JP5163094B2 - 2−アクリルアミド−2−メチルプロパンスルホン酸の連続製造方法 - Google Patents
2−アクリルアミド−2−メチルプロパンスルホン酸の連続製造方法 Download PDFInfo
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- JP5163094B2 JP5163094B2 JP2007326810A JP2007326810A JP5163094B2 JP 5163094 B2 JP5163094 B2 JP 5163094B2 JP 2007326810 A JP2007326810 A JP 2007326810A JP 2007326810 A JP2007326810 A JP 2007326810A JP 5163094 B2 JP5163094 B2 JP 5163094B2
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- 238000000034 method Methods 0.000 title claims description 15
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 title claims description 11
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 title claims description 11
- 238000010924 continuous production Methods 0.000 title claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 78
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 54
- 239000007788 liquid Substances 0.000 claims description 34
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 27
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 26
- 239000002002 slurry Substances 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 8
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 37
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 21
- 239000006227 byproduct Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000012066 reaction slurry Substances 0.000 description 6
- 239000010779 crude oil Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- XXMFJKNOJSDQBM-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrate Chemical compound [OH3+].[O-]C(=O)C(F)(F)F XXMFJKNOJSDQBM-UHFFFAOYSA-N 0.000 description 1
- WTEXTEJRYNLGNC-UHFFFAOYSA-N 2-methylidenepropane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CC(=C)CS(O)(=O)=O WTEXTEJRYNLGNC-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
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- 229920006158 high molecular weight polymer Polymers 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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Description
以下、上記検討結果を反映するATBSの製造方法について説明する。
HPLC条件;Waters社製 高速液体クロマトグラフ
カラム;Waters社製 X-bridge Shield RP18 (カラムサイズ: 4.6mm(内径)x150mm(長さ))
溶離液;0.03質量%トリフルオロ酢酸水/アセトニトリル(90/10(容量基準))
溶離液流量;0.8ml/min
検出波長;200nm
攪拌機及び入口管と出口管とを備えたガラス反応槽を2個連結し、第1反応槽、第2反応槽を構成した。下記条件でアクリロニトリルおよび発煙硫酸を第1反応槽に仕込み、アクリロニトリルと発煙硫酸とを混合した後、この混合液を第2反応槽に供給した。第2反応槽において、前記混合物中にイソブチレンガスを吹き込み、ATBSを合成した。上記反応は連続的に行った。
表2に示す条件以外は、比較例1と同様に操作した。結果を表2に記載した。
表2に示す条件以外は、比較例1と同様に操作した。結果を表2に記載した。
4、14 ジャケット
6、16 温度調整機
8 アクリロニトリル
10 発煙硫酸
12 第2反応槽
18 イソブチレン
20 取出し管
100 連続製造装置
Claims (3)
- 第1反応槽でアクリロニトリルと発煙硫酸とを混合してこれらの混合液を得、次いで前記第1反応槽で混合した混合液を第2反応槽に供給して第2反応槽で前記混合液とイソブチレンとを反応させて生成するスラリー液を第2反応槽から取出す下記式(3)
で示される2−アクリルアミド-2-メチルプロパンスルホン酸の連続製造方法であって、前記第2反応槽から取出すスラリー液中の下記式(1)
で示される2−メチル−2−プロペニル−1−スルホン酸の濃度が12000質量ppm又は下記式(2)
