SK27893A3 - Two-step process for liquid-phase production of oximes - Google Patents

Two-step process for liquid-phase production of oximes Download PDF

Info

Publication number: SK27893A3
Authority: SK; Slovakia
Prior art keywords: range; reaction; carbonyl compound; hydroxylamine; process according
Prior art date: 1992-04-01

Application number

SK278-93A

Other languages

English (en)

Slovak (sk)

Inventor

Maria A Mantegazza

Guido Petrini

Original Assignee

Enichem Anic Srl

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.)

1992-04-01

Filing date

1993-04-01

Publication date

1993-11-10

1993-04-01 Application filed by Enichem Anic Srl filed Critical Enichem Anic Srl

1993-11-10 Publication of SK27893A3 publication Critical patent/SK27893A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 12
239000007791 liquid phase Substances 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title claims description 3
150000002923 oximes Chemical class 0.000 title abstract description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 33
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 23
239000003054 catalyst Substances 0.000 claims abstract description 21
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 20
229910021529 ammonia Inorganic materials 0.000 claims abstract description 13
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 6
239000010703 silicon Substances 0.000 claims abstract description 6
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
230000001590 oxidative effect Effects 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
229910052710 silicon Inorganic materials 0.000 claims abstract description 5
229910052719 titanium Inorganic materials 0.000 claims abstract description 5
239000010936 titanium Substances 0.000 claims abstract description 5
229910000069 nitrogen hydride Inorganic materials 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 31
150000001728 carbonyl compounds Chemical class 0.000 claims description 19
239000007788 liquid Substances 0.000 claims description 8
239000012429 reaction media Substances 0.000 claims description 7
230000035484 reaction time Effects 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
238000006555 catalytic reaction Methods 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 5
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 25
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 3
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 3
239000004005 microsphere Substances 0.000 description 3
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GNKTZDSRQHMHLZ-UHFFFAOYSA-N [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] Chemical compound [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] GNKTZDSRQHMHLZ-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003509 tertiary alcohols Chemical class 0.000 description 2
FSHMPNBRNOGDDK-UHFFFAOYSA-N 1,2,3,4,4a,5,5a,6-octahydrophenazine Chemical compound C1=CCC2NC(CCCC3)C3=NC2=C1 FSHMPNBRNOGDDK-UHFFFAOYSA-N 0.000 description 1
AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 1
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
JLYNSPSTPQAEAX-UHFFFAOYSA-N 4-cyclohexylcyclohexan-1-one Chemical compound C1CC(=O)CCC1C1CCCCC1 JLYNSPSTPQAEAX-UHFFFAOYSA-N 0.000 description 1
JYYRTWNCBVRKMN-UHFFFAOYSA-N Octahydrophenazine Natural products C1CCCC2=C1N=C1CCCCC1=N2 JYYRTWNCBVRKMN-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
SFBLKWGYRDDITM-UHFFFAOYSA-J [Ti+4].[O-]S([O-])=O.[O-]S([O-])=O Chemical compound [Ti+4].[O-]S([O-])=O.[O-]S([O-])=O SFBLKWGYRDDITM-UHFFFAOYSA-J 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
-1 alicyclic alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
RFAZFSACZIVZDV-UHFFFAOYSA-N butan-2-one Chemical compound CCC(C)=O.CCC(C)=O RFAZFSACZIVZDV-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
NTDWKOBRLRKJOC-UHFFFAOYSA-N n-cyclohex-2-yn-1-ylidenehydroxylamine Chemical compound ON=C1CCCC#C1 NTDWKOBRLRKJOC-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000006146 oximation reaction Methods 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
239000011148 porous material Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

SK278-93A 1992-04-01 1993-04-01 Two-step process for liquid-phase production of oximes SK27893A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ITMI920776A IT1255745B (it)	1992-04-01	1992-04-01	Processo in due stadi per la produzione in fase liquida di ossime

Publications (1)

Publication Number	Publication Date
SK27893A3 true SK27893A3 (en)	1993-11-10

Family

ID=11362723

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK278-93A SK27893A3 (en)	1992-04-01	1993-04-01	Two-step process for liquid-phase production of oximes

Country Status (10)

Country	Link
US (1)	US5312987A (de)
EP (1)	EP0564040B1 (de)
JP (1)	JP3409144B2 (de)
KR (1)	KR960007724B1 (de)
CZ (1)	CZ284458B6 (de)
DE (1)	DE69302739T2 (de)
ES (1)	ES2087642T3 (de)
IT (1)	IT1255745B (de)
PL (1)	PL171270B1 (de)
SK (1)	SK27893A3 (de)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5451701A (en) *	1994-03-11	1995-09-19	Arco Chemical Technology, L.P.	Integrated process for cyclohexanone oxime production
DE10047435A1 (de) *	2000-09-26	2002-04-11	Degussa	Verfahren zur Herstellung von Oximen
US7091381B2 (en) *	2001-07-25	2006-08-15	Asahi Kasei Chemicals Corporation	Process for preparation of cyclohexanone oxime
DE10142620A1 (de)	2001-08-31	2003-03-20	Degussa	Ammoximation von Ketonen und Aufarbeitung durch Pervaporation/Dampfpermeation
DE10142621A1 (de)	2001-08-31	2003-03-20	Degussa	Aufarbeitung der Ammoximationsprodukte von Ketonen durch Flüssig-Flüssig-Extraktion in einem ternären Lösemittelsystem
DE10158352A1 (de)	2001-11-28	2003-06-12	Degussa	Zweiphasige Ammoximierung
US7408080B2 (en)	2002-05-31	2008-08-05	China Petroleum & Chemical Corporation	Process for ammoximation of carbonyl compounds
EP1552886B1 (de)	2002-05-31	2020-05-06	China Petroleum & Chemical Corporation	Verfahren zur regeneration eines titanhaltigen katalysators
TWI324990B (en)	2002-06-28	2010-05-21	Sumitomo Chemical Co	Method for producing cyclohexanone oxime
DE10260717A1 (de) *	2002-12-23	2004-07-01	Degussa Ag	Verfahren zur Herstellung von Oximen
JP4534428B2 (ja) *	2003-04-09	2010-09-01	住友化学株式会社	シクロヘキサノンオキシムの製造方法
JP4552435B2 (ja) *	2003-12-22	2010-09-29	住友化学株式会社	オキシムの製造方法
JP4577003B2 (ja) *	2004-12-16	2010-11-10	住友化学株式会社	オキシムの製造方法
JP4639792B2 (ja)	2004-12-22	2011-02-23	住友化学株式会社	シクロヘキサノンオキシムの製造方法
SG123723A1 (en)	2004-12-22	2006-07-26	Sumitomo Chemical Co	Process for producing cyclohexanone oxime
SG123716A1 (en)	2004-12-22	2006-07-26	Sumitomo Chemical Co	Process for producing cyclohexanone oxime
JP4635644B2 (ja)	2005-02-28	2011-02-23	住友化学株式会社	シクロヘキサノンオキシムの製造方法
JP4577077B2 (ja) *	2005-04-25	2010-11-10	住友化学株式会社	シクロヘキサノンオキシムの製造方法
US7372776B2 (en) *	2006-02-23	2008-05-13	Image Acoustics, Inc.	Modal acoustic array transduction apparatus
JP2012067044A (ja)	2010-09-27	2012-04-05	Sumitomo Chemical Co Ltd	シクロヘキサノンオキシムの製造方法
TWI480100B (zh)	2011-04-27	2015-04-11	China Petrochemical Dev Corp Taipei Taiwan	Titanium-silicon molecular sieve and its preparation method and method for producing cyclohexanone oxime using the molecular sieve
TWI508935B (zh)	2011-08-11	2015-11-21	China Petrochemical Dev Corp Taipei Taiwan	Titanium-silicon molecular sieve and its preparation method and method for producing cyclohexanone oxime using the molecular sieve
CN103896801B (zh)	2012-12-25	2016-03-16	中国石油化学工业开发股份有限公司	制造酮肟的方法
CN103193212B (zh) *	2013-03-15	2016-01-20	华东师范大学	一种游离羟胺的制备方法
CN104262196B (zh) *	2014-09-02	2016-07-27	河北美邦工程科技有限公司	一种氨肟化反应与分离耦合工艺及装置
CN110803999A (zh) *	2019-12-04	2020-02-18	长沙兴和新材料有限公司	一种提高环己酮肟质量和收率的生产工艺及设备系统
CN114230482A (zh) *	2021-09-09	2022-03-25	浙江吉瑞通新材料有限公司	一种环己酮氨肟化生产环已酮肟的方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB677386A (en) *	1949-11-07	1952-08-13	Inventa Ag	Improvements relating to the production of oximes
DE1568504A1 (de) *	1966-03-19	1970-04-09	Bayer Ag	Verfahren zur Herstellung von gegebenenfalls alkylsubstituiertem Cyclohexanonoxim
IT1214622B (it) *	1985-07-10	1990-01-18	Montedipe Spa	Processo catalitico per laproduzione di cicloesanonossima.
US4794198A (en) *	1986-11-14	1988-12-27	Montedipe S.P.A.	Catalytic process for the manufacture of oximes
IT1222022B (it) *	1987-07-14	1990-08-31	Montedipe Spa	Metodo per la preparazione di un catalizzatore per l' ammossimazione di composti carbonilici
IT1217899B (it) *	1988-06-23	1990-03-30	Montedipe Spa	Processo catalitico per la produzione di ossime
IT1244680B (it) *	1991-01-23	1994-08-08	Montedipe Srl	Processo a piu' stadi per l'ammossimazione in fase liquida dei composti carbonilici

