DE2264932C3 - Verfahren zur Herstellung von 1,4-Dicyanbutenen - Google Patents
Verfahren zur Herstellung von 1,4-DicyanbutenenInfo
- Publication number
- DE2264932C3 DE2264932C3 DE2264932A DE2264932A DE2264932C3 DE 2264932 C3 DE2264932 C3 DE 2264932C3 DE 2264932 A DE2264932 A DE 2264932A DE 2264932 A DE2264932 A DE 2264932A DE 2264932 C3 DE2264932 C3 DE 2264932C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- mixture
- cyanide
- adiponitrile
- mmol
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 23
- 230000008569 process Effects 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 4
- ZQOHAQBXINVHHC-UHFFFAOYSA-N hex-2-enedinitrile Chemical class N#CCCC=CC#N ZQOHAQBXINVHHC-UHFFFAOYSA-N 0.000 title description 16
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 41
- 239000003054 catalyst Substances 0.000 claims description 31
- NGCJVMZXRCLPRQ-UHFFFAOYSA-N 2-methylidenepentanedinitrile Chemical compound N#CC(=C)CCC#N NGCJVMZXRCLPRQ-UHFFFAOYSA-N 0.000 claims description 22
- VSDGXRKPOJEXFE-UHFFFAOYSA-N butane-1,2,4-tricarbonitrile Chemical compound N#CCCC(C#N)CC#N VSDGXRKPOJEXFE-UHFFFAOYSA-N 0.000 claims description 13
- 239000002243 precursor Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000000203 mixture Substances 0.000 description 20
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 17
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 15
- 238000006317 isomerization reaction Methods 0.000 description 12
- -1 phosphonium cations Chemical class 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000006471 dimerization reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 238000001030 gas--liquid chromatography Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000003003 phosphines Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- BSVZXPLUMFUWHW-OWOJBTEDSA-N (e)-hex-3-enedinitrile Chemical compound N#CC\C=C\CC#N BSVZXPLUMFUWHW-OWOJBTEDSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- ZQOHAQBXINVHHC-HNQUOIGGSA-N (e)-hex-2-enedinitrile Chemical compound N#CCC\C=C\C#N ZQOHAQBXINVHHC-HNQUOIGGSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JKBPBRLDGFKIIA-UHFFFAOYSA-N 2-propylidenepropanedinitrile Chemical compound CCC=C(C#N)C#N JKBPBRLDGFKIIA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- JORQDGTZGKHEEO-UHFFFAOYSA-N lithium cyanide Chemical compound [Li+].N#[C-] JORQDGTZGKHEEO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910052716 thallium Inorganic materials 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 description 1
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 description 1
- 229940068372 acetyl salicylate Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- XTCPEYCUFMHXBI-UHFFFAOYSA-N cesium;cyanide Chemical compound [Cs+].N#[C-] XTCPEYCUFMHXBI-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QLQYLCRMTTXKHS-UHFFFAOYSA-N hexa-2,4-dienedinitrile Chemical compound N#CC=CC=CC#N QLQYLCRMTTXKHS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical class O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006578 reductive coupling reaction Methods 0.000 description 1
- 238000006456 reductive dimerization reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- OHUVHDUNQKJDKW-UHFFFAOYSA-N sodium;cyclopenta-1,3-diene Chemical compound [Na+].C=1C=C[CH-]C=1 OHUVHDUNQKJDKW-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- MPULMSAVZAPUQG-UHFFFAOYSA-N tri(cyclooctyl)phosphane Chemical compound C1CCCCCCC1P(C1CCCCCCC1)C1CCCCCCC1 MPULMSAVZAPUQG-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19898771A | 1971-11-15 | 1971-11-15 | |
| US28527272A | 1972-08-31 | 1972-08-31 | |
| US28527172A | 1972-08-31 | 1972-08-31 | |
| US28678472A | 1972-09-06 | 1972-09-06 | |
| US29811572A | 1972-10-16 | 1972-10-16 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2264932A1 DE2264932A1 (de) | 1975-06-26 |
| DE2264932B2 DE2264932B2 (de) | 1977-08-18 |
| DE2264932C3 true DE2264932C3 (de) | 1978-04-06 |
Family
ID=27539397
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2264932A Expired DE2264932C3 (de) | 1971-11-15 | 1972-11-15 | Verfahren zur Herstellung von 1,4-Dicyanbutenen |
| DE2256039A Expired DE2256039C3 (de) | 1971-11-15 | 1972-11-15 | Herstellung von 1,4-Dicyanbutenen |
| DE2265299A Expired DE2265299C3 (de) | 1971-11-15 | 1972-11-15 | Verfahren zur Herstellung von 1,4-Dicyanbutenen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2256039A Expired DE2256039C3 (de) | 1971-11-15 | 1972-11-15 | Herstellung von 1,4-Dicyanbutenen |
| DE2265299A Expired DE2265299C3 (de) | 1971-11-15 | 1972-11-15 | Verfahren zur Herstellung von 1,4-Dicyanbutenen |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS4861423A (https=) |
| AR (2) | AR199886A1 (https=) |
| AU (1) | AU471821B2 (https=) |
| BE (1) | BE791339A (https=) |
| CA (1) | CA1001657A (https=) |
