CN101104586B - 丙烯酸酯的制备方法 - Google Patents
丙烯酸酯的制备方法 Download PDFInfo
- Publication number
- CN101104586B CN101104586B CN2007101124800A CN200710112480A CN101104586B CN 101104586 B CN101104586 B CN 101104586B CN 2007101124800 A CN2007101124800 A CN 2007101124800A CN 200710112480 A CN200710112480 A CN 200710112480A CN 101104586 B CN101104586 B CN 101104586B
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- China
- Prior art keywords
- acrylate
- tower
- acid
- knockout tower
- boils
- 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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- 238000000034 method Methods 0.000 title claims abstract description 32
- -1 acrylic ester Chemical class 0.000 title abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000002253 acid Substances 0.000 claims abstract description 87
- 238000009835 boiling Methods 0.000 claims abstract description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000010409 thin film Substances 0.000 claims abstract description 33
- 239000002994 raw material Substances 0.000 claims abstract description 32
- 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 23
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 139
- 238000002360 preparation method Methods 0.000 claims description 73
- 239000000470 constituent Substances 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 239000002351 wastewater Substances 0.000 claims description 36
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- 239000012074 organic phase Substances 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 26
- 238000005886 esterification reaction Methods 0.000 claims description 23
- 238000000605 extraction Methods 0.000 claims description 22
- 241000282326 Felis catus Species 0.000 claims description 20
- 230000032050 esterification Effects 0.000 claims description 20
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 150000002191 fatty alcohols Chemical class 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000010408 film Substances 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000011084 recovery Methods 0.000 abstract description 13
- 238000000926 separation method Methods 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 50
- 239000007788 liquid Substances 0.000 description 34
- 239000002699 waste material Substances 0.000 description 34
- 238000005516 engineering process Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- 230000009466 transformation Effects 0.000 description 14
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 125000005396 acrylic acid ester group Chemical group 0.000 description 7
- 238000003809 water extraction Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 230000006837 decompression Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 238000004065 wastewater treatment Methods 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000008676 import Effects 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006-190889 | 2006-07-11 | ||
| JP2006190889A JP4160087B2 (ja) | 2006-07-11 | 2006-07-11 | アクリル酸エステルの製造方法 |
| JP2006190889 | 2006-07-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101104586A CN101104586A (zh) | 2008-01-16 |
| CN101104586B true CN101104586B (zh) | 2011-06-08 |
Family
ID=38950102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007101124800A Active CN101104586B (zh) | 2006-07-11 | 2007-06-28 | 丙烯酸酯的制备方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7491841B2 (enExample) |
| JP (1) | JP4160087B2 (enExample) |
| CN (1) | CN101104586B (enExample) |
| SA (1) | SA07280369B1 (enExample) |
| TW (1) | TW200808716A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008060218A1 (de) * | 2008-12-04 | 2010-06-10 | Evonik Stockhausen Gmbh | Aufarbeitungsverfahren bei der Herstellung von (Meth)Acrylsäurealkylestern |
