JP5689131B2 - 5−スルホイソフタル酸から、低硫酸塩の5−スルホイソフタル酸・モノ−リチウム塩を調製するための、酢酸/水混合溶媒の使用 - Google Patents
5−スルホイソフタル酸から、低硫酸塩の5−スルホイソフタル酸・モノ−リチウム塩を調製するための、酢酸/水混合溶媒の使用 Download PDFInfo
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- JP5689131B2 JP5689131B2 JP2012535298A JP2012535298A JP5689131B2 JP 5689131 B2 JP5689131 B2 JP 5689131B2 JP 2012535298 A JP2012535298 A JP 2012535298A JP 2012535298 A JP2012535298 A JP 2012535298A JP 5689131 B2 JP5689131 B2 JP 5689131B2
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- lithium
- sulfoisophthalic acid
- mixture
- lithium salt
- acetic acid
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 133
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 41
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 title claims description 19
- 239000012046 mixed solvent Substances 0.000 title description 10
- GQRUOOBVEYCCGN-UHFFFAOYSA-M [Li+].S(=O)(=O)(O)C=1C=C(C=C(C(=O)O)C1)C(=O)O.S(=O)(=O)([O-])O Chemical compound [Li+].S(=O)(=O)(O)C=1C=C(C=C(C(=O)O)C1)C(=O)O.S(=O)(=O)([O-])O GQRUOOBVEYCCGN-UHFFFAOYSA-M 0.000 title description 7
- 238000000034 method Methods 0.000 claims description 46
- 230000008569 process Effects 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 38
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- AHYFYYVVAXRMKB-UHFFFAOYSA-N 3-(1h-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CC(C(=O)O)NC(=O)OCC1=CC=CC=C1 AHYFYYVVAXRMKB-UHFFFAOYSA-N 0.000 claims description 14
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 14
- 229940006487 lithium cation Drugs 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 9
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 claims description 7
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 claims description 7
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 claims description 7
- 229910003002 lithium salt Inorganic materials 0.000 claims description 7
- 159000000002 lithium salts Chemical class 0.000 claims description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000012035 limiting reagent Substances 0.000 claims description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 2
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 claims description 2
- ROSJRNCQPUYTEX-UHFFFAOYSA-N 5-sulfobenzene-1,3-dicarboxylic acid;sulfuric acid Chemical compound OS(O)(=O)=O.OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 ROSJRNCQPUYTEX-UHFFFAOYSA-N 0.000 claims 1
- RDUQIPJRJKFWBS-UHFFFAOYSA-N S(=O)(=O)(O)C=1C=C(C=C(C(=O)O)C1)C(=O)O.S(=O)(=O)(O)C=1C=C(C=C(C(=O)O)C1)C(=O)O Chemical compound S(=O)(=O)(O)C=1C=C(C=C(C(=O)O)C1)C(=O)O.S(=O)(=O)(O)C=1C=C(C=C(C(=O)O)C1)C(=O)O RDUQIPJRJKFWBS-UHFFFAOYSA-N 0.000 claims 1
