JP2014532650A5 - - Google Patents
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- JP2014532650A5 JP2014532650A5 JP2014538976A JP2014538976A JP2014532650A5 JP 2014532650 A5 JP2014532650 A5 JP 2014532650A5 JP 2014538976 A JP2014538976 A JP 2014538976A JP 2014538976 A JP2014538976 A JP 2014538976A JP 2014532650 A5 JP2014532650 A5 JP 2014532650A5
- Authority
- JP
- Japan
- Prior art keywords
- product stream
- stream
- solid support
- acrylic acid
- ethylene oxide
- 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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- 238000000034 method Methods 0.000 claims description 94
- 229910052751 metal Inorganic materials 0.000 claims description 42
- 239000002184 metal Substances 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 39
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 32
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 31
- 239000007787 solid Substances 0.000 claims description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 27
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 25
- 230000006315 carbonylation Effects 0.000 claims description 25
- 238000005810 carbonylation reaction Methods 0.000 claims description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 18
- 229960000380 propiolactone Drugs 0.000 claims description 18
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
- 239000005977 Ethylene Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000005909 Kieselgur Chemical class 0.000 claims description 10
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 10
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical class O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 10
- -1 ceramics Chemical class 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000011521 glass Chemical class 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000129 anionic group Chemical group 0.000 claims description 8
- 239000000919 ceramic Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 229910003480 inorganic solid Inorganic materials 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 239000002808 molecular sieve Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 5
- 239000004408 titanium dioxide Substances 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 239000003957 anion exchange resin Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003729 cation exchange resin Substances 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 4
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
- 229920002717 polyvinylpyridine Polymers 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011973 solid acid Substances 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims 2
- 239000002994 raw material Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 1
- 229920000070 poly-3-hydroxybutyrate Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161551496P | 2011-10-26 | 2011-10-26 | |
| US61/551,496 | 2011-10-26 | ||
| PCT/US2012/061791 WO2013063191A1 (en) | 2011-10-26 | 2012-10-25 | Process for production of acrylates from epoxides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017122352A Division JP6486992B2 (ja) | 2011-10-26 | 2017-06-22 | エポキシドからアクリレートの生成のためのプロセス |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014532650A JP2014532650A (ja) | 2014-12-08 |
| JP2014532650A5 true JP2014532650A5 (enExample) | 2016-12-08 |
| JP6219834B2 JP6219834B2 (ja) | 2017-10-25 |
Family
ID=48168463
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014538976A Active JP6219834B2 (ja) | 2011-10-26 | 2012-10-25 | エポキシドからアクリレートの生成のためのプロセス |
