CN101148404B - (甲基)丙烯酸的制备方法 - Google Patents
(甲基)丙烯酸的制备方法 Download PDFInfo
- Publication number
- CN101148404B CN101148404B CN2007101518111A CN200710151811A CN101148404B CN 101148404 B CN101148404 B CN 101148404B CN 2007101518111 A CN2007101518111 A CN 2007101518111A CN 200710151811 A CN200710151811 A CN 200710151811A CN 101148404 B CN101148404 B CN 101148404B
- Authority
- CN
- China
- Prior art keywords
- acrylic acid
- methyl
- acid solution
- quality
- moisture concentration
- 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.)
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Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 26
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 228
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 296
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 239
- 238000002425 crystallisation Methods 0.000 claims abstract description 102
- 230000008025 crystallization Effects 0.000 claims abstract description 101
- 239000007788 liquid Substances 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 23
- 230000003197 catalytic effect Effects 0.000 claims description 20
- 238000007254 oxidation reaction Methods 0.000 claims description 20
- 230000014759 maintenance of location Effects 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 238000007086 side reaction Methods 0.000 claims description 11
- 239000012808 vapor phase Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 9
- 238000011144 upstream manufacturing Methods 0.000 claims description 5
- 230000000717 retained effect Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 abstract description 25
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 212
- 238000007670 refining Methods 0.000 description 61
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 42
- 239000012535 impurity Substances 0.000 description 25
- 239000011259 mixed solution Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 230000003647 oxidation Effects 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 9
- 230000002441 reversible effect Effects 0.000 description 9
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 230000008676 import Effects 0.000 description 6
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 amine compound Chemical class 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000015073 liquid stocks Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006-254955 | 2006-09-20 | ||
| JP2006254955A JP4256887B2 (ja) | 2006-09-20 | 2006-09-20 | （メタ）アクリル酸の製造方法 |
| JP2006254955 | 2006-09-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101148404A CN101148404A (zh) | 2008-03-26 |
| CN101148404B true CN101148404B (zh) | 2012-07-18 |
Family
ID=38961750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007101518111A Active CN101148404B (zh) | 2006-09-20 | 2007-09-18 | (甲基)丙烯酸的制备方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7714164B2 (enExample) |
| EP (1) | EP1903025B1 (enExample) |
| JP (1) | JP4256887B2 (enExample) |
| CN (1) | CN101148404B (enExample) |
| BR (1) | BRPI0705682B1 (enExample) |
| DE (1) | DE602007012971D1 (enExample) |
| SA (1) | SA07280502B1 (enExample) |
| TW (1) | TW200821282A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5606692B2 (ja) * | 2009-06-25 | 2014-10-15 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
| JP5318602B2 (ja) * | 2009-02-03 | 2013-10-16 | 株式会社日本触媒 | アクリル酸結晶の融解方法 |
| US8680330B2 (en) | 2009-02-03 | 2014-03-25 | Nippon Shokubai Co., Ltd. | Process for producing (meth) acrylic acid |
| JP5485585B2 (ja) * | 2009-05-15 | 2014-05-07 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