1992
- 1992-04-01 IT ITMI920776A patent/IT1255745B/it active IP Right Grant
1993
- 1993-03-30 EP EP93200901A patent/EP0564040B1/de not_active Expired - Lifetime
- 1993-03-30 ES ES93200901T patent/ES2087642T3/es not_active Expired - Lifetime
- 1993-03-30 US US08/039,839 patent/US5312987A/en not_active Expired - Lifetime
- 1993-03-30 PL PL93298303A patent/PL171270B1/pl unknown
- 1993-03-30 DE DE69302739T patent/DE69302739T2/de not_active Expired - Lifetime
- 1993-03-31 KR KR1019930005261A patent/KR960007724B1/ko not_active Expired - Lifetime
- 1993-04-01 SK SK278-93A patent/SK27893A3/sk unknown
- 1993-04-01 CZ CZ93562A patent/CZ284458B6/cs not_active IP Right Cessation
- 1993-04-01 JP JP09648693A patent/JP3409144B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE69302739T2 (de)	1996-10-31
EP0564040B1 (de)	1996-05-22
IT1255745B (it)	1995-11-15
JPH0649015A (ja)	1994-02-22
ITMI920776A0 (it)	1992-04-01
CZ284458B6 (cs)	1998-12-16
US5312987A (en)	1994-05-17
ITMI920776A1 (it)	1993-10-01
DE69302739D1 (de)	1996-06-27
CZ56293A3 (en)	1994-02-16
PL171270B1 (pl)	1997-03-28
JP3409144B2 (ja)	2003-05-26
EP0564040A2 (de)	1993-10-06
KR960007724B1 (ko)	1996-06-11
PL298303A1 (en)	1994-03-07
ES2087642T3 (es)	1996-07-16
KR930021606A (ko)	1993-11-22
EP0564040A3 (en)	1993-11-24

Publication	Publication Date	Title
SK27893A3 (en)	1993-11-10	Two-step process for liquid-phase production of oximes
JP3009285B2 (ja)	2000-02-14	カルボニル化合物の液相アンモオキシム化多段法
EP0522634B1 (de)	2001-01-24	Verfahren zur direkten katalytischen Produktion von Hydroxylamin
CN101531615A (zh)	2009-09-16	制备肟的方法
US6566555B2 (en)	2003-05-20	Process for preparing oximes
US20020143210A1 (en)	2002-10-03	Process for production of oximes cocatalyzed by ammonium salts or substituted ammonium salts
US5498793A (en)	1996-03-12	Catalytic process for the production of oximes
JP2010195835A (ja)	2010-09-09	カルボニル化合物のアンモオキシム化法
US5239119A (en)	1993-08-24	Catalytic synthesis of azines from H2 O2 /NH3 /carbonyl compounds
US7005547B2 (en)	2006-02-28	Process for the preparation of cyclohexanone oxime
US6759556B2 (en)	2004-07-06	Process for the production of cyclohexanone oxime
KR100257629B1 (ko)	2000-06-01	히드록실암모늄 염 용액의 제조 및 정제방법
CN103492312B (zh)	2016-11-02	制备羟胺的方法
KR20010079651A (ko)	2001-08-22	히드라진 수화물의 제조 방법