JPS621946B2 - - Google Patents

Info

Publication number: JPS621946B2
Authority: JP; Japan
Prior art keywords: cyanoacetaldehyde; reaction; aminomethylene; solvent; amines
Prior art date: 1982-09-14
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

JP15891582A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5948451A (ja

Inventor

Mamoru Nakai

Hiroshi Yoshida

Teruhiko Inoe

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.)

Ube Corp

Original Assignee

Ube Industries 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.)

1982-09-14

Filing date

1982-09-14

Publication date

1987-01-16

1982-09-14 Application filed by Ube Industries Ltd filed Critical Ube Industries Ltd

1982-09-14 Priority to JP15891582A priority Critical patent/JPS5948451A/ja

1984-03-19 Publication of JPS5948451A publication Critical patent/JPS5948451A/ja

1987-01-16 Publication of JPS621946B2 publication Critical patent/JPS621946B2/ja

Status Granted legal-status Critical Current

Links

LOFUZRUXVYHVQW-UHFFFAOYSA-N 3-amino-2-formylprop-2-enenitrile Chemical class NC=C(C=O)C#N LOFUZRUXVYHVQW-UHFFFAOYSA-N 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 11
ZMMOYIXZGHJMNI-UHFFFAOYSA-N 3-oxopropanenitrile Chemical class O=CCC#N ZMMOYIXZGHJMNI-UHFFFAOYSA-N 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 description 17
239000002904 solvent Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
NCQIJCZRPDYLHS-UHFFFAOYSA-N 2-formyl-3-methoxyprop-2-enenitrile Chemical compound COC=C(C=O)C#N NCQIJCZRPDYLHS-UHFFFAOYSA-N 0.000 description 4
ZRJLAYJQCBEKRO-UHFFFAOYSA-N 3-ethoxy-2-formylprop-2-enenitrile Chemical compound CCOC=C(C=O)C#N ZRJLAYJQCBEKRO-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000002994 raw material Substances 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
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
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
ACYMGUSQXQEHGA-UHFFFAOYSA-N cyclohex-2-en-1-amine Chemical compound NC1CCCC=C1 ACYMGUSQXQEHGA-UHFFFAOYSA-N 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
-1 propoxymethylene cyanoacetaldehyde Chemical compound 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
239000002002 slurry Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
NAWOUBPWTIVLAO-UHFFFAOYSA-N 3-butoxy-2-formylprop-2-enenitrile Chemical compound CCCCOC=C(C=O)C#N NAWOUBPWTIVLAO-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000010813 internal standard method Methods 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
YVCLRNJQIURSKF-UHFFFAOYSA-N 2-(diethoxymethyl)-3-hydroxyprop-2-enenitrile Chemical compound CCOC(OCC)C(=CO)C#N YVCLRNJQIURSKF-UHFFFAOYSA-N 0.000 description 1
JVQUIFRKEPFYBR-UHFFFAOYSA-N 2-(dimethoxymethyl)-3-hydroxyprop-2-enenitrile Chemical compound COC(OC)C(=CO)C#N JVQUIFRKEPFYBR-UHFFFAOYSA-N 0.000 description 1
OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
XHGFTCMTKSDVJK-UHFFFAOYSA-N 3,3-dibutoxypropanenitrile Chemical compound CCCCOC(CC#N)OCCCC XHGFTCMTKSDVJK-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
NRHDCQLCSOWVTF-UHFFFAOYSA-N azonane Chemical compound C1CCCCNCCC1 NRHDCQLCSOWVTF-UHFFFAOYSA-N 0.000 description 1
238000007664 blowing Methods 0.000 description 1
YLBIBZCIFHPPKA-UHFFFAOYSA-N but-2-yn-1-amine Chemical compound CC#CCN YLBIBZCIFHPPKA-UHFFFAOYSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
HFWIMJHBCIGYFH-UHFFFAOYSA-N cyanoform Chemical compound N#CC(C#N)C#N HFWIMJHBCIGYFH-UHFFFAOYSA-N 0.000 description 1
KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229940100684 pentylamine Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

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

JP15891582A 1982-09-14 1982-09-14 アミノメチレンシアノアセトアルデヒド類の製造法 Granted JPS5948451A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP15891582A JPS5948451A (ja)	1982-09-14	1982-09-14	アミノメチレンシアノアセトアルデヒド類の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15891582A JPS5948451A (ja)	1982-09-14	1982-09-14	アミノメチレンシアノアセトアルデヒド類の製造法

Publications (2)

Publication Number	Publication Date
JPS5948451A JPS5948451A (ja)	1984-03-19
JPS621946B2 true JPS621946B2 (xx)	1987-01-16

Family

ID=15682118

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15891582A Granted JPS5948451A (ja)	1982-09-14	1982-09-14	アミノメチレンシアノアセトアルデヒド類の製造法

Country Status (1)

Country	Link
JP (1)	JPS5948451A (xx)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0573716U (ja) *	1992-02-26	1993-10-08	日本電気ホームエレクトロニクス株式会社	光ディスク装置の光ヘッド

1982
- 1982-09-14 JP JP15891582A patent/JPS5948451A/ja active Granted

Also Published As

Publication number	Publication date
JPS5948451A (ja)	1984-03-19

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