DE1668837C - - Google Patents
Info
- Publication number
- DE1668837C DE1668837C DE19671668837 DE1668837A DE1668837C DE 1668837 C DE1668837 C DE 1668837C DE 19671668837 DE19671668837 DE 19671668837 DE 1668837 A DE1668837 A DE 1668837A DE 1668837 C DE1668837 C DE 1668837C
- Authority
- DE
- Germany
- Prior art keywords
- dinitrile
- oxygen
- adipic
- temperature
- acid
- 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
- BTGRAWJCKBQKAO-UHFFFAOYSA-N Adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- DVARTQFDIMZBAA-UHFFFAOYSA-O Ammonium nitrate Chemical compound [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 claims description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N Copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 3
- BGTOWKSIORTVQH-UHFFFAOYSA-N Cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating Effects 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 230000001264 neutralization Effects 0.000 claims description 3
- -1 nitrate anion Chemical class 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- UXJVWJGDHIZPLD-UHFFFAOYSA-O Ammonium vanadate Chemical compound [NH4+].O=[V-](=O)=O UXJVWJGDHIZPLD-UHFFFAOYSA-O 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011780 sodium chloride Substances 0.000 claims 5
- VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- 229910001385 heavy metal Inorganic materials 0.000 claims 2
- 230000002452 interceptive Effects 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 150000002823 nitrates Chemical class 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000011109 contamination Methods 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 150000003997 cyclic ketones Chemical class 0.000 claims 1
- 230000009089 cytolysis Effects 0.000 claims 1
- 230000002349 favourable Effects 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- 238000003958 fumigation Methods 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 230000002934 lysing Effects 0.000 claims 1
- LBSANEJBGMCTBH-UHFFFAOYSA-N manganate Chemical compound [O-][Mn]([O-])(=O)=O LBSANEJBGMCTBH-UHFFFAOYSA-N 0.000 claims 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative Effects 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N α-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 claims 1
- NPDODHDPVPPRDJ-UHFFFAOYSA-N permanganate Chemical compound [O-][Mn](=O)(=O)=O NPDODHDPVPPRDJ-UHFFFAOYSA-N 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- IPMQSLPLJDKUPI-UHFFFAOYSA-N 2-oxocyclopentane-1-carbonitrile Chemical compound O=C1CCCC1C#N IPMQSLPLJDKUPI-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV0035098 | 1967-12-23 | ||
| DEV0035098 | 1967-12-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1668837A1 DE1668837A1 (de) | 1971-12-23 |
| DE1668837C true DE1668837C (US08080257-20111220-C00005.png) | 1973-04-19 |
Family
ID=7589433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671668837 Granted DE1668837A1 (de) | 1967-12-23 | 1967-12-23 | Verfahren zur Reinigung von Adipinsaeuredinitril |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1668837A1 (US08080257-20111220-C00005.png) |
-
1967
- 1967-12-23 DE DE19671668837 patent/DE1668837A1/de active Granted
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