DE2051548C3 - Verfahren zur Stabilisierung aliphatischer Diene - Google Patents
Verfahren zur Stabilisierung aliphatischer DieneInfo
- Publication number
- DE2051548C3 DE2051548C3 DE2051548A DE2051548A DE2051548C3 DE 2051548 C3 DE2051548 C3 DE 2051548C3 DE 2051548 A DE2051548 A DE 2051548A DE 2051548 A DE2051548 A DE 2051548A DE 2051548 C3 DE2051548 C3 DE 2051548C3
- Authority
- DE
- Germany
- Prior art keywords
- stabilizers
- dienes
- butadiene
- compounds
- weight
- 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 12
- -1 aliphatic dienes Chemical class 0.000 title claims description 5
- 230000000087 stabilizing effect Effects 0.000 title claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 17
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 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 claims description 5
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 claims description 4
- 238000006471 dimerization reaction Methods 0.000 claims description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 24
- 239000000539 dimer Substances 0.000 description 19
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003860 storage Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical class O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- PXNJGLAVKOXITN-UHFFFAOYSA-N 2-(4-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=C(CC#N)C=C1 PXNJGLAVKOXITN-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- SYUYTOYKQOAVDW-UHFFFAOYSA-N 2-nitrosonaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C(N=O)C=CC2=C1 SYUYTOYKQOAVDW-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- VVOUQFXJSCDIAO-UHFFFAOYSA-L lead(2+);dinitrite Chemical compound [Pb+2].[O-]N=O.[O-]N=O VVOUQFXJSCDIAO-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2051548A DE2051548C3 (de) | 1970-10-21 | 1970-10-21 | Verfahren zur Stabilisierung aliphatischer Diene |
| US00190260A US3711565A (en) | 1970-10-21 | 1971-10-18 | Process for stabilizing dienes |
| NL717114303A NL151971B (nl) | 1970-10-21 | 1971-10-18 | Werkwijze voor het tegen sterke dimeervorming stabiliseren van alifatische dienen. |
| IT53563/71A IT939612B (it) | 1970-10-21 | 1971-10-19 | Procedimento per stabilizzare dieni alifatici |
| CA125,484A CA954144A (en) | 1970-10-21 | 1971-10-19 | Process for the stabilisation of aliphatic dienes |
| BE774190A BE774190A (fr) | 1970-10-21 | 1971-10-20 | Procede de stabilisation des dienes aliphatiques |
| GB4877471A GB1356831A (en) | 1970-10-21 | 1971-10-20 | Process for the stabilisation of aliphatic dienes |
| JP46082554A JPS5029441B1 (enExample) | 1970-10-21 | 1971-10-20 | |
| ES396240A ES396240A1 (es) | 1970-10-21 | 1971-10-21 | Procedimiento para estabilizar dienos alifaticos. |
| FR7137933A FR2113093A5 (enExample) | 1970-10-21 | 1971-10-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2051548A DE2051548C3 (de) | 1970-10-21 | 1970-10-21 | Verfahren zur Stabilisierung aliphatischer Diene |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2051548A1 DE2051548A1 (de) | 1972-04-27 |
| DE2051548B2 DE2051548B2 (de) | 1974-04-04 |
| DE2051548C3 true DE2051548C3 (de) | 1974-10-31 |
Family
ID=5785674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2051548A Expired DE2051548C3 (de) | 1970-10-21 | 1970-10-21 | Verfahren zur Stabilisierung aliphatischer Diene |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3711565A (enExample) |
| JP (1) | JPS5029441B1 (enExample) |
| BE (1) | BE774190A (enExample) |
| CA (1) | CA954144A (enExample) |
| DE (1) | DE2051548C3 (enExample) |
| ES (1) | ES396240A1 (enExample) |
| FR (1) | FR2113093A5 (enExample) |
| GB (1) | GB1356831A (enExample) |
| IT (1) | IT939612B (enExample) |
| NL (1) | NL151971B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3307486A1 (de) * | 1983-03-03 | 1984-09-06 | Bunawerke Hüls GmbH, 4370 Marl | Verfahren zum verhindern der bildung von polymeren nebenprodukten bei der herstellung von diels-alder-addukten |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2787634A (en) * | 1953-08-19 | 1957-04-02 | Eastman Kodak Co | Inhibition of autopolymerization in vinyl-type compounds |
| JPS4519683B1 (enExample) * | 1967-04-26 | 1970-07-06 |
-
1970
- 1970-10-21 DE DE2051548A patent/DE2051548C3/de not_active Expired
-
1971
- 1971-10-18 US US00190260A patent/US3711565A/en not_active Expired - Lifetime
- 1971-10-18 NL NL717114303A patent/NL151971B/xx not_active IP Right Cessation
- 1971-10-19 CA CA125,484A patent/CA954144A/en not_active Expired
- 1971-10-19 IT IT53563/71A patent/IT939612B/it active
- 1971-10-20 GB GB4877471A patent/GB1356831A/en not_active Expired
- 1971-10-20 JP JP46082554A patent/JPS5029441B1/ja active Pending
- 1971-10-20 BE BE774190A patent/BE774190A/xx unknown
- 1971-10-21 FR FR7137933A patent/FR2113093A5/fr not_active Expired
- 1971-10-21 ES ES396240A patent/ES396240A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7114303A (enExample) | 1972-04-25 |
| DE2051548B2 (de) | 1974-04-04 |
| DE2051548A1 (de) | 1972-04-27 |
| FR2113093A5 (enExample) | 1972-06-23 |
| US3711565A (en) | 1973-01-16 |
| JPS5029441B1 (enExample) | 1975-09-23 |
| NL151971B (nl) | 1977-01-17 |
| CA954144A (en) | 1974-09-03 |
| GB1356831A (en) | 1974-06-19 |
| ES396240A1 (es) | 1974-04-16 |
| BE774190A (fr) | 1972-04-20 |
| IT939612B (it) | 1973-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1086226B (de) | Verfahren zur Herstellung von Cyclododecatrien-(1, 5, 9) | |
| DE2051548C3 (de) | Verfahren zur Stabilisierung aliphatischer Diene | |
| DE1271115C2 (de) | Verfahren zum destillativen Reinigen von reduzierbaren, cyclischen, organischen Verbindungen | |
| DE1090194B (de) | Verfahren zur Herstellung von 1, 2-Dichlorbuten-2, 2, 3-Dichlorbuten-1 und gegebenenfalls 1, 3-Dichlorbuten-2 aus 1, 2, 3-Trichlorbutan | |
| DE1518461A1 (de) | Stabilisierte Massen auf der Grundlage von Chlorfluoralkanen | |
| EP2813490B1 (de) | Verfahren zur Herstellung von lagerstabilem 3-Methylmercaptopropionaldehyd | |
| DE2500106A1 (de) | Verfahren zur herstellung von 1- methyl-3-phenyl-indan | |
| DE812248C (de) | Verfahren zur Herstellung von stabilem Perborat | |
| DE2200977A1 (de) | Trimerisierung von Butadien | |
| DE811952C (de) | Verfahren zum Stabilisieren von Cyanhydrinen | |
| DE551805C (de) | Verfahren zur Beschleunigung der Vulkanisation von natuerlichen und kuenstlichen Kautschukarten | |
| DE857373C (de) | Aufarbeitungsverfahren fuer waessrige Loesungen von Acrylnitril | |
| DE2820394A1 (de) | Verfahren zur oxidation von p-methylbenzoesaeure | |
| DE2156285C3 (de) | Verfahren zur kontinuierlichen Herstellung von m-Chlornitrobenzol | |
| DE898737C (de) | Verfahren zur Herstellung von Chlormethylmethylaether | |
| DE1003207B (de) | Verfahren zur Reinigung von nieder-polymere Acetylenverbindungen enthaltendem Acrylsaeurenitril | |
| DE2332777C3 (de) | Verfahren zur Rückgewinnung von Tetraalkylammoniumsalzen aus einer Mischung, die Wasser, Adiponitril, gelöste Tetraalkylammoniumsalze und Acrylnitril enthält | |
| DE57621C (de) | Verfahren zur Darstellung von Chlor- I methylalkohol und Oxychlormethyläther | |
| DE2332170A1 (de) | Verfahren fuer die chlorierung von c tief 8-c tief 16-kohlenwasserstoffen in fluessiger phase | |
| DE2145877A1 (de) | Stabilisatoren zur verhinderung der rueckisomerisierung von 3,4-dichlorbuten1 zu 1,4-dichlorbuten-2 | |
| DE1274106B (de) | Verfahren zur Gewinnung von stabilen konzentrierten waessrigen Loesungen von Peressigsaeure | |
| DE1240074B (de) | Verfahren zur Herstellung von Cycloalkanonoximen durch Photonitrosierung von C-C-Cycloalkanen | |
| DE1027654B (de) | Verfahren zur Herstellung von gesaettigten, aliphatischen Ketonen | |
| DE1177145B (de) | Verfahren zur Herstellung von ª-Chloracrylsaeurenitril | |
| DE1242593B (de) | Verfahren zur kontinuierlichen Herstellung von Monovinylacetylen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |