ZA200504177B - Method for inhibiting polymerization during the recovery and purification of unsaturated mononitriles. - Google Patents
Method for inhibiting polymerization during the recovery and purification of unsaturated mononitriles. Download PDFInfo
- Publication number
- ZA200504177B ZA200504177B ZA200504177A ZA200504177A ZA200504177B ZA 200504177 B ZA200504177 B ZA 200504177B ZA 200504177 A ZA200504177 A ZA 200504177A ZA 200504177 A ZA200504177 A ZA 200504177A ZA 200504177 B ZA200504177 B ZA 200504177B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenylenediamine
- aqueous solution
- butyl
- group
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 89
- 238000011084 recovery Methods 0.000 title claims abstract description 52
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 41
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 32
- 238000000746 purification Methods 0.000 title claims description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 74
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 70
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 62
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 41
- -1 nitrogen-containing organic compounds Chemical class 0.000 claims abstract description 39
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000004821 distillation Methods 0.000 claims abstract description 37
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 35
- 238000010791 quenching Methods 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000007788 liquid Substances 0.000 claims abstract description 24
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims abstract description 20
- 230000003197 catalytic effect Effects 0.000 claims abstract description 19
- 239000001294 propane Substances 0.000 claims abstract description 19
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001282 iso-butane Substances 0.000 claims abstract description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 85
- 238000009835 boiling Methods 0.000 claims description 28
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 22
- 229910001882 dioxygen Inorganic materials 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
- 150000002894 organic compounds Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 claims description 9
- CMGXCZJLZPWTGL-UHFFFAOYSA-N 1-n,4-n-ditert-butylbenzene-1,4-diamine Chemical compound CC(C)(C)NC1=CC=C(NC(C)(C)C)C=C1 CMGXCZJLZPWTGL-UHFFFAOYSA-N 0.000 claims description 9
- 150000002430 hydrocarbons Chemical group 0.000 claims description 9
- 150000004986 phenylenediamines Chemical class 0.000 claims description 9
- KDLIPGJLQQTGKY-UHFFFAOYSA-N 1-n,4-n-bis(2-methylpropyl)benzene-1,4-diamine Chemical compound CC(C)CNC1=CC=C(NCC(C)C)C=C1 KDLIPGJLQQTGKY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 11
- 230000003647 oxidation Effects 0.000 abstract description 10
- 238000005191 phase separation Methods 0.000 abstract description 9
- 150000004989 p-phenylenediamines Chemical class 0.000 abstract description 5
- 238000007670 refining Methods 0.000 abstract description 5
- 230000000171 quenching effect Effects 0.000 abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 50
- 239000000047 product Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 239000003112 inhibitor Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000007789 gas Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- ZUROCNHARMFRKA-UHFFFAOYSA-N 4,5-dibromo-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(Br)=C(Br)N1 ZUROCNHARMFRKA-UHFFFAOYSA-N 0.000 description 10
- 101100431668 Homo sapiens YBX3 gene Proteins 0.000 description 10
- 102100022221 Y-box-binding protein 3 Human genes 0.000 description 10
- 238000010908 decantation Methods 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 6
