CS208454B2 - Method of producing the halogenides alpha-halogenalkylcarbon acid - Google Patents
Method of producing the halogenides alpha-halogenalkylcarbon acid Download PDFInfo
- Publication number
- CS208454B2 CS208454B2 CS794924A CS492479A CS208454B2 CS 208454 B2 CS208454 B2 CS 208454B2 CS 794924 A CS794924 A CS 794924A CS 492479 A CS492479 A CS 492479A CS 208454 B2 CS208454 B2 CS 208454B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- alpha
- bromo
- bromide
- chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 239000002253 acid Substances 0.000 title description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000004820 halides Chemical class 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- -1 alkenyl isocyanates Chemical class 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000007858 starting material Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 description 5
- 239000012433 hydrogen halide Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- RDSCMNBQKJQNEU-UHFFFAOYSA-N n-(1-bromo-2-phenylpropyl)carbamoyl bromide Chemical compound BrC(=O)NC(Br)C(C)C1=CC=CC=C1 RDSCMNBQKJQNEU-UHFFFAOYSA-N 0.000 description 2
- FHJVZGZGORHHPA-UHFFFAOYSA-N n-(1-chloro-3-methylbutyl)carbamoyl chloride Chemical class CC(C)CC(Cl)NC(Cl)=O FHJVZGZGORHHPA-UHFFFAOYSA-N 0.000 description 2
- WBCGUIQLJNJHMT-UHFFFAOYSA-N n-(1-chlorodecyl)carbamoyl chloride Chemical compound CCCCCCCCCC(Cl)NC(Cl)=O WBCGUIQLJNJHMT-UHFFFAOYSA-N 0.000 description 2
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- YPXJOWQHBUFHBK-UHFFFAOYSA-N 1,1-dibromodec-1-ene Chemical compound CCCCCCCCC=C(Br)Br YPXJOWQHBUFHBK-UHFFFAOYSA-N 0.000 description 1
- SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-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
- MOXLHAPKZWTHEX-UHFFFAOYSA-N 1,2-dichloronaphthalene Chemical compound C1=CC=CC2=C(Cl)C(Cl)=CC=C21 MOXLHAPKZWTHEX-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-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
- 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
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-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
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- DCOVNGPBTDQOGF-UHFFFAOYSA-N 1-isocyanato-3-methylbut-1-ene Chemical compound CC(C)C=CN=C=O DCOVNGPBTDQOGF-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- XTDQDBVBDLYELW-UHFFFAOYSA-N 2,2,3-trimethylpentane Chemical compound CCC(C)C(C)(C)C XTDQDBVBDLYELW-UHFFFAOYSA-N 0.000 description 1
- OKVWYBALHQFVFP-UHFFFAOYSA-N 2,3,3-trimethylpentane Chemical compound CCC(C)(C)C(C)C OKVWYBALHQFVFP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KGSXLXDXLSAZCL-UHFFFAOYSA-N IC(CCC)NC(=O)I Chemical compound IC(CCC)NC(=O)I KGSXLXDXLSAZCL-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- YYPFLFDDJFLUIX-UHFFFAOYSA-N isocyanatomethylidenecyclohexane Chemical compound O=C=NC=C1CCCCC1 YYPFLFDDJFLUIX-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HMRROBKAACRWBP-UHFFFAOYSA-N methyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=CC2=C1 HMRROBKAACRWBP-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YYDJFUFTIXZTOW-UHFFFAOYSA-N n-(1-bromo-2-ethylhexyl)carbamoyl bromide Chemical compound CCCCC(CC)C(Br)NC(Br)=O YYDJFUFTIXZTOW-UHFFFAOYSA-N 0.000 description 1
