KR970065532A - 고리형 n-비닐 카르복실산 아미드의 제조 방법 - Google Patents
고리형 n-비닐 카르복실산 아미드의 제조 방법 Download PDFInfo
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- KR970065532A KR970065532A KR1019970009220A KR19970009220A KR970065532A KR 970065532 A KR970065532 A KR 970065532A KR 1019970009220 A KR1019970009220 A KR 1019970009220A KR 19970009220 A KR19970009220 A KR 19970009220A KR 970065532 A KR970065532 A KR 970065532A
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- cyclic
- carboxylic acid
- acid amide
- hydroxyethyl
- vinyl
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- 125000004122 cyclic group Chemical group 0.000 title claims abstract 13
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 title claims abstract 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- -1 cyclic carboxylic acid ester Chemical class 0.000 claims abstract 5
- 239000003054 catalyst Substances 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- 238000006297 dehydration reaction Methods 0.000 claims abstract 4
- BAMUPQJDKBGDPU-UHFFFAOYSA-N n-(2-hydroxyethyl)formamide Chemical compound OCCNC=O BAMUPQJDKBGDPU-UHFFFAOYSA-N 0.000 claims abstract 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 3
- 229910052710 silicon Inorganic materials 0.000 claims abstract 3
- 239000010703 silicon Substances 0.000 claims abstract 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 2
- TWYIPMITVXPNEM-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidine-2,5-dione Chemical group OCCN1C(=O)CCC1=O TWYIPMITVXPNEM-UHFFFAOYSA-N 0.000 claims 1
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical group C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 claims 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical group ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- LSDRPIKPZUFDLE-UHFFFAOYSA-N n-ethenylformamide;1-ethenylpyrrolidin-2-one Chemical compound C=CNC=O.C=CN1CCCC1=O LSDRPIKPZUFDLE-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 229940014800 succinic anhydride Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 abstract 2
- 230000018044 dehydration Effects 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/04—Seven-membered rings not condensed with other rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
본 발명은, 출발 물질로서, 값싸면서도 용이하게 얻을 수가 있는 고리형 카르복실산 에스테르와 모노에탄올아민을 사용하여 안전하면서도 저가로 고리형 N-비닐카르복실산 아미드를 안정되게 제조하는 방법을 제공한다. 본 발명의 방법은 고리형 카르복실산 에스테르와 모노에탄올아민을 액체상에서 분자간 탈수 반응(제1-단계 반응)시켜 고리형 N-(2-히드록시에틸) 카르복실산 아미드를 제조하는 단계 그 다음에는 이 고리형 N-(2-히드록시에틸) 카르복실산 아미드를 알칼리 금속 원소 및/또는 알칼리 토금속 원소 및 규소를 함유하는 산화물 촉매의 존재하에 기체상에서 분자내 탈수 반응(제2-단계 반응)시켜 고리형 N-비닐 카르복실산 아미드를 제조하는 단계로 구성되어 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 모노에탄올아민과 다음의 일반 화학식(1):(여기서 m은 0 또는 1이고: m과 n의 합은 3-5의 어떤 정수이며; CH2들 중의 하나는 산소 원자 또는 황원자로 치환될 수 있음)로 표시되는 고리형 카르복실산 에스테르를 액체상에서 분자간 탈수 반응(제1-단계반응)시켜 다음의 일반 화학식(2):(여기서 m은 0 또는 1이고; m 과 n의 합은 3-5의 어떤 정수이며; CH2들 중의 하나는 산소 원자 또는 황원자로 치환될 수 있음)로 표시되는 고리형 N-2(2-히드록시에틸) 카르복실산 아미드를 만들어 내는 단계, 그 다음에는 이 고리형 n-(2-히드록시에틸) 카르복실산 아미드를 알칼리 금속 원소 및/또는 알칼리 토금속 원소 및 규소를 함유하는 산화물 촉매의 존재하에 기체상에서 분자내 탈수 반응(제2-단계반응)시켜 다음의 일반 화학식(3):(여기서 m은 0 또는 1이고; m 과n의 합은 3-5의 어떤 정수이며; CH2들 중의 하나는 산소 원자 또는 황원자로 치환될 수 있음)로 표시되는 고리형 N-비닐카르복실산 아미드를 만들어 내는 단계를 포함함을 특징으로 하는, 고리형 N-비닐카르복실산 아미드의 제조 방법.
- 청구항 1에 있어서, 촉매는 다음의 일반 화학식(4):MaSibXcOd(4)(여기서 M은 알칼리 금속 원소들 및 알칼리 토금속 원소들로 구성된 군에서 선택된 1종 이상의 원소이고; Si는 규소이며; X는 붕소, 알루미늄 및 인으로 구성된 군에서 선택된 1종 이상의 원소이고; O는 산소이며; a,b,c 및 d는, 각각 M, Si, X 및 O의 원자 수들로서, a=1인 경우, b는 1-500이고 c는 0-1이며, d는 a,b 및 c의 값들과 각 구성 원소들의 결합 상태들에 의해 결정되는 값임을 조건으로 함)로 표시되는 산화물임을 특징으로 하는 방법.
