DE1090197B - Process for the preparation of optionally substituted aliphatic and cycloaliphatic mono- and polyvalent isocyanates - Google Patents
Process for the preparation of optionally substituted aliphatic and cycloaliphatic mono- and polyvalent isocyanatesInfo
- Publication number
- DE1090197B DE1090197B DEF29204A DEF0029204A DE1090197B DE 1090197 B DE1090197 B DE 1090197B DE F29204 A DEF29204 A DE F29204A DE F0029204 A DEF0029204 A DE F0029204A DE 1090197 B DE1090197 B DE 1090197B
- Authority
- DE
- Germany
- Prior art keywords
- optionally substituted
- substituted aliphatic
- preparation
- polyvalent isocyanates
- cycloaliphatic mono
- Prior art date
- 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.)
- Pending
Links
- 239000012948 isocyanate Substances 0.000 title claims description 13
- 150000002513 isocyanates Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 7
- 125000001931 aliphatic group Chemical group 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- -1 Alkyl hypochlorites Chemical class 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IIBOGKHTXBPGEI-UHFFFAOYSA-N N-benzylformamide Chemical compound O=CNCC1=CC=CC=C1 IIBOGKHTXBPGEI-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- VTQINHDYJQCMGU-UHFFFAOYSA-N n-(3-methoxypropyl)formamide Chemical compound COCCCNC=O VTQINHDYJQCMGU-UHFFFAOYSA-N 0.000 description 2
- SUUDTPGCUKBECW-UHFFFAOYSA-N n-propylformamide Chemical compound CCCNC=O SUUDTPGCUKBECW-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- IQOIAHPAAZJVOX-UHFFFAOYSA-N 1-isocyanato-3-methoxypropane Chemical compound COCCCN=C=O IQOIAHPAAZJVOX-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QQGNLKJAIVSNCO-UHFFFAOYSA-N N-butylformamide Chemical compound CCCCNC=O QQGNLKJAIVSNCO-UHFFFAOYSA-N 0.000 description 1
- SWGXDLRCJNEEGZ-UHFFFAOYSA-N N-cyclohexylformamide Chemical compound O=CNC1CCCCC1 SWGXDLRCJNEEGZ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- TYCXRAVZVQSHSC-UHFFFAOYSA-N n-dodecylformamide Chemical compound CCCCCCCCCCCCNC=O TYCXRAVZVQSHSC-UHFFFAOYSA-N 0.000 description 1
- OFYOLZSDWXUNJV-UHFFFAOYSA-N n-methylcarbamoyl bromide Chemical compound CNC(Br)=O OFYOLZSDWXUNJV-UHFFFAOYSA-N 0.000 description 1
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/12—Preparation of derivatives of isocyanic acid from or via nitrogen analogues of carboxylic acids, e.g. from hydroxamic acids, involving a Hofmann, Curtius or Lossen-type rearrangement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von gegebenenfalls substituierten aliphatischen und cycloaliphatischen ein- und mehrwertigen Isocyanaten Es ist bekannt, aliphatische und cycloaliphatische ein-und zweiwertige Isocyanate in der Weise herzustellen, daß man N-Alkyl-formamide mit tert. Alkylhypochloriten in die N-Chloralkyl-formamide und diese dann in Gegenwart eines tert. Amins in die Isocyanate überführt entsprechend folgendem Reaktionsschema: Dieses aus zwei Reaktionsstufen bestehende Verfahren Liefert j e nach Ausgangsmaterial in der ersten Stufe zwischen etwa 75 und 95 % und in der zweiten Stufe zwischen etwa 50 und 75 °/o schwankende Ausbeuten. Nachteilig ist die Verwendung des tert. Alkylhypochlorits und der tert. Base, die nach Ablauf der Reaktion beide aus dem Reaktionsgut entfernt werden müssen.Process for the preparation of optionally substituted aliphatic and cycloaliphatic mono- and polyvalent isocyanates It is known to prepare aliphatic and cycloaliphatic mono- and divalent isocyanates in such a way that N-alkyl-formamides with tert. Alkyl hypochlorites in the N-chloroalkyl formamides and then in the presence of a tert. Amine is converted into isocyanates according to the following reaction scheme: This process, which consists of two reaction stages, provides between about 75 and 95% in the first stage and between about 50 and 75% fluctuating yields in the second stage, depending on the starting material. The disadvantage is the use of the tert. Alkyl hypochlorite and the tert. Base, both of which have to be removed from the reaction mixture after the reaction has ended.
Es wurde nun gefunden, daB man aliphatische und cycloaliphatische ein- und mehrwertige Isocyanate in einfacher Weise dadurch erhält, daB man N-Alkyl- bzw. N-Cycloalkyl-formamide mit freiem Halogen oder einer freies Halogen abspaltenden Verbindung umsetzt. Die Reaktion verläuft nach folgendem Formelschema: Für das neue Verfahren verwendbare Formylverbindungen sind beispielsweise N-Methyl-formamid, N-Propylformamid, N-tert. Butyl-formamid, N-Dodecyl-formamid, N-Cyclohexyl-formamid, N-Benzyl-formamid, N-(ß-Phenyl-äthyl)-formamid, N-(ß-Chloräthyl)-formamid, N-(3-Methoxypropyl)-formamid sowie die Bisformyl-Verbindungen von primären Diaminen, wie z. B. des 1,4-Tetramethylendiamins,1,6-Hexamethylendiamins und des Cyclohexan-1,4-diamins.It has now been found that aliphatic and cycloaliphatic monovalent and polyvalent isocyanates are obtained in a simple manner by reacting N-alkyl- or N-cycloalkyl-formamides with free halogen or a compound which splits off free halogen. The reaction proceeds according to the following equation: Formyl compounds which can be used for the new process are, for example, N-methylformamide, N-propylformamide, N-tert. Butyl-formamide, N-dodecyl-formamide, N-cyclohexyl-formamide, N-benzyl-formamide, N- (ß-phenyl-ethyl) -formamide, N- (ß-chloroethyl) -formamide, N- (3-methoxypropyl ) formamide and the bisformyl compounds of primary diamines, such as. B. of 1,4-tetramethylene diamine, 1,6-hexamethylene diamine and cyclohexane-1,4-diamine.
Zur Umsetzung mit den Formylverbindungen kommen neben den Halogenen selbst, wie z. B. Chlor und Brom, auch freies Halogen abspaltende Agenzien, wie z. B. Sulfurylchlorid oder Phosphorpentachlorid, in Frage.In addition to the halogens, the reaction with the formyl compounds is also used itself, such as B. chlorine and bromine, also free halogen-releasing agents, such as z. B. sulfuryl chloride or phosphorus pentachloride in question.
Zur Durchführung der Reaktion kann man das N-Alkylformamid in einem organischen Lösungsmittel, z. B. in Tetrachlorkohlenstoff, Chloroform, o-Dichlorbenzol lösen bzw. suspendieren und leitet das Halogen bzw. das freies Halogen abspaltende Mittel bei Raumtemperatur oder auch bei erhöhter Temperatur, vorteilhaft bei etwa 20 bis 50°C, ein. Das N-Alkyl-formamid läBt sich auch ohne Lösungsmittel in dieser Weise umsetzen. Aus dem Reaktionsgemisch wird das erhaltene Isocyanat in üblicher Weise isoliert, bei flüssigen Verfahrensprodukten vorteilhaft durch einfache Destillation.To carry out the reaction, the N-alkylformamide can be used in one organic solvents, e.g. B. in carbon tetrachloride, chloroform, o-dichlorobenzene dissolve or suspend and conduct the halogen or the free halogen which splits off Medium at room temperature or at elevated temperature, advantageously at about 20 to 50 ° C. The N-alkylformamide can also be used in this without a solvent Way to implement. The isocyanate obtained is made from the reaction mixture in a conventional manner Isolated manner, in the case of liquid process products advantageously by simple distillation.
Wenn man vom Methyl-, Äthyl- oder Propyl-formamid ausgeht, erhält man neben den Isocyanaten die zugehörigenN-Alkyl-carbamidsäurechloride, dasichwährend der Destillation das Isocyanat mit dem frei werdenden Halogenwasserstoff teilweise in der Kälte reversibel vereinigt. Man hat in diesen speziellen Fällen das Carbamidsäurechlorid in bekannter Weise in das Isocyanat zu überführen.If you start from methyl, ethyl or propyl formamide, you get in addition to the isocyanates, the associated N-alkyl-carbamic acid chlorides are used the isocyanate with the liberated hydrogen halide is partially removed from the distillation reversibly united in the cold. In these special cases, the carbamic acid chloride is used to be converted into the isocyanate in a known manner.
Die einwertigen Isocyanate dienen als Zwischenprodukte für die Herstellung von Pflanzenschutz- und Heilmitteln, während die mehrwertigen Isocyanate für die Herstellung von Kunststoffen nach dem Isocyanat-Polyadditions-Verfahren Verwendung finden.The monovalent isocyanates are used as intermediate products for the production of pesticides and medicinal products, while the polyvalent isocyanates for that Production of plastics using the isocyanate polyaddition process Find.
Beispiel 1 In die Lösung von 59 g N-Methyl-formamid in 150 ml o-Dichlorbenzol tropft man bei Zimmertemperatur innerhalb von 1 Stunde 135 g Sulfurylchlorid ein und sorgt durch Wasserkühlung dafür, daB die Temperatur 30'C nicht übersteigt. Man rührt einige Stunden nach und destilliert die aus zwei Schichten bestehende Reaktionslösung unter Rühren bei Atmosphärendruck. Man erhält 63 g eines Gemisches aus Methylisocyanat und Methylcarbamidsäurechlorid vom Kp. 90 bis 91'C. EXAMPLE 1 135 g of sulfuryl chloride are added dropwise to the solution of 59 g of N-methylformamide in 150 ml of o-dichlorobenzene at room temperature over the course of 1 hour, and the water is cooled to ensure that the temperature does not exceed 30.degree. The mixture is stirred for a few hours and the reaction solution, which consists of two layers, is distilled with stirring at atmospheric pressure. 63 g of a mixture of methyl isocyanate and methyl carbamic acid chloride with a boiling point of 90 to 91 ° C. are obtained.
Beispiel 2 30g N-Methyl-formamid werden bei Zimmertemperatur tropfenweise mit 80 g Brom versetzt. Nach mehrstündigem Rühren destilliert man die Lösung im Vakuum. Nach einem kurzen Vorlauf erhält man 50 g eines Gemisches aus Methylisocyanat und N-Methylcarbamidsäurebromid vom Kp." 30 bis 31'C. Beispiel 3 Unter Wasserkühlung läßt man 67,5 g Sulfurylchlorid in 60 g N-n-Butyl-formamid eintropfen. Hierbei steigt die Temperatur bis etwa 45°C an. Bis zur Beendigung der S 02 und H Cl-Entwicklung erhitzt man 1/2 Stünde auf dem Wasserbad und destilliert anschließend bei Atmosphärendruck, man erhält 21 g = 42 % der Theorie an N-n-Butyl-isocyanat vom Kp. 112 bis 114°C. Beispiel 4 90g N-Benzyl-formamid werden bei Zimmertemperatur in eine Lösung von 90 g Sulfurylchlorid und 300 ml Thionylchlorid eingetragen. Der Reaktionsansatz wird mehrere Stunden gerührt und nach Entfernung des Lösungsmittels im Vakuum destilliert. Man erhält 63 g = 71 % der Theorie an Benzyl-isocyanat vom Kp." 96 bis 100°C. Beispiel 5 37g Hexahydroformanilid werden unterhalb 309C in 60m1 Sulfurylchlorid eingetropft. Nach dreistündigem Rühren wird das überschüssige Sulfurylchlorid abdestilliert und der Rückstand im Vakuum fraktioniert. Dabei gehen 26 g = 72 % der Theorie an Cyclohexylisocyanat vom Kp." 55 bis 56°C über.Example 2 80 g of bromine are added dropwise to 30 g of N-methylformamide at room temperature. After several hours of stirring, the solution is distilled in vacuo. After a short forerun, 50 g of a mixture of methyl isocyanate and N-methylcarbamic acid bromide with a boiling point of 30 ° to 31 ° C. are obtained Temperature up to about 45 ° C. Until the evolution of S 02 and H Cl has ended, the mixture is heated for 1/2 hour on a water bath and then distilled at atmospheric pressure, 21 g = 42 % of theory of Nn-butyl isocyanate from Bp 112 ° to 114 ° C. Example 4 90 g of N-benzylformamide are introduced into a solution of 90 g of sulfuryl chloride and 300 ml of thionyl chloride at room temperature, the reaction mixture is stirred for several hours and, after removal of the solvent, distilled in vacuo g = 71 % of theory of benzyl isocyanate of bp. " 96 to 100 ° C. Example 5 37 g of hexahydroformanilide are added dropwise to 60 ml of sulfuryl chloride below 309C. After three hours of stirring, the excess sulfuryl chloride is distilled off and the residue is fractionated in vacuo. In this case, 26 g = 72 % of theory of cyclohexyl isocyanate with a boiling point of 55 to 56 ° C. pass over.
Beispiel 6 72g der Bis-formyl-Verbindung des Tetramethylendiamins werden unterhalb 209C langsam in 150 ccm Sulfurylchlorid eingetragen. Unter allmählicher Verflüssigung tritt eine geringe Wärmetönung auf. Nach kurzer Zeit kristallisiert die Lösung wieder. Man gibt 400m1 Toluol zu, destilliert überschüssiges Sulfurylchlorid ab, erwärmt eine Zeitlang auf dem Wasserbad, dekantiert die 'Toluollösung vom unlöslichen Harz und engt im Vakuum ein. Nach Abdestillieren des Lösungsmittels erhält man 20 g = 29 °/p der Theorie an Tetramethylendiisocyanat vom Kp.l, 108 bis 110°C. Beispiel 7 58,5 g (1/2 Mol) N-(3-Methoxypropyl)-formamid werden bei Raumtemperatur in 80 ml Sulfurylchlorid eingetropft. Durch Kühlung sorgt man dafür, daß die Temperatur 30'C nicht übersteigt. Man rührt nach dem Eintropfen eine Zeitlang nach, destilliert das überschüssige Sulfurylchlorid ab und fraktioniert anschließend im Vakuum. Hierbei gehen beim Kp.2o = 54 bis 559C 42 g = 73 % der Theorie 3-Methoxypropylisocyanat über.Example 6 72 g of the bis-formyl compound of tetramethylenediamine are slowly introduced into 150 cc of sulfuryl chloride below 209C. With gradual liquefaction, a slight heat release occurs. After a short time the solution crystallizes again. 400 ml of toluene are added, excess sulfuryl chloride is distilled off, the mixture is warmed for a while on the water bath, the toluene solution is decanted from the insoluble resin and concentrated in vacuo. After the solvent has been distilled off, 20 g = 29 ° / p theoretical of tetramethylene diisocyanate with a boiling point of 108 to 110 ° C. is obtained. Example 7 58.5 g (1/2 mol) of N- (3-methoxypropyl) formamide are added dropwise to 80 ml of sulfuryl chloride at room temperature. Cooling ensures that the temperature does not exceed 30 ° C. After the dropwise addition, the mixture is stirred for a while, the excess sulfuryl chloride is distilled off and then fractionated in vacuo. Here, at a boiling point of 54 to 559C, 42 g = 73% of theory 3-methoxypropyl isocyanate are transferred.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29204A DE1090197B (en) | 1959-08-19 | 1959-08-19 | Process for the preparation of optionally substituted aliphatic and cycloaliphatic mono- and polyvalent isocyanates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29204A DE1090197B (en) | 1959-08-19 | 1959-08-19 | Process for the preparation of optionally substituted aliphatic and cycloaliphatic mono- and polyvalent isocyanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1090197B true DE1090197B (en) | 1960-10-06 |
Family
ID=7093202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF29204A Pending DE1090197B (en) | 1959-08-19 | 1959-08-19 | Process for the preparation of optionally substituted aliphatic and cycloaliphatic mono- and polyvalent isocyanates |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1090197B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025907A1 (en) * | 1979-09-13 | 1981-04-01 | BASF Aktiengesellschaft | Halogenated tertiary alkyl isocyanates and process for their preparation |
-
1959
- 1959-08-19 DE DEF29204A patent/DE1090197B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025907A1 (en) * | 1979-09-13 | 1981-04-01 | BASF Aktiengesellschaft | Halogenated tertiary alkyl isocyanates and process for their preparation |
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