- LZODMWSAUMRDGN-UHFFFAOYSA-N n-(1-bromo-2-ethylpentyl)carbamoyl bromide Chemical compound CCCC(CC)C(Br)NC(Br)=O LZODMWSAUMRDGN-UHFFFAOYSA-N 0.000 description 1
- PTVKUFKHHAYBAT-UHFFFAOYSA-N n-(1-bromo-2-methylbutyl)carbamoyl bromide Chemical compound CCC(C)C(Br)NC(Br)=O PTVKUFKHHAYBAT-UHFFFAOYSA-N 0.000 description 1
- CETVGARGCPAVMC-UHFFFAOYSA-N n-(1-bromo-2-methyldecyl)carbamoyl bromide Chemical compound CCCCCCCCC(C)C(Br)NC(Br)=O CETVGARGCPAVMC-UHFFFAOYSA-N 0.000 description 1
- OJGWXKACVYRUHU-UHFFFAOYSA-N n-(1-bromo-2-methylhexyl)carbamoyl bromide Chemical compound CCCCC(C)C(Br)NC(Br)=O OJGWXKACVYRUHU-UHFFFAOYSA-N 0.000 description 1
- IMQQCWUFGGIECL-UHFFFAOYSA-N n-(1-bromo-2-methylnonyl)carbamoyl bromide Chemical compound CCCCCCCC(C)C(Br)NC(Br)=O IMQQCWUFGGIECL-UHFFFAOYSA-N 0.000 description 1
- CIXUEKUGDNITFY-UHFFFAOYSA-N n-(1-bromo-2-methyloctyl)carbamoyl bromide Chemical compound CCCCCCC(C)C(Br)NC(Br)=O CIXUEKUGDNITFY-UHFFFAOYSA-N 0.000 description 1
- VHZOPDDYANHJER-UHFFFAOYSA-N n-(1-bromo-2-phenylethyl)carbamoyl bromide Chemical compound BrC(=O)NC(Br)CC1=CC=CC=C1 VHZOPDDYANHJER-UHFFFAOYSA-N 0.000 description 1
- IAZORTLAVLJYMY-UHFFFAOYSA-N n-(1-bromo-3-methylbutyl)carbamoyl bromide Chemical compound CC(C)CC(Br)NC(Br)=O IAZORTLAVLJYMY-UHFFFAOYSA-N 0.000 description 1
- TYOXXLZALDOCBJ-UHFFFAOYSA-N n-(1-bromo-3-methylhexyl)carbamoyl bromide Chemical class CCCC(C)CC(Br)NC(Br)=O TYOXXLZALDOCBJ-UHFFFAOYSA-N 0.000 description 1
- ZTJZCHBMLBHDRF-UHFFFAOYSA-N n-(1-bromo-3-methylpentyl)carbamoyl bromide Chemical compound CCC(C)CC(Br)NC(Br)=O ZTJZCHBMLBHDRF-UHFFFAOYSA-N 0.000 description 1
- MFAZRLFTQGIINX-UHFFFAOYSA-N n-(1-bromobutyl)carbamoyl bromide Chemical compound CCCC(Br)NC(Br)=O MFAZRLFTQGIINX-UHFFFAOYSA-N 0.000 description 1
- UUPLUTFIPNAJPB-UHFFFAOYSA-N n-(1-bromodecyl)carbamoyl bromide Chemical compound CCCCCCCCCC(Br)NC(Br)=O UUPLUTFIPNAJPB-UHFFFAOYSA-N 0.000 description 1
- BWSGHZMZUXYIHN-UHFFFAOYSA-N n-(1-bromoheptyl)carbamoyl bromide Chemical compound CCCCCCC(Br)NC(Br)=O BWSGHZMZUXYIHN-UHFFFAOYSA-N 0.000 description 1
- QSNYWRMNNWLDOE-UHFFFAOYSA-N n-(1-bromohexyl)carbamoyl bromide Chemical compound CCCCCC(Br)NC(Br)=O QSNYWRMNNWLDOE-UHFFFAOYSA-N 0.000 description 1
- JOUQNTBVALWKQG-UHFFFAOYSA-N n-(1-bromononyl)carbamoyl bromide Chemical compound CCCCCCCCC(Br)NC(Br)=O JOUQNTBVALWKQG-UHFFFAOYSA-N 0.000 description 1
- JWVJHFSZUVNPBZ-UHFFFAOYSA-N n-(1-bromooctyl)carbamoyl bromide Chemical compound CCCCCCCC(Br)NC(Br)=O JWVJHFSZUVNPBZ-UHFFFAOYSA-N 0.000 description 1
- PXIXBFXHQIMFKT-UHFFFAOYSA-N n-(1-bromopentyl)carbamoyl bromide Chemical compound CCCCC(Br)NC(Br)=O PXIXBFXHQIMFKT-UHFFFAOYSA-N 0.000 description 1
