CH626055A5 - - Google Patents

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Info

Publication number: CH626055A5
Authority: CH; Switzerland
Prior art keywords: reaction; water; tertiary; formula; phosgene
Prior art date: 1976-01-16

Application number

CH42077A

Other languages

German (de)

English (en)

Inventor

Chem Karl-Heinz Dr Koenig

Chem Christian Dr Reitel

Chem Dietrich Dr Mangold

Original Assignee

Basf 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.)

1976-01-16

Filing date

1977-01-13

Publication date

1981-10-30

1977-01-13 Application filed by Basf Ag filed Critical Basf Ag

1981-10-30 Publication of CH626055A5 publication Critical patent/CH626055A5/de

Links

OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 25
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 19
239000007795 chemical reaction product Substances 0.000 claims description 19
238000000034 method Methods 0.000 claims description 19
239000011541 reaction mixture Substances 0.000 claims description 16
-1 tertiary amine salts Chemical class 0.000 claims description 15
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 14
239000008346 aqueous phase Substances 0.000 claims description 14
239000012074 organic phase Substances 0.000 claims description 14
150000003512 tertiary amines Chemical class 0.000 claims description 12
239000002262 Schiff base Substances 0.000 claims description 11
150000004753 Schiff bases Chemical class 0.000 claims description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
150000003973 alkyl amines Chemical class 0.000 claims description 3
239000002253 acid Substances 0.000 claims 2
150000001805 chlorine compounds Chemical class 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
239000007858 starting material Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000004821 distillation Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000012071 phase Substances 0.000 description 7
150000001412 amines Chemical class 0.000 description 6
239000002904 solvent Substances 0.000 description 6
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 5
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical class CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 5
238000000926 separation method Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000576 coating method Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
KBXRGBYSPXRSOZ-UHFFFAOYSA-N cyclohexyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)C1CCCCC1 KBXRGBYSPXRSOZ-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003973 paint Substances 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
AMCBMCWLCDERHY-UHFFFAOYSA-N 1,3-dichloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC(Cl)=C21 AMCBMCWLCDERHY-UHFFFAOYSA-N 0.000 description 1
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
ZEOVXNVKXIPWMS-UHFFFAOYSA-N 2,2-dichloropropane Chemical compound CC(C)(Cl)Cl ZEOVXNVKXIPWMS-UHFFFAOYSA-N 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
125000006414 CCl Chemical group ClC* 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
150000003939 benzylamines Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000004566 building material Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
KFUSEUYYWQURPO-UPHRSURJSA-N cis-1,2-dichloroethene Chemical group Cl\C=C/Cl KFUSEUYYWQURPO-UPHRSURJSA-N 0.000 description 1
239000004567 concrete Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
125000005397 methacrylic acid ester group Chemical group 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
LEBUWIZXFLKBIY-UHFFFAOYSA-N n,n-ditert-butylcyclohexanamine Chemical compound CC(C)(C)N(C(C)(C)C)C1CCCCC1 LEBUWIZXFLKBIY-UHFFFAOYSA-N 0.000 description 1
GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
SMBYUOXUISCLCF-UHFFFAOYSA-N n-ethyl-n-methylpropan-1-amine Chemical compound CCCN(C)CC SMBYUOXUISCLCF-UHFFFAOYSA-N 0.000 description 1
IYRHAQYBWOQDPW-UHFFFAOYSA-N n-prop-1-enylpropan-1-amine Chemical class CCCNC=CC IYRHAQYBWOQDPW-UHFFFAOYSA-N 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
DUXCOTKQMWMAPC-UHFFFAOYSA-N n-tert-butyl-n-ethenylcarbamoyl chloride Chemical compound CC(C)(C)N(C=C)C(Cl)=O DUXCOTKQMWMAPC-UHFFFAOYSA-N 0.000 description 1
RPVBCVQKDPOMII-UHFFFAOYSA-N n-tert-butylethanimine Chemical compound CC=NC(C)(C)C RPVBCVQKDPOMII-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004575 stone Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH42077A 1976-01-16 1977-01-13 CH626055A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19762601542 DE2601542A1 (de)	1976-01-16	1976-01-16	Verfahren zur herstellung von n-vinyl-n-alkyl-carbamidsaeurechloriden

Publications (1)

Publication Number	Publication Date
CH626055A5 true CH626055A5 (fr)	1981-10-30

Family

ID=5967608

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH42077A CH626055A5 (fr)	1976-01-16	1977-01-13

Country Status (12)

Country	Link
US (1)	US4137261A (fr)
JP (1)	JPS5287120A (fr)
BE (1)	BE850112A (fr)
CH (1)	CH626055A5 (fr)
DD (1)	DD128906A5 (fr)
DE (1)	DE2601542A1 (fr)
FR (1)	FR2338255A1 (fr)
GB (1)	GB1566527A (fr)
HU (1)	HU175699B (fr)
IL (1)	IL51152A (fr)
IT (1)	IT1065437B (fr)
NL (1)	NL7700337A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2830969A1 (de) *	1978-07-14	1980-01-31	Basf Ag	Neue alpha -halogenalkylcarbamidsaeurehalogenide und verfahren zur herstellung von alpha -halogenalkylcarbamidsaeurehalogeniden

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4038311A (en) *	1969-01-14	1977-07-26	Basf Aktiengesellschaft	Production of n-(1-alkenyl)-carbamyl chlorides
DE2054660C3 (de) *	1970-11-06	1980-08-21	Basf Ag, 6700 Ludwigshafen	N-Methyl-N- a -methoxyvinylcarbamidsäurechlorid sowie ein Verfahren zur Herstellung von N-( 1-Alken-IyI)carbamidsäurechloriden
CH547779A (de) *	1971-02-16	1974-04-11	Ciba Geigy Ag	N,n-disubstituierte carbaminsaeurehalogenide.
DE2146069A1 (de)	1971-09-15	1973-03-22	Bayer Ag	Verfahren zur herstellung von phosgenierungsprodukten schiff'scher basen
US4001318A (en) *	1972-11-22	1977-01-04	Bayer Aktiengesellschaft	Preparation of n-chloroformyl-carbamic acid amides and esters

1976
- 1976-01-16 DE DE19762601542 patent/DE2601542A1/de not_active Withdrawn
- 1976-12-21 IT IT30708/76A patent/IT1065437B/it active
- 1976-12-23 IL IL51152A patent/IL51152A/xx unknown
- 1976-12-27 US US05/754,598 patent/US4137261A/en not_active Expired - Lifetime
1977
- 1977-01-05 BE BE173859A patent/BE850112A/fr not_active IP Right Cessation
- 1977-01-11 FR FR7700567A patent/FR2338255A1/fr active Granted
- 1977-01-13 NL NL7700337A patent/NL7700337A/xx not_active Application Discontinuation
- 1977-01-13 CH CH42077A patent/CH626055A5/de not_active IP Right Cessation
- 1977-01-13 JP JP200877A patent/JPS5287120A/ja active Pending
- 1977-01-14 DD DD7700196935A patent/DD128906A5/xx unknown
- 1977-01-14 GB GB1463/77A patent/GB1566527A/en not_active Expired
- 1977-01-14 HU HU77BA3497A patent/HU175699B/hu unknown

Also Published As

Publication number	Publication date
FR2338255B1 (fr)	1981-10-23
IL51152A (en)	1979-05-31
NL7700337A (nl)	1977-07-19
HU175699B (hu)	1980-10-28
IT1065437B (it)	1985-02-25
US4137261A (en)	1979-01-30
BE850112A (fr)	1977-07-05
GB1566527A (en)	1980-04-30
FR2338255A1 (fr)	1977-08-12
IL51152A0 (en)	1977-02-28
JPS5287120A (en)	1977-07-20
DD128906A5 (de)	1977-12-14
DE2601542A1 (de)	1977-07-21

Legal Events

Date	Code	Title	Description
1988-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE1215365B (de)	1966-04-28	Verfahren zur Herstellung von hoehermolekularen Polyisocyanaten mit Biuret-Struktur
CH626055A5 (fr)	1981-10-30
DE2548508C2 (fr)	1988-07-14
DE69604513T2 (de)	2000-02-03	Verfahren zur Herstellung substituierter Carbodiimide
DE2824648C2 (de)	1982-06-24	Verfahren zur Herstellung von Isocyanaten
DE2258453C2 (de)	1982-12-02	Verfahren zur Gewinnung reiner sekundärer Ammonium-N,N-disubstituierter-thiolcarbamate
EP0025906B1 (fr)	1982-10-27	Isocyanates monohalogénés en position 1; procédé pour la préparation de mélanges d'isocyanates 1-monohalogénés avec des isocyanates insaturés en position 1,2
DE1770428A1 (de)	1972-03-09	Verfahren zur Herstellung von N-Carboxyanhydriden von Aminosaeuren
DE2249459A1 (de)	1973-04-19	Verfahren zur herstellung von isocyanaten
DE2625539C2 (de)	1982-11-04	Cyclische Ester des 3,4-Dihydroxy-2,5-diphenyl-thiophen-1,1-dioxids und des 3,4-Dihydroxy-2,5-diphenyl-cyclopentadienons und deren Verwendung
DE2856384B2 (de)	1980-10-23	Quartäre Ammoniumgruppen enthaltende Acrylyl- bzw. Methacrylylharnstoffe und Verfahren zu ihrer Herstellung
DE2102809A1 (de)	1972-05-31	Mehrphasen- Aminierungsverfahren
DE2054660C3 (de)	1980-08-21	N-Methyl-N- a -methoxyvinylcarbamidsäurechlorid sowie ein Verfahren zur Herstellung von N-( 1-Alken-IyI)carbamidsäurechloriden
EP0265668B1 (fr)	1991-01-09	Procédé por la préparation d'un isocyanate
DE2304589A1 (de)	1974-08-01	3-alkyloxazolinone-(2)
DE2653150A1 (de)	1977-06-02	Verfahren zur herstellung von n-(3-chlorphenyl)-carbaminsaeure-4'- chlorbutin-2'-ylester
DE2856216A1 (de)	1979-06-28	Verfahren zur herstellung von aethern
DE2700680A1 (de)	1978-07-20	Verfahren zur herstellung von n-substituierten morpholiniumsalzen
DE2360248C3 (de)	1982-04-01	Verfahren zur Herstellung von Estern von Thiolcarbaminsäuren
DE1272286C2 (de)	1969-03-06	Verfahren zur Herstellung von N-substituierten aliphatischen Thiocarbonsaeureamiden
DE2438725A1 (de)	1976-02-26	Piperazinderivate
DE1081453B (de)	1960-05-12	Verfahren zur Herstellung von selektiv herbizid wirksamen Harnstoffderivaten
DE1568203C (de)	1971-11-18	Verfahren zur Herstellung von N-Phenyl-N-methyl-N-(2.3-dibrom-l-methylallyl)-harnstoffen
EP0017205A1 (fr)	1980-10-15	Procédé de préparation de N-aryl-oxazolidine-2,4-diones
DE2043235C3 (de)	1979-06-07	Verfahren zur Herstellung von aChloralkylcarbamidsäurechloriden