JPS6210216B2 - - Google Patents

Info

Publication number: JPS6210216B2
Authority: JP; Japan
Prior art keywords: reaction; stirring; hydrogen chloride; alcoholysis; ethanol
Prior art date: 1978-12-26
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

JP53161815A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5587734A (en

Inventor

Norihiko Masunari

Nobuhiro Danno

Toshuki Kusuda

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.)

Nippon Synthetic Chemical Industry Co Ltd

Original Assignee

Nippon Synthetic Chemical Industry 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.)

1978-12-26

Filing date

1978-12-26

Publication date

1987-03-05

1978-12-26 Application filed by Nippon Synthetic Chemical Industry Co Ltd filed Critical Nippon Synthetic Chemical Industry Co Ltd

1978-12-26 Priority to JP16181578A priority Critical patent/JPS5587734A/ja

1980-07-02 Publication of JPS5587734A publication Critical patent/JPS5587734A/ja

1987-03-05 Publication of JPS6210216B2 publication Critical patent/JPS6210216B2/ja

Status Granted legal-status Critical Current

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 19
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 19
238000006136 alcoholysis reaction Methods 0.000 claims description 16
-1 imide ether hydrochloride Chemical class 0.000 claims description 15
150000002905 orthoesters Chemical class 0.000 claims description 12
229910021529 ammonia Inorganic materials 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
238000003756 stirring Methods 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 26
235000019270 ammonium chloride Nutrition 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000007789 gas Substances 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 13
239000000203 mixture Substances 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000007788 liquid Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
238000007664 blowing Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000002002 slurry Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
125000003710 aryl alkyl group Chemical group 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 6
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 5
238000000034 method Methods 0.000 description 5
239000011259 mixed solution Substances 0.000 description 5
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
125000000392 cycloalkenyl group Chemical group 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 2
239000002184 metal Substances 0.000 description 2
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000004065 wastewater treatment Methods 0.000 description 2
FQJMHCIJFGVJAA-UHFFFAOYSA-N 1,1,1-triethoxy-2-methylpropane Chemical compound CCOC(OCC)(OCC)C(C)C FQJMHCIJFGVJAA-UHFFFAOYSA-N 0.000 description 1
KOPMZTKUZCNGFY-UHFFFAOYSA-N 1,1,1-triethoxybutane Chemical compound CCCC(OCC)(OCC)OCC KOPMZTKUZCNGFY-UHFFFAOYSA-N 0.000 description 1
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
DIKAUBKIDNXNNW-UHFFFAOYSA-N 1,1,1-triethoxypentane Chemical compound CCCCC(OCC)(OCC)OCC DIKAUBKIDNXNNW-UHFFFAOYSA-N 0.000 description 1
FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
YAXJYZHZHZDYPG-UHFFFAOYSA-N 1-ethylaziridine-2,3-dione Chemical compound C(C)N1C(C1=O)=O YAXJYZHZHZDYPG-UHFFFAOYSA-N 0.000 description 1
UNYMPEIBWGQKLM-UHFFFAOYSA-N 1-methylaziridine-2,3-dione Chemical compound CN1C(=O)C1=O UNYMPEIBWGQKLM-UHFFFAOYSA-N 0.000 description 1
PNHBFCDPHOKOPO-UHFFFAOYSA-N 3-ethylazetidine-2,4-dione Chemical compound C(C)C1C(=O)NC1=O PNHBFCDPHOKOPO-UHFFFAOYSA-N 0.000 description 1
SZQUNAOZNFKTHM-UHFFFAOYSA-N 3-ethylpiperidine-2,6-dione Chemical compound CCC1CCC(=O)NC1=O SZQUNAOZNFKTHM-UHFFFAOYSA-N 0.000 description 1
RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003342 alkenyl 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
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
SDAXRHHPNYTELL-UHFFFAOYSA-N heptanenitrile Chemical compound CCCCCCC#N SDAXRHHPNYTELL-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003002 pH adjusting agent Substances 0.000 description 1
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Landscapes

