CH437248A - Verfahren zur Herstellung von Derivaten aliphatischer Dicarbonsäuren - Google Patents

Verfahren zur Herstellung von Derivaten aliphatischer Dicarbonsäuren

Info

Publication number: CH437248A
Authority: CH; Switzerland
Prior art keywords: amalgam; mol; reaction; acrylonitrile; vinyl
Prior art date: 1961-05-26

Application number

CH602762A

Other languages

German (de)

English (en)

Inventor

Kurt Dr Sennewald

Alexander Dr Ohorodnik

Hugo Dr Gudernatsch

Vierling Hermann

Original Assignee

Knapsack 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.)

1961-05-26

Filing date

1962-05-18

Publication date

1967-06-15

1961-05-26 Priority claimed from DEK43829A external-priority patent/DE1151791B/de

1961-08-09 Priority claimed from DEK44461A external-priority patent/DE1155769B/de

1962-04-12 Priority claimed from DEK46455A external-priority patent/DE1171414B/de

1962-05-18 Application filed by Knapsack Ag filed Critical Knapsack Ag

1967-06-15 Publication of CH437248A publication Critical patent/CH437248A/de

Links

238000000034 method Methods 0.000 title claims description 54
-1 derivatives of aliphatic dicarboxylic acids Chemical class 0.000 title claims description 40
238000002360 preparation method Methods 0.000 title claims description 8
229910000497 Amalgam Inorganic materials 0.000 claims description 57
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 47
BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 32
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 22
229910052753 mercury Inorganic materials 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
239000003513 alkali Substances 0.000 claims description 21
125000004429 atom Chemical group 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
229920002554 vinyl polymer Polymers 0.000 claims description 20
229910052783 alkali metal Inorganic materials 0.000 claims description 19
150000001340 alkali metals Chemical class 0.000 claims description 18
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 16
235000014113 dietary fatty acids Nutrition 0.000 claims description 16
229930195729 fatty acid Natural products 0.000 claims description 16
239000000194 fatty acid Substances 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 12
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
239000007858 starting material Substances 0.000 claims description 11
150000004665 fatty acids Chemical class 0.000 claims description 10
239000007788 liquid Substances 0.000 claims description 10
238000006116 polymerization reaction Methods 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
239000003112 inhibitor Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000005868 electrolysis reaction Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
229910001023 sodium amalgam Inorganic materials 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
239000012433 hydrogen halide Substances 0.000 claims description 4
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
150000001805 chlorine compounds Chemical class 0.000 claims description 3
239000011261 inert gas Substances 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 claims description 2
238000006053 organic reaction Methods 0.000 claims description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
229910001508 alkali metal halide Inorganic materials 0.000 claims 1
229910001615 alkaline earth metal halide Inorganic materials 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
239000011734 sodium Substances 0.000 description 25
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 18
238000004821 distillation Methods 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 16
229910052708 sodium Inorganic materials 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 11
GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 10
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 8
150000002825 nitriles Chemical class 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
229910000567 Amalgam (chemistry) Inorganic materials 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 4
238000006471 dimerization reaction Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000012295 chemical reaction liquid Substances 0.000 description 3
238000010924 continuous production Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
WNZKWBYFYOMJRC-UHFFFAOYSA-N methyl 2-cyanopentanoate Chemical compound CCCC(C#N)C(=O)OC WNZKWBYFYOMJRC-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
GZGJIACHBCQSPC-UHFFFAOYSA-N methyl 3-chloropropanoate Chemical compound COC(=O)CCCl GZGJIACHBCQSPC-UHFFFAOYSA-N 0.000 description 2
UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
238000006886 vinylation reaction Methods 0.000 description 2
STSRVFAXSLNLLI-ONEGZZNKSA-N (2e)-penta-2,4-dienenitrile Chemical compound C=C\C=C\C#N STSRVFAXSLNLLI-ONEGZZNKSA-N 0.000 description 1
GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
SBDSWNLTVOAIPQ-UHFFFAOYSA-N 2-methylhexanedinitrile Chemical compound N#CC(C)CCCC#N SBDSWNLTVOAIPQ-UHFFFAOYSA-N 0.000 description 1
JKBPBRLDGFKIIA-UHFFFAOYSA-N 2-propylidenepropanedinitrile Chemical compound CCC=C(C#N)C#N JKBPBRLDGFKIIA-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
101150046432 Tril gene Proteins 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000007278 cyanoethylation reaction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000020169 heat generation Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
239000010815 organic waste Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 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
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH602762A 1961-05-26 1962-05-18 Verfahren zur Herstellung von Derivaten aliphatischer Dicarbonsäuren CH437248A (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DEK43829A DE1151791B (de)	1961-05-26	1961-05-26	Verfahren zur Herstellung von Adipinsaeuredinitril
DEK44461A DE1155769B (de)	1961-08-09	1961-08-09	Verfahren zur Herstellung von Adipinsaeuredinitril
DEK46455A DE1171414B (de)	1962-04-12	1962-04-12	Verfahren zur Herstellung von insbesondere Cyangruppen enthaltenden Derivaten aliphatischer Dicarbonsaeuren

