JP7029740B2 - ２－メチルアリルアルコールを連続的に製造する方法 - Google Patents

２－メチルアリルアルコールを連続的に製造する方法 Download PDF

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Publication number: JP7029740B2
Authority: JP; Japan
Prior art keywords: methylallyl; reaction; sodium acetate; water; solution
Prior art date: 2017-12-22
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.): Active

Application number

JP2020554344A

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English (en)

Japanese (ja)

Other versions

JP2021506981A (ja

Inventor

紅尹

志栄陳

偉松王

新栄王

勝利王

一豊金

楠董

洪軍高

定連馬

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Zhejiang University ZJU

Zhejiang Huangma Technology Co Ltd

Original Assignee

Zhejiang University ZJU

Zhejiang Huangma Technology Co Ltd

Priority date (The priority date 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 date listed.)

2017-12-22

Filing date

2018-10-10

Publication date

2022-03-04

2018-10-10 Application filed by Zhejiang University ZJU, Zhejiang Huangma Technology Co Ltd filed Critical Zhejiang University ZJU

2021-02-22 Publication of JP2021506981A publication Critical patent/JP2021506981A/ja

2022-03-04 Application granted granted Critical

2022-03-04 Publication of JP7029740B2 publication Critical patent/JP7029740B2/ja

Status Active legal-status Critical Current

2038-10-10 Anticipated expiration legal-status Critical

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BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 title claims description 49
238000000034 method Methods 0.000 title claims description 40
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 77
238000006243 chemical reaction Methods 0.000 claims description 48
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 45
239000001632 sodium acetate Substances 0.000 claims description 45
235000017281 sodium acetate Nutrition 0.000 claims description 45
239000000243 solution Substances 0.000 claims description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 43
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 claims description 23
238000003756 stirring Methods 0.000 claims description 23
239000011780 sodium chloride Substances 0.000 claims description 22
239000013078 crystal Substances 0.000 claims description 11
238000010992 reflux Methods 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 5
239000012452 mother liquor Substances 0.000 claims description 4
239000012071 phase Substances 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 4
239000008346 aqueous phase Substances 0.000 claims description 3
239000011259 mixed solution Substances 0.000 claims description 2
239000000047 product Substances 0.000 description 16
238000001914 filtration Methods 0.000 description 9
238000002156 mixing Methods 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
239000003513 alkali Substances 0.000 description 7
239000006227 byproduct Substances 0.000 description 7
239000002994 raw material Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000005886 esterification reaction Methods 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
238000007127 saponification reaction Methods 0.000 description 6
239000012670 alkaline solution Substances 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
-1 aluminum alkoxide Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000005394 methallyl group Chemical group 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000003444 phase transfer catalyst Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000002253 acid Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
238000001514 detection method Methods 0.000 description 3
238000006266 etherification reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012530 fluid Substances 0.000 description 3
229940051841 polyoxyethylene ether Drugs 0.000 description 3
229920000056 polyoxyethylene ether Polymers 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
230000002194 synthesizing effect Effects 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000002699 waste material Substances 0.000 description 3
239000002351 wastewater Substances 0.000 description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000005265 energy consumption Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000178 monomer Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
238000005705 Cannizzaro reaction Methods 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
STNJBCKSHOAVAJ-UHFFFAOYSA-N alpha-methyl acrolein Natural products CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000012267 brine Substances 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000016507 interphase Effects 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000010248 power generation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002910 solid waste Substances 0.000 description 1
238000013517 stratification Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1

Images

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
- C07C29/12—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 mineral acids
- C07C29/124—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 mineral acids of halides
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
- C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP2020554344A 2017-12-22 2018-10-10 ２－メチルアリルアルコールを連続的に製造する方法 Active JP7029740B2 (ja)

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Application Number	Priority Date	Filing Date	Title
CN201711400139.5		2017-12-22
CN201711400139.5A CN108191604B (zh)	2017-12-22	2017-12-22	一种连续制备2-甲基烯丙醇的方法
PCT/CN2018/109595 WO2019119934A1 (zh)	2017-12-22	2018-10-10	一种连续制备2-甲基烯丙醇的方法

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JP2021506981A JP2021506981A (ja)	2021-02-22
JP7029740B2 true JP7029740B2 (ja)	2022-03-04

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JP (1)	JP7029740B2 (zh)
KR (1)	KR102364274B1 (zh)
CN (1)	CN108191604B (zh)
RU (1)	RU2734548C1 (zh)
WO (1)	WO2019119934A1 (zh)

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CN108191604B (zh) *	2017-12-22	2020-03-27	浙江大学	一种连续制备2-甲基烯丙醇的方法
CN111099990B (zh) *	2019-12-31	2023-12-26	山东广通新材料有限公司	长碳链二元羧酸精制结晶母液的回收利用方法
CN111170828B (zh) *	2020-01-17	2023-01-03	浙江大学宁波理工学院	利用原位生成Cu(I)催化剂制备甲基烯丙醇的方法
CN111499515A (zh) *	2020-04-28	2020-08-07	南京简迪环境工程有限公司	硝基氯苯连续水解合成硝基酚钠工艺
CN112546658A (zh) *	2020-11-13	2021-03-26	南通百川新材料有限公司	一种新型的2-甲氧基-1-丙醇乙酸酯脱酯精馏提纯方法
CN114015034A (zh) *	2021-12-08	2022-02-08	江苏奥克化学有限公司	用于合成减水剂聚醚的醇钠催化剂的制备方法与应用
CN114560752A (zh) *	2022-02-24	2022-05-31	浙江皇马科技股份有限公司	一种2-甲基烯丙醇的合成方法

Citations (2)

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Publication number	Priority date	Publication date	Assignee	Title
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
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

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JPS5210296A (en) *	1975-07-15	1977-01-26	Kohjin Co Ltd	A process for preparing 6,2'-cyclo-5- substituted isocytidines
KR100676304B1 (ko) *	2004-12-24	2007-01-30	주식회사 엘지화학	네오펜틸글리콜의 제조방법
JP2009107949A (ja) *	2007-10-29	2009-05-21	Nippon Shokubai Co Ltd	アリルアルコール化合物の製造方法
CN104341255B (zh) *	2014-09-19	2016-08-24	江苏苏博特新材料股份有限公司	一种不饱和醇的制备方法
CN108191604B (zh) *	2017-12-22	2020-03-27	浙江大学	一种连续制备2-甲基烯丙醇的方法

2017
- 2017-12-22 CN CN201711400139.5A patent/CN108191604B/zh active Active
2018
- 2018-10-10 WO PCT/CN2018/109595 patent/WO2019119934A1/zh active Application Filing
- 2018-10-10 KR KR1020207010732A patent/KR102364274B1/ko active IP Right Grant
- 2018-10-10 RU RU2020112924A patent/RU2734548C1/ru active
- 2018-10-10 JP JP2020554344A patent/JP7029740B2/ja active Active

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
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

Also Published As

Publication number	Publication date
WO2019119934A1 (zh)	2019-06-27
CN108191604B (zh)	2020-03-27
KR102364274B1 (ko)	2022-02-17
JP2021506981A (ja)	2021-02-22
KR20200047716A (ko)	2020-05-07
RU2734548C1 (ru)	2020-10-20
CN108191604A (zh)	2018-06-22

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