DE2128001A1 - Verfahren zur Herstellung von 3,4-ungesättigten Nitrilen - Google Patents
Verfahren zur Herstellung von 3,4-ungesättigten NitrilenInfo
- Publication number
- DE2128001A1 DE2128001A1 DE19712128001 DE2128001A DE2128001A1 DE 2128001 A1 DE2128001 A1 DE 2128001A1 DE 19712128001 DE19712128001 DE 19712128001 DE 2128001 A DE2128001 A DE 2128001A DE 2128001 A1 DE2128001 A1 DE 2128001A1
- Authority
- DE
- Germany
- Prior art keywords
- allyl
- reaction
- cyanide
- hydrocyanic acid
- copper
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 18
- 150000002825 nitriles Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 65
- 239000003054 catalyst Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000012876 carrier material Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 150000001879 copper Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- NGZNCESUZDJUTH-UHFFFAOYSA-N cyanic acid;hydrate Chemical compound O.OC#N NGZNCESUZDJUTH-UHFFFAOYSA-N 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 32
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 8
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- STSRVFAXSLNLLI-ONEGZZNKSA-N (2e)-penta-2,4-dienenitrile Chemical compound C=C\C=C\C#N STSRVFAXSLNLLI-ONEGZZNKSA-N 0.000 description 2
- BSVZXPLUMFUWHW-OWOJBTEDSA-N (e)-hex-3-enedinitrile Chemical compound N#CC\C=C\CC#N BSVZXPLUMFUWHW-OWOJBTEDSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- KMTFOQPBLCPPTP-UHFFFAOYSA-N 4-bromo-2-methyl-5-propylpyrazole-3-carboxylic acid Chemical compound CCCC1=NN(C)C(C(O)=O)=C1Br KMTFOQPBLCPPTP-UHFFFAOYSA-N 0.000 description 1
- MZTSMFMGZMDYGL-UHFFFAOYSA-N 5-chloropent-3-enenitrile Chemical compound ClCC=CCC#N MZTSMFMGZMDYGL-UHFFFAOYSA-N 0.000 description 1
- WPVGCOZUWLMELF-UHFFFAOYSA-N 5-hydroxypent-3-enenitrile Chemical compound OCC=CCC#N WPVGCOZUWLMELF-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- ITMIAZBRRZANGB-UHFFFAOYSA-N but-3-ene-1,2-diol Chemical compound OCC(O)C=C ITMIAZBRRZANGB-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- -1 copper (I) halides Chemical class 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712128001 DE2128001A1 (de) | 1971-06-05 | 1971-06-05 | Verfahren zur Herstellung von 3,4-ungesättigten Nitrilen |
| GB2526772A GB1384796A (en) | 1971-06-05 | 1972-05-30 | Process for the production of 3,4-unsaturated nitriles |
| NL7207540A NL7207540A (enExample) | 1971-06-05 | 1972-06-02 | |
| CH821072A CH582133A5 (enExample) | 1971-06-05 | 1972-06-02 | |
| BE784327A BE784327A (fr) | 1971-06-05 | 1972-06-02 | Procede de preparation de nitriles 3,4-insatures |
| CA143,696A CA962282A (en) | 1971-06-05 | 1972-06-02 | Process for the production of 3,4-unsaturated nitriles |
| IT2522872A IT961214B (it) | 1971-06-05 | 1972-06-03 | Procedimento per la preparazione di nitrili 3 4 insaturi |
| FR7220159A FR2141187A5 (enExample) | 1971-06-05 | 1972-06-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712128001 DE2128001A1 (de) | 1971-06-05 | 1971-06-05 | Verfahren zur Herstellung von 3,4-ungesättigten Nitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2128001A1 true DE2128001A1 (de) | 1972-12-28 |
Family
ID=5809947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712128001 Pending DE2128001A1 (de) | 1971-06-05 | 1971-06-05 | Verfahren zur Herstellung von 3,4-ungesättigten Nitrilen |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE784327A (enExample) |
| CA (1) | CA962282A (enExample) |