- 150000002642 lithium compounds Chemical class 0.000 claims 1
- HPCCWDVOHHFCKM-UHFFFAOYSA-M lithium;hydrogen sulfate Chemical compound [Li+].OS([O-])(=O)=O HPCCWDVOHHFCKM-UHFFFAOYSA-M 0.000 claims 1
- 238000013021 overheating Methods 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 37
- 239000000047 product Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011175 product filtration Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012776 robust process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Claims (12)
- 低硫酸塩の5−スルホイソフタル酸の塩を調製するプロセスであって、その方法が
酢酸、水、ある量のリチウムカチオン生成化合物、及びある量の5−スルホイソフタル酸を含む混合物を形成するステップ、及び
酢酸、水、ある量のリチウムカチオン生成化合物、及びある量の5−スルホイソフタル酸を含む前記混合物を、5−スルホイソフタル酸・モノ−リチウム塩を含む混合物を生成するのに十分な期間十分な温度で過熱するステップ、と
を含む、プロセス。 - 前記リチウムカチオン生成化合物が、水酸化リチウム一水和物、無水水酸化リチウム、有機リチウム塩、及び無機リチウム塩から成る群から選択される、請求項1に記載のプロセス。
- 前記有機リチウム塩が、酢酸リチウム、炭酸リチウム、重炭酸リチウムから成る群から選択される、請求項2に記載のプロセス。
- 前記リチウム化合物が、水酸化リチウム一水和物である、請求項2に記載のプロセス。
- 混合物を形成する前記プロセスが、酢酸、水、ある量のリチウムカチオン生成化合物、及びある量の5−スルホイソフタル酸を含む混合物を、0℃〜118℃の間の温度で混合することを含む、請求項1に記載のプロセス。
- 前記酢酸が、過剰である、請求項1に記載のプロセス。
- 前記リチウムカチオンが、制限試薬として、5−スルホイソフタル酸に対するリチウムカチオンのモル比が1.0以下に保持される、請求項1に記載のプロセス。
- 酢酸、水、リチウムカチオン生成化合物、及び5−スルホイソフタル酸を含む前記混合物が、還流まで過熱され、5−スルホイソフタル酸・モノ−リチウム塩を含む混合物を生成するのに十分な期間還流で保持される、請求項1に記載のプロセス。
- 前記十分な期間が、5分〜2時間の間である、請求項8に記載のプロセス。
- 5−スルホイソフタル酸・モノ−リチウム塩を含む前記混合物を冷却するステップと、
5−スルホイソフタル酸・モノ−リチウム塩を含む前記混合物をろ過して、5−スルホイソフタル酸・モノ−リチウム塩を含むケーキを得るステップと、
5−スルホイソフタル酸・モノ−リチウム塩を含む前記ケーキを乾燥させるステップと
を更に含む、請求項1に記載のプロセス。 - 5−スルホイソフタル酸・モノ−リチウム塩を含む、前記乾燥したケーキが、200ppm未満の硫酸塩を含む、請求項10に記載のプロセス。
- 低硫酸塩の5−スルホイソフタル酸のモノ−リチウム塩を調製するプロセスであって、その方法が、
酢酸、水、ある量のリチウムカチオン生成化合物、及びある量の5−スルホイソフタル酸を含む混合物を形成するステップと、
酢酸、水、リチウムカチオン生成化合物、及び5−スルホイソフタル酸を含む前記混合物を、5−スルホイソフタル酸・モノ−リチウム塩を生成するために、5分〜2時間還流するために加熱するステップと、
5−スルホイソフタル酸・モノ−リチウム塩を含む前記混合物を冷却するステップと、
5−スルホイソフタル酸・モノ−リチウム塩を含む前記混合物を、5−スルホイソフタル酸・モノ−リチウム塩を含むケーキを得るためにろ過するステップと、
5−スルホイソフタル酸・モノ−リチウム塩を含む前記ケーキを、酢酸を用いて洗浄するステップと、
5−スルホイソフタル酸・モノ−リチウム塩を含む前記洗浄したケーキ(前記、5−スルホイソフタル酸・モノ−リチウム塩は200ppm未満の硫酸塩を含む)を乾燥させるステップと、
を含む、プロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25341509P | 2009-10-20 | 2009-10-20 | |
US61/253,415 | 2009-10-20 | ||
PCT/US2010/053186 WO2011049940A2 (en) | 2009-10-20 | 2010-10-19 | Use of an acetic acid/water solvent mixture for the preparation of low-sulfate 5-sulfoisophthalic acid, mono-lithium salt from 5-sulfoisophthalic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013508377A JP2013508377A (ja) | 2013-03-07 |
JP5689131B2 true JP5689131B2 (ja) | 2015-03-25 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2012535298A Expired - Fee Related JP5689131B2 (ja) | 2009-10-20 | 2010-10-19 | 5−スルホイソフタル酸から、低硫酸塩の5−スルホイソフタル酸・モノ−リチウム塩を調製するための、酢酸/水混合溶媒の使用 |
Country Status (8)
Country | Link |
