BE866404A - Procede pour la synthese de dinitriles, produits ainsi obtenus et leurs derives - Google Patents

Procede pour la synthese de dinitriles, produits ainsi obtenus et leurs derives

Info

Publication number: BE866404A
Authority: BE; Belgium
Prior art keywords: emi; formula; strong base; diamines; reaction
Prior art date: 1977-04-26

Application number

BE187128A

Other languages

English (en)

French (fr)

Original Assignee

Anic Spa

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.)

1977-04-26

Filing date

1978-04-26

Publication date

1978-10-26

1978-04-26 Application filed by Anic Spa filed Critical Anic Spa

1978-10-26 Publication of BE866404A publication Critical patent/BE866404A/fr

Links

238000000034 method Methods 0.000 title claims description 28
230000008569 process Effects 0.000 title claims description 17
230000015572 biosynthetic process Effects 0.000 title description 18
238000003786 synthesis reaction Methods 0.000 title description 14
150000002825 nitriles Chemical class 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 23
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
239000002904 solvent Substances 0.000 claims description 18
239000002585 base Substances 0.000 claims description 16
150000004985 diamines Chemical class 0.000 claims description 16
229920006395 saturated elastomer Polymers 0.000 claims description 14
239000004952 Polyamide Substances 0.000 claims description 13
229920002647 polyamide Polymers 0.000 claims description 13
-1 aromatic dicarboxylic acids Chemical class 0.000 claims description 11
229910021529 ammonia Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
HAKWQVNMQOZCMB-UHFFFAOYSA-N 1-(1-cyano-2-methylpropan-2-yl)cyclohexane-1-carbonitrile Chemical compound N#CCC(C)(C)C1(C#N)CCCCC1 HAKWQVNMQOZCMB-UHFFFAOYSA-N 0.000 claims description 2
VYQJJFMIRPSJEV-UHFFFAOYSA-N 2-ethyl-3,3-dimethylpentanedinitrile Chemical compound CCC(C#N)C(C)(C)CC#N VYQJJFMIRPSJEV-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
159000000032 aromatic acids Chemical class 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
150000003841 chloride salts Chemical class 0.000 claims 3
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 2
239000003513 alkali Substances 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
239000007810 chemical reaction solvent Substances 0.000 claims 1
150000004678 hydrides Chemical class 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
229920000642 polymer Polymers 0.000 description 8
239000000126 substance Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 6
239000000203 mixture Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000010941 cobalt Substances 0.000 description 4
229910017052 cobalt Inorganic materials 0.000 description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
238000006068 polycondensation reaction Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
125000000217 alkyl group Chemical group 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 3
238000002076 thermal analysis method Methods 0.000 description 3
ACRWYXSKEHUQDB-UHFFFAOYSA-N 3-phenylpropionitrile Chemical compound N#CCCC1=CC=CC=C1 ACRWYXSKEHUQDB-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
229920006020 amorphous polyamide Polymers 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
HLCSDJLATUNSSI-JXMROGBWSA-N (2e)-3,7-dimethylocta-2,6-dienenitrile Chemical compound CC(C)=CCC\C(C)=C\C#N HLCSDJLATUNSSI-JXMROGBWSA-N 0.000 description 1
QMICLBLOVTXNIY-ZZXKWVIFSA-N (e)-3-(3-methylphenyl)prop-2-enenitrile Chemical compound CC1=CC=CC(\C=C\C#N)=C1 QMICLBLOVTXNIY-ZZXKWVIFSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical class OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 description 1
WBIGZXWZARXXBI-UHFFFAOYSA-N 2,2-dimethylpentane-1,1-diamine Chemical compound CCCC(C)(C)C(N)N WBIGZXWZARXXBI-UHFFFAOYSA-N 0.000 description 1
HWWOHMMQTVKWAP-UHFFFAOYSA-N 2,3,3-trimethylpentanedinitrile Chemical compound N#CC(C)C(C)(C)CC#N HWWOHMMQTVKWAP-UHFFFAOYSA-N 0.000 description 1
BJWNKFVWHPJKQZ-UHFFFAOYSA-N 2,3-dimethylbut-2-enenitrile Chemical compound CC(C)=C(C)C#N BJWNKFVWHPJKQZ-UHFFFAOYSA-N 0.000 description 1
VGSAPFZMBQTQGA-UHFFFAOYSA-N 2-(2-methylcyclopentyl)acetonitrile Chemical compound CC1CCCC1CC#N VGSAPFZMBQTQGA-UHFFFAOYSA-N 0.000 description 1
MXFPACNADGXIQY-UHFFFAOYSA-N 2-cyclohexylacetonitrile Chemical compound N#CCC1CCCCC1 MXFPACNADGXIQY-UHFFFAOYSA-N 0.000 description 1
JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 1
CGCIFJIHFPIUEC-UHFFFAOYSA-N 2-ethyl-3,3-dimethylpentane-1,5-diamine Chemical compound CCC(CN)C(C)(C)CCN CGCIFJIHFPIUEC-UHFFFAOYSA-N 0.000 description 1
UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 description 1
RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
XIQMVSHUFUZTST-UHFFFAOYSA-N 3-butoxy-3-oxo-2-phenylpropanoic acid Chemical compound CCCCOC(=O)C(C(O)=O)C1=CC=CC=C1 XIQMVSHUFUZTST-UHFFFAOYSA-N 0.000 description 1
WDXJOKBPTSUUNJ-UHFFFAOYSA-N 3-ethylpent-2-enenitrile Chemical compound CCC(CC)=CC#N WDXJOKBPTSUUNJ-UHFFFAOYSA-N 0.000 description 1
AUGKLUNRHYPDAM-UHFFFAOYSA-N 3-methylbut-2-enenitrile Chemical compound CC(C)=CC#N AUGKLUNRHYPDAM-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
239000004953 Aliphatic polyamide Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
238000012696 Interfacial polycondensation Methods 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 1
RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229920003231 aliphatic polyamide Polymers 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
238000000137 annealing Methods 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
GTMWGXABXQTZRJ-UHFFFAOYSA-N cyclohexene-1-carbonitrile Chemical compound N#CC1=CCCCC1 GTMWGXABXQTZRJ-UHFFFAOYSA-N 0.000 description 1
SVPZJHKVRMRREG-UHFFFAOYSA-N cyclopentanecarbonitrile Chemical compound N#CC1CCCC1 SVPZJHKVRMRREG-UHFFFAOYSA-N 0.000 description 1
XBVZRFXCDCYXAX-UHFFFAOYSA-N cyclopentene-1-carbonitrile Chemical compound N#CC1=CCCC1 XBVZRFXCDCYXAX-UHFFFAOYSA-N 0.000 description 1
150000001470 diamides Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005669 hydrocyanation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007689 inspection Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
238000011068 loading method Methods 0.000 description 1
230000004807 localization Effects 0.000 description 1
239000010687 lubricating oil Substances 0.000 description 1
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006456 reductive dimerization reaction Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
239000002966 varnish Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyamides (AREA)

BE187128A 1977-04-26 1978-04-26 Procede pour la synthese de dinitriles, produits ainsi obtenus et leurs derives BE866404A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT2280677A IT1075501B (it)	1977-04-26	1977-04-26	Procedimento per la sintesi di dinitrili e prodotti cosi' ottenuti

Publications (1)

Publication Number	Publication Date
BE866404A true BE866404A (fr)	1978-10-26

Family

ID=11200630

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE187128A BE866404A (fr)	1977-04-26	1978-04-26	Procede pour la synthese de dinitriles, produits ainsi obtenus et leurs derives

Country Status (5)

Country	Link
AT (1)	AT361454B (de)
BE (1)	BE866404A (de)
ES (1)	ES469827A1 (de)
IT (1)	IT1075501B (de)
SE (1)	SE7804741L (de)

1977
- 1977-04-26 IT IT2280677A patent/IT1075501B/it active
1978
- 1978-04-24 AT AT292378A patent/AT361454B/de not_active IP Right Cessation
- 1978-04-25 ES ES469827A patent/ES469827A1/es not_active Expired
- 1978-04-25 SE SE7804741A patent/SE7804741L/xx unknown
- 1978-04-26 BE BE187128A patent/BE866404A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1075501B (it)	1985-04-22
ES469827A1 (es)	1979-09-16
SE7804741L (sv)	1978-10-27
ATA292378A (de)	1980-08-15
AT361454B (de)	1981-03-10

Legal Events

Date

Code

Title

Description

1984-10-31

RE

Patent lapsed

Owner name: ANIC S.P.A.

Effective date: 19840426

Publication	Publication Date	Title
EP2780319B1 (de)	2016-03-30	Verfahren zur herstellung von verbindungen mit nitrilfunktionen
EP2729446A1 (de)	2014-05-14	Verfahren zur herstellung von verbindungen mit nitrilfunktionen
FR2711365A1 (fr)	1995-04-28	Procédé d'hydroxycarbonylation du butadiène.
CH637102A5 (fr)	1983-07-15	Procede de preparation de chlorure de chloracetyle.
BE866404A (fr)	1978-10-26	Procede pour la synthese de dinitriles, produits ainsi obtenus et leurs derives
EP0680465B1 (de)	1998-04-22	Verfahren zur herstellung von alpha-amino omega-ester-monoamid
US4279834A (en)	1981-07-21	Method for synthesizing dinitriles, products obtained thereby and their derivatives
CH518904A (fr)	1972-02-15	Procédé de préparation d'un acide dicarboxylique monomère
JP3355215B2 (ja)	2002-12-09	４，４，５，５，６，６，６−ヘプタフルオロ−３，３―ビス（トリフルオロメチル）−１−ヘキサノール、及びその製造方法
JP2006193434A (ja)	2006-07-27	４，４’−ジアミノビフェニル化合物
FR2499558A1 (fr)	1982-08-13	Metathese de composes non satures portant des groupes fonctionnels
US4465822A (en)	1984-08-14	Polyamide from aralkylene diamine, dicarboxylic acid and tricarboxylic acid
JPH0316354B2 (de)	1991-03-05
FR2551747A1 (fr)	1985-03-15	Procede de production d'aminobenzylamines
EP0378022A1 (de)	1990-07-18	Funktionalisierte Chlorfluorverbindungen und ihre Herstellung
JPH01272558A (ja)	1989-10-31	ジアミノジフェニルエーテル類の精製方法
WO2016042045A1 (fr)	2016-03-24	Procede de synthese d'aminoesters et de polyamides
FR2618148A1 (fr)	1989-01-20	Nouveau procede de preparation enantiospecifique du (s) ethylamino-2 (trifluoromethyl-3 phenyl)-1 propane
GB1604697A (en)	1981-12-16	Diamines their production and their use in the production of polyamides
WO2015132519A1 (fr)	2015-09-11	Procédé de préparation de dérives de l'acide 11-aminoundecanoique et de l'acide 12-aminododecanoique
EP1494994A2 (de)	2005-01-12	Aminierte verbindungen, die wenigstens ein allyl und ein difluormethyl tragen, und bei deren synthese angewendete verfahren
EP0322279A2 (de)	1989-06-28	Verfahren zur Acylierung von N,N-Diallylanilin
BE504403A (de)
BE628971A (de)
BE443466A (de)