ZA200409151B - Process for producing (meth)acrolein or (meth)acrylic acid - Google Patents
Process for producing (meth)acrolein or (meth)acrylic acid Download PDFInfo
- Publication number
- ZA200409151B ZA200409151B ZA200409151A ZA200409151A ZA200409151B ZA 200409151 B ZA200409151 B ZA 200409151B ZA 200409151 A ZA200409151 A ZA 200409151A ZA 200409151 A ZA200409151 A ZA 200409151A ZA 200409151 B ZA200409151 B ZA 200409151B
- Authority
- ZA
- South Africa
- Prior art keywords
- low
- steps
- boiling fraction
- series
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 96
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims description 48
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 19
- 238000009835 boiling Methods 0.000 claims description 105
- 238000007254 oxidation reaction Methods 0.000 claims description 89
- 239000012495 reaction gas Substances 0.000 claims description 74
- 238000001816 cooling Methods 0.000 claims description 69
- 238000000926 separation method Methods 0.000 claims description 64
- 238000000746 purification Methods 0.000 claims description 30
- 238000000354 decomposition reaction Methods 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 230000003647 oxidation Effects 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 10
- 230000003197 catalytic effect Effects 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 33
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 31
- 238000004519 manufacturing process Methods 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 15
- 238000012856 packing Methods 0.000 description 15
- 238000004821 distillation Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
- 239000002994 raw material Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 7
- 238000004064 recycling Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000003889 chemical engineering Methods 0.000 description 2
- KGGZTXSNARMULX-UHFFFAOYSA-L copper;dicarbamodithioate Chemical class [Cu+2].NC([S-])=S.NC([S-])=S KGGZTXSNARMULX-UHFFFAOYSA-L 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000002990 phenothiazines Chemical class 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- STGFANHLXUILNY-UHFFFAOYSA-N 3,7-dioctyl-10h-phenothiazine Chemical compound C1=C(CCCCCCCC)C=C2SC3=CC(CCCCCCCC)=CC=C3NC2=C1 STGFANHLXUILNY-UHFFFAOYSA-N 0.000 description 1
- BCFGABRSRXBITB-UHFFFAOYSA-N 4-carbamothioylsulfanylbutyl carbamodithioate Chemical compound NC(=S)SCCCCSC(N)=S BCFGABRSRXBITB-UHFFFAOYSA-N 0.000 description 1
- QNTARNCGFNQQRP-UHFFFAOYSA-N 5-carbamothioylsulfanylpentyl carbamodithioate Chemical compound NC(=S)SCCCCCSC(N)=S QNTARNCGFNQQRP-UHFFFAOYSA-N 0.000 description 1
- 229910002909 Bi-Te Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- IULVMSRZVAOLEB-UHFFFAOYSA-N azepane-1-carbodithioic acid Chemical compound SC(=S)N1CCCCCC1 IULVMSRZVAOLEB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 description 1
- OBBCYCYCTJQCCK-UHFFFAOYSA-L copper;n,n-diethylcarbamodithioate Chemical compound [Cu+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S OBBCYCYCTJQCCK-UHFFFAOYSA-L 0.000 description 1
- ZOUQIAGHKFLHIA-UHFFFAOYSA-L copper;n,n-dimethylcarbamodithioate Chemical compound [Cu+2].CN(C)C([S-])=S.CN(C)C([S-])=S ZOUQIAGHKFLHIA-UHFFFAOYSA-L 0.000 description 1
- UQMKZLGQBFCRSN-UHFFFAOYSA-L copper;n,n-dipropylcarbamodithioate Chemical compound [Cu+2].CCCN(C([S-])=S)CCC.CCCN(C([S-])=S)CCC UQMKZLGQBFCRSN-UHFFFAOYSA-L 0.000 description 1