- 第1反応槽でアクリロニトリルと発煙硫酸とを30分間以上混合してこれらの混合液を得、次いで前記第1反応槽で混合した混合液を第2反応槽に供給して第2反応槽で前記混合液とイソブチレンとを反応させて生成するスラリー液を第2反応槽から取出す下記式(3)
で示される2−メチル−2−プロペニル−1−スルホン酸の濃度を12000質量ppm以下に保ち、かつ下記式(2)
- 請求項1または請求項2に記載の連続製造方法で製造して得られるスラリー液中の2−アクリルアミド-2-メチルプロパンスルホン酸の粗体を濾別してケーキを得、次いでアクリロニトリル、アセトニトリル、アセトン、メタノール、エタノール、2−プロパノール、ブタノール、酢酸エチル、酢酸からなる群から選ばれる1の溶媒又はこれらの混合溶媒を用いて前記ケーキを洗浄する2−アクリルアミド-2-メチルプロパンスルホン酸の連続製造方法。
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JP2007326810A JP5163094B2 (ja) | 2007-12-19 | 2007-12-19 | 2−アクリルアミド−2−メチルプロパンスルホン酸の連続製造方法 |
CN200880117913.4A CN101874017B (zh) | 2007-12-06 | 2008-12-02 | 2-丙烯酰胺-2-甲基丙烷磺酸及其制造方法 |
US12/746,124 US8247601B2 (en) | 2007-12-06 | 2008-12-02 | 2-acrylamide-2-methylpropanesulfonic acid and process for producing the same |
PCT/JP2008/071845 WO2009072480A1 (ja) | 2007-12-06 | 2008-12-02 | 2-アクリルアミド-2-メチルプロパンスルホン酸、及びその製造方法 |
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JP5163094B2 true JP5163094B2 (ja) | 2013-03-13 |
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JP5391824B2 (ja) * | 2009-05-19 | 2014-01-15 | 東亞合成株式会社 | 水系増粘剤及びその製造方法並びにそれを用いた水性増粘液 |
EP3310736B1 (de) | 2015-06-17 | 2019-01-30 | Clariant International Ltd | Wasserlösliche oder wasserquellbare polymere als wasserverlustreduzierer in zementschlämmen |
WO2018108610A1 (en) * | 2016-12-12 | 2018-06-21 | Clariant International Ltd | Polymer comprising certain level of bio-based carbon |
CN110267997B (zh) * | 2016-12-12 | 2022-07-22 | 科莱恩国际有限公司 | 包含某种水平的生物基碳的聚合物 |
BR112019011780B1 (pt) * | 2016-12-12 | 2023-03-07 | Clariant International Ltd | Polímero compreendendo carbono de material biológico, seu processo de obtenção e seu uso |
CN110300573B (zh) | 2016-12-12 | 2023-07-25 | 科莱恩国际有限公司 | 生物基聚合物在化妆、皮肤病学或药物学组合物中的用途 |
US11401362B2 (en) | 2016-12-15 | 2022-08-02 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
US11542343B2 (en) | 2016-12-15 | 2023-01-03 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
EP3554646A1 (en) | 2016-12-15 | 2019-10-23 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
WO2018108664A1 (en) | 2016-12-15 | 2018-06-21 | Clariant International Ltd | Water-soluble and/or water-swellable hybrid polymer |
FR3064004B1 (fr) * | 2017-03-20 | 2019-03-29 | S.P.C.M. Sa | Forme cristalline hydratee de l'acide 2-acrylamido-2-methylpropane sulfonique |
CN112430198A (zh) * | 2020-11-24 | 2021-03-02 | 潍坊奥瑞环保科技有限公司 | 一种2-丙烯酰胺基-2-甲基丙磺酸的制备方法 |
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JP3885555B2 (ja) * | 2001-10-31 | 2007-02-21 | 東亞合成株式会社 | 2−アクリルアミド−2−メチルプロパンスルホン酸の製造方法 |
JP4178909B2 (ja) * | 2002-10-24 | 2008-11-12 | 東亞合成株式会社 | アクリルアミドアルカンスルホン酸溶液の製造方法 |
JP4285035B2 (ja) * | 2003-03-18 | 2009-06-24 | 東亞合成株式会社 | アクリルアミドアルカンスルホン酸の精製方法 |
JP4277110B2 (ja) * | 2003-06-04 | 2009-06-10 | 東亞合成株式会社 | アクリルアミドアルカンスルホン酸の精製方法 |
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