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

JP16181578A 1978-12-26 1978-12-26 Preparation of orthoester Granted JPS5587734A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP16181578A JPS5587734A (en)	1978-12-26	1978-12-26	Preparation of orthoester

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP16181578A JPS5587734A (en)	1978-12-26	1978-12-26	Preparation of orthoester

Publications (2)

Publication Number	Publication Date
JPS5587734A JPS5587734A (en)	1980-07-02
JPS6210216B2 true JPS6210216B2 (fr)	1987-03-05

Family

ID=15742428

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16181578A Granted JPS5587734A (en)	1978-12-26	1978-12-26	Preparation of orthoester

Country Status (1)

Country	Link
JP (1)	JPS5587734A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5401885A (en) *	1993-06-01	1995-03-28	Huls America, Inc.	Method of preparing ortho esters and 1.1-dialkoxycycloalkanes
TWI546306B (zh) *	2007-04-11	2016-08-21	第一三共股份有限公司	神經胺酸衍生物之製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS51108012A (en) *	1975-03-19	1976-09-25	Kuraray Co	Orutoesuteruno seizohoho

1978
- 1978-12-26 JP JP16181578A patent/JPS5587734A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS51108012A (en) *	1975-03-19	1976-09-25	Kuraray Co	Orutoesuteruno seizohoho

Also Published As

Publication number	Publication date
JPS5587734A (en)	1980-07-02

Publication	Publication Date	Title
CA1340549C (fr)	1999-05-18	Methode pour preparer des derives de la sphingosine
JPH05213838A (ja)	1993-08-24	フルオキセチンの製法
HU206202B (en)	1992-09-28	Process for producing pyrimidine derivatives
FR2470763A1 (fr)	1981-06-12	Procede de preparation d'un b-aminopropionamide
US6806380B2 (en)	2004-10-19	Modified safe and efficient process for the environmentally friendly synthesis of imidoesters
JPS6210216B2 (fr)	1987-03-05
US4157342A (en)	1979-06-05	Process for preparation of 3-acylamino-4-homoisotwistane
CA1249590A (fr)	1989-01-31	Preparation d'un acetal d'amide bicyclique
US4169208A (en)	1979-09-25	Process for producing unsaturated quaternary ammonium salt
JPH1067755A (ja)	1998-03-10	４，６−ジヒドロキシピリミジンの製法
US4492792A (en)	1985-01-08	Process for preparing 4-amino-5-dialkoxy-methylpyrimidine derivatives
JPH039898B2 (fr)	1991-02-12
US3402193A (en)	1968-09-17	Preparation of imido ester hydrochlorides
EP0244810B1 (fr)	1992-03-11	Procédé de préparation de 2-oxazolidinones
KR900001179B1 (ko)	1990-02-27	4-아미노-5-디알콕시메틸피리미딘 유도체의 제조방법
EP0893436B1 (fr)	2002-03-27	Procédé pour la préparation d'esters d'acide cyanoformique
US5550299A (en)	1996-08-27	Method of preparing 1.1-dialkoxycycloalkanes
JPS6210215B2 (fr)	1987-03-05
JPH0353298B2 (fr)	1991-08-14
JP2021181407A (ja)	2021-11-25	アミドアルコール化合物の水和物及びその製造方法、並びに、及びラクトン化合物の製造方法
US4189444A (en)	1980-02-19	Process for the preparation of N,N'-disubstituted 2-naphthaleneethanimidamide and intermediates used therein
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
JP3719736B2 (ja)	2005-11-24	ピラゾロン類の製造法
JPH02273653A (ja)	1990-11-08	３―置換アミノアクリル酸エステル類の製造法
JPS6317869A (ja)	1988-01-25	２−低級アルキル−４−アミノ−５−ホルミルピリミジンの製造法