- 청구항 1 또는 청구항 2에 있어서, 고리형 카르복실산 에스테르는 γ-부티로락톤이고, 고리형 N-(2-히드록시에틸) 카르복실산 아미드는 N-(2-히드록시에틸)-2-피롤리돈이며, 고리형 N-비닐 카르복실산 아미드 N-비닐-2-피롤리돈임을 특징으로 하는 방법.
- 청구항 1 또는 청구항 2에 있어서, 고리형 카르복실산 에스테르는 무수 숙신산이고, 고리형 N-(2-히드록시에틸) 카르복실산 아미드는 N-(2-히드록시에틸)-숙신이미드이며, 고리형 N-비닐 카르복실산 아미드는 N-비닐숙신이미드임을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP96-60,455 | 1996-03-18 | ||
| JP8060455A JP2939433B2 (ja) | 1996-03-18 | 1996-03-18 | 環式ｎ−ビニルカルボン酸アミドの製造方法 |
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| Publication Number | Publication Date |
|---|---|
| KR970065532A true KR970065532A (ko) | 1997-10-13 |
| KR100337683B1 KR100337683B1 (ko) | 2002-10-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019970009220A KR100337683B1 (ko) | 1996-03-18 | 1997-03-18 | 고리형n-비닐카르복실산아미드의제조방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5801252A (ko) |
| EP (1) | EP0796844B1 (ko) |
| JP (1) | JP2939433B2 (ko) |
| KR (1) | KR100337683B1 (ko) |
| DE (1) | DE69704802T2 (ko) |
| TW (1) | TW453998B (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3315105B2 (ja) * | 2000-02-10 | 2002-08-19 | 株式会社日本触媒 | ビニルピロリドン系重合体の製造法 |
| KR100377504B1 (ko) * | 2000-05-12 | 2003-03-26 | 애경유화 주식회사 | 감마-부티로락톤으로부터 피롤리돈 유도체를 제조하는 방법 |
| JP3999022B2 (ja) | 2002-04-04 | 2007-10-31 | 株式会社日本触媒 | ビニルピロリドン系重合体 |
| US6982337B1 (en) | 2004-07-28 | 2006-01-03 | Lyondell Chemical Technology, L.P. | Process for making N-vinyl-2-pyrrolidone |
| US7045639B2 (en) * | 2004-09-15 | 2006-05-16 | Lyondell Chemical Technology, L.P. | Method for purifying N-(2-hydroxyethyl)-2-pyrrolidone |
| WO2011146449A1 (en) * | 2010-05-19 | 2011-11-24 | Bioamber S.A.S. | Processes for the production of pyrrolidones |
| CN105837489B (zh) * | 2016-05-11 | 2019-08-20 | 西安元创化工科技股份有限公司 | 一种由n-羟乙基吡咯烷酮脱水制备n-乙烯基吡咯烷酮的方法 |
| CN106622309B (zh) * | 2016-09-27 | 2019-06-11 | 西安元创化工科技股份有限公司 | 一种n-羟乙基吡咯烷酮脱水催化剂及其制备方法 |
| CN106699629A (zh) * | 2016-12-28 | 2017-05-24 | 贵州省欣紫鸿药用辅料有限公司 | 一种n‑乙烯基吡咯烷酮的制备工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2669570A (en) * | 1951-08-24 | 1954-02-16 | Celanese Corp | Production of n-vinyl pyrrolidone |
| JPS5421330B2 (ko) * | 1971-10-14 | 1979-07-30 | ||
| JPS5422973B2 (ko) * | 1972-03-17 | 1979-08-10 | ||
| DE4302325A1 (de) * | 1993-01-28 | 1994-08-04 | Basf Ag | Verfahren zur Herstellung von N-Alkenylpyrrolidonen |
| KR100388696B1 (ko) * | 1994-09-19 | 2003-11-14 | 니폰 쇼쿠바이 컴파니 리미티드 | 3급n-알케닐카르복실산아미드류의제조용촉매및이촉매를이용한3급n-알케닐카르복실산아미드류의제조방법 |
-
1996
- 1996-03-18 JP JP8060455A patent/JP2939433B2/ja not_active Expired - Lifetime
-
1997
- 1997-03-18 EP EP97301783A patent/EP0796844B1/en not_active Expired - Lifetime
- 1997-03-18 TW TW086103352A patent/TW453998B/zh not_active IP Right Cessation
- 1997-03-18 DE DE69704802T patent/DE69704802T2/de not_active Expired - Lifetime
- 1997-03-18 KR KR1019970009220A patent/KR100337683B1/ko not_active IP Right Cessation
- 1997-03-18 US US08/820,283 patent/US5801252A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5801252A (en) | 1998-09-01 |
| JPH09249644A (ja) | 1997-09-22 |
| EP0796844A1 (en) | 1997-09-24 |
| JP2939433B2 (ja) | 1999-08-25 |
| TW453998B (en) | 2001-09-11 |
| EP0796844B1 (en) | 2001-05-16 |
| KR100337683B1 (ko) | 2002-10-25 |
| DE69704802T2 (de) | 2001-09-06 |
| DE69704802D1 (de) | 2001-06-21 |
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