ZA200302087B - Nitrile process. - Google Patents
Nitrile process. Download PDFInfo
- Publication number
- ZA200302087B ZA200302087B ZA200302087A ZA200302087A ZA200302087B ZA 200302087 B ZA200302087 B ZA 200302087B ZA 200302087 A ZA200302087 A ZA 200302087A ZA 200302087 A ZA200302087 A ZA 200302087A ZA 200302087 B ZA200302087 B ZA 200302087B
- Authority
- ZA
- South Africa
- Prior art keywords
- acid
- product mixture
- process according
- acrylonitrile
- nitrile
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- 150000002825 nitriles Chemical class 0.000 title claims description 29
- 239000002253 acid Substances 0.000 claims description 51
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 36
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 30
- 229910021529 ammonia Inorganic materials 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 5
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 5
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 5
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 5
- 229940018557 citraconic acid Drugs 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 239000004310 lactic acid Substances 0.000 claims description 5
- 235000014655 lactic acid Nutrition 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000011084 recovery Methods 0.000 description 6
- -1 surface coatings Substances 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 241001550224 Apha Species 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
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 |
|---|---|---|---|
| US09/710,996 US6355828B1 (en) | 2000-11-10 | 2000-11-10 | Nitrile process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302087B true ZA200302087B (en) | 2004-07-12 |
Family
ID=24856362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200302087A ZA200302087B (en) | 2000-11-10 | 2003-03-14 | Nitrile process. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6355828B1 (fr) |
| EP (1) | EP1332177B1 (fr) |
| JP (1) | JP2004526677A (fr) |
| CN (1) | CN1296348C (fr) |
| AU (1) | AU2002241600A1 (fr) |
| BR (1) | BR0115459A (fr) |
| DE (1) | DE60135923D1 (fr) |
| ES (1) | ES2311557T3 (fr) |
| TW (1) | TWI291949B (fr) |
| WO (1) | WO2002046293A2 (fr) |
| ZA (1) | ZA200302087B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6355828B1 (en) * | 2000-11-10 | 2002-03-12 | E. I. Du Pont De Nemours And Company | Nitrile process |
| US8585870B2 (en) * | 2008-03-05 | 2013-11-19 | E I Du Pont De Nemours And Company | Process to C-manufacture acrylonitrile and hydrogen cyanide |
| CN103984369A (zh) | 2014-05-19 | 2014-08-13 | 英尼奥斯欧洲股份公司 | 丙烯腈产物的在线分析 |
| CN103991653B (zh) * | 2014-06-09 | 2018-03-20 | 英尼奥斯欧洲股份公司 | 粗制丙烯腈罐 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3049408A (en) | 1960-05-12 | 1962-08-14 | Monsanto Chemicals | Stabilization of hydrogen cyanide |
| US3936360A (en) | 1971-04-07 | 1976-02-03 | The Standard Oil Company | Process for distillation and recovery of olefinic nitriles |
| US3734943A (en) | 1971-05-06 | 1973-05-22 | Standard Oil Co | Deep well disposal process for acrylonitrile process waste water |
| US4238295A (en) | 1978-12-04 | 1980-12-09 | Standard Oil Company | Energy efficient recovery of acrylonitrile |
| US4269667A (en) | 1979-08-02 | 1981-05-26 | Standard Oil Company | Acrylonitrile purification by extractive distillation |
| US4981670A (en) | 1989-12-15 | 1991-01-01 | Bp America Inc. | HCN from crude aceto |
| US6084121A (en) | 1999-09-09 | 2000-07-04 | E. I. Du Pont De Nemours And Company | Nitrile process |
| US6355828B1 (en) * | 2000-11-10 | 2002-03-12 | E. I. Du Pont De Nemours And Company | Nitrile process |
-
2000
- 2000-11-10 US US09/710,996 patent/US6355828B1/en not_active Expired - Lifetime
-
2001
- 2001-10-17 TW TW090125669A patent/TWI291949B/zh active
- 2001-11-06 WO PCT/US2001/046985 patent/WO2002046293A2/fr active Application Filing
- 2001-11-06 CN CNB018186742A patent/CN1296348C/zh not_active Expired - Lifetime
- 2001-11-06 DE DE60135923T patent/DE60135923D1/de not_active Expired - Lifetime
- 2001-11-06 AU AU2002241600A patent/AU2002241600A1/en not_active Abandoned
- 2001-11-06 BR BR0115459-1A patent/BR0115459A/pt not_active Application Discontinuation
- 2001-11-06 ES ES01988279T patent/ES2311557T3/es not_active Expired - Lifetime
- 2001-11-06 EP EP01988279A patent/EP1332177B1/fr not_active Expired - Lifetime
- 2001-11-06 JP JP2002548021A patent/JP2004526677A/ja active Pending
-
2003
- 2003-03-14 ZA ZA200302087A patent/ZA200302087B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE60135923D1 (de) | 2008-11-06 |
| TWI291949B (en) | 2008-01-01 |
| JP2004526677A (ja) | 2004-09-02 |
| AU2002241600A1 (en) | 2002-06-18 |
| EP1332177A4 (fr) | 2005-12-28 |
| ES2311557T3 (es) | 2009-02-16 |
| WO2002046293B1 (fr) | 2003-05-15 |
| US6355828B1 (en) | 2002-03-12 |
| BR0115459A (pt) | 2003-08-19 |
| EP1332177B1 (fr) | 2008-09-24 |
| CN1296348C (zh) | 2007-01-24 |
| CN1529693A (zh) | 2004-09-15 |
| WO2002046293A2 (fr) | 2002-06-13 |
| EP1332177A2 (fr) | 2003-08-06 |
| WO2002046293A3 (fr) | 2003-03-13 |
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