CN111170828B - 利用原位生成Cu(I)催化剂制备甲基烯丙醇的方法 - Google Patents
利用原位生成Cu(I)催化剂制备甲基烯丙醇的方法 Download PDFInfo
- Publication number
- CN111170828B CN111170828B CN202010053617.5A CN202010053617A CN111170828B CN 111170828 B CN111170828 B CN 111170828B CN 202010053617 A CN202010053617 A CN 202010053617A CN 111170828 B CN111170828 B CN 111170828B
- Authority
- CN
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- Prior art keywords
- methallyl
- methallyl alcohol
- salt
- catalyst
- cupric
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- 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.)
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Links
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 239000003054 catalyst Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000011065 in-situ storage Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000010949 copper Substances 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 239000005416 organic matter Substances 0.000 claims abstract description 15
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 13
- 150000001879 copper Chemical class 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 claims description 20
- -1 methallyl carboxylate Chemical class 0.000 claims description 12
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims description 9
- 239000012266 salt solution Substances 0.000 claims description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 5
- 229930003268 Vitamin C Natural products 0.000 claims description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 5
- 235000019154 vitamin C Nutrition 0.000 claims description 5
- 239000011718 vitamin C Substances 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 4
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 claims description 3
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 3
- 239000000176 sodium gluconate Substances 0.000 claims description 3
- 229940005574 sodium gluconate Drugs 0.000 claims description 3
- 235000012207 sodium gluconate Nutrition 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 229960004106 citric acid Drugs 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- 229940076286 cupric acetate Drugs 0.000 claims description 2
- 229960003280 cupric chloride Drugs 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 229960001031 glucose Drugs 0.000 claims description 2
- 235000001727 glucose Nutrition 0.000 claims description 2
- 235000010378 sodium ascorbate Nutrition 0.000 claims description 2
- 229960005055 sodium ascorbate Drugs 0.000 claims description 2
- 239000001509 sodium citrate Substances 0.000 claims description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 2
- 229960001790 sodium citrate Drugs 0.000 claims description 2
- 235000011083 sodium citrates Nutrition 0.000 claims description 2
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 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
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052802 copper Inorganic materials 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- XMHDLKFMJMNOAX-UHFFFAOYSA-N 2-methyl-3-(2-methylprop-2-enoxy)prop-1-ene Chemical compound CC(=C)COCC(C)=C XMHDLKFMJMNOAX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- FASUFOTUSHAIHG-UHFFFAOYSA-N 3-methoxyprop-1-ene Chemical compound COCC=C FASUFOTUSHAIHG-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- 229910001431 copper ion Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- IVKYUXHYUAMPMT-UHFFFAOYSA-N 2-methylprop-2-enyl acetate Chemical compound CC(=C)COC(C)=O IVKYUXHYUAMPMT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- SHCSFZHSNSGTOP-UHFFFAOYSA-N Methyl 4-pentenoate Chemical compound COC(=O)CCC=C SHCSFZHSNSGTOP-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- PTVDYARBVCBHSL-UHFFFAOYSA-N copper;hydrate Chemical class O.[Cu] PTVDYARBVCBHSL-UHFFFAOYSA-N 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000010352 sodium erythorbate Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
