SU689616A3 - Способ получени амида алифатической или ароматической одноосновной карбоновой кислоты - Google Patents

Способ получени амида алифатической или ароматической одноосновной карбоновой кислоты

Info

Publication number: SU689616A3
Authority: SU; USSR - Soviet Union
Prior art keywords: copper; promoter; nitrile; amide; catalyst
Prior art date: 1973-06-05

Application number

SU742031563A

Other languages

English (en)

Russian (ru)

Inventor

Асано Сиро

Иосимура Киетака

Хасимото Масао

Original Assignee

Мицуи Тоатцу Кемикалз Инкорпорейтед (Фирма)

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.)

1973-06-05

Filing date

1974-06-05

Publication date

1979-09-30

1973-06-05 Priority claimed from JP6251073A external-priority patent/JPS5720294B2/ja

1974-06-05 Application filed by Мицуи Тоатцу Кемикалз Инкорпорейтед (Фирма) filed Critical Мицуи Тоатцу Кемикалз Инкорпорейтед (Фирма)

1979-09-30 Application granted granted Critical

1979-09-30 Publication of SU689616A3 publication Critical patent/SU689616A3/ru

Links

238000000034 method Methods 0.000 title claims description 12
150000001408 amides Chemical class 0.000 title claims description 8
125000001931 aliphatic group Chemical group 0.000 title claims 2
125000003118 aryl group Chemical group 0.000 title claims 2
150000001732 carboxylic acid derivatives Chemical class 0.000 title claims 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 25
239000003054 catalyst Substances 0.000 claims description 24
229910052802 copper Inorganic materials 0.000 claims description 24
239000010949 copper Substances 0.000 claims description 24
150000002825 nitriles Chemical class 0.000 claims description 15
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 11
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 3
230000036571 hydration Effects 0.000 claims description 3
238000006703 hydration reaction Methods 0.000 claims description 3
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 claims description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
229910001960 metal nitrate Inorganic materials 0.000 claims 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
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
229910052791 calcium Inorganic materials 0.000 claims 1
239000011575 calcium Substances 0.000 claims 1
230000007423 decrease Effects 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
235000010344 sodium nitrate Nutrition 0.000 description 11
239000004317 sodium nitrate Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
238000002474 experimental method Methods 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
239000005749 Copper compound Substances 0.000 description 4
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 4
239000005751 Copper oxide Substances 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
150000001880 copper compounds Chemical class 0.000 description 4
229910000431 copper oxide Inorganic materials 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
239000007788 liquid Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 3
239000005750 Copper hydroxide Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000956 alloy Substances 0.000 description 3
229910045601 alloy Inorganic materials 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
229910001956 copper hydroxide Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
239000012295 chemical reaction liquid Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
238000000151 deposition Methods 0.000 description 2
-1 for example Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000000758 substrate Substances 0.000 description 2
ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
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
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical group N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000032683 aging Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000010923 batch production Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229910001431 copper ion Inorganic materials 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
QYCVHILLJSYYBD-UHFFFAOYSA-L copper;oxalate Chemical compound [Cu+2].[O-]C(=O)C([O-])=O QYCVHILLJSYYBD-UHFFFAOYSA-L 0.000 description 1
HFORGINKVIYNFC-UHFFFAOYSA-N copper;oxochromium Chemical compound [Cr].[Cu]=O HFORGINKVIYNFC-UHFFFAOYSA-N 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004227 thermal cracking Methods 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1

Landscapes

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

SU742031563A 1973-06-05 1974-06-05 Способ получени амида алифатической или ароматической одноосновной карбоновой кислоты SU689616A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP6251073A JPS5720294B2 (it)	1973-06-05	1973-06-05

Publications (1)

Publication Number	Publication Date
SU689616A3 true SU689616A3 (ru)	1979-09-30

Family

ID=13202231

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU742031563A SU689616A3 (ru)	1973-06-05	1974-06-05	Способ получени амида алифатической или ароматической одноосновной карбоновой кислоты

Country Status (2)

Country	Link
IT (1)	IT1014747B (it)
SU (1)	SU689616A3 (it)

1974
- 1974-06-04 IT IT2357274A patent/IT1014747B/it active
- 1974-06-05 SU SU742031563A patent/SU689616A3/ru active

Also Published As

Publication number	Publication date
IT1014747B (it)	1977-04-30

Publication	Publication Date	Title
US4083809A (en)	1978-04-11	Hydrogenation catalyst and method of producing same
US3696152A (en)	1972-10-03	Hydration of nitriles to amides using heterogeneous cupreous catalysts
US5097073A (en)	1992-03-17	Production of aliphatic primary of secondary amine
US4263175A (en)	1981-04-21	Catalyst for the production of pyrrolidone
EP0013578B1 (en)	1981-11-04	Process for producing methacrylic acid
SU689616A3 (ru)	1979-09-30	Способ получени амида алифатической или ароматической одноосновной карбоновой кислоты
USRE36719E (en)	2000-05-30	Process for the manufacture of 2,5-dihydrofurans from γ,δ-epoxybutenes
US4922023A (en)	1990-05-01	Preparation of aliphatic N,N-dialkyl-substituted amino alcohols
US4169107A (en)	1979-09-25	Process for manufacturing an amide compound using aluminum nitrate promoter
US3994973A (en)	1976-11-30	Catalysts for the hydration of nitriles to amides
US4036879A (en)	1977-07-19	Catalysts for the hydration of nitriles of amides
JPS6362525B2 (it)	1988-12-02
US4100361A (en)	1978-07-11	Manufacture of butenediol diacetates
US6384263B1 (en)	2002-05-07	Process for making 3-hydroxyalkanelnitriles and conversion of the 3-hydroxyalkanelnitrile to an hydroxyaminoalkane
EP0435445A1 (en)	1991-07-03	Method for preparing alpha beta-unsaturated nitriles
JP3330404B2 (ja)	2002-09-30	酢酸エチルの製造方法
JPS60146885A (ja)	1985-08-02	フルフリルアミン及び／又はテトラヒドロフルフリルアミンの製造法
US5124485A (en)	1992-06-23	Catalysts and methods of separation thereof
US4966970A (en)	1990-10-30	Process for manufacturing pyrazines
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JP3274301B2 (ja)	2002-04-15	ヒドロキシアルカナールの製造方法
KR790000923B1 (ko)	1979-07-31	아미드 화합물의 제조법
JP2998377B2 (ja)	2000-01-11	メタクリルアミドの製造方法