DE2052167C3 - Verfahren zur Herstellung des gereinigten Ammoniumsalzes der 11-Cyanundecansäure bzw. der reinen freien 11-Cyanundecansäure - Google Patents
Verfahren zur Herstellung des gereinigten Ammoniumsalzes der 11-Cyanundecansäure bzw. der reinen freien 11-CyanundecansäureInfo
- Publication number
- DE2052167C3 DE2052167C3 DE19702052167 DE2052167A DE2052167C3 DE 2052167 C3 DE2052167 C3 DE 2052167C3 DE 19702052167 DE19702052167 DE 19702052167 DE 2052167 A DE2052167 A DE 2052167A DE 2052167 C3 DE2052167 C3 DE 2052167C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- cyanundecanoic
- ammonium salt
- crude
- solvent
- 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
- YKHZGLKQBYTRHO-UHFFFAOYSA-N 11-cyanoundecanoic acid Chemical compound OC(=O)CCCCCCCCCCC#N YKHZGLKQBYTRHO-UHFFFAOYSA-N 0.000 title claims description 49
- 150000003863 ammonium salts Chemical class 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 33
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 16
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 16
- 239000012535 impurity Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 238000000197 pyrolysis Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- YCVJHQSECYGGPB-UHFFFAOYSA-N azane;11-cyanoundecanoic acid Chemical compound [NH4+].[O-]C(=O)CCCCCCCCCCC#N YCVJHQSECYGGPB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical class CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 2
- OXFDTUUEWDRMGG-UHFFFAOYSA-N 3,4-dibutylpyrrolidine-2,5-dione Chemical compound CCCCC1C(CCCC)C(=O)NC1=O OXFDTUUEWDRMGG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- -1 cyclic imides Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012808 vapor phase 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5219569 | 1969-10-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2052167A1 DE2052167A1 (de) | 1971-05-06 |
| DE2052167B2 DE2052167B2 (de) | 1980-02-21 |
| DE2052167C3 true DE2052167C3 (de) | 1980-11-20 |
Family
ID=10463001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702052167 Expired DE2052167C3 (de) | 1969-10-24 | 1970-10-23 | Verfahren zur Herstellung des gereinigten Ammoniumsalzes der 11-Cyanundecansäure bzw. der reinen freien 11-Cyanundecansäure |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5015B1 (enrdf_load_stackoverflow) |
| BE (1) | BE757806A (enrdf_load_stackoverflow) |
| DE (1) | DE2052167C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2066426A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1266213A (enrdf_load_stackoverflow) |
| NL (1) | NL7014969A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1575282A (en) * | 1977-05-04 | 1980-09-17 | Ube Industries | Process for separating 11-cyanoundecanoic acid cyclohexanone and -caprolactam |
-
0
- BE BE757806D patent/BE757806A/xx unknown
-
1969
- 1969-10-24 GB GB1266213D patent/GB1266213A/en not_active Expired
-
1970
- 1970-10-13 NL NL7014969A patent/NL7014969A/xx not_active Application Discontinuation
- 1970-10-23 FR FR7038282A patent/FR2066426A5/fr not_active Expired
- 1970-10-23 DE DE19702052167 patent/DE2052167C3/de not_active Expired
- 1970-10-24 JP JP9390070A patent/JPS5015B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2052167A1 (de) | 1971-05-06 |
| GB1266213A (enrdf_load_stackoverflow) | 1972-03-08 |
| DE2052167B2 (de) | 1980-02-21 |
| NL7014969A (enrdf_load_stackoverflow) | 1971-04-27 |
| BE757806A (fr) | 1971-04-21 |
| JPS5015B1 (enrdf_load_stackoverflow) | 1975-01-06 |
| FR2066426A5 (enrdf_load_stackoverflow) | 1971-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |