JP2014519476A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014519476A5 JP2014519476A5 JP2014502512A JP2014502512A JP2014519476A5 JP 2014519476 A5 JP2014519476 A5 JP 2014519476A5 JP 2014502512 A JP2014502512 A JP 2014502512A JP 2014502512 A JP2014502512 A JP 2014502512A JP 2014519476 A5 JP2014519476 A5 JP 2014519476A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- catalyst system
- unreacted
- lactone
- catalyst
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 29
- 239000003054 catalyst Substances 0.000 claims 20
- 239000002253 acid Substances 0.000 claims 11
- 150000002596 lactones Chemical class 0.000 claims 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 6
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical group CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 claims 5
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims 4
- 229910052763 palladium Inorganic materials 0.000 claims 4
- 235000011037 adipic acid Nutrition 0.000 claims 3
- 239000001361 adipic acid Substances 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 125000004437 phosphorous atom Chemical group 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 2
- 229920002302 Nylon 6,6 Polymers 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 2
- 239000001913 cellulose Substances 0.000 claims 2
- 229920002678 cellulose Polymers 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 2
- 229940040102 levulinic acid Drugs 0.000 claims 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- 125000000962 organic group Chemical group 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- MCUBJMCZRUOHOK-UHFFFAOYSA-N 2,4,6-trioxa-1-phosphatricyclo[3.3.1.13,7]decane Chemical group C1P(O2)CC3OC1CC2O3 MCUBJMCZRUOHOK-UHFFFAOYSA-N 0.000 claims 1
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 229910052570 clay Inorganic materials 0.000 claims 1
- 230000000593 degrading effect Effects 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- SFCNPIUDAIFHRD-UHFFFAOYSA-N ditert-butyl-[[2-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC=CC=C1CP(C(C)(C)C)C(C)(C)C SFCNPIUDAIFHRD-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000002941 palladium compounds Chemical class 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 claims 1
- 238000000066 reactive distillation Methods 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 239000011949 solid catalyst Substances 0.000 claims 1
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161468494P | 2011-03-28 | 2011-03-28 | |
| US61/468,494 | 2011-03-28 | ||
| PCT/SG2012/000107 WO2012134397A1 (en) | 2011-03-28 | 2012-03-28 | Synthesis of diacids |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016205882A Division JP2017057204A (ja) | 2011-03-28 | 2016-10-20 | 二価酸の合成 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014519476A JP2014519476A (ja) | 2014-08-14 |
| JP2014519476A5 true JP2014519476A5 (enExample) | 2015-05-14 |
Family
ID=46931753
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014502512A Pending JP2014519476A (ja) | 2011-03-28 | 2012-03-28 | 二価酸の合成 |
| JP2016205882A Pending JP2017057204A (ja) | 2011-03-28 | 2016-10-20 | 二価酸の合成 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016205882A Pending JP2017057204A (ja) | 2011-03-28 | 2016-10-20 | 二価酸の合成 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20150183703A1 (enExample) |
| EP (1) | EP2691361A4 (enExample) |
| JP (2) | JP2014519476A (enExample) |
| SG (1) | SG193629A1 (enExample) |
| WO (1) | WO2012134397A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA201500756A1 (ru) | 2013-01-18 | 2015-12-30 | ДСМ АйПи АССЕТС Б.В. | Способ получения формилвалериановой кислоты и адипиновой кислоты |
| WO2017135897A1 (en) * | 2016-02-02 | 2017-08-10 | Agency For Science, Technology And Research | A catalyst for the carbonylation of alkenes |
| WO2017135898A1 (en) * | 2016-02-02 | 2017-08-10 | Agency For Science, Technology And Research | Process for preparing mono and dicarboxylic acids |
| TW201802061A (zh) * | 2016-03-21 | 2018-01-16 | 諾沃梅爾公司 | 丙烯酸及其製造方法 |
| US20180282251A1 (en) * | 2017-03-21 | 2018-10-04 | Novomer, Inc. | Systems and processes for producing organic acids direct from beta-lactones |
| US20180305286A1 (en) | 2016-03-21 | 2018-10-25 | Novomer, Inc. | Systems and Processes for Producing Organic Acids Direct from Beta-Lactones |
| JP2021532244A (ja) * | 2018-08-01 | 2021-11-25 | ブラスケム・アメリカ・インコーポレイテッド | 向上した堅牢性を有する熱可塑性組成物、その物品、及びその方法 |
| CN111979819B (zh) * | 2020-08-10 | 2022-08-09 | 齐鲁工业大学 | 分离木质纤维生物质组分的方法 |
| EP4306515A4 (en) * | 2021-03-12 | 2025-04-16 | Toray Industries, Inc. | 3-hydroxyadipic acid 3,6-lactone composition |
| WO2025033045A1 (ja) * | 2023-08-04 | 2025-02-13 | 国立研究開発法人農業・食品産業技術総合研究機構 | 植物病原菌の生育を抑制するための組成物及び方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2130948A (en) * | 1937-04-09 | 1938-09-20 | Du Pont | Synthetic fiber |
| JPS59116247A (ja) * | 1982-12-23 | 1984-07-05 | Soda Koryo Kk | 不飽和脂肪酸の製法 |
| US4788333A (en) * | 1985-01-07 | 1988-11-29 | E. I. Du Pont De Nemours And Company | Hydrocarboxylation of unsaturated carboxylic acids to linear dicarboxylic acids |
| US4897497A (en) * | 1988-04-26 | 1990-01-30 | Biofine Incorporated | Lignocellulose degradation to furfural and levulinic acid |
| JPH026427A (ja) * | 1988-06-27 | 1990-01-10 | Idemitsu Kosan Co Ltd | ジカルボン酸およびホルミルカルボン酸の製造方法 |
| FR2693459B1 (fr) * | 1992-07-09 | 1994-08-26 | Rhone Poulenc Chimie | Procédé de préparation de l'acide adipique par hydrocarboxylation d'acides penténoïques. |
| WO1994007835A1 (fr) * | 1992-10-02 | 1994-04-14 | Rhone-Poulenc Chimie | Procede d'isomerisation de lactones en acides pentenoiques par catalyse acide ou basique |
| FR2749300B1 (fr) * | 1996-06-04 | 1998-07-17 | Rhone Poulenc Fibres | Procede de purification de l'acide adipique par cristallisation |
| FR2749582B1 (fr) * | 1996-06-07 | 1998-07-17 | Rhone Poulenc Fibres | Procede d'hydroxycarbonylation des acides pentenoiques |
| US5710325A (en) * | 1996-11-01 | 1998-01-20 | E. I. Du Pont De Nemours And Company | Manufacture of adipic acid |
| CN1795159A (zh) * | 2003-05-22 | 2006-06-28 | 国际壳牌研究有限公司 | 烯属不饱和羧酸加氢羧基化的方法 |
| EP1699771A1 (en) * | 2003-12-15 | 2006-09-13 | Shell Internationale Researchmaatschappij B.V. | A process for the liquefaction of lignocellulosic material |
| WO2006125801A1 (en) * | 2005-05-27 | 2006-11-30 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of adipic acid from n-pentenoic acid |
-
2012
- 2012-03-28 SG SG2013072400A patent/SG193629A1/en unknown
- 2012-03-28 JP JP2014502512A patent/JP2014519476A/ja active Pending
- 2012-03-28 EP EP12764925.9A patent/EP2691361A4/en not_active Withdrawn
- 2012-03-28 WO PCT/SG2012/000107 patent/WO2012134397A1/en not_active Ceased
- 2012-03-28 US US14/007,169 patent/US20150183703A1/en not_active Abandoned
-
2016
- 2016-10-20 JP JP2016205882A patent/JP2017057204A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014519476A5 (enExample) | ||
| US20150183703A1 (en) | Synthesis of diacids | |
| EP3527551B1 (en) | Methods for the production of alpha,beta-unsaturated carboxylic acids and salts thereof | |
| US8598303B2 (en) | Process to produce valerolactone from levulinic acid | |
| RU2016145670A (ru) | Улучшенные каталитические характеристики в способах получения уксусной кислоты | |
| JPH0834761A (ja) | ５−ホルミル吉草酸エステルの製造法 | |
| TW201604181A (zh) | 用於純化乙酸甲酯混合物之方法 | |
| TWI455760B (zh) | 羰基化催化劑之再生技術 | |
| RU2015129636A (ru) | Объединенный способ получения метанола и метилацетата | |
| IN2014DN05822A (enExample) | ||
| DE60127446T2 (de) | Verfahren zur herstellung von 5-cyanovaleriansäure oder adipinsäure | |
| JP2017521379A (ja) | 酢酸およびジメチルエーテルの併産用プロセス | |
| TWI386388B (zh) | 從高沸物取得脂族ｃ3－ｃ10醛類之製法 | |
| JP2014504278A5 (enExample) | ||
| US20150133685A1 (en) | Process to produce a diene from a lactone | |
| CN105102413B (zh) | 制备甲酰戊酸和己二酸的方法 | |
| JP5895293B2 (ja) | ラクトンからのアルケン酸エステルの製造方法 | |
| US20140128631A1 (en) | Process for the preparation of alkanoic acid esters in a carbonylation process using palladium bidentate biphosphate ligands | |
| JP2002105021A (ja) | １，４−二置換ブテン−２又は３，４−二置換ブテン−１の製造方法 | |
| JP7215421B2 (ja) | ペンテン酸エステル誘導体の製造方法 | |
| WO2013107904A1 (en) | Process to produce alkanoic acid esters in a carbonylation process using lewis acids as acid promotor | |
| WO2012131028A1 (en) | Process to produce adipic acid and diesters thereof in a carbonylation process using palladium bidentate biphosphate ligands | |
| CN107737610A (zh) | 一种含膦配体的催化剂组合物 | |
| CN103172597A (zh) | 钛硅分子筛催化合成环氧脂肪酸甲酯的方法 | |
| TW201249536A (en) | Process to produce adipic acid and diesters thereof in a carbonylation process using palladium bidentate biphosphate ligands |