| JP2017122352A Active JP6486992B2 (ja) | 2011-10-26 | 2017-06-22 | エポキシドからアクリレートの生成のためのプロセス |
| JP2018088351A Pending JP2018119010A (ja) | 2011-10-26 | 2018-05-01 | エポキシドからアクリレートの生成のためのプロセス |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017122352A Active JP6486992B2 (ja) | 2011-10-26 | 2017-06-22 | エポキシドからアクリレートの生成のためのプロセス |
| JP2018088351A Pending JP2018119010A (ja) | 2011-10-26 | 2018-05-01 | エポキシドからアクリレートの生成のためのプロセス |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US9096510B2 (enExample) |
| EP (2) | EP2771307B1 (enExample) |
| JP (3) | JP6219834B2 (enExample) |
| KR (1) | KR101894709B1 (enExample) |
| CN (2) | CN107382699B (enExample) |
| CY (1) | CY1120779T1 (enExample) |
| DK (1) | DK2771307T3 (enExample) |
| ES (1) | ES2684970T3 (enExample) |
| HK (1) | HK1245240B (enExample) |
| HR (1) | HRP20181284T1 (enExample) |
| HU (1) | HUE039449T2 (enExample) |
| LT (1) | LT2771307T (enExample) |
| PL (1) | PL2771307T3 (enExample) |
| PT (1) | PT2771307T (enExample) |
| SI (1) | SI2771307T1 (enExample) |
| SM (1) | SMT201800438T1 (enExample) |
| WO (1) | WO2013063191A1 (enExample) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529950A (zh) | 2009-04-08 | 2015-04-22 | 诺沃梅尔公司 | β-内酯的制造方法 |
| JP2014527456A (ja) | 2011-05-13 | 2014-10-16 | ノボマー， インコーポレイテッド | 触媒的カルボニル化用触媒および方法 |
| US9096510B2 (en) | 2011-10-26 | 2015-08-04 | Novomer, Inc. | Process for production of acrylates from epoxides |
| US9403788B2 (en) | 2012-02-13 | 2016-08-02 | Novomer, Inc. | Process for the production of acid anhydrides from epoxides |
| HK1231431A1 (zh) | 2013-12-07 | 2017-12-22 | 诺沃梅尔公司 | 纳米过滤膜和使用方法 |
| JP2017511303A (ja) | 2014-03-14 | 2017-04-20 | ノボマー， インコーポレイテッド | エポキシドカルボニル化のための触媒 |
| WO2015171372A1 (en) | 2014-05-05 | 2015-11-12 | Novomer, Inc. | Catalyst recycle methods |
| CN106488899B (zh) | 2014-05-30 | 2020-08-18 | 诺沃梅尔公司 | 用于化学合成的综合方法 |
| CN104014227B (zh) * | 2014-06-05 | 2016-03-09 | 万华化学集团股份有限公司 | 一种含环氧丙烷或环氧乙烷有机废气的净化方法 |
| JP6670011B2 (ja) | 2014-07-25 | 2020-03-18 | ノボマー， インコーポレイテッド | 金属錯体の合成およびその使用 |
| KR20170129735A (ko) * | 2015-02-13 | 2017-11-27 | 노보머, 인코포레이티드 | 유연한 화학 제조 플랫폼 |
| MA41510A (fr) * | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de production d'acide acrylique |
| MA41507A (fr) * | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production de polymères |
| MA41513A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de distillation pour la production d'acide acrylique |
| CA2976255A1 (en) * | 2015-02-13 | 2016-08-18 | Novomer, Inc. | Process and system for production of polypropiolactone |
| CA2976253A1 (en) | 2015-02-13 | 2016-08-18 | Novomer, Inc. | Continuous carbonylation processes |
| MA41514A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédés intégrés de synthèse chimique |
| MA41508A (fr) * | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production d'acide polyacrylique |
| CN107949554A (zh) * | 2015-07-01 | 2018-04-20 | 诺沃梅尔公司 | 由环氧乙烷共同制造对苯二甲酸和苯乙烯的方法 |
| WO2017004349A2 (en) | 2015-07-01 | 2017-01-05 | Novomer, Inc. | Methods for production of terephthalic acid from ethylene oxide |
| HK1249496A1 (zh) | 2015-07-31 | 2018-11-02 | 诺沃梅尔公司 | 用於丙烯酸及其前体的生产系统/生产方法 |
| JP2019512585A (ja) * | 2016-03-21 | 2019-05-16 | ノボマー， インコーポレイテッド | 高吸収性ポリマーを生成するためのシステムおよび方法 |
| US20180282251A1 (en) | 2017-03-21 | 2018-10-04 | Novomer, Inc. | Systems and processes for producing organic acids direct from beta-lactones |
| WO2020005951A1 (en) | 2018-06-29 | 2020-01-02 | Novomer, Inc. | Systems and processes for producing organic acids directly from beta-lactones |
| KR20180118797A (ko) * | 2016-03-21 | 2018-10-31 | 노보머, 인코포레이티드 | 개선된 아크릴산 제조 방법 |