---|---|
US (1) | US9359292B2 (ja) |
EP (1) | EP2491012B1 (ja) |
JP (1) | JP5689131B2 (ja) |
CA (1) | CA2775965A1 (ja) |
ES (1) | ES2524977T3 (ja) |
MX (1) | MX2012004562A (ja) |
PL (1) | PL2491012T3 (ja) |
WO (1) | WO2011049940A2 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8404886B2 (en) | 2009-02-27 | 2013-03-26 | Future Fuel Chemical Company | Purification of 5-sulfoisophthalic acid by the use of an acetic acid wash on a crude cake |
WO2011049940A2 (en) | 2009-10-20 | 2011-04-28 | Futurefuel Chemical Company | Use of an acetic acid/water solvent mixture for the preparation of low-sulfate 5-sulfoisophthalic acid, mono-lithium salt from 5-sulfoisophthalic acid |
EP2630119A4 (en) * | 2010-10-19 | 2014-04-23 | Futurefuel Chemical Co | USE OF ACETIC ACID FLOWS FOR THE PREPARATION OF 5-SULPHOSOPHTHALINIC ACID AND A MONO-LITHIUM SALT WITH LOW SULFUR PARTICULARITY |
US8884045B2 (en) | 2010-10-19 | 2014-11-11 | Future Fuel Chemical Company | Use of an acetic acid wash to prepare low-sulfate 5-sulfoisophthalic acid, mono-lithium salt |
WO2012118973A2 (en) | 2011-03-02 | 2012-09-07 | Futurefuel Chemical Company | Metal salts of a dialkyl ester of 5-sulfoisophthalic acid and method of preparing same |
EP2744813A4 (en) * | 2011-08-16 | 2015-03-18 | Futurefuel Chemical Co | 5-SULPHOSOPHTHALIC ACID SALTS AND METHOD FOR THE PRODUCTION THEREOF |
US8809565B2 (en) | 2011-08-29 | 2014-08-19 | Futurefuel Chemical Company | 5-sulfoisophthalic acid salts and process for the preparation thereof |
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-
2010
- 2010-10-19 WO PCT/US2010/053186 patent/WO2011049940A2/en active Application Filing
- 2010-10-19 US US13/502,333 patent/US9359292B2/en active Active
- 2010-10-19 ES ES10825516.7T patent/ES2524977T3/es active Active
- 2010-10-19 MX MX2012004562A patent/MX2012004562A/es not_active Application Discontinuation
- 2010-10-19 EP EP10825516.7A patent/EP2491012B1/en not_active Not-in-force
- 2010-10-19 CA CA2775965A patent/CA2775965A1/en not_active Abandoned
- 2010-10-19 JP JP2012535298A patent/JP5689131B2/ja not_active Expired - Fee Related
- 2010-10-19 PL PL10825516T patent/PL2491012T3/pl unknown
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WO2011049940A2 (en) | 2011-04-28 |
EP2491012A4 (en) | 2013-03-20 |
US9359292B2 (en) | 2016-06-07 |
US20120245378A1 (en) | 2012-09-27 |
CA2775965A1 (en) | 2011-04-28 |
MX2012004562A (es) | 2012-09-07 |
PL2491012T3 (pl) | 2015-04-30 |
ES2524977T3 (es) | 2014-12-16 |
EP2491012B1 (en) | 2014-10-08 |
EP2491012A2 (en) | 2012-08-29 |
JP2013508377A (ja) | 2013-03-07 |
WO2011049940A3 (en) | 2011-09-15 |
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