| CH (2) | CH551951A (https=) |
| DD (2) | DD109863A5 (https=) |
| DE (3) | DE2264932C3 (https=) |
| DK (3) | DK132320C (https=) |
| EG (1) | EG10867A (https=) |
| FR (1) | FR2161597A5 (https=) |
| IE (1) | IE37078B1 (https=) |
| IL (3) | IL40830A (https=) |
| IT (1) | IT986887B (https=) |
| NL (2) | NL162633C (https=) |
| NO (1) | NO137938C (https=) |
| RO (2) | RO72799A (https=) |
| SE (1) | SE405353B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080374A (en) * | 1977-02-23 | 1978-03-21 | E. I. Du Pont De Nemours And Company | Product recovery |
-
0
- BE BE791339D patent/BE791339A/xx not_active IP Right Cessation
-
1972
- 1972-11-12 EG EG465/72A patent/EG10867A/xx active
- 1972-11-14 FR FR7240275A patent/FR2161597A5/fr not_active Expired
- 1972-11-14 CA CA156,329A patent/CA1001657A/en not_active Expired
- 1972-11-14 IE IE1566/72A patent/IE37078B1/xx unknown
- 1972-11-14 CH CH1655672A patent/CH551951A/fr not_active IP Right Cessation
- 1972-11-14 DK DK565072A patent/DK132320C/da active
- 1972-11-14 NL NL7215387.A patent/NL162633C/xx not_active IP Right Cessation
- 1972-11-14 IL IL40830A patent/IL40830A/en unknown
- 1972-11-14 AR AR245114A patent/AR199886A1/es active
- 1972-11-14 AU AU48833/72A patent/AU471821B2/en not_active Expired
- 1972-11-14 NO NO724134A patent/NO137938C/no unknown
- 1972-11-14 DD DD176199*A patent/DD109863A5/xx unknown
- 1972-11-14 IL IL48000A patent/IL48000A/en unknown
- 1972-11-14 DD DD173192*A patent/DD106367A5/xx unknown
- 1972-11-14 CH CH373874A patent/CH553165A/fr not_active IP Right Cessation
- 1972-11-15 RO RO7272824A patent/RO72799A/ro unknown
- 1972-11-15 DE DE2264932A patent/DE2264932C3/de not_active Expired
- 1972-11-15 DE DE2256039A patent/DE2256039C3/de not_active Expired
- 1972-11-15 DE DE2265299A patent/DE2265299C3/de not_active Expired
- 1972-11-15 IT IT54031/72A patent/IT986887B/it active
- 1972-11-15 RO RO7287241A patent/RO72552A/ro unknown
- 1972-11-15 JP JP47114655A patent/JPS4861423A/ja active Pending
-
1973
- 1973-10-31 AR AR250788A patent/AR198539A1/es active
-
1974
- 1974-11-13 DK DK590074A patent/DK590074A/da unknown
- 1974-11-13 DK DK589974A patent/DK589974A/da unknown
-
1975
- 1975-05-22 SE SE7505822A patent/SE405353B/xx unknown
- 1975-08-27 IL IL48000A patent/IL48000A0/xx unknown
-
1979
- 1979-09-24 NL NL7907083A patent/NL7907083A/nl not_active Application Discontinuation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2502247A1 (de) | Verfahren zur herstellung von n-(tert. aminoalkyl)acrylamiden | |
| EP0957075A1 (de) | Verbessertes Verfahren zur Herstellung von 3,5,5-Trimethylcyclohexa-3-en-1-on (Beta-Isophoron) durch Isomerisierung von 3,5,5-Trimethylcyclohexa-2-en-1-on (Alpha-Isophoron) (II) | |
| DE2431378C2 (de) | Verfahren zur Herstellung von 4-Methyl-1-penten | |
| DE2264932C3 (de) | Verfahren zur Herstellung von 1,4-Dicyanbutenen | |
| DE2811722C2 (https=) | ||
| DE3504732A1 (de) | Verfahren zur herstellung eines gemisches von phosphornitridchlorid-oligomeren | |
| DE69604327T2 (de) | Herstellung von polyalkylierten Cyclopentadienen aus Isobornylcarboxylaten | |
| DE2747999C3 (de) | Verfahren zur Herstellung von Dimethylformamid | |
| DE2028329C3 (de) | Kontinuierliches Verfahren zur Herstellung von Cyclododecatrien-(13,9) aus Butadien mittels Alkylaluminiumsesquichlorid-Titanhalogenid-Mischkatalysatoren | |
| DE3509911C2 (de) | Verfahren zur Herstellung von Trifluoressigsäure aus Trichlortrifluorethan | |
| DE2329545A1 (de) | Verfahren zur herstellung von 2-vinyloxazolinen | |
| DE2211231C3 (de) | Verfahren zur Herstellung von Jodwasserstoff und/oder Alkyljodiden | |
| DE2921551A1 (de) | Verfahren zur herstellung von dimethylformamid | |
| DE2102263A1 (de) | Verfahren zur kontinuierlichen Herstellung ungesättigter Nitrile | |
| DE954238C (de) | Verfahren zur Herstellung von Fluoralkanen durch chemische Reduktion von Dichlordifluormethan | |
| DE1643348C3 (de) | Verfahren zur Herstellung von Phenylestern aus Benzol | |
| DE2050562A1 (de) | Verfahren zur Herstellung von Dichloracetylchlorid | |
| DE1916533C3 (de) | Verfahren zur Herstellung von Methyl-2,5-hexadienoat | |
| DE848806C (de) | Verfahren zur Herstellung von ª-Oxypropionsaeurelacton | |
| DE1720519B2 (de) | Verfahren zur herstellung von polyestern | |
| DE1805989A1 (de) | Verfahren zur Herstellung von N-Alkylpyrrolen | |
| DE1643920A1 (de) | Verfahren zur Herstellung von Cyclohexadienen-(1,4) | |
| DE2734368A1 (de) | Verfahren zur herstellung von 3,5-dichloranilin | |
| DE1793446A1 (de) | Verfahren zur Herstellung von Dichloracetylchlorid | |
| DE2006456A1 (en) | O-alkylisoueas and salts from cyanamide - and alkanols |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HALCON RESEARCH AND DEVELOPMENT CORP., 10016 NEW Y |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |