JPS6135977B2 - - Google Patents
Info
- Publication number
- JPS6135977B2 JPS6135977B2 JP53003753A JP375378A JPS6135977B2 JP S6135977 B2 JPS6135977 B2 JP S6135977B2 JP 53003753 A JP53003753 A JP 53003753A JP 375378 A JP375378 A JP 375378A JP S6135977 B2 JPS6135977 B2 JP S6135977B2
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- dimer
- acid dimer
- decomposition
- liquid
- 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.)
- Expired
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 129
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 125
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 100
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 99
- 239000007788 liquid Substances 0.000 claims description 62
- 238000000354 decomposition reaction Methods 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 38
- 238000001704 evaporation Methods 0.000 claims description 35
- 230000008020 evaporation Effects 0.000 claims description 32
- 238000006116 polymerization reaction Methods 0.000 claims description 28
- 239000003112 inhibitor Substances 0.000 claims description 27
- 238000000926 separation method Methods 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 13
- 238000000746 purification Methods 0.000 claims description 13
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000011084 recovery Methods 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000539 dimer Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- JTEIDNQWGDEGMK-UHFFFAOYSA-N benzene-1,4-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC1=CC=C(O)C=C1 JTEIDNQWGDEGMK-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- -1 that is Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP375378A JPS5498718A (en) | 1978-01-19 | 1978-01-19 | Recovery of acrylic acid |
| US06/003,405 US4317926A (en) | 1978-01-19 | 1979-01-15 | Process for preparing and recovering acrylic acid |
| DE19792901783 DE2901783A1 (de) | 1978-01-19 | 1979-01-18 | Verfahren zur rueckgewinnung von akrylsaeure |
| SU792713493A SU1169528A3 (ru) | 1978-01-19 | 1979-01-18 | Способ выделени акриловой кислоты |
| FR7901403A FR2415092A1 (fr) | 1978-01-19 | 1979-01-19 | Procede pour valoriser les oligomeres de l'acide acrylique obtenus a la preparation de ce compose en recuperant simultanement l'hydroquinone utilisee comme inhibiteur de polymerisation |
| GB792038A GB2012760B (en) | 1978-01-19 | 1979-01-19 | Process for recovering acrylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP375378A JPS5498718A (en) | 1978-01-19 | 1978-01-19 | Recovery of acrylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5498718A JPS5498718A (en) | 1979-08-03 |
| JPS6135977B2 true JPS6135977B2 (ru) | 1986-08-15 |
Family
ID=11565941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP375378A Granted JPS5498718A (en) | 1978-01-19 | 1978-01-19 | Recovery of acrylic acid |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5498718A (ru) |
| SU (1) | SU1169528A3 (ru) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009133813A1 (ja) | 2008-04-27 | 2009-11-05 | 株式会社日本触媒 | アクリル酸の製造方法ならびにその製造方法を用いた親水性樹脂の製造方法および吸水性樹脂の製造方法 |
| US10239815B2 (en) | 2015-02-05 | 2019-03-26 | Nippon Shokubai Co., Ltd. | Method for producing acrylic acid |