- XPLSDXJBKRIVFZ-UHFFFAOYSA-L copper;prop-2-enoate Chemical compound [Cu+2].[O-]C(=O)C=C.[O-]C(=O)C=C XPLSDXJBKRIVFZ-UHFFFAOYSA-L 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- -1 methoquinone Chemical compound 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| JP2004154105A JP2005336065A (ja) | 2004-05-25 | 2004-05-25 | （メタ）アクロレイン又は（メタ）アクリル酸の製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200409151B true ZA200409151B (en) | 2008-01-30 |
Family
ID=35350119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200409151A ZA200409151B (en) | 2004-05-25 | 2004-11-11 | Process for producing (meth)acrolein or (meth)acrylic acid |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20050267313A1 (pt) |
| EP (1) | EP1749811A4 (pt) |
| JP (1) | JP2005336065A (pt) |
| CN (1) | CN1697798A (pt) |
| AU (1) | AU2004233471A1 (pt) |
| BR (1) | BRPI0405226A (pt) |
| RU (1) | RU2004136183A (pt) |
| WO (1) | WO2005115953A1 (pt) |
| ZA (1) | ZA200409151B (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103391914B (zh) * | 2011-03-11 | 2016-01-20 | Lg化学株式会社 | 一种（甲基）丙烯酸的连续收集方法及收集装置 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51136611A (en) * | 1975-05-23 | 1976-11-26 | Asahi Glass Co Ltd | Separation and recovery of unsaturated aldehyde and/or unsaturated car boxylic acid |
| FR2727964B1 (fr) * | 1994-12-12 | 1997-01-24 | Atochem Elf Sa | Procede de recuperation des produits nobles legers contenus dans les residus de distillation des procedes de fabrication de l'acide acrylique et de ses esters |
| DE19838783A1 (de) * | 1998-08-26 | 2000-03-02 | Basf Ag | Verfahren zur kontinuierlichen Gewinnung von (Meth)acrylsäure |
| WO2000051954A1 (fr) * | 1999-03-03 | 2000-09-08 | Asahi Kasei Kabushiki Kaisha | Procede d'elaboration continue de carbonate dialcoyle et de diol |
| JP4416889B2 (ja) * | 1999-12-15 | 2010-02-17 | 株式会社日本触媒 | 固体触媒の廃棄方法 |
| KR100740728B1 (ko) * | 2000-06-14 | 2007-07-19 | 바스프 악티엔게젤샤프트 | 아크롤레인 및(또는) 아크릴산의 제조 방법 |
| JP2003073327A (ja) * | 2001-09-03 | 2003-03-12 | Nippon Shokubai Co Ltd | 有機酸の製造方法 |
| KR100594671B1 (ko) * | 2002-03-06 | 2006-06-30 | 미쯔비시 레이온 가부시끼가이샤 | 중합 용이성 물질의 취급방법 및 중합 용이성 물질의취급장치 |
| JP4440518B2 (ja) * | 2002-07-16 | 2010-03-24 | 株式会社日本触媒 | アクリル酸の製造方法 |
| JP3971974B2 (ja) * | 2002-09-03 | 2007-09-05 | 三菱化学株式会社 | （メタ）アクリル酸類の製造方法 |
-
2004
- 2004-05-25 JP JP2004154105A patent/JP2005336065A/ja active Pending
- 2004-08-09 CN CNA2004800003428A patent/CN1697798A/zh active Pending
- 2004-08-09 AU AU2004233471A patent/AU2004233471A1/en not_active Abandoned
- 2004-08-09 EP EP04771434A patent/EP1749811A4/en not_active Withdrawn
- 2004-08-09 BR BRPI0405226-9A patent/BRPI0405226A/pt not_active IP Right Cessation
- 2004-08-09 RU RU2004136183/04A patent/RU2004136183A/ru not_active Application Discontinuation
- 2004-08-09 WO PCT/JP2004/011447 patent/WO2005115953A1/ja not_active Application Discontinuation
- 2004-11-10 US US10/985,015 patent/US20050267313A1/en not_active Abandoned
- 2004-11-11 ZA ZA200409151A patent/ZA200409151B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0405226A (pt) | 2006-02-21 |
| WO2005115953A1 (ja) | 2005-12-08 |
| CN1697798A (zh) | 2005-11-16 |
| RU2004136183A (ru) | 2006-01-27 |
| JP2005336065A (ja) | 2005-12-08 |
| AU2004233471A1 (en) | 2005-12-15 |
| US20050267313A1 (en) | 2005-12-01 |
| EP1749811A4 (en) | 2007-11-14 |
| EP1749811A1 (en) | 2007-02-07 |
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