| CN102414159B (zh) | 2009-05-15 | 2014-02-26 | 株式会社日本触媒 | 制备(甲基)丙烯酸的方法 |
| JP5485584B2 (ja) * | 2009-05-15 | 2014-05-07 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法および晶析システム |
| SG175379A1 (en) | 2009-05-15 | 2011-12-29 | Nippon Catalytic Chem Ind | Process for producing (meth)acrylic acid and crystallization system |
| JP5932506B2 (ja) * | 2012-06-12 | 2016-06-08 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
| DE102014114193A1 (de) * | 2014-09-30 | 2015-08-13 | Basf Se | Verfahren und Anlage zur Rückgewinnung von Acrylsäure |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10036881A1 (de) * | 2000-07-28 | 2002-02-07 | Basf Ag | Verfahren zur Regelung einer Waschkolonne in einem Schmelzkristallisationsprozess und Vorrichtung zur Durchführung des Verfahrens |
| US6677482B2 (en) * | 1999-06-10 | 2004-01-13 | Nippon Shokubai Co, Ltd. | Method of manufacturing (meth) acrylic acid |
| CN1480441A (zh) * | 2002-08-08 | 2004-03-10 | ��ʽ�����ձ���ý | 生产丙烯酸的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3659507B2 (ja) | 1993-09-13 | 2005-06-15 | 月島機械株式会社 | アクリル酸の精製方法 |
| DE50108001D1 (de) | 2000-04-11 | 2005-12-15 | Basf Ag | Verfahren zur reinigung einer rohacrylsäureschmelze |
| JP4601772B2 (ja) | 2000-06-06 | 2010-12-22 | 株式会社日本触媒 | （メタ）アクリル酸およびそのエステルの重合防止方法ならびにこれらの製造方法 |
| JP4456730B2 (ja) | 2000-06-06 | 2010-04-28 | 株式会社日本触媒 | （メタ）アクリル酸またはそのエステルの重合防止方法ならびにこれらの製造方法 |
| JP2001348359A (ja) | 2000-06-06 | 2001-12-18 | Nippon Shokubai Co Ltd | （メタ）アクリル酸およびそのエステルの重合防止方法ならびにこれらの製造方法 |
| JP3957297B2 (ja) | 2003-06-05 | 2007-08-15 | 株式会社日本触媒 | アクリル酸の製造方法 |
| JP2005015478A (ja) | 2003-06-05 | 2005-01-20 | Nippon Shokubai Co Ltd | アクリル酸の製造方法 |
| JP3957298B2 (ja) * | 2003-06-05 | 2007-08-15 | 株式会社日本触媒 | アクリル酸の製造方法 |
| JP2005336110A (ja) | 2004-05-27 | 2005-12-08 | Mitsubishi Chemicals Corp | （メタ）アクリル酸および（メタ）アクリル酸エステルの製造方法 |
-
2006
- 2006-09-20 JP JP2006254955A patent/JP4256887B2/ja active Active
-
2007
- 2007-09-12 TW TW096134029A patent/TW200821282A/zh unknown
- 2007-09-17 SA SA07280502A patent/SA07280502B1/ar unknown
- 2007-09-18 EP EP07018315A patent/EP1903025B1/en active Active
- 2007-09-18 CN CN2007101518111A patent/CN101148404B/zh active Active
- 2007-09-18 DE DE602007012971T patent/DE602007012971D1/de active Active
- 2007-09-19 US US11/902,162 patent/US7714164B2/en active Active
- 2007-09-19 BR BRPI0705682A patent/BRPI0705682B1/pt active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6677482B2 (en) * | 1999-06-10 | 2004-01-13 | Nippon Shokubai Co, Ltd. | Method of manufacturing (meth) acrylic acid |
| DE10036881A1 (de) * | 2000-07-28 | 2002-02-07 | Basf Ag | Verfahren zur Regelung einer Waschkolonne in einem Schmelzkristallisationsprozess und Vorrichtung zur Durchführung des Verfahrens |
| CN1480441A (zh) * | 2002-08-08 | 2004-03-10 | ��ʽ�����ձ���ý | 生产丙烯酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101148404A (zh) | 2008-03-26 |
| EP1903025A1 (en) | 2008-03-26 |
| TW200821282A (en) | 2008-05-16 |
| JP2008074759A (ja) | 2008-04-03 |
| BRPI0705682A (pt) | 2008-06-03 |
| EP1903025B1 (en) | 2011-03-09 |
| JP4256887B2 (ja) | 2009-04-22 |
| BRPI0705682B1 (pt) | 2016-11-08 |
| US20080071111A1 (en) | 2008-03-20 |
| DE602007012971D1 (de) | 2011-04-21 |
| TWI354661B (enExample) | 2011-12-21 |
| US7714164B2 (en) | 2010-05-11 |
| SA07280502B1 (ar) | 2011-08-20 |
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| C06 | Publication | ||
| PB01 | Publication | ||
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| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |