JP2023524710A - アクリル酸の製造方法 - Google Patents
アクリル酸の製造方法 Download PDFInfo
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- JP2023524710A JP2023524710A JP2022566252A JP2022566252A JP2023524710A JP 2023524710 A JP2023524710 A JP 2023524710A JP 2022566252 A JP2022566252 A JP 2022566252A JP 2022566252 A JP2022566252 A JP 2022566252A JP 2023524710 A JP2023524710 A JP 2023524710A
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- JP
- Japan
- Prior art keywords
- lactic acid
- distillation column
- acrylic acid
- stage
- producing acrylic
- 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.)
- Granted
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 49
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 40
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 353
- 235000014655 lactic acid Nutrition 0.000 claims description 178
- 239000004310 lactic acid Substances 0.000 claims description 174
- 238000004821 distillation Methods 0.000 claims description 98
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 239000002994 raw material Substances 0.000 claims description 36
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 230000000052 comparative effect Effects 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000006200 vaporizer Substances 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 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 2
- 238000000926 separation method Methods 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229930182843 D-Lactic acid Natural products 0.000 description 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910001069 Ti alloy Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 229910000963 austenitic stainless steel Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940022769 d- lactic acid Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001039 duplex stainless steel Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910001258 titanium gold Inorganic materials 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- 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
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本明細書において、ある部分がある構成要素を「含む」とする際、これは、特に反対の記載がない限り、他の構成要素を除くものではなく、他の構成要素をさらに含んでもよいことを意味する。
下記の実施例および比較例は、アスペンテック社のアスペンプラスでシミュレーションされた。
蒸留塔は、コンデンサ(condenser)なしにリボイラ(reboiler)だけを有するタイプとして5段で構成した。精製された濃縮乳酸原料を希釈するステップなしに蒸留塔の1段(最上段)に投入した。蒸留塔下段の乳酸オリゴマーを分解して運転温度を低くするために、水は蒸留塔の5段(最下段)に投入した。
乳酸原料と水を別に投入せず、精製された濃縮乳酸原料を水で希釈して乳酸原料(乳酸および乳酸オリゴマー)が40%となるように水溶液を作った後に蒸留塔の1段(最上段)に投入し、水は蒸留塔の5段(最下段)に投入してないことを除いては、前記実施例1と同様に運転した。
精製された濃縮乳酸原料を水で希釈して乳酸原料(乳酸および乳酸オリゴマー)が40%となるように水溶液に作った後に熱交換器に投入し、熱交換器にて3%が気化し、気化していない液相は再び再循環した。再循環液相の流量は、液相乳酸水溶液と比べて50倍レベルであり、希釈された乳酸水溶液と合流して熱交換器に投入された。熱交換器にて気化した気相乳酸の流れを反応器フィードとして用いた。
200 ・・・熱交換器
1 ・・・液相乳酸水溶液
2 ・・・水
3 ・・・第1乳酸蒸気
4 ・・・第2乳酸水溶液
Claims (9)
- 乳酸原料を蒸留塔の上段部に供給するステップ;
前記蒸留塔の下段部に水を供給するステップ;
前記蒸留塔にて気化した第1乳酸蒸気を反応器に供給するステップ;および
前記蒸留塔にて気化していない第2乳酸水溶液を前記蒸留塔の中段部に供給するステップ;
を含む、アクリル酸の製造方法。 - 前記乳酸原料は、水;乳酸;および乳酸オリゴマーを含み、前記乳酸原料100重量部に対して、前記水を20重量部以下で含む、請求項1に記載のアクリル酸の製造方法。
- 前記蒸留塔の上段部の温度は150℃以上200℃以下であり、前記蒸留塔の下段部の温度は200℃以上250℃以下である、請求項1又は2に記載のアクリル酸の製造方法。
- 前記第1乳酸蒸気中の乳酸:乳酸オリゴマーの割合が100:0~95:5である、請求項1から3のいずれか一項に記載のアクリル酸の製造方法。