- 238000005194 fractionation Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000008246 gaseous mixture Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 150000002826 nitrites Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000003134 recirculating effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- LJSAJMXWXGSVNA-UHFFFAOYSA-N a805044 Chemical compound OC1=CC=C(O)C=C1.OC1=CC=C(O)C=C1 LJSAJMXWXGSVNA-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910000413 arsenic oxide Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000010908 plant waste Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten 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
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
- C07C255/07—Mononitriles
- C07C255/08—Acrylonitrile; Methacrylonitrile
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/309,962 US6984749B2 (en) | 2002-12-04 | 2002-12-04 | Method for inhibiting polymerization during the recovery and purification of unsaturated mononitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200504177B true ZA200504177B (en) | 2006-02-22 |
Family
ID=32467951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200504177A ZA200504177B (en) | 2002-12-04 | 2005-05-23 | Method for inhibiting polymerization during the recovery and purification of unsaturated mononitriles. |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US6984749B2 (zh) |
| EP (1) | EP1567481B1 (zh) |
| JP (2) | JP2006509030A (zh) |
| KR (1) | KR101026343B1 (zh) |
| CN (1) | CN100390139C (zh) |
| AT (1) | ATE400549T1 (zh) |
| AU (1) | AU2003287702A1 (zh) |
| BR (1) | BR0316857A (zh) |
| CA (1) | CA2506409A1 (zh) |
| DE (1) | DE60322095D1 (zh) |
| ES (1) | ES2306907T3 (zh) |
| MX (1) | MXPA05005847A (zh) |
| MY (1) | MY141089A (zh) |
| RU (1) | RU2324677C2 (zh) |
| TW (1) | TWI312774B (zh) |
| WO (1) | WO2004052842A1 (zh) |
| ZA (1) | ZA200504177B (zh) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090299087A1 (en) * | 2008-05-28 | 2009-12-03 | Solutia, Inc. | Process for manufacturing unsaturated mononitriles to improve on-stream time and reduce fouling |
| JP5643064B2 (ja) * | 2010-11-18 | 2014-12-17 | 旭化成ケミカルズ株式会社 | 重合性化合物の精製方法 |
| CN106892843A (zh) * | 2015-12-17 | 2017-06-27 | 英尼奥斯欧洲股份公司 | 回收塔控制 |
| CN107941039B (zh) * | 2016-10-12 | 2020-03-03 | 英尼奥斯欧洲股份公司 | 骤冷塔后冷却器 |
| CN112439310B (zh) * | 2019-09-05 | 2023-08-11 | 中石油吉林化工工程有限公司 | 一种丙烯腈装置急冷塔用水的补充方法 |
| WO2024089543A1 (en) * | 2022-10-26 | 2024-05-02 | Inv Nylon Chemicals Americas, Llc | Production of cyano-containing compounds |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3691226A (en) * | 1970-11-12 | 1972-09-12 | Du Pont | Anti-foulant in acrylonitrile manufacture |
| US4720566A (en) * | 1986-10-23 | 1988-01-19 | Betz Laboratories, Inc. | Method and composition for inhibiting acrylonitrile polymerization |
| JPH02248402A (ja) * | 1989-03-22 | 1990-10-04 | Mitsubishi Petrochem Co Ltd | アクリル酸エステル類の重合禁止剤及び重合禁止方法 |
| CA2099168A1 (en) * | 1992-10-21 | 1994-04-22 | Betzdearborn Inc. | Compositions and methods for inhibiting styrene polymerization |
| ES2096220T3 (es) * | 1992-10-21 | 1997-03-01 | Betz Europ Inc | Composiciones y metodos para inhibir la polimerizacion de monomeros vinil-aromaticos. |
| US5648574A (en) * | 1992-10-21 | 1997-07-15 | Betzdearborn Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| US5416258A (en) * | 1994-01-14 | 1995-05-16 | Betz Laboratories, Inc. | Methods for inhibiting ethylenically unsaturated monomers |
| US5396005A (en) * | 1994-01-19 | 1995-03-07 | Betz Laboratories, Inc. | Compositions and methods for inhibiting polymerization of ethlenically unsaturated monomers |
| US5446220A (en) * | 1994-08-24 | 1995-08-29 | Betz Laboratories, Inc. | Methods for inhibiting vinyl aromatic monomer polymerization |
| US5426257A (en) * | 1994-06-30 | 1995-06-20 | Betz Laboratories, Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| US5489720A (en) * | 1994-06-30 | 1996-02-06 | Betz Laboratories, Inc. | Methods for inhibiting vinyl aromatic monomer polymerization |
| JP3673292B2 (ja) * | 1994-07-27 | 2005-07-20 | 伯東株式会社 | ビニル化合物を扱う工程でのファウリング防止方法 |
| US6608226B1 (en) * | 1995-06-07 | 2003-08-19 | Baker Hughes Incorporated | Use of phenylenediamines and hindered phenols to inhibit polymer formation during the manufacture of acrylonitrile |
| EP0938469B1 (en) * | 1996-10-23 | 2001-06-20 | Solutia Inc. | Process for purifying acrylonitrile |
| BR9811126A (pt) * | 1997-08-07 | 2000-07-18 | Basf Ag | Processo de estabilizar os ésteres do ácido (met) acrìlico |
| JPH11246495A (ja) * | 1998-03-05 | 1999-09-14 | Nippon Shokubai Co Ltd | アルキルアミノ（メタ）アクリレートを製造する方法 |
| US5869730A (en) * | 1998-05-13 | 1999-02-09 | The Standard Oil Company | Oxidant reduction by manipulation and/or treatment of aqueous acrylonitrile process streams |
| US6238574B1 (en) * | 1998-10-30 | 2001-05-29 | The Standard Oil Company | Oxidation and ammoxidation of acrylonitrile process waste water organics |
| US6107509A (en) * | 1999-03-31 | 2000-08-22 | The Standard Oil Company | Process for the recovery of acrylonitrile and methacrylontrile |
| US6084121A (en) * | 1999-09-09 | 2000-07-04 | E. I. Du Pont De Nemours And Company | Nitrile process |
| US6262323B1 (en) * | 1999-12-14 | 2001-07-17 | Baker Hughes Incorporated | Polymerization inhibition of isoprene |
| US6403850B1 (en) | 2000-01-18 | 2002-06-11 | Uniroyal Chemical Company, Inc. | Inhibition of polymerization of unsaturated monomers |
-
2002
- 2002-12-04 US US10/309,962 patent/US6984749B2/en not_active Expired - Fee Related
-
2003
- 2003-11-12 CN CNB2003801052380A patent/CN100390139C/zh not_active Expired - Fee Related
- 2003-11-12 JP JP2004559113A patent/JP2006509030A/ja not_active Withdrawn
- 2003-11-12 WO PCT/US2003/036060 patent/WO2004052842A1/en active Application Filing
- 2003-11-12 ES ES03781907T patent/ES2306907T3/es not_active Expired - Lifetime
- 2003-11-12 AT AT03781907T patent/ATE400549T1/de not_active IP Right Cessation
- 2003-11-12 CA CA002506409A patent/CA2506409A1/en not_active Abandoned
- 2003-11-12 AU AU2003287702A patent/AU2003287702A1/en not_active Abandoned
- 2003-11-12 BR BR0316857-3A patent/BR0316857A/pt not_active Application Discontinuation
- 2003-11-12 EP EP03781907A patent/EP1567481B1/en not_active Expired - Lifetime
- 2003-11-12 MX MXPA05005847A patent/MXPA05005847A/es active IP Right Grant
- 2003-11-12 KR KR1020057010225A patent/KR101026343B1/ko not_active IP Right Cessation
- 2003-11-12 RU RU2005120625/04A patent/RU2324677C2/ru not_active IP Right Cessation
- 2003-11-12 DE DE60322095T patent/DE60322095D1/de not_active Expired - Lifetime
- 2003-11-20 TW TW092132590A patent/TWI312774B/zh active
- 2003-11-28 MY MYPI20034567A patent/MY141089A/en unknown
-
2004
- 2004-05-24 US US10/852,277 patent/US7282600B2/en not_active Expired - Fee Related
-
2005
- 2005-05-23 ZA ZA200504177A patent/ZA200504177B/en unknown
-
2010
- 2010-11-12 JP JP2010253574A patent/JP2011063607A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US7282600B2 (en) | 2007-10-16 |
| MXPA05005847A (es) | 2005-09-21 |
| RU2324677C2 (ru) | 2008-05-20 |
| ATE400549T1 (de) | 2008-07-15 |
| BR0316857A (pt) | 2005-10-18 |
| US6984749B2 (en) | 2006-01-10 |
| WO2004052842A1 (en) | 2004-06-24 |
| EP1567481B1 (en) | 2008-07-09 |
| TWI312774B (en) | 2009-08-01 |
| TW200420528A (en) | 2004-10-16 |
| KR20050088410A (ko) | 2005-09-06 |
| CA2506409A1 (en) | 2004-06-24 |
| US20040110977A1 (en) | 2004-06-10 |
| RU2005120625A (ru) | 2006-01-20 |
| AU2003287702A1 (en) | 2004-06-30 |
| KR101026343B1 (ko) | 2011-04-04 |
| DE60322095D1 (de) | 2008-08-21 |
| CN100390139C (zh) | 2008-05-28 |
| JP2011063607A (ja) | 2011-03-31 |
| ES2306907T3 (es) | 2008-11-16 |
| US20040249182A1 (en) | 2004-12-09 |
| CN1720220A (zh) | 2006-01-11 |
| EP1567481A1 (en) | 2005-08-31 |
| JP2006509030A (ja) | 2006-03-16 |
| MY141089A (en) | 2010-03-15 |
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