Publications (1)

Publication Number	Publication Date
CH437248A true CH437248A (de)	1967-06-15

Family

ID=27211196

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH602762A CH437248A (de)	1961-05-26	1962-05-18	Verfahren zur Herstellung von Derivaten aliphatischer Dicarbonsäuren

Country Status (3)

Country	Link
BE (1)	BE618095A (fr)
CH (1)	CH437248A (fr)
GB (1)	GB1011552A (fr)

1962
- 1962-05-18 CH CH602762A patent/CH437248A/de unknown
- 1962-05-25 BE BE618095A patent/BE618095A/fr unknown
- 1962-05-28 GB GB2051762A patent/GB1011552A/en not_active Expired

Also Published As

Publication number	Publication date
GB1011552A (en)	1965-12-01
BE618095A (fr)	1962-09-17

Publication	Publication Date	Title
DE2502247C3 (de)	1983-01-05	Verfahren zur Herstellung von N-(tert.-Aminoalkyl)acrylamiden
DE849109C (de)	1952-09-11	Verfahren zur Herstellung aliphatischer Azoverbindungen
DE2336852C2 (de)	1984-10-04	Verfahren zur Herstellung von 3-Pentennitril
DE69909619T2 (de)	2004-06-09	Verfahren zur herstellung eines aminonitrils und eines diamins
DE69109166T2 (de)	1995-12-07	Cyanobutylation von Aminen mit 2-Pentennitril.
DE1281446B (de)	1968-10-31	Verfahren zur Herstellung von Carbonsaeureestern aus Nitrilen unter Wiedergewinnung von Ammoniak
CH437248A (de)	1967-06-15	Verfahren zur Herstellung von Derivaten aliphatischer Dicarbonsäuren
AT235820B (de)	1964-09-25	Verfahren zur Herstellung von Derivaten aliphatischer Dicarbonsäuren
DE2236040C2 (de)	1974-06-27	Verfahren zur Herstellung von Carbonsäureamiden
DE2245892B2 (de)	1981-08-06	Verfahren zur Herstellung von Citronensäure
DE3029205A1 (de)	1982-03-11	Verfahren zur herstellung von aminonitrilen
EP1511720B1 (fr)	2006-08-09	Procede de reduction de la teneur en amine insaturee d'un melange contenant aminonitrile, diamine, dinitrile ou des melanges de ceux-ci
DE2005515C3 (de)	1980-12-11	Verfahren zur Herstellung von γ -Cyanbutyraldinünen
AT209326B (de)	1960-05-25	Verfahren zur Herstellung von 1,4-Dicyanbutenen
DE69007706T2 (de)	1994-08-11	Verfahren zur Herstellung von Carbonsäureestern und Formamid.
DE2626675A1 (de)	1977-01-20	Verfahren zur herstellung von 2-pyrrolidon
CH404634A (de)	1965-12-31	Verfahren zur Herstellung von y-Ketocarbonsäurenitrilen aus a,B-ungesättigten Ketonen
DE4321273A1 (de)	1995-01-05	Verfahren zur Herstellung von Aminopropionitrilen
DE2102263A1 (de)	1972-08-03	Verfahren zur kontinuierlichen Herstellung ungesättigter Nitrile
DE1287057B (de)	1969-01-16	Verfahren zur Herstellung von Nitrilgruppen enthaltenden Derivaten gesaettigter aliphatischer Carbonsaeuren
DE1927528C3 (de)	1978-01-19	Verfahren zur herstellung von alpha- aethinylaminen
DE1171414B (de)	1964-06-04	Verfahren zur Herstellung von insbesondere Cyangruppen enthaltenden Derivaten aliphatischer Dicarbonsaeuren
CH378868A (de)	1964-06-30	Verfahren zur Herstellung des w-Amino-caprylsäureamids
EP1339672B1 (fr)	2004-10-06	Procede de reduction de la teneur en une amine insaturee d'un melange contenant une amine et un nitrile
DE3339386A1 (de)	1985-05-30	Verfahren zur herstellung unterschiedlich derivatisierter, in 2-stellung substituierter bernsteinsaeuren