| CH (1) | CH582133A5 (enExample) |
| DE (1) | DE2128001A1 (enExample) |
| FR (1) | FR2141187A5 (enExample) |
| GB (1) | GB1384796A (enExample) |
| IT (1) | IT961214B (enExample) |
| NL (1) | NL7207540A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2092277A1 (en) * | 1992-04-01 | 1993-10-02 | Katsuharu Imi | Process for producing 1,4-dicyano-2-butene and catalyst therefor |
| JPH06306037A (ja) * | 1993-02-26 | 1994-11-01 | Sumitomo Chem Co Ltd | １，４−ジシアノ−２−ブテンの製造方法 |
-
1971
- 1971-06-05 DE DE19712128001 patent/DE2128001A1/de active Pending
-
1972
- 1972-05-30 GB GB2526772A patent/GB1384796A/en not_active Expired
- 1972-06-02 CH CH821072A patent/CH582133A5/xx not_active IP Right Cessation
- 1972-06-02 NL NL7207540A patent/NL7207540A/xx unknown
- 1972-06-02 CA CA143,696A patent/CA962282A/en not_active Expired
- 1972-06-02 BE BE784327A patent/BE784327A/xx unknown
- 1972-06-03 IT IT2522872A patent/IT961214B/it active
- 1972-06-05 FR FR7220159A patent/FR2141187A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1384796A (en) | 1975-02-19 |
| NL7207540A (enExample) | 1972-12-07 |
| FR2141187A5 (enExample) | 1973-01-19 |
| IT961214B (it) | 1973-12-10 |
| CA962282A (en) | 1975-02-04 |
| BE784327A (fr) | 1972-12-04 |
| CH582133A5 (enExample) | 1976-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1543427C3 (enExample) | ||
| CH622235A5 (enExample) | ||
| CH624920A5 (en) | Process for the preparation of trans-2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane-1-carboxylic acid and its esters | |
| DE2631222C3 (de) | Verfahren zur Herstellung basisch substituierter Phenylacetonitrile | |
| DD229126A5 (de) | Verfahren zur herstellung von tetronsaeure | |
| CH615431A5 (enExample) | ||
| DE2128001A1 (de) | Verfahren zur Herstellung von 3,4-ungesättigten Nitrilen | |
| DE2749437A1 (de) | Verfahren zur herstellung von resorcin oder alkylsubstituierten derivaten desselben | |
| DE2404306C3 (de) | Optisch aktive Pinanderivate | |
| DE2352922A1 (de) | Verfahren zur herstellung von perchlormethylmercaptan | |
| DE2005515C3 (de) | Verfahren zur Herstellung von γ -Cyanbutyraldinünen | |
| DE1493752A1 (de) | Verfahren zur Herstellung von reinem wasserfreiem 2-Amino-propionitril | |
| AT500971B1 (de) | Verfahren zur herstellung von 2,2-dimethyl-3- (1-propenyl)cyclopropancarboxylatester | |
| DE2206849C2 (de) | Verfahren zur Aufspaltung von 2-(2β-Benzyloxymethyl-3α-hydroxy-4-cyclopenten-1α-yl)- essigsäure | |
| DE2316374A1 (de) | 3-alkyl-2-(omega-carboxyalkyl) cyclopentanone sowie ester und salze davon | |
| DE2721265A1 (de) | Verfahren zur herstellung von di- n-propylacetonitril | |
| DE3144765A1 (de) | Verfahren zur herstellung von chlorlactonen aus ungesaettigten carbonsaeuren | |
| DE836797C (de) | Verfahren zur Herstellung ª,ª-ungesaettigter, ª-chlorsubstituierter Carbonsaeurenitrile | |
| DE904650C (de) | Verfahren zur Herstellung von Adipinsaeurenitril | |
| DE1135887B (de) | Verfahren zur Herstellung eines Gemisches aus 2, 3- und 2, 6-Dichlorbenzonitril | |
| AT333981B (de) | Verfahren zur herstellung des neuen n-(d-6-methyl-8-isoergolin-i-yl)-n',n'-diathylharnstoffs | |
| DE1906493A1 (de) | Verfahren zur Herstellung von 3,4-ungesaettigten Nitrilen | |
| EP0525579A2 (de) | Verfahren zur Herstellung von substituierten Hexensäuren | |
| DE1114812B (de) | Verfahren zur Herstellung von ª-Carotin | |
| CH581625A5 (en) | 2-dimethylallylbenzomorphans - analgesics |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |