CN107903164A - 同时制备有机酸和环氧丁烷的方法 - Google Patents
同时制备有机酸和环氧丁烷的方法 Download PDFInfo
- Publication number
- CN107903164A CN107903164A CN201711000802.2A CN201711000802A CN107903164A CN 107903164 A CN107903164 A CN 107903164A CN 201711000802 A CN201711000802 A CN 201711000802A CN 107903164 A CN107903164 A CN 107903164A
- Authority
- CN
- China
- Prior art keywords
- epoxy butane
- organic acid
- reaction
- butylene
- organic
- 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
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 239000007800 oxidant agent Substances 0.000 claims abstract description 5
- 230000001590 oxidative effect Effects 0.000 claims abstract description 5
- 150000003233 pyrroles Chemical class 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 150000001299 aldehydes Chemical class 0.000 claims description 19
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 6
- 229940090181 propyl acetate Drugs 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000007086 side reaction Methods 0.000 abstract description 5
- 238000006555 catalytic reaction Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- -1 polyoxybutylene Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- PLGXRTUGMZEVII-UHFFFAOYSA-N 2-chloro-1h-pyrrole Chemical class ClC1=CC=CN1 PLGXRTUGMZEVII-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- IRTLROCMFSDSNF-UHFFFAOYSA-N 2-phenyl-1h-pyrrole Chemical compound C1=CNC(C=2C=CC=CC=2)=C1 IRTLROCMFSDSNF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711000802.2A CN107903164A (zh) | 2017-10-24 | 2017-10-24 | 同时制备有机酸和环氧丁烷的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711000802.2A CN107903164A (zh) | 2017-10-24 | 2017-10-24 | 同时制备有机酸和环氧丁烷的方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN107903164A true CN107903164A (zh) | 2018-04-13 |
Family
ID=61841639
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711000802.2A Pending CN107903164A (zh) | 2017-10-24 | 2017-10-24 | 同时制备有机酸和环氧丁烷的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN107903164A (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113292518A (zh) * | 2021-06-22 | 2021-08-24 | 中山大学 | 一种有机小分子绿色、高效催化丁烯制备环氧丁烷的方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0342615A1 (en) * | 1988-05-17 | 1989-11-23 | ISTITUTO GUIDO DONEGANI S.p.A. | Process for the preparation of epoxides |
US6229028B1 (en) * | 1997-05-29 | 2001-05-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Process for the epoxidation of alkenes |
CN101899022A (zh) * | 2010-07-27 | 2010-12-01 | 中山大学 | 一种仿生催化丙烯环氧化制备环氧丙烷的方法 |
CN105085438A (zh) * | 2015-07-31 | 2015-11-25 | 中山大学惠州研究院 | 一种环氧丙烷的制备方法 |
-
2017
- 2017-10-24 CN CN201711000802.2A patent/CN107903164A/zh active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0342615A1 (en) * | 1988-05-17 | 1989-11-23 | ISTITUTO GUIDO DONEGANI S.p.A. | Process for the preparation of epoxides |
US6229028B1 (en) * | 1997-05-29 | 2001-05-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Process for the epoxidation of alkenes |
CN101899022A (zh) * | 2010-07-27 | 2010-12-01 | 中山大学 | 一种仿生催化丙烯环氧化制备环氧丙烷的方法 |
CN105085438A (zh) * | 2015-07-31 | 2015-11-25 | 中山大学惠州研究院 | 一种环氧丙烷的制备方法 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113292518A (zh) * | 2021-06-22 | 2021-08-24 | 中山大学 | 一种有机小分子绿色、高效催化丁烯制备环氧丁烷的方法 |
CN113292518B (zh) * | 2021-06-22 | 2022-05-31 | 中山大学 | 一种有机小分子绿色、高效催化丁烯制备环氧丁烷的方法 |
WO2022267081A1 (zh) * | 2021-06-22 | 2022-12-29 | 中山大学 | 一种有机小分子绿色、高效催化丁烯制备环氧丁烷的方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101492370B (zh) | Co偶联制草酸酯的方法 | |
CN102000559B (zh) | 一种采用负载氧化铌催化剂制备甲缩醛的方法 | |
CN102698799A (zh) | 一种聚合物负载的季铵盐离子催化剂及其制备方法与应用 | |
CN103360224A (zh) | 一种制备聚甲氧基二甲醚的组合工艺 | |
CN102260147A (zh) | 一种在离子液体溶剂中烯烃氢甲酰化反应的方法 | |
CN105085438B (zh) | 一种环氧丙烷的制备方法 | |
CN104557784A (zh) | 一种生产环氧丙烷的方法 | |
CN110818566A (zh) | 一种环戊烯制备环戊醇的方法 | |
CN101899022B (zh) | 一种仿生催化丙烯环氧化制备环氧丙烷的方法 | |
CN110240540A (zh) | 一种连续制备2-甲氧基丙烯的方法 | |
CN107866282A (zh) | 一类含氮膦配体在烯烃氢甲酰化串联反应中的应用 | |
KR101862042B1 (ko) | 폴리옥시메틸렌 디메틸 에테르 카보닐 화합물 및 메틸 메톡시아세테이트의 제조방법 | |
CN103588618B (zh) | 醋酸甲酯加氢生产乙醇的反应精馏方法及装置 | |
CN100448857C (zh) | 一种选择性催化烯烃环氧化制备环氧化物的方法 | |
CN107903164A (zh) | 同时制备有机酸和环氧丁烷的方法 | |
CN102452934A (zh) | 一种乙酸仲丁酯的制备方法 | |
EP2628735B1 (en) | Method for producing oxidized olefin through olefin epoxidation | |
CN103894232B (zh) | 一种亚硝酸甲酯甲酰化合成甲酸甲酯的催化剂及其制备方法和应用 | |
CN106554299A (zh) | 一种联产3-甲基吲哚和吲哚的方法 | |
CN105170180A (zh) | 4,5-亚甲基-L-脯氨酸在直接不对称Aldol反应中作为催化剂的应用 | |
CN102755910A (zh) | 一种钛硅分子筛与树脂复合改性催化剂及其制备方法 | |
CN102219679B (zh) | Co气相偶联生产草酸酯的方法 | |
CN109134538B (zh) | 碘膦氧配体及其制备方法和络合物、包括该络合物的催化剂体系和用途 | |
CN103772175B (zh) | 一种合成异丙叉丙酮及仲丁醇的组合工艺方法 | |
CN108503595B (zh) | 一种制备喹唑啉酮类化合物的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
CB02 | Change of applicant information |
Address after: 255000 Shandong Province, East District, Zhangdian, chemical District, Chang Dong Road, No. 219 Applicant after: Shandong Lianchuang Industrial Development Group Co.,Ltd. Applicant after: SHANDONG LECRON POLYMER CO.,LTD. Applicant after: ZIBO LIANCHUANG POLYURETHANE Co.,Ltd. Address before: 255000 Shandong Province, East District, Zhangdian, chemical District, Chang Dong Road, No. 219 Applicant before: SHANDONG LECRON INTERNET MEDIA Co.,Ltd. Applicant before: SHANDONG LECRON POLYMER Co.,Ltd. Applicant before: ZIBO LIANCHUANG POLYURETHANE Co.,Ltd. |
|
CB02 | Change of applicant information | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180413 |
|
RJ01 | Rejection of invention patent application after publication |