| US20180305286A1 (en) * | 2016-03-21 | 2018-10-25 | Novomer, Inc. | Systems and Processes for Producing Organic Acids Direct from Beta-Lactones |
| TW201808926A (zh) * | 2016-06-30 | 2018-03-16 | 捷恩智股份有限公司 | 含有乙烯性不飽和基的γ-丁內酯衍生物的製造方法 |
| EP3535235A4 (en) | 2016-11-02 | 2020-07-08 | Novomer, Inc. | ABSORBENT POLYMERS, METHODS AND SYSTEMS OF PRODUCTION AND USES THEREOF |
| US10144802B2 (en) | 2016-12-05 | 2018-12-04 | Novomer, Inc. | Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof |
| US10500104B2 (en) | 2016-12-06 | 2019-12-10 | Novomer, Inc. | Biodegradable sanitary articles with higher biobased content |
| CN110546187A (zh) | 2017-03-17 | 2019-12-06 | 诺沃梅尔公司 | 聚酰胺和其制造方法 |
| US10065914B1 (en) | 2017-04-24 | 2018-09-04 | Novomer, Inc. | Thermolysis of polypropiolactone to produce acrylic acid |
| US10781156B2 (en) | 2017-06-30 | 2020-09-22 | Novomer, Inc. | Compositions for improved production of acrylic acid |
| US10676426B2 (en) | 2017-06-30 | 2020-06-09 | Novomer, Inc. | Acrylonitrile derivatives from epoxide and carbon monoxide reagents |
| US10899622B2 (en) * | 2017-06-30 | 2021-01-26 | Novomer, Inc. | Biobased carbon fibers and carbon black and methods of making the same |
| US10590099B1 (en) | 2017-08-10 | 2020-03-17 | Novomer, Inc. | Processes for producing beta-lactone with heterogenous catalysts |
| US10961209B2 (en) * | 2017-08-10 | 2021-03-30 | Novomer, Inc. | Processes for producing beta-lactone and beta-lactone derivatives with heterogenous catalysts |
| KR102529865B1 (ko) * | 2017-09-09 | 2023-05-09 | 노보머, 인코포레이티드 | 아마이드 및 니트릴 화합물 및 이의 제조 및 사용 방법 |
| TW201922692A (zh) * | 2017-10-05 | 2019-06-16 | 美商諾沃梅爾公司 | 異氰酸酯、其衍生物及製造彼等之方法 |
| JP7676023B2 (ja) | 2018-07-13 | 2025-05-14 | ノボマー， インコーポレイテッド | ポリラクトン発泡体及びその製造方法 |
| WO2020033248A1 (en) * | 2018-08-07 | 2020-02-13 | Novomer, Inc. | Processes for producing beta-lactone and beta-lactone derivatives with heterogenous catalysts |
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| CN113573798A (zh) * | 2019-03-18 | 2021-10-29 | 诺沃梅尔公司 | 膜分离系统和其用途 |
| CN114127052A (zh) * | 2019-11-01 | 2022-03-01 | 埃克森美孚研究工程公司 | 用于生产被取代内酯的方法 |
| FR3110570B1 (fr) * | 2020-05-19 | 2022-05-20 | Commissariat Energie Atomique | PROCEDE DE PREPARATION D’ACIDE ACRYLIQUE A PARTIR DE β-PROPIOLACTONE |
| EP4015077A1 (de) * | 2020-12-15 | 2022-06-22 | Covestro Deutschland AG | Verfahren zur carbonylierung von epoxiden |
| CN116964128A (zh) | 2021-02-26 | 2023-10-27 | 诺沃梅尔公司 | 用于生产可生物降解聚酯的方法 |
| KR20230170697A (ko) | 2021-04-16 | 2023-12-19 | 노보머, 인코포레이티드 | 폴리프로피오락톤 및 제조 방법 |
| WO2023003890A1 (en) | 2021-07-21 | 2023-01-26 | Novomer, Inc. | Methods for beta-lactone copolymerization |
| CN113786864A (zh) * | 2021-09-07 | 2021-12-14 | 安徽建筑大学 | 一种催化剂及其催化乙酰丙酸加氢制γ-戊内酯的方法 |
| CN115850065B (zh) * | 2022-10-14 | 2024-12-20 | 水燃宝(北京)新能源有限公司 | 一种以硫酸氢钠为催化剂催化聚3-羟基丁酸酯降解制备r-3-羟基丁酸酯的方法 |
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| CN116273120B (zh) * | 2023-03-07 | 2024-07-05 | 青岛国恩科技股份有限公司 | 一种碳氮掺杂负载型钴基催化剂及其制备方法与应用 |
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2012
- 2012-10-25 US US14/353,532 patent/US9096510B2/en active Active
- 2012-10-25 HU HUE12842768A patent/HUE039449T2/hu unknown
- 2012-10-25 LT LTEP12842768.9T patent/LT2771307T/lt unknown
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- 2012-10-25 KR KR1020147013829A patent/KR101894709B1/ko active Active
- 2012-10-25 PT PT12842768T patent/PT2771307T/pt unknown
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- 2012-10-25 CN CN201710361942.6A patent/CN107382699B/zh active Active
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