JPH0414653B2 - - Google Patents

Info

Publication number: JPH0414653B2
Authority: JP; Japan
Prior art keywords: alcohol; compound; lower alkyl; alkyl group; complex
Prior art date: 1984-06-09
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.): Expired

Application number

JP11859384A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6132A (ja

Inventor

Fumio Toda

Koichi Tanaka

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.)

Individual

Original Assignee

Individual

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.)

1984-06-09

Filing date

1984-06-09

Publication date

1992-03-13

1984-06-09 Application filed by Individual filed Critical Individual

1984-06-09 Priority to JP11859384A priority Critical patent/JPS6132A/ja

1986-01-06 Publication of JPS6132A publication Critical patent/JPS6132A/ja

1992-03-13 Publication of JPH0414653B2 publication Critical patent/JPH0414653B2/ja

Status Granted legal-status Critical Current

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
125000000217 alkyl group Chemical group 0.000 claims description 13
-1 acetylene alcohol compound Chemical class 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 10
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
235000019441 ethanol Nutrition 0.000 description 50
150000001875 compounds Chemical class 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 12
239000013078 crystal Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000000034 method Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
238000001914 filtration Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000011160 research Methods 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
GLQWGVMBEKNKTP-UHFFFAOYSA-N 1,1-bis(2,4-dimethylphenyl)prop-2-yn-1-ol Chemical compound CC1=CC(C)=CC=C1C(O)(C#C)C1=CC=C(C)C=C1C GLQWGVMBEKNKTP-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
AHEOVUWANYQNIZ-UHFFFAOYSA-N 9-prop-1-ynylfluoren-9-ol Chemical compound C1=CC=C2C(C#CC)(O)C3=CC=CC=C3C2=C1 AHEOVUWANYQNIZ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
229910016870 Fe(NO3)3-9H2O Inorganic materials 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000010633 broth Nutrition 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000012827 research and development Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP11859384A 1984-06-09 1984-06-09 アルコ−ル分離剤 Granted JPS6132A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP11859384A JPS6132A (ja)	1984-06-09	1984-06-09	アルコ−ル分離剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP11859384A JPS6132A (ja)	1984-06-09	1984-06-09	アルコ−ル分離剤

Publications (2)

Publication Number	Publication Date
JPS6132A JPS6132A (ja)	1986-01-06
JPH0414653B2 true JPH0414653B2 (fr)	1992-03-13

Family

ID=14740419

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11859384A Granted JPS6132A (ja)	1984-06-09	1984-06-09	アルコ−ル分離剤

Country Status (1)

Country	Link
JP (1)	JPS6132A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5871633A (ja) *	1981-10-23	1983-04-28	Toshiba Corp	圧接型半導体装置

1984
- 1984-06-09 JP JP11859384A patent/JPS6132A/ja active Granted

Also Published As

Publication number	Publication date
JPS6132A (ja)	1986-01-06

Publication	Publication Date	Title
EP0281627A1 (fr)	1988-09-14	Procede de reduction d'aldehydes ou de cetones
US4176138A (en)	1979-11-27	Process for preparing p-aminophenol in the presence of dimethyldodecylamine sulfate
US2122813A (en)	1938-07-05	Production of polyhydric alcohols
JP2001139508A (ja)	2001-05-22	光学活性含弗素ビナフトール誘導体
JPS6132A (ja)	1986-01-06	アルコ−ル分離剤
CA1052815A (fr)	1979-04-17	Precipitation du benzoate de sodium
EP0178331A1 (fr)	1986-04-23	Composes d'alkynol et agents de separation d'alcool
CN116715573B (zh)	2025-08-19	一种2,2-二甲基丁酰氯的合成方法
CN117142934B (zh)	2026-02-06	一种（s）-3-环己烯-1-甲酸及其中间体的制备方法
US7250529B2 (en)	2007-07-31	Synthesis process for 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid
JPS6365053B2 (fr)	1988-12-14
JPS5892647A (ja)	1983-06-02	アゾイミノエ−テル塩酸塩およびその製造方法
JP2003335715A (ja)	2003-11-28	アダマンタノール類の分離方法
JPS60202836A (ja)	1985-10-14	アセチレンアルコ−ル系化合物及びアルコ−ル分離剤
JP3959178B2 (ja)	2007-08-15	ヒドラジン誘導体の製造方法、その中間体および中間体の製造方法
JP2792883B2 (ja)	1998-09-03	トリメチロール化合物の精製法
JP3539152B2 (ja)	2004-07-07	シトシンの製法
JPS60202837A (ja)	1985-10-14	ジインジオ−ル系化合物及びアルコ−ル分離剤
JP3539153B2 (ja)	2004-07-07	シトシンの製造法
JPH04120039A (ja)	1992-04-21	水素結合性包接錯体形成剤及びこれを用いたアルコールの分離方法
US3081338A (en)	1963-03-12	Method of reacting hydrocarboyl manganese polycarbonyls
JPS62263140A (ja)	1987-11-16	α−フエニルプロピオン酸誘導体の製造法
EP0612760B1 (fr)	1997-01-02	Procédé de purification du phosphate d'estramustin ou ses sels
JPS63301843A (ja)	1988-12-08	パラヒドロキシベンズアルデヒドの精製法
JP2928856B2 (ja)	1999-08-03	ビス（４―アリルオキシ―３，５―ジブロモフェニル）スルホンの製造を行う方法