JP2014523422A5 - - Google Patents
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- JP2014523422A5 JP2014523422A5 JP2014516076A JP2014516076A JP2014523422A5 JP 2014523422 A5 JP2014523422 A5 JP 2014523422A5 JP 2014516076 A JP2014516076 A JP 2014516076A JP 2014516076 A JP2014516076 A JP 2014516076A JP 2014523422 A5 JP2014523422 A5 JP 2014523422A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfate
- salt
- produce
- ethyl
- following structure
- 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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- -1 heteroatom compound Chemical class 0.000 claims description 18
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 4
- 229940008406 diethyl sulfate Drugs 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 19
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical class OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical class CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 230000007062 hydrolysis Effects 0.000 claims 4
- 238000006460 hydrolysis reaction Methods 0.000 claims 4
- 230000003301 hydrolyzing effect Effects 0.000 claims 4
- 230000003472 neutralizing effect Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- PKFQJZUKSYRCRI-UHFFFAOYSA-L 1-ethyl-2,3-dimethylimidazol-3-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCN1C=C[N+](C)=C1C.CCN1C=C[N+](C)=C1C PKFQJZUKSYRCRI-UHFFFAOYSA-L 0.000 claims 2
- LXSZYUJSMQYYLZ-UHFFFAOYSA-L 4-ethyl-4-methylmorpholin-4-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.CC[N+]1(C)CCOCC1.CC[N+]1(C)CCOCC1 LXSZYUJSMQYYLZ-UHFFFAOYSA-L 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 239000002608 ionic liquid Substances 0.000 claims 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 claims 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims 1
- PYEWZDAEJUUIJX-UHFFFAOYSA-N 3-(dimethylamino)-2,2-dimethylpropan-1-ol Chemical compound CN(C)CC(C)(C)CO PYEWZDAEJUUIJX-UHFFFAOYSA-N 0.000 claims 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- 150000001334 alicyclic compounds Chemical class 0.000 claims 1
- 150000007824 aliphatic compounds Chemical class 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161498308P | 2011-06-17 | 2011-06-17 | |
| US61/498,308 | 2011-06-17 | ||
| PCT/US2012/042955 WO2012174531A1 (en) | 2011-06-17 | 2012-06-18 | Methods of producing sulfate salts of cations from heteroatomic compounds and dialkyl sulfates and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017099327A Division JP2017200917A (ja) | 2011-06-17 | 2017-05-18 | ヘテロ原子化合物のカチオン及びジアルキルスルフェートの硫酸塩の製造方法及びその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014523422A JP2014523422A (ja) | 2014-09-11 |
| JP2014523422A5 true JP2014523422A5 (enExample) | 2017-07-27 |
| JP6235469B2 JP6235469B2 (ja) | 2017-11-22 |
Family
ID=46172880
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014516076A Expired - Fee Related JP6235469B2 (ja) | 2011-06-17 | 2012-06-18 | ヘテロ原子化合物のカチオン及びジアルキルスルフェートの硫酸塩の製造方法及びその使用 |
| JP2017099327A Pending JP2017200917A (ja) | 2011-06-17 | 2017-05-18 | ヘテロ原子化合物のカチオン及びジアルキルスルフェートの硫酸塩の製造方法及びその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017099327A Pending JP2017200917A (ja) | 2011-06-17 | 2017-05-18 | ヘテロ原子化合物のカチオン及びジアルキルスルフェートの硫酸塩の製造方法及びその使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (5) | US8741491B2 (enExample) |
| EP (2) | EP2721686B1 (enExample) |
| JP (2) | JP6235469B2 (enExample) |
| CN (2) | CN103534867B (enExample) |
| AU (1) | AU2012271326B2 (enExample) |
| ES (2) | ES2702487T3 (enExample) |
| WO (2) | WO2012173694A1 (enExample) |
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| CN203225320U (zh) | 2011-11-04 | 2013-10-02 | 流体公司 | 电化学电池系统 |
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-
2012
- 2012-04-17 ES ES12723975T patent/ES2702487T3/es active Active
- 2012-04-17 EP EP12723975.4A patent/EP2721686B1/en not_active Not-in-force
- 2012-04-17 CN CN201280023680.8A patent/CN103534867B/zh not_active Expired - Fee Related
- 2012-04-17 US US13/448,923 patent/US8741491B2/en active Active
- 2012-04-17 WO PCT/US2012/033940 patent/WO2012173694A1/en not_active Ceased
- 2012-06-18 EP EP12731836.8A patent/EP2721681B1/en not_active Not-in-force
- 2012-06-18 AU AU2012271326A patent/AU2012271326B2/en not_active Ceased
- 2012-06-18 WO PCT/US2012/042955 patent/WO2012174531A1/en not_active Ceased
- 2012-06-18 US US13/526,432 patent/US9793586B2/en active Active
- 2012-06-18 JP JP2014516076A patent/JP6235469B2/ja not_active Expired - Fee Related
- 2012-06-18 CN CN201280040053.5A patent/CN103748731B/zh not_active Expired - Fee Related
- 2012-06-18 US US13/526,058 patent/US9147919B2/en active Active
- 2012-06-18 ES ES12731836T patent/ES2702032T3/es active Active
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