KR102106763B1 - 알칸 및 올레움으로부터 알칸설폰산류를 제조하기 위한 신규 개시제 - Google Patents
알칸 및 올레움으로부터 알칸설폰산류를 제조하기 위한 신규 개시제 Download PDFInfo
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- KR102106763B1 KR102106763B1 KR1020167012178A KR20167012178A KR102106763B1 KR 102106763 B1 KR102106763 B1 KR 102106763B1 KR 1020167012178 A KR1020167012178 A KR 1020167012178A KR 20167012178 A KR20167012178 A KR 20167012178A KR 102106763 B1 KR102106763 B1 KR 102106763B1
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- alkaline earth
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- 239000002253 acid Substances 0.000 title claims description 30
- 239000003999 initiator Substances 0.000 title claims description 18
- 150000007513 acids Chemical class 0.000 title claims description 14
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 9
- 239000011701 zinc Chemical group 0.000 claims abstract description 9
- 229910052784 alkaline earth metal Chemical group 0.000 claims abstract description 8
- 150000001342 alkaline earth metals Chemical group 0.000 claims abstract description 8
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 48
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 30
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- -1 methanesulfonic acid halide Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 5
- 150000008045 alkali metal halides Chemical class 0.000 claims description 5
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 238000011049 filling Methods 0.000 claims description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 238000009713 electroplating Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- XJPAEZVERBCSTJ-UHFFFAOYSA-N methylsulfonyloxy methanesulfonate Chemical compound CS(=O)(=O)OOS(C)(=O)=O XJPAEZVERBCSTJ-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical compound OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- FVIRGMIYFJWRGC-UHFFFAOYSA-N sulfurobromidic acid Chemical compound OS(Br)(=O)=O FVIRGMIYFJWRGC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/42—Peroxy compounds containing sulfur atoms
- C07C409/44—Peroxy compounds containing sulfur atoms with sulfur atoms directly bound to the —O—O— groups, e.g. persulfonic acids
-
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
-
- 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
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
-
- 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
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13193349.1 | 2013-11-18 | ||
| EP13193349 | 2013-11-18 | ||
| PCT/EP2014/074747 WO2015071455A1 (en) | 2013-11-18 | 2014-11-17 | Novel initiator for preparing alkanesulfonic acids from alkane and oleum |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160086832A KR20160086832A (ko) | 2016-07-20 |
| KR102106763B1 true KR102106763B1 (ko) | 2020-05-06 |
Family
ID=49674152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167012178A Active KR102106763B1 (ko) | 2013-11-18 | 2014-11-17 | 알칸 및 올레움으로부터 알칸설폰산류를 제조하기 위한 신규 개시제 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US10329251B2 (enExample) |
| EP (1) | EP3071549B1 (enExample) |
| JP (1) | JP6412570B2 (enExample) |
| KR (1) | KR102106763B1 (enExample) |
| CN (1) | CN105705486B (enExample) |
| MY (1) | MY179376A (enExample) |
| SG (1) | SG11201607264XA (enExample) |
| WO (1) | WO2015071455A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3068760B1 (en) | 2013-11-13 | 2023-06-07 | Grillo Chemie GmbH | Process for preparing alkanesulfonic acids from sulfur trioxide and an alkane |
| EP3071549B1 (en) | 2013-11-18 | 2017-10-18 | Grillo-Werke AG | Novel initiator for preparing alkanesulfonic acids from alkane and oleum |
| MY191259A (en) | 2016-11-28 | 2022-06-11 | Basf Se | Solvent-free alkane sulfonation |
| CN110267938A (zh) * | 2017-02-07 | 2019-09-20 | 格里洛工厂股份有限公司 | 烷烃磺酸的生产方法 |
| US10899703B2 (en) | 2017-03-10 | 2021-01-26 | Veolia North American Regeneration Services, LLC | Radical initiators and chain extenders for converting methane gas into methane-sulfonic acid |
| US10995063B2 (en) | 2017-03-10 | 2021-05-04 | Veolia North America Regeneration Services, Llc | Integrated processing system with continuous acid loop for converting methane to methane-sulfonic acid |
| TW201841881A (zh) * | 2017-04-18 | 2018-12-01 | 德商巴斯夫歐洲公司 | 純化烷烴磺酸酐的方法及使用純化的烷烴磺酸酐製造烷烴磺酸的方法 |
| US10669232B2 (en) * | 2017-05-11 | 2020-06-02 | Arkema Inc. | Processes and systems for recovering methanesulfonic acid in purified form |
| MY199501A (en) * | 2017-05-30 | 2023-11-01 | Basf Se | Process for the production of alkanesulfonic acids |
| TW201904938A (zh) | 2017-06-30 | 2019-02-01 | 德商葛里洛沃克股份有限公司 | 用於生產烷磺酸的調節劑 |
| US11247967B2 (en) | 2018-02-07 | 2022-02-15 | Basf Se | Process for the manufacturing of alkanesulfonic acids |
| FR3077817B1 (fr) * | 2018-02-14 | 2020-02-28 | Arkema France | Procede de synthese industrielle en continu d'acide alcane-sulfonique |
| TWI714964B (zh) * | 2018-02-16 | 2021-01-01 | 巴斯夫歐洲公司 | 用於烷磺酸之合成的催化劑 |
| WO2019212835A2 (en) | 2018-03-10 | 2019-11-07 | Richards Alan K | Compounds, processes, and machinery for converting methane gas into methane-sulfonic acid |
| TWI799586B (zh) * | 2018-05-25 | 2023-04-21 | 德商格里洛工廠股份有限公司 | 自三氧化硫及鹵烷製備鹵代烷磺酸的方法 |
| WO2020048965A1 (en) * | 2018-09-04 | 2020-03-12 | Basf Se | Method for the production of alkane sulfonic acids |
| WO2020064573A1 (en) | 2018-09-25 | 2020-04-02 | Basf Se | Catalysts for the synthesis of alkanesulfonic acids |
| CN112739681A (zh) | 2018-09-25 | 2021-04-30 | 巴斯夫欧洲公司 | 作为生产链烷磺酸中的催化剂的阳离子 |
| WO2020064466A1 (en) | 2018-09-25 | 2020-04-02 | Basf Se | Catalyst for the synthesis of alkanesulfonic acids |
| WO2020126855A1 (en) | 2018-12-21 | 2020-06-25 | Basf Se | Mixture comprising methanesulfonic acid and sulfuric acid |
| EP3941876B1 (en) * | 2019-03-21 | 2023-09-20 | Basf Se | Method for the purification of alkanes |
| ES2950933T3 (es) | 2019-04-18 | 2023-10-16 | Basf Se | Procedimiento de producción de ácido metanosulfónico anhidro a partir de metano y SO3 |
| ES2966787T3 (es) | 2019-07-10 | 2024-04-24 | Basf Se | Procedimiento para reducir la concentración de SO3 en una mezcla de reacción que comprende ácido metano sulfónico y SO3 |
| EP3763701A1 (en) | 2019-07-10 | 2021-01-13 | Grillo-Werke AG | Improved process for the purification of methane sulfonic acid |
| CN114174257B (zh) * | 2019-08-07 | 2024-05-14 | 巴斯夫欧洲公司 | 制备链烷磺酸的方法 |
| KR102886808B1 (ko) | 2019-08-07 | 2025-11-14 | 바스프 에스이 | 증류 칼럼의 저부 스트림으로부터 물-비함유 메탄설폰산의 회수 |
| EP3782981A1 (en) | 2019-08-20 | 2021-02-24 | Basf Se | Catalysts for the synthesis of alkanesulfonic acids |
| US20220340518A1 (en) * | 2019-10-01 | 2022-10-27 | Basf Se | Process for manufacturing alkanesulfonic acids |
| CA3156635A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | Process for manufacturing alkanesulfonic acids |
| CN111302978A (zh) * | 2020-04-17 | 2020-06-19 | 凯瑞环保科技股份有限公司 | 一种烷基磺酸的合成装置及合成方法 |
| US20230322662A1 (en) * | 2020-08-24 | 2023-10-12 | University Of Kansas | Alkane multi-sulfonic acids, compositions thereof, and related methods |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5304360A (en) | 1990-10-27 | 1994-04-19 | Interox Chemicals Limited | Peroxoacid manufacture |
| US20050070614A1 (en) | 2003-06-21 | 2005-03-31 | Richards Alan K. | Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds |
| WO2007136425A2 (en) | 2006-05-19 | 2007-11-29 | Richards, Alan, K. | Manufacture of dimethyl ether or olefins from methane, using di(methyl-sulfonyl) peroxide as radical initiator |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2493038A (en) | 1946-05-31 | 1950-01-03 | Houdry Process Corp | Reaction of methane with sulfur trioxide |
| US2619507A (en) | 1951-01-05 | 1952-11-25 | Dow Chemical Co | Di(methanesulfonyl) peroxide and its preparation |
| US4680095A (en) | 1986-11-03 | 1987-07-14 | Pennwalt Corporation | Continuous preparation of dialkanesulfonyl peroxide |
| FR2610320A1 (fr) | 1987-02-03 | 1988-08-05 | Atochem | Composes peroxydes renfermant l'isotope 17o |
| US4910335A (en) | 1989-08-01 | 1990-03-20 | Pennwalt Corporation | Decolorization of alkanesulfonic and arenesulfonic acids |
| CN1318361C (zh) * | 2002-11-05 | 2007-05-30 | 艾伦·K·理查兹 | 使用自由基路线和链反应,在最小废物的情况下,使甲烷和其它轻质烷烃无水转化成甲醇和其它衍生物 |
| ES2591253T3 (es) | 2002-11-05 | 2016-11-25 | Alan K. Richards | Conversión anhidra de metano y otros alcanos ligeros en metanol y otros derivados, que utiliza vías de radicales y reacciones en cadena con productos de desecho mínimos |
| US20080161591A1 (en) * | 2003-06-21 | 2008-07-03 | Richards Alan K | Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds |
| US7119226B2 (en) | 2004-04-20 | 2006-10-10 | The Penn State Research Foundation | Process for the conversion of methane |
| JP5068813B2 (ja) | 2006-05-24 | 2012-11-07 | ライブニッツ インスティトゥート フォー ナチュラル プロダクト リサーチ アンド インフェクション バイオロジー エー．ファウ． ハンス−クネル−インスティトゥート（ハーカーイー） | 新規なベンゾチアジノン誘導体、及び抗菌剤としてのその使用 |
| WO2015071351A1 (en) | 2013-11-13 | 2015-05-21 | Grillo Chemie Gmbh | Process for preparing bis(alkanesulfonyl peroxide) |
| EP3068760B1 (en) | 2013-11-13 | 2023-06-07 | Grillo Chemie GmbH | Process for preparing alkanesulfonic acids from sulfur trioxide and an alkane |
| WO2015071371A1 (en) | 2013-11-13 | 2015-05-21 | Grillo Chemie Gmbh | Process for preparing bis(alkanesulfonyl) peroxide by oxidation |
| EP3071549B1 (en) | 2013-11-18 | 2017-10-18 | Grillo-Werke AG | Novel initiator for preparing alkanesulfonic acids from alkane and oleum |
-
2014
- 2014-11-17 EP EP14799443.8A patent/EP3071549B1/en active Active
- 2014-11-17 KR KR1020167012178A patent/KR102106763B1/ko active Active
- 2014-11-17 US US15/035,865 patent/US10329251B2/en active Active
- 2014-11-17 JP JP2016528892A patent/JP6412570B2/ja active Active
- 2014-11-17 MY MYPI2016704208A patent/MY179376A/en unknown
- 2014-11-17 WO PCT/EP2014/074747 patent/WO2015071455A1/en not_active Ceased
- 2014-11-17 SG SG11201607264XA patent/SG11201607264XA/en unknown
- 2014-11-17 CN CN201480061403.5A patent/CN105705486B/zh active Active
-
2019
- 2019-05-03 US US16/403,112 patent/US11180448B2/en active Active
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| US5304360A (en) | 1990-10-27 | 1994-04-19 | Interox Chemicals Limited | Peroxoacid manufacture |
| US20050070614A1 (en) | 2003-06-21 | 2005-03-31 | Richards Alan K. | Anhydrous processing of methane into methane-sulfonic acid, methanol, and other compounds |
| WO2007136425A2 (en) | 2006-05-19 | 2007-11-29 | Richards, Alan, K. | Manufacture of dimethyl ether or olefins from methane, using di(methyl-sulfonyl) peroxide as radical initiator |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105705486B (zh) | 2019-03-01 |
| EP3071549B1 (en) | 2017-10-18 |
| US10329251B2 (en) | 2019-06-25 |
| JP2016540743A (ja) | 2016-12-28 |
| EP3071549A1 (en) | 2016-09-28 |
| KR20160086832A (ko) | 2016-07-20 |
| US20190256461A1 (en) | 2019-08-22 |
| US11180448B2 (en) | 2021-11-23 |
| SG11201607264XA (en) | 2016-10-28 |
| MY179376A (en) | 2020-11-05 |
| WO2015071455A1 (en) | 2015-05-21 |
| CN105705486A (zh) | 2016-06-22 |
| JP6412570B2 (ja) | 2018-10-24 |
| US20160289181A1 (en) | 2016-10-06 |
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