DE1081006B - Verfahren zur Herstellung von ª,ª-ungesaettigten Carbonsaeurenitrilen - Google Patents
Verfahren zur Herstellung von ª,ª-ungesaettigten CarbonsaeurenitrilenInfo
- Publication number
- DE1081006B DE1081006B DEK34407A DEK0034407A DE1081006B DE 1081006 B DE1081006 B DE 1081006B DE K34407 A DEK34407 A DE K34407A DE K0034407 A DEK0034407 A DE K0034407A DE 1081006 B DE1081006 B DE 1081006B
- Authority
- DE
- Germany
- Prior art keywords
- butadiene
- cyanohydrin
- reaction
- cyano
- crotonaldehyde
- 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
- -1 carboxylic acid nitriles Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 16
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 12
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 9
- 235000011007 phosphoric acid Nutrition 0.000 claims description 9
- 230000008030 elimination Effects 0.000 claims description 7
- 238000003379 elimination reaction Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- STSRVFAXSLNLLI-ONEGZZNKSA-N (2e)-penta-2,4-dienenitrile Chemical compound C=C\C=C\C#N STSRVFAXSLNLLI-ONEGZZNKSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- LEKIODFWYFCUER-UHFFFAOYSA-N 2-methylidenebut-3-enenitrile Chemical compound C=CC(=C)C#N LEKIODFWYFCUER-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 150000003016 phosphoric acids Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 238000000926 separation method Methods 0.000 claims 3
- 238000005406 washing Methods 0.000 claims 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 claims 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 241001448862 Croton Species 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 239000003546 flue gas Substances 0.000 claims 2
- 238000002156 mixing Methods 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 238000000889 atomisation Methods 0.000 claims 1
- 239000001273 butane Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 239000000567 combustion gas Substances 0.000 claims 1
- 238000002485 combustion reaction Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- USKZHEQYENVSMH-UHFFFAOYSA-N hepta-1,3,5-triene Chemical compound CC=CC=CC=C USKZHEQYENVSMH-UHFFFAOYSA-N 0.000 claims 1
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000003595 mist Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- GXHAENUAJYZNOA-UHFFFAOYSA-N oxolane-2-carboxamide Chemical compound NC(=O)C1CCCO1 GXHAENUAJYZNOA-UHFFFAOYSA-N 0.000 claims 1
- STSRVFAXSLNLLI-UHFFFAOYSA-N penta-2,4-dienenitrile Chemical compound C=CC=CC#N STSRVFAXSLNLLI-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 229910001220 stainless steel Inorganic materials 0.000 claims 1
- 239000010935 stainless steel Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 2
- JFVBCXHSPKJLRP-UHFFFAOYSA-N 4-oxopentanenitrile Chemical compound CC(=O)CCC#N JFVBCXHSPKJLRP-UHFFFAOYSA-N 0.000 description 1
- HLWLDVVQFGABQI-UHFFFAOYSA-N C(C)(=O)OC(CC(C)OC(C)=O)C#N Chemical compound C(C)(=O)OC(CC(C)OC(C)=O)C#N HLWLDVVQFGABQI-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE576955D BE576955A (en, 2012) | 1958-03-22 | ||
| BE531097D BE531097A (en, 2012) | 1958-03-22 | ||
| NL109651D NL109651C (en, 2012) | 1958-03-22 | ||
| DEK34407A DE1081006B (de) | 1958-03-22 | 1958-03-22 | Verfahren zur Herstellung von ª,ª-ungesaettigten Carbonsaeurenitrilen |
| DEK39648A DE1108685B (de) | 1958-03-22 | 1958-03-22 | Verfahren zur Herstellung von ª‡ú¼ ª‰-ungesaettigten Carbonsaeurenitrilen |
| GB36496/60A GB866182A (en) | 1958-03-22 | 1959-03-11 | Process for the preparation of unsaturated nitriles |
| GB8469/59A GB866181A (en) | 1958-03-22 | 1959-03-11 | Process for the preparation of unsaturated carboxylic acids and their derivatives |
| US799860A US3022332A (en) | 1958-03-22 | 1959-03-17 | Process for the preparation of unsaturated carboxylic acid nitriles |
| FR790029A FR75500E (fr) | 1958-03-22 | 1959-03-21 | Procédé de préparation d'acides carboxyliques alpha, bêta-éthyléniques non substitués en position alpha, et de leurs dérivés |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK34407A DE1081006B (de) | 1958-03-22 | 1958-03-22 | Verfahren zur Herstellung von ª,ª-ungesaettigten Carbonsaeurenitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1081006B true DE1081006B (de) | 1960-05-05 |
Family
ID=7220025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK34407A Pending DE1081006B (de) | 1958-03-22 | 1958-03-22 | Verfahren zur Herstellung von ª,ª-ungesaettigten Carbonsaeurenitrilen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3022332A (en, 2012) |
| BE (2) | BE531097A (en, 2012) |
| DE (1) | DE1081006B (en, 2012) |
| GB (2) | GB866182A (en, 2012) |
| NL (1) | NL109651C (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03220166A (ja) * | 1989-11-30 | 1991-09-27 | Mitsui Toatsu Chem Inc | α，β―不飽和ニトリルの製造方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2205239A (en) * | 1938-11-19 | 1940-06-18 | Du Pont | Process for preparing cyano-2-butadiene-1,3 |
| US2264026A (en) * | 1938-12-09 | 1941-11-25 | Ici Ltd | Manufacture of 1-cyanobutadiene-1,3 |
| US2264025A (en) * | 1938-04-13 | 1941-11-25 | Ici Ltd | Manufacture of 1-cyanobutadiene-1:3 |
| US2334192A (en) * | 1941-03-19 | 1943-11-16 | Du Pont | Preparation of alpha-cyanobutadiene |
| US2503710A (en) * | 1948-01-24 | 1950-04-11 | Rohm & Haas | Method for making 1-cyano-1,3-butadiene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2790822A (en) * | 1953-08-12 | 1957-04-30 | Knapsack Ag | Process for the preparation of aliphatic alpha-unsubstituted alpha-beta-unsatureated carboxylic acids and their derivatives |
-
0
- BE BE576955D patent/BE576955A/xx unknown
- BE BE531097D patent/BE531097A/xx unknown
- NL NL109651D patent/NL109651C/xx active
-
1958
- 1958-03-22 DE DEK34407A patent/DE1081006B/de active Pending
-
1959
- 1959-03-11 GB GB36496/60A patent/GB866182A/en not_active Expired
- 1959-03-11 GB GB8469/59A patent/GB866181A/en not_active Expired
- 1959-03-17 US US799860A patent/US3022332A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2264025A (en) * | 1938-04-13 | 1941-11-25 | Ici Ltd | Manufacture of 1-cyanobutadiene-1:3 |
| US2205239A (en) * | 1938-11-19 | 1940-06-18 | Du Pont | Process for preparing cyano-2-butadiene-1,3 |
| US2264026A (en) * | 1938-12-09 | 1941-11-25 | Ici Ltd | Manufacture of 1-cyanobutadiene-1,3 |
| US2334192A (en) * | 1941-03-19 | 1943-11-16 | Du Pont | Preparation of alpha-cyanobutadiene |
| US2503710A (en) * | 1948-01-24 | 1950-04-11 | Rohm & Haas | Method for making 1-cyano-1,3-butadiene |
Also Published As
| Publication number | Publication date |
|---|---|
| BE576955A (en, 2012) | |
| BE531097A (en, 2012) | |
| US3022332A (en) | 1962-02-20 |
| NL109651C (en, 2012) | |
| GB866182A (en) | 1961-04-26 |
| GB866181A (en) | 1961-04-26 |
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