LU84241A1 - Isocyanurates et leur preparation - Google Patents

Isocyanurates et leur preparation Download PDF

Info

Publication number: LU84241A1
Authority: LU; Luxembourg
Prior art keywords: cyanate; formula; denotes; equal; trione
Prior art date: 1982-06-29

Application number

LU84241A

Other languages

English (en)

French (fr)

Inventor

Pierre Lambert

Ignacio De Aguirre-Otegui

Original Assignee

Carbochimique Sa

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.)

1982-06-29

Filing date

1982-06-29

Publication date

1984-03-07

1982-06-29 Application filed by Carbochimique Sa filed Critical Carbochimique Sa

1982-06-29 Priority to LU84241A priority Critical patent/LU84241A1/fr

1983-06-20 Priority to EP83200906A priority patent/EP0098006A3/de

1983-06-29 Priority to JP58118036A priority patent/JPS5931770A/ja

1984-03-07 Publication of LU84241A1 publication Critical patent/LU84241A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 27
238000000034 method Methods 0.000 claims description 41
-1 salt cyanate Chemical class 0.000 claims description 29
230000008569 process Effects 0.000 claims description 26
MUNGMRPYTCHBFX-UHFFFAOYSA-N 1,5-diphenylpentane-1,3,5-trione Chemical compound C=1C=CC=CC=1C(=O)CC(=O)CC(=O)C1=CC=CC=C1 MUNGMRPYTCHBFX-UHFFFAOYSA-N 0.000 claims description 24
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
239000004215 Carbon black (E152) Substances 0.000 claims description 16
229930195733 hydrocarbon Natural products 0.000 claims description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 16
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 16
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical class [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 claims description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims description 9
LTMQZVLXCLQPCT-UHFFFAOYSA-N 1,1,6-trimethyltetralin Chemical compound C1CCC(C)(C)C=2C1=CC(C)=CC=2 LTMQZVLXCLQPCT-UHFFFAOYSA-N 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 7
150000001913 cyanates Chemical class 0.000 claims description 7
150000005063 oxadiazines Chemical class 0.000 claims description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
229920000642 polymer Polymers 0.000 claims description 6
239000011780 sodium chloride Substances 0.000 claims description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
VCBMYOGJZQELET-UHFFFAOYSA-M tetrapropylazanium;cyanate Chemical compound [O-]C#N.CCC[N+](CCC)(CCC)CCC VCBMYOGJZQELET-UHFFFAOYSA-M 0.000 claims description 5
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 4
ORWNMXQXOLHWIK-UHFFFAOYSA-N 3-methyl-2,4-dihydrooxadiazine Chemical compound CN1CC=CON1 ORWNMXQXOLHWIK-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 3
229910021653 sulphate ion Inorganic materials 0.000 claims description 3
PEFQHPVDKJBRFF-UHFFFAOYSA-M tetrabutylazanium;cyanate Chemical compound [O-]C#N.CCCC[N+](CCCC)(CCCC)CCCC PEFQHPVDKJBRFF-UHFFFAOYSA-M 0.000 claims description 3
ZKZBGSDRPHLIBM-UHFFFAOYSA-M tetrapentylazanium;cyanate Chemical compound [O-]C#N.CCCCC[N+](CCCCC)(CCCCC)CCCCC ZKZBGSDRPHLIBM-UHFFFAOYSA-M 0.000 claims description 3
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical group ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 claims description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
LSNYEHQFJWMQHP-UHFFFAOYSA-N 1-(3-propyl-2,4-dihydrooxadiazin-5-yl)ethanone Chemical compound C(CC)N1NOC=C(C1)C(C)=O LSNYEHQFJWMQHP-UHFFFAOYSA-N 0.000 claims description 2
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000000129 anionic group Chemical group 0.000 claims description 2
229910052785 arsenic Inorganic materials 0.000 claims description 2
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
KRUWJKLQAMEPRW-UHFFFAOYSA-M benzyl(triethyl)arsanium;cyanate Chemical compound [O-]C#N.CC[As+](CC)(CC)CC1=CC=CC=C1 KRUWJKLQAMEPRW-UHFFFAOYSA-M 0.000 claims description 2
ACHYTNILNDIYSZ-UHFFFAOYSA-M benzyl(triethyl)azanium;cyanate Chemical compound [O-]C#N.CC[N+](CC)(CC)CC1=CC=CC=C1 ACHYTNILNDIYSZ-UHFFFAOYSA-M 0.000 claims description 2
VUGKCDVRCRKITO-UHFFFAOYSA-M benzyl(tripropyl)azanium;cyanate Chemical compound [O-]C#N.CCC[N+](CCC)(CCC)CC1=CC=CC=C1 VUGKCDVRCRKITO-UHFFFAOYSA-M 0.000 claims description 2
229920001429 chelating resin Polymers 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 claims description 2
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
229920005989 resin Polymers 0.000 claims description 2
239000011347 resin Substances 0.000 claims description 2
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 claims description 2
NKEVUMSCVLJVFU-UHFFFAOYSA-N tetraethylazanium isocyanate Chemical compound [N-]=C=O.CC[N+](CC)(CC)CC NKEVUMSCVLJVFU-UHFFFAOYSA-N 0.000 claims description 2
AGFGLNYPBNYVJA-UHFFFAOYSA-M tetramethylazanium;cyanate Chemical compound [O-]C#N.C[N+](C)(C)C AGFGLNYPBNYVJA-UHFFFAOYSA-M 0.000 claims description 2
AMSIWBVFTMQDME-UHFFFAOYSA-M tetraphenylarsanium;cyanate Chemical compound [O-]C#N.C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AMSIWBVFTMQDME-UHFFFAOYSA-M 0.000 claims description 2
VZNMBPHHWXRXRE-UHFFFAOYSA-M trimethyl(phenyl)azanium;cyanate Chemical compound [O-]C#N.C[N+](C)(C)C1=CC=CC=C1 VZNMBPHHWXRXRE-UHFFFAOYSA-M 0.000 claims description 2
JKPSCLPFXNWYAW-UHFFFAOYSA-N CCCCCCCC.N#CO Chemical compound CCCCCCCC.N#CO JKPSCLPFXNWYAW-UHFFFAOYSA-N 0.000 claims 1
CGXUKNKFRNOKCG-UHFFFAOYSA-N [O-]C#N.C[NH+](C)C Chemical compound [O-]C#N.C[NH+](C)C CGXUKNKFRNOKCG-UHFFFAOYSA-N 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
WIJRMGQOERPOJA-UHFFFAOYSA-N benzyl cyanate Chemical compound N#COCC1=CC=CC=C1 WIJRMGQOERPOJA-UHFFFAOYSA-N 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
125000005496 phosphonium group Chemical group 0.000 claims 1
AMLYACBLTXQKAS-UHFFFAOYSA-M tetrabutylphosphanium;cyanate Chemical compound [O-]C#N.CCCC[P+](CCCC)(CCCC)CCCC AMLYACBLTXQKAS-UHFFFAOYSA-M 0.000 claims 1
SIUAVVAWJSSORE-UHFFFAOYSA-M tetrahexylazanium;cyanate Chemical compound [O-]C#N.CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SIUAVVAWJSSORE-UHFFFAOYSA-M 0.000 claims 1
PCCGUVMOVSMIDK-UHFFFAOYSA-M tetraphenylphosphanium;cyanate Chemical compound [O-]C#N.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PCCGUVMOVSMIDK-UHFFFAOYSA-M 0.000 claims 1
LJOGKCBBQFMJPW-UHFFFAOYSA-M tetrapropylarsanium;cyanate Chemical compound [O-]C#N.CCC[As+](CCC)(CCC)CCC LJOGKCBBQFMJPW-UHFFFAOYSA-M 0.000 claims 1
VJDKNMHQJBKBCX-UHFFFAOYSA-M triethyl(phenyl)azanium;cyanate Chemical compound [O-]C#N.CC[N+](CC)(CC)C1=CC=CC=C1 VJDKNMHQJBKBCX-UHFFFAOYSA-M 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 16
238000003756 stirring Methods 0.000 description 10
239000012948 isocyanate Substances 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000002513 isocyanates Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000126 substance Substances 0.000 description 4
150000003918 triazines Chemical class 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
QYTOONVFPBUIJG-UHFFFAOYSA-N azane;cyanic acid Chemical class [NH4+].[O-]C#N QYTOONVFPBUIJG-UHFFFAOYSA-N 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
XVGVNOVEJAWYEO-UHFFFAOYSA-N 3,4-dihydro-2h-oxadiazine Chemical compound C1NNOC=C1 XVGVNOVEJAWYEO-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
AVVGUSAFSPYGAC-UHFFFAOYSA-N 5-benzyl-3-methyl-2,4-dihydrooxadiazine Chemical compound CN1NOC=C(C1)CC1=CC=CC=C1 AVVGUSAFSPYGAC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000003495 polar organic solvent Substances 0.000 description 2
229920000582 polyisocyanurate Polymers 0.000 description 2
239000011495 polyisocyanurate Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 2
230000009466 transformation Effects 0.000 description 2
238000005829 trimerization reaction Methods 0.000 description 2
QYAPHLRPFNSDNH-MRFRVZCGSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O QYAPHLRPFNSDNH-MRFRVZCGSA-N 0.000 description 1
SWSOIFQIPTXLOI-HNQUOIGGSA-N (e)-1,4-dichlorobut-1-ene Chemical compound ClCC\C=C\Cl SWSOIFQIPTXLOI-HNQUOIGGSA-N 0.000 description 1
GRJWOKACBGZOKT-UHFFFAOYSA-N 1,3-bis(chloromethyl)benzene Chemical group ClCC1=CC=CC(CCl)=C1 GRJWOKACBGZOKT-UHFFFAOYSA-N 0.000 description 1
OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
ABNGESMFWMTZHX-UHFFFAOYSA-N 1-chlorohexane Chemical compound [CH2]CCCCCCl ABNGESMFWMTZHX-UHFFFAOYSA-N 0.000 description 1
GMNKLDXOSOVSKZ-UHFFFAOYSA-N 1-methyl-2h-triazine Chemical compound CN1NN=CC=C1 GMNKLDXOSOVSKZ-UHFFFAOYSA-N 0.000 description 1
XIOLUARFGKUPBK-UHFFFAOYSA-N 3,5-dimethyl-2,4-dihydrooxadiazine Chemical compound CC1=CONN(C1)C XIOLUARFGKUPBK-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WOHWWJAWIZTXNL-UHFFFAOYSA-N CC(=O)N1C=C(CN(N1)C)CC2=CC=CC=C2 Chemical compound CC(=O)N1C=C(CN(N1)C)CC2=CC=CC=C2 WOHWWJAWIZTXNL-UHFFFAOYSA-N 0.000 description 1
MVRDANIRYFDQGN-UHFFFAOYSA-N CCC1=CONN(C1)C Chemical compound CCC1=CONN(C1)C MVRDANIRYFDQGN-UHFFFAOYSA-N 0.000 description 1
241000551547 Dione <red algae> Species 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
241000428198 Lutrinae Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
ISRXTPJAHZNVHB-UHFFFAOYSA-M benzyl(trimethyl)azanium;cyanate Chemical compound [O-]C#N.C[N+](C)(C)CC1=CC=CC=C1 ISRXTPJAHZNVHB-UHFFFAOYSA-M 0.000 description 1
QGLYFXPXNKWSHU-UHFFFAOYSA-N benzyl-dimethyl-propan-2-ylazanium Chemical compound CC(C)[N+](C)(C)CC1=CC=CC=C1 QGLYFXPXNKWSHU-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
238000010586 diagram Methods 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000003918 potentiometric titration Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
DTIFFPXSSXFQCJ-UHFFFAOYSA-N tetrahexylazanium Chemical compound CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC DTIFFPXSSXFQCJ-UHFFFAOYSA-N 0.000 description 1
GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 1
PJMJFVQKDBRMIP-UHFFFAOYSA-N tetraphenylarsonium Chemical compound C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PJMJFVQKDBRMIP-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

LU84241A 1982-06-29 1982-06-29 Isocyanurates et leur preparation LU84241A1 (fr)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
LU84241A LU84241A1 (fr)	1982-06-29	1982-06-29	Isocyanurates et leur preparation
EP83200906A EP0098006A3 (de)	1982-06-29	1983-06-20	Isocyanurate und ihre Herstellung
JP58118036A JPS5931770A (ja)	1982-06-29	1983-06-29	イソシアヌレ−ト類およびその製法

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU84241		1982-06-29
LU84241A LU84241A1 (fr)	1982-06-29	1982-06-29	Isocyanurates et leur preparation

Publications (1)

Publication Number	Publication Date
LU84241A1 true LU84241A1 (fr)	1984-03-07

Family

ID=19729912

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU84241A LU84241A1 (fr)	1982-06-29	1982-06-29	Isocyanurates et leur preparation

Country Status (3)

Country	Link
EP (1)	EP0098006A3 (de)
JP (1)	JPS5931770A (de)
LU (1)	LU84241A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4171920B2 (ja)	2002-10-09	2008-10-29	日産化学工業株式会社	リソグラフィー用反射防止膜形成組成物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3549630A (en) *	1967-11-13	1970-12-22	Marathon Oil Co	Method of preparing isocyanuric acids and their salts

1982
- 1982-06-29 LU LU84241A patent/LU84241A1/fr unknown
1983
- 1983-06-20 EP EP83200906A patent/EP0098006A3/de not_active Withdrawn
- 1983-06-29 JP JP58118036A patent/JPS5931770A/ja active Pending

Also Published As

Publication number	Publication date
JPS5931770A (ja)	1984-02-20
EP0098006A2 (de)	1984-01-11
EP0098006A3 (de)	1984-09-05

Publication	Publication Date	Title
EP3313823B1 (de)	2022-11-09	Verfahren zur synthese von molekülen mit nitriloxidfunktion
EP0098006A2 (de)	1984-01-11	Isocyanurate und ihre Herstellung
EP0360709B1 (de)	1992-12-16	Verfahren zur Herstellung von Diorganopolysiloxan-Gruppen enthaltenden thermostabilen Copolyimidamiden
LU84238A1 (fr)	1984-03-07	Nouveaux sels de polyisocyanates organiques et leur preparation
US3422143A (en)	1969-01-14	Alpha,alpha,alpha',alpha'-tetramethyl-p-xylylenediamine
EP0053981B1 (de)	1985-04-10	Verfahren zur Herstellung von Thiochlorameisensäureestern
JP7627257B2 (ja)	2025-02-05	アルカンジスルホン酸化合物の製造方法
LU84242A1 (fr)	1984-03-07	Sels d'oxadiazines 1,3,5 triones 2,4,6,oxadiazines 1,3,5 triones 2,4,6 et leur preparation
US2890248A (en)	1959-06-09	Preparation of alpha-chlorocyclooctanone oxime
US4151193A (en)	1979-04-24	Process for the preparation of aliphatic isocyanates
CH616147A5 (de)	1980-03-14
JP7851572B2 (ja)	2026-04-27	硬化性組成物
US4076941A (en)	1978-02-28	Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins
US3637811A (en)	1972-01-25	Production of organic isocyanates
EP0157661B1 (de)	1988-02-24	Diisocyanat-1-10-Dekan und Verfahren zu ihrer Herstellung
EP0268507B1 (de)	1991-03-06	Verfahren zur Herstellung von Alkylthiochloroformiaten
US3337621A (en)	1967-08-22	N, n'-disubstituted allophanyl chlorides and their preparation
FR3037952A1 (fr)	2016-12-30	Procede de synthese d'oximes aromatiques
EP4733293A1 (de)	2026-04-29	Verfahren zur herstellung einer alkylfluoridverbindung und verfahren zur herstellung einer optisch aktiven alkylfluoridverbindung
BE706410A (de)	1968-05-13
KR950011118B1 (ko)	1995-09-28	유기 n-히드록시이미데이트의 제조방법
JPS6130580A (ja)	1986-02-12	チアゾリジン−２−オン類の製造法
US3267143A (en)	1966-08-16	Process for obtaining alpha-chloro-oximes and sulphates thereof
FR2525216A1 (fr)	1983-10-21	Isocyanates aromatiques halogenes, ou leurs melanges, a structure diphenylmethane et leur procede de fabrication
CH403796A (fr)	1965-12-15	Procédé de préparation de dicarbamates de 5,5-bis-hydroxyméthyl-dioxane-1,3-substitués en position 2