DE1468872A1 - Verfahren zur Herstellung von 2,4-Dicyanobuten-(1) - Google Patents
Verfahren zur Herstellung von 2,4-Dicyanobuten-(1)Info
- Publication number
- DE1468872A1 DE1468872A1 DE19641468872 DE1468872A DE1468872A1 DE 1468872 A1 DE1468872 A1 DE 1468872A1 DE 19641468872 DE19641468872 DE 19641468872 DE 1468872 A DE1468872 A DE 1468872A DE 1468872 A1 DE1468872 A1 DE 1468872A1
- Authority
- DE
- Germany
- Prior art keywords
- acrylonitrile
- reaction
- dicyanobutene
- hydroquinone
- preparation
- 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 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 15
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- NGCJVMZXRCLPRQ-UHFFFAOYSA-N 2-methylidenepentanedinitrile Chemical compound N#CC(=C)CCC#N NGCJVMZXRCLPRQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- -1 aromatic phosphines Chemical class 0.000 description 5
- 150000003003 phosphines Chemical group 0.000 description 5
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 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 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003060 catalysis inhibitor Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- NLIIZKKTTLNFRW-UHFFFAOYSA-N cyclobutane-1,1-dicarbonitrile Chemical compound N#CC1(C#N)CCC1 NLIIZKKTTLNFRW-UHFFFAOYSA-N 0.000 description 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZQOHAQBXINVHHC-UHFFFAOYSA-N hex-2-enedinitrile Chemical compound N#CCCC=CC#N ZQOHAQBXINVHHC-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- IELLVVGAXDLVSW-UHFFFAOYSA-N tricyclohexyl phosphate Chemical compound C1CCCCC1OP(OC1CCCCC1)(=O)OC1CCCCC1 IELLVVGAXDLVSW-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR935908A FR1366081A (fr) | 1963-05-24 | 1963-05-24 | Dicyano-2, 4 butène-1 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1468872A1 true DE1468872A1 (de) | 1969-06-26 |
Family
ID=8804586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641468872 Pending DE1468872A1 (de) | 1963-05-24 | 1964-05-22 | Verfahren zur Herstellung von 2,4-Dicyanobuten-(1) |
Country Status (5)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE655214A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-11-04 | |||
| BE662661A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-04-16 | |||
| GB1143539A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1965-03-02 | |||
| DE1293155B (de) * | 1966-05-14 | 1969-04-24 | Basf Ag | Verfahren zur Herstellung von 1, 3-Dicyan-3-buten durch Dimerisieren von Acrylsaeurenitril |
| US3538141A (en) * | 1967-01-23 | 1970-11-03 | Halcon International Inc | Dimerization of acrylonitrile |
| US3954831A (en) * | 1974-12-30 | 1976-05-04 | Halcon International, Inc. | Dimerization process |
| AU499165B2 (en) | 1975-10-31 | 1979-04-05 | Ici Limited | Dimerisation process |
| GB1547432A (en) * | 1976-11-24 | 1979-06-20 | Ici Ltd | Process for the dimerisation of acrylonitrile |
| US4500468A (en) * | 1983-11-21 | 1985-02-19 | The Standard Oil Company | Catalytic dimerization of acrylonitrile |
| CN107935886B (zh) * | 2017-11-29 | 2020-06-02 | 碳氢联合科技（北京）有限公司 | 一种丙烯腈装置用阻聚剂的制备及其使用方法 |
-
1963
- 1963-05-24 FR FR935908A patent/FR1366081A/fr not_active Expired
-
1964
- 1964-05-11 GB GB1954864A patent/GB1003656A/en not_active Expired
- 1964-05-22 NL NL6405733A patent/NL6405733A/xx unknown
- 1964-05-22 DE DE19641468872 patent/DE1468872A1/de active Pending
- 1964-05-22 BE BE648319A patent/BE648319A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6405733A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-11-25 |
| BE648319A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-11-23 |
| FR1366081A (fr) | 1964-07-10 |
| GB1003656A (en) | 1965-09-08 |
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