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CN202010053617.5A CN111170828B (zh) | 2020-01-17 | 2020-01-17 | 利用原位生成Cu(I)催化剂制备甲基烯丙醇的方法 |
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CN202010053617.5A CN111170828B (zh) | 2020-01-17 | 2020-01-17 | 利用原位生成Cu(I)催化剂制备甲基烯丙醇的方法 |
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CN111170828A CN111170828A (zh) | 2020-05-19 |
CN111170828B true CN111170828B (zh) | 2023-01-03 |
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CN112625257B (zh) * | 2020-12-11 | 2022-05-20 | 江苏大学 | MOF-Cu的制备方法及其在二芳基砜类化合物合成中的应用 |
Citations (14)
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US2072015A (en) * | 1932-10-04 | 1937-02-23 | Shell Dev | Process for the treatment of unsaturated halides |
US2313767A (en) * | 1940-11-22 | 1943-03-16 | Pittsburgh Plate Glass Co | Hydrolysis of allyl halides |
FR2302991A1 (fr) * | 1975-03-07 | 1976-10-01 | Ube Industries | Procede pour la preparation d'ortho-alcoxy-para-allylphenols |
US4152530A (en) * | 1978-07-24 | 1979-05-01 | Rhone-Poulenc Inc. | Process for preparing allylic alcohols from allylic halides |
CN1803352A (zh) * | 2005-09-29 | 2006-07-19 | 江苏大学 | 一种制备纳米铜的方法 |
CN101759528A (zh) * | 2010-01-12 | 2010-06-30 | 宁波尖锋紫星生物科技有限公司 | 2-甲基烯丙醇的合成方法 |
CN103242139A (zh) * | 2013-05-22 | 2013-08-14 | 南京工业大学 | 酯化水解两步法制备2-甲基烯丙基醇的方法 |
CN103588622A (zh) * | 2013-11-29 | 2014-02-19 | 上海多纶化工有限公司 | 连续水解反应合成2-甲基烯丙醇的方法 |
CN104014816A (zh) * | 2014-06-21 | 2014-09-03 | 吉林大学 | 一种具有抗氧化性铜纳米颗粒的制备方法 |
CN105037097A (zh) * | 2015-06-23 | 2015-11-11 | 浙江绿科安化学有限公司 | 一种2-甲基烯丙醇的合成方法 |
CN105819489A (zh) * | 2016-03-13 | 2016-08-03 | 河南师范大学 | 一种氯化亚铜的绿色合成方法 |
CN108059584A (zh) * | 2017-11-02 | 2018-05-22 | 浙江大学宁波理工学院 | 甲基烯丙醇的制备方法 |
CN108191604A (zh) * | 2017-12-22 | 2018-06-22 | 浙江大学 | 一种连续制备2-甲基烯丙醇的方法 |
CN108558600A (zh) * | 2018-04-08 | 2018-09-21 | 襄阳金达成精细化工有限公司 | 一种低污染2-甲基烯丙醇的合成方法 |
-
2020
- 2020-01-17 CN CN202010053617.5A patent/CN111170828B/zh active Active
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2072015A (en) * | 1932-10-04 | 1937-02-23 | Shell Dev | Process for the treatment of unsaturated halides |
US2313767A (en) * | 1940-11-22 | 1943-03-16 | Pittsburgh Plate Glass Co | Hydrolysis of allyl halides |
FR2302991A1 (fr) * | 1975-03-07 | 1976-10-01 | Ube Industries | Procede pour la preparation d'ortho-alcoxy-para-allylphenols |
US4152530A (en) * | 1978-07-24 | 1979-05-01 | Rhone-Poulenc Inc. | Process for preparing allylic alcohols from allylic halides |
CN1803352A (zh) * | 2005-09-29 | 2006-07-19 | 江苏大学 | 一种制备纳米铜的方法 |
CN101759528A (zh) * | 2010-01-12 | 2010-06-30 | 宁波尖锋紫星生物科技有限公司 | 2-甲基烯丙醇的合成方法 |
CN103242139A (zh) * | 2013-05-22 | 2013-08-14 | 南京工业大学 | 酯化水解两步法制备2-甲基烯丙基醇的方法 |
CN103588622A (zh) * | 2013-11-29 | 2014-02-19 | 上海多纶化工有限公司 | 连续水解反应合成2-甲基烯丙醇的方法 |
CN104014816A (zh) * | 2014-06-21 | 2014-09-03 | 吉林大学 | 一种具有抗氧化性铜纳米颗粒的制备方法 |
CN105037097A (zh) * | 2015-06-23 | 2015-11-11 | 浙江绿科安化学有限公司 | 一种2-甲基烯丙醇的合成方法 |
CN105819489A (zh) * | 2016-03-13 | 2016-08-03 | 河南师范大学 | 一种氯化亚铜的绿色合成方法 |
CN108059584A (zh) * | 2017-11-02 | 2018-05-22 | 浙江大学宁波理工学院 | 甲基烯丙醇的制备方法 |
CN108191604A (zh) * | 2017-12-22 | 2018-06-22 | 浙江大学 | 一种连续制备2-甲基烯丙醇的方法 |
CN108558600A (zh) * | 2018-04-08 | 2018-09-21 | 襄阳金达成精细化工有限公司 | 一种低污染2-甲基烯丙醇的合成方法 |
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Address after: 315100 No. 1, Qian Hunan Road, Ningbo Higher Education Park, Zhejiang Patentee after: Zhejiang University of science and engineering Ningbo Address before: 315100 No. 1, Qian Hunan Road, Yinzhou District Higher Education Park, Ningbo, Zhejiang Patentee before: Ningbo Institute of Technology, Zhejiang University |
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TR01 | Transfer of patent right |
Effective date of registration: 20231225 Address after: 6 Guangxing Road, Binhai Industrial Park, xiaocao'e Town, Yuyao City, Ningbo City, Zhejiang Province Patentee after: Ningbo Jinlai Chemical Co.,Ltd. Address before: 315100 No.1 Qianhu South Road, Ningbo Higher Education Park, Ningbo City, Zhejiang Province Patentee before: Zhejiang University of science and engineering Ningbo |