04-24 AT AT331163A patent/AT237608B/de active
- 1963-05-06 GB GB1781063A patent/GB989313A/en not_active Expired
- 1963-05-09 FR FR934189A patent/FR1356627A/fr not_active Expired
- 1963-05-09 BE BE632073A patent/BE632073A/fr unknown

Also Published As

Publication number	Publication date
FR1356627A (fr)	1964-03-27
AT237608B (de)	1964-12-28
GB989313A (en)	1965-04-14
BE632073A (fr)	1963-09-02
DE1157601B (de)	1963-11-21

Publication	Publication Date	Title
DE4326952A1 (de)	1995-02-16	Verfahren zur Herstellung von Triphenylphosphin
DE2837341C2 (de)	1983-02-17	Verfahren zur Herstellung von organischen Mono- und Polyisocyanaten durch thermische Spaltung der Hydrochloride trisubstituierter Harnstoffe
EP0083442B1 (fr)	1986-08-20	Procédé de préparation de 2,4,6-trichloroaniline
CH431499A (de)	1967-03-15	Verfahren zur Herstellung perchlorierter Arylisocyanate
EP0057844B1 (fr)	1983-12-28	Procédé de préparation de chlorures de polychlorobenzoyle
EP0270906B1 (fr)	1990-02-21	Diisocyanates et mélanges de diisocyanates, un procédé pour leur préparation et leur utilisation pour la préparation de plastiques de polyuréthane
DE1123663B (de)	1962-02-15	Verfahren zur Herstellung von hochchlorierten Arylsulfiden
DE232071C (fr)	1900-01-01
DE1158500B (de)	1963-12-05	Verfahren zur Herstellung von Polyisonitrilen
EP0034711A2 (fr)	1981-09-02	Procédé de préparation d'isocyanates aromatiques portant des groupes sulfochlorures à noyau aromatique
DE954919C (de)	1956-12-27	Verfahren zur Herstellung von Polyisocyanaten
DE2258747C2 (de)	1982-07-08	Verfahren zur Herstellung von 2,4-Dichlortoluol
EP0755908B1 (fr)	2000-01-12	Procédé pour la préparation des composés aromatiques chlorés substitués
CH630593A5 (de)	1982-06-30	Verfahren zur herstellung von 4-brom-2-chlorphenol.
DE2452714A1 (de)	1975-05-22	Diisocyanato-diphenylmethan-derivate und ihre verwendung
DE2016985C3 (de)	1977-12-29	Verfahren zur Herstellung von PoIyisocyanatverbindungen, die Isocyanuratringe und Halogenalkylgruppen enthalten
EP0037481B1 (fr)	1983-06-29	Procédé de préparation du chlorure de 1-monochloroéthyl-carbamoyle
EP0195928B1 (fr)	1989-10-18	4,4'-Diisocyanato-phényl benzyl éther, son procédé de préparation et son utilisation comme partie isocyanate dans la préparation de polyuréthanes
DE3047376C2 (fr)	1991-07-18
AT214425B (de)	1961-04-10	Verfahren zur Herstellung von N-substituierten Malonimiden und deren Polymeren
DE947470C (de)	1956-08-16	Verfahren zur Herstellung in der aliphatischen Seitenkette halogensubstituierter aromatischer Mono- und Polyisocyanate
DE2126105C3 (de)	1980-06-26	Verfahren zur Herstellung von wasserstofffreien Halogenmethanen
CH639054A5 (en)	1983-10-31	Process for the preparation of 4-bromo-2,5-dichlorophenol
DE1186844B (de)	1965-02-11	Verfahren zur Herstellung von Trifluoracetylchlorid
DE1620346C3 (de)	1975-11-13	Verfahren zur Herstellung von 1,2,4,5-Tetrachlorimidazol