- 前記第2乳酸水溶液中の乳酸:乳酸オリゴマーの割合が1:99~20:80である、請求項1から4のいずれか一項に記載のアクリル酸の製造方法。
- 前記蒸留塔の内部圧力が0.1bar以上2.0bar以下である、請求項1から5のいずれか一項に記載のアクリル酸の製造方法。
- 前記蒸留塔は3段~7段で構成され、前記上段部は1段、前記中段部は前記上段部と下段部との間の段、前記下段部は最後の段である、請求項1から6のいずれか一項に記載のアクリル酸の製造方法。
- 前記第1乳酸蒸気は、水;乳酸;および乳酸オリゴマーを含み、前記第1乳酸蒸気100重量部に対して、前記乳酸および乳酸オリゴマーを5重量部以上80重量部以下で含む、請求項1から7のいずれか一項に記載のアクリル酸の製造方法。
- 前記蒸留塔にて気化した第1乳酸蒸気を反応器に供給するステップ以後、前記第1乳酸蒸気の脱水反応によりアクリル酸を生成する、請求項1から8のいずれか一項に記載のアクリル酸の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2020-0159107 | 2020-11-24 | ||
KR1020200159107A KR20220071687A (ko) | 2020-11-24 | 2020-11-24 | 아크릴산의 제조 공정 |
PCT/KR2021/015174 WO2022114545A1 (ko) | 2020-11-24 | 2021-10-27 | 아크릴산의 제조 공정 |
Publications (2)
Publication Number | Publication Date |
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JP2023524710A true JP2023524710A (ja) | 2023-06-13 |
JP7408225B2 JP7408225B2 (ja) | 2024-01-05 |
Family
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JP2022566252A Active JP7408225B2 (ja) | 2020-11-24 | 2021-10-27 | アクリル酸の製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20230159428A1 (ja) |
EP (1) | EP4122912A4 (ja) |
JP (1) | JP7408225B2 (ja) |
KR (1) | KR20220071687A (ja) |
CN (1) | CN115697960A (ja) |
WO (1) | WO2022114545A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20240037087A (ko) * | 2022-09-14 | 2024-03-21 | 주식회사 엘지화학 | 아크릴산 제조방법 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE1011197A3 (fr) | 1997-06-06 | 1999-06-01 | Brussels Biotech En Abrege Bb | Procede de purification d'acide lactique. |
NL1013682C2 (nl) | 1999-11-26 | 2001-05-30 | Purac Biochem Bv | Werkwijze en inrichting voor het zuiveren van een waterige oplossing van melkzuur. |
JP2002128727A (ja) | 2000-10-18 | 2002-05-09 | Toyota Motor Corp | 乳酸の蒸留精製方法 |
EP1732874A1 (en) | 2004-04-02 | 2006-12-20 | Ciba Speciality Chemicals Water Treatments Limited | Preparation of acrylic acid derivatives from alpha or beta-hydroxy carboxylic acids |
JP2016175840A (ja) * | 2013-07-30 | 2016-10-06 | 株式会社日本触媒 | アクリル酸の製造方法 |
WO2016026761A1 (en) * | 2014-08-18 | 2016-02-25 | Basf Se | Process for preparing acrylic acid by dehydration of 3-hydroxypropionic acid |
US9758463B1 (en) | 2014-09-17 | 2017-09-12 | Nippon Shokubai Co., Ltd. | Method for producing vapor composition containing lactic acid |
KR101870503B1 (ko) * | 2016-02-12 | 2018-06-22 | 에스케이이노베이션 주식회사 | 히드록시프로피온산을 이용한 아크릴산의 제조방법 |
-
2020
- 2020-11-24 KR KR1020200159107A patent/KR20220071687A/ko not_active Application Discontinuation
-
2021
- 2021-10-27 WO PCT/KR2021/015174 patent/WO2022114545A1/ko unknown
- 2021-10-27 JP JP2022566252A patent/JP7408225B2/ja active Active
- 2021-10-27 CN CN202180035197.0A patent/CN115697960A/zh active Pending
- 2021-10-27 EP EP21898371.6A patent/EP4122912A4/en active Pending
- 2021-10-27 US US17/921,412 patent/US20230159428A1/en active Pending
Also Published As
Publication number | Publication date |
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EP4122912A1 (en) | 2023-01-25 |
CN115697960A (zh) | 2023-02-03 |
WO2022114545A1 (ko) | 2022-06-02 |
JP7408225B2 (ja) | 2024-01-05 |
KR20220071687A (ko) | 2022-05-31 |
US20230159428A1 (en) | 2023-05-25 |
EP4122912A4 (en) | 2023-11-08 |
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