| US11001955B2 (en) | 2017-09-29 | 2021-05-11 | Samsung Electronics Co., Ltd. | Bubble generator and washing machine having the same |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4542214B2 (ja) * | 1999-08-20 | 2010-09-08 | 株式会社日本触媒 | アクリル酸の精製方法 |
| WO2003043968A1 (en) | 2001-11-20 | 2003-05-30 | Mitsubishi Chemical Corporation | Process for producing (meth)acrylic acid compounds |
| JP2005179352A (ja) * | 2003-11-28 | 2005-07-07 | Mitsubishi Chemicals Corp | （メタ）アクリル酸の精製方法 |
| AU2004293262A1 (en) | 2003-11-28 | 2005-06-09 | Mitsubishi Chemical Corporation | Method and apparatus for collecting (meth)acrolein or (meth)acrylic acid |
| DE102004008575A1 (de) * | 2004-02-19 | 2005-09-08 | Stockhausen Gmbh | Spaltung oligomerer (Meth)acrylsäure in flüssiger Phase unter Druck |
| JP2005239636A (ja) * | 2004-02-26 | 2005-09-08 | Mitsubishi Chemicals Corp | 高粘性物質の取扱い方法 |
| KR101861855B1 (ko) * | 2008-07-28 | 2018-05-28 | 바스프 에스이 | 탄소원자 수가 ３개인 아크릴산의 전구체 화합물의 기체상 생성물 혼합물로부터 주성분으로서 함유된 아크릴산과 부산물로서 함유된 글리옥살을 분리시키는 방법 |
| US10703702B2 (en) | 2015-07-31 | 2020-07-07 | Novomer, Inc. | Production system/production process for acrylic acid and precursors thereof |
| WO2020185420A1 (en) | 2019-03-08 | 2020-09-17 | Novomer, Inc. | Integrated methods and systems for producing amide and nitrile compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5452038A (en) * | 1977-09-28 | 1979-04-24 | Nippon Shokubai Kagaku Kogyo Co Ltd | Recovery hydroquinone |
-
1978
- 1978-01-19 JP JP375378A patent/JPS5498718A/ja active Granted
-
1979
- 1979-01-18 SU SU792713493A patent/SU1169528A3/ru active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5452038A (en) * | 1977-09-28 | 1979-04-24 | Nippon Shokubai Kagaku Kogyo Co Ltd | Recovery hydroquinone |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009133813A1 (ja) | 2008-04-27 | 2009-11-05 | 株式会社日本触媒 | アクリル酸の製造方法ならびにその製造方法を用いた親水性樹脂の製造方法および吸水性樹脂の製造方法 |
| US10239815B2 (en) | 2015-02-05 | 2019-03-26 | Nippon Shokubai Co., Ltd. | Method for producing acrylic acid |
| US11001955B2 (en) | 2017-09-29 | 2021-05-11 | Samsung Electronics Co., Ltd. | Bubble generator and washing machine having the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5498718A (en) | 1979-08-03 |
| SU1169528A3 (ru) | 1985-07-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3938646B2 (ja) | アクリル酸の製造方法 | |
| EP0887334B1 (en) | Method for recovering acrylic acid | |
| JP3332594B2 (ja) | 酢酸の精製方法 | |
| EP1818324B1 (en) | Process for producing (Meth) acrylic acid | |
| US8308913B2 (en) | Apparatus for recovering acrylic acid | |
| US4199410A (en) | Purification of crude acrylic acid | |
| US4599144A (en) | Process for recovery of methacrylic acid | |
| JPS6135977B2 (ru) | ||
| WO2018216699A1 (ja) | （メタ）アクリル酸の製造方法 | |
| JP4759153B2 (ja) | （メタ）アクリル酸溶液の蒸留方法 | |
| JPH089567B2 (ja) | アクリル酸製造においてアクリル酸を高純度に精製する方法 | |
| JP3905810B2 (ja) | アクリル酸製造プロセスにおける重合防止方法 | |
| JPS582219B2 (ja) | メタクリル酸の回収法 | |
| JPS6059889B2 (ja) | ハイドロキノンの回収方法 | |
| JP2980366B2 (ja) | アクリル酸の精製方法 | |
| JP3832868B2 (ja) | アクリル酸の精製法 | |
| JPS6136501B2 (ru) | ||
| JPH0425259B2 (ru) | ||
| US6494996B2 (en) | Process for removing water from aqueous methanol | |
| JP2002193875A (ja) | メタクリル酸の回収方法 | |
| JPS58140039A (ja) | アクリル酸の精製方法 | |
| JPH0725814A (ja) | 高純度酢酸の製造方法 | |
| JP3937495B2 (ja) | アクリル酸の回収方法 | |
| JPH0764776B2 (ja) | メタクロレインの吸収方法 | |
| JPS5938233B2 (ja) | プロピレンオキシド含有溶液の分離方法 |