- YNTSCWJOORTNGX-UHFFFAOYSA-N n-(1-chloro-2-ethylhexyl)carbamoyl chloride Chemical compound CCCCC(CC)C(Cl)NC(Cl)=O YNTSCWJOORTNGX-UHFFFAOYSA-N 0.000 description 1
- FPPBZESFSKDKBY-UHFFFAOYSA-N n-(1-chloro-2-methylbutyl)carbamoyl chloride Chemical compound CCC(C)C(Cl)NC(Cl)=O FPPBZESFSKDKBY-UHFFFAOYSA-N 0.000 description 1
- VWTGNJCEEZEUFB-UHFFFAOYSA-N n-(1-chloro-2-methyldecyl)carbamoyl chloride Chemical compound CCCCCCCCC(C)C(Cl)NC(Cl)=O VWTGNJCEEZEUFB-UHFFFAOYSA-N 0.000 description 1
- DLQKBSNFAGOQIL-UHFFFAOYSA-N n-(1-chloro-2-methylheptyl)carbamoyl chloride Chemical compound CCCCCC(C)C(Cl)NC(Cl)=O DLQKBSNFAGOQIL-UHFFFAOYSA-N 0.000 description 1
- JCSFBNLKNLJOPI-UHFFFAOYSA-N n-(1-chloro-2-methylhexyl)carbamoyl chloride Chemical compound CCCCC(C)C(Cl)NC(Cl)=O JCSFBNLKNLJOPI-UHFFFAOYSA-N 0.000 description 1
- DSKZYXUXGHWSOO-UHFFFAOYSA-N n-(1-chloro-2-methylnonyl)carbamoyl chloride Chemical compound CCCCCCCC(C)C(Cl)NC(Cl)=O DSKZYXUXGHWSOO-UHFFFAOYSA-N 0.000 description 1
- JXPMVPDMHNYVLB-UHFFFAOYSA-N n-(1-chloro-2-methyloctyl)carbamoyl chloride Chemical compound CCCCCCC(C)C(Cl)NC(Cl)=O JXPMVPDMHNYVLB-UHFFFAOYSA-N 0.000 description 1
- QOVGMHUALGUSOI-UHFFFAOYSA-N n-(1-chloro-2-methylpropyl)carbamoyl chloride Chemical compound CC(C)C(Cl)NC(Cl)=O QOVGMHUALGUSOI-UHFFFAOYSA-N 0.000 description 1
- SSMLUIVXCCNINS-UHFFFAOYSA-N n-(1-chloro-2-phenylethyl)carbamoyl chloride Chemical compound ClC(=O)NC(Cl)CC1=CC=CC=C1 SSMLUIVXCCNINS-UHFFFAOYSA-N 0.000 description 1
- BABRJJZRISTEAO-UHFFFAOYSA-N n-(1-chloro-3-methylhexyl)carbamoyl chloride Chemical compound CCCC(C)CC(Cl)NC(Cl)=O BABRJJZRISTEAO-UHFFFAOYSA-N 0.000 description 1
- CIUVOSOGKGBKED-UHFFFAOYSA-N n-(1-chloro-3-methylpentyl)carbamoyl chloride Chemical compound CCC(C)CC(Cl)NC(Cl)=O CIUVOSOGKGBKED-UHFFFAOYSA-N 0.000 description 1
- GHZRQDNXDBTQAQ-UHFFFAOYSA-N n-(1-chloroheptyl)carbamoyl chloride Chemical compound CCCCCCC(Cl)NC(Cl)=O GHZRQDNXDBTQAQ-UHFFFAOYSA-N 0.000 description 1
- COFMKXZDRAFNLM-UHFFFAOYSA-N n-(1-chlorooctyl)carbamoyl chloride Chemical compound CCCCCCCC(Cl)NC(Cl)=O COFMKXZDRAFNLM-UHFFFAOYSA-N 0.000 description 1
- XYOUAACTCDDOMH-UHFFFAOYSA-N n-(2-bromobutan-2-yl)carbamoyl bromide Chemical compound CCC(C)(Br)NC(Br)=O XYOUAACTCDDOMH-UHFFFAOYSA-N 0.000 description 1
- WTTDAMAJBINSSA-UHFFFAOYSA-N n-(3-bromohexan-3-yl)carbamoyl bromide Chemical class CCCC(Br)(CC)NC(Br)=O WTTDAMAJBINSSA-UHFFFAOYSA-N 0.000 description 1
- OPUIGIPMFPSMJV-UHFFFAOYSA-N n-(3-chlorohexan-3-yl)carbamoyl chloride Chemical compound CCCC(Cl)(CC)NC(Cl)=O OPUIGIPMFPSMJV-UHFFFAOYSA-N 0.000 description 1
- BYGDQZARVAGMRF-UHFFFAOYSA-N n-(chloromethyl)-n-cyclohexylcarbamoyl chloride Chemical compound ClCN(C(Cl)=O)C1CCCCC1 BYGDQZARVAGMRF-UHFFFAOYSA-N 0.000 description 1
- NLOKUTFTNLUHJD-UHFFFAOYSA-N n-[bromo(cyclohexyl)methyl]carbamoyl bromide Chemical compound BrC(=O)NC(Br)C1CCCCC1 NLOKUTFTNLUHJD-UHFFFAOYSA-N 0.000 description 1
- STIPXQURPWSSDO-UHFFFAOYSA-N n-[chloro(cyclohexyl)methyl]carbamoyl chloride Chemical compound ClC(=O)NC(Cl)C1CCCCC1 STIPXQURPWSSDO-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/04—Carbamic acid halides
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782830969 DE2830969A1 (de) | 1978-07-14 | 1978-07-14 | Neue alpha -halogenalkylcarbamidsaeurehalogenide und verfahren zur herstellung von alpha -halogenalkylcarbamidsaeurehalogeniden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208454B2 true CS208454B2 (en) | 1981-09-15 |
Family
ID=6044375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS794924A CS208454B2 (en) | 1978-07-14 | 1979-07-13 | Method of producing the halogenides alpha-halogenalkylcarbon acid |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4297300A (pl) |
| EP (1) | EP0007498A1 (pl) |
| JP (1) | JPS5543067A (pl) |
| AU (1) | AU4886479A (pl) |
| CA (1) | CA1132609A (pl) |
| CS (1) | CS208454B2 (pl) |
| DD (1) | DD145100A5 (pl) |
| DE (1) | DE2830969A1 (pl) |
| HU (1) | HU179117B (pl) |
| PL (1) | PL116342B2 (pl) |
| ZA (1) | ZA793544B (pl) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA763948A (en) | 1967-07-25 | Koenig Karl-Heinz | PRODUCTION OF .alpha.,.beta.-UNSATURATED ALIPHATIC ISOCYANATES AND CARBAMYL HALIDES | |
| CH425768A (de) * | 1961-05-26 | 1966-12-15 | Basf Ag | Verfahren zur Herstellung von a,B-ungesättigten Isocyanaten und Carbamidsäurehalogeniden |
| DE2146069A1 (de) * | 1971-09-15 | 1973-03-22 | Bayer Ag | Verfahren zur herstellung von phosgenierungsprodukten schiff'scher basen |
| DE2601542A1 (de) * | 1976-01-16 | 1977-07-21 | Basf Ag | Verfahren zur herstellung von n-vinyl-n-alkyl-carbamidsaeurechloriden |
| IT1096870B (it) * | 1977-07-16 | 1985-08-26 | Basf Ag | Processo per la preparazione di alogenuri di acidi alfa-alogenoalchil-carbamici |
| DE2732284A1 (de) * | 1977-07-16 | 1979-02-01 | Basf Ag | Verfahren zur herstellung von alpha- halogenaethylcarbamidsaeurehalogeniden |
-
1978
- 1978-07-14 DE DE19782830969 patent/DE2830969A1/de active Pending
-
1979
- 1979-06-25 US US06/051,744 patent/US4297300A/en not_active Expired - Lifetime
- 1979-06-28 CA CA330,976A patent/CA1132609A/en not_active Expired
- 1979-07-04 JP JP8407379A patent/JPS5543067A/ja active Pending
- 1979-07-09 EP EP79102313A patent/EP0007498A1/de not_active Withdrawn
- 1979-07-11 AU AU48864/79A patent/AU4886479A/en not_active Abandoned
- 1979-07-12 PL PL1979217050A patent/PL116342B2/pl unknown
- 1979-07-12 DD DD79214299A patent/DD145100A5/de unknown
- 1979-07-13 HU HU79BA3814A patent/HU179117B/hu unknown
- 1979-07-13 CS CS794924A patent/CS208454B2/cs unknown
- 1979-07-13 ZA ZA00793544A patent/ZA793544B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1132609A (en) | 1982-09-28 |
| PL217050A2 (pl) | 1980-08-11 |
| PL116342B2 (en) | 1981-06-30 |
| DD145100A5 (de) | 1980-11-19 |
| JPS5543067A (en) | 1980-03-26 |
| AU4886479A (en) | 1980-01-17 |
| DE2830969A1 (de) | 1980-01-31 |
| HU179117B (en) | 1982-08-28 |
| EP0007498A1 (de) | 1980-02-06 |
| US4297300A (en) | 1981-10-27 |
| ZA793544B (en) | 1980-08-27 |
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