| TWI415836B (zh) * | 2011-10-19 | 2013-11-21 | Shiny Chemical Ind Co Ltd | A process for preparing an alkyl diol alkyl ether (meth) acrylate |
| FR2982258B1 (fr) * | 2011-11-04 | 2013-11-15 | Arkema France | Procede de production d'acrylate de 2-octyle par esterification directe |
| CN102675098A (zh) * | 2012-05-29 | 2012-09-19 | 江门谦信化工发展有限公司 | 一种丙烯酸丁酯连续生产新工艺 |
| CN104761450B (zh) * | 2012-12-20 | 2016-08-24 | 常州市松盛香料有限公司 | 丙酸乙酯的制备方法 |
| FR3024143B1 (fr) * | 2014-07-28 | 2016-07-15 | Arkema France | Procede perfectionne de fabrication de (meth)acrylates d'alkyle |
| CN107011165B (zh) * | 2017-04-24 | 2020-07-03 | 朱大春 | Uv光固化单体连续化生产方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3882167A (en) * | 1972-06-02 | 1975-05-06 | Hoechst Ag | Process for the manufacture of acrylic acid esters |
| US4956493A (en) * | 1987-04-16 | 1990-09-11 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Process for producing methacrylic ester |
| CN1164528A (zh) * | 1996-02-06 | 1997-11-12 | 巴斯福股份公司 | (甲基)丙烯酸烷基酯的连续制备方法 |
| CN1326431A (zh) * | 1998-11-11 | 2001-12-12 | 巴斯福股份公司 | (甲基)丙烯酸烷基酯的连续制备 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2548561C2 (de) | 1975-10-30 | 1983-09-29 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen Herstellung dioctylätherfreien 2-Äthyl- hexylacrylats |
| JPS58159442A (ja) | 1982-03-17 | 1983-09-21 | Nippon Kayaku Co Ltd | アクリル酸エステル又はメタクリル酸エステルの製造方法 |
| JPS63275544A (ja) | 1987-05-06 | 1988-11-14 | Osaka Yuki Kagaku Kogyo Kk | エステルの安定化方法 |
| JPH0686406B2 (ja) | 1989-04-21 | 1994-11-02 | 株式会社日本触媒 | アクリル酸エステルの製造方法 |
| JPH0764791B2 (ja) | 1989-06-30 | 1995-07-12 | 出光石油化学株式会社 | アクリル酸エステル又はメタクリル酸エステルの製造方法 |
| JPH0686407B2 (ja) | 1989-07-21 | 1994-11-02 | 株式会社日本触媒 | メタクリル酸エステルの製造方法 |
| JPH0699365B2 (ja) | 1989-07-21 | 1994-12-07 | 株式会社日本触媒 | アクリル酸エステルの製造法 |
| DE3935470A1 (de) | 1989-10-25 | 1991-05-02 | Hoechst Ag | Verfahren zur kontinuierlichen herstellung von estern niederer aliphatischer carbonsaeuren mit niederen alkoholen |
| US6649787B1 (en) * | 1999-10-12 | 2003-11-18 | Nippon Shokubai Co., Ltd. | Method for preparing (meth) acrylic acid ester |
| JP3981550B2 (ja) | 2001-12-03 | 2007-09-26 | 三菱化学株式会社 | アクリル酸エステルの製造方法 |
| JP2003226669A (ja) | 2001-11-28 | 2003-08-12 | Mitsubishi Chemicals Corp | (メタ)アクリル酸エステルの製造方法 |
| DE10200171A1 (de) * | 2002-01-04 | 2003-07-10 | Roehm Gmbh | Verfahren zur kontinuierlichen Herstellung von Alkyl(meth)acrylaten |
-
2006
- 2006-07-11 JP JP2006190889A patent/JP4160087B2/ja active Active
-
2007
- 2007-06-28 CN CN2007101124800A patent/CN101104586B/zh active Active
- 2007-06-28 TW TW096123438A patent/TW200808716A/zh unknown
- 2007-07-06 US US11/822,521 patent/US7491841B2/en active Active
- 2007-07-10 SA SA07280369A patent/SA07280369B1/ar unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3882167A (en) * | 1972-06-02 | 1975-05-06 | Hoechst Ag | Process for the manufacture of acrylic acid esters |
| US4956493A (en) * | 1987-04-16 | 1990-09-11 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Process for producing methacrylic ester |
| CN1164528A (zh) * | 1996-02-06 | 1997-11-12 | 巴斯福股份公司 | (甲基)丙烯酸烷基酯的连续制备方法 |
| CN1326431A (zh) * | 1998-11-11 | 2001-12-12 | 巴斯福股份公司 | (甲基)丙烯酸烷基酯的连续制备 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101104586A (zh) | 2008-01-16 |
| JP2008019189A (ja) | 2008-01-31 |
| SA07280369B1 (ar) | 2011-10-08 |
| TWI353976B (enExample) | 2011-12-11 |
| JP4160087B2 (ja) | 2008-10-01 |
| US7491841B2 (en) | 2009-02-17 |
| TW200808716A (en) | 2008-02-16 |
| US20080015384A1 (en) | 2008-01-17 |
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| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |