KR840005422A - 글리옥실산 및 글리옥실산 유도체의 제조방법 - Google Patents
글리옥실산 및 글리옥실산 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840005422A KR840005422A KR1019830003023A KR830003023A KR840005422A KR 840005422 A KR840005422 A KR 840005422A KR 1019830003023 A KR1019830003023 A KR 1019830003023A KR 830003023 A KR830003023 A KR 830003023A KR 840005422 A KR840005422 A KR 840005422A
- Authority
- KR
- South Korea
- Prior art keywords
- glyoxylic acid
- process according
- hydrogenation reaction
- hydrogenation
- general formula
- Prior art date
Links
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 title claims 11
- 238000000034 method Methods 0.000 title claims 10
- 238000005984 hydrogenation reaction Methods 0.000 claims 7
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 238000000354 decomposition reaction Methods 0.000 claims 3
- 150000002978 peroxides Chemical class 0.000 claims 3
- -1 alkyl glyoxylate Chemical compound 0.000 claims 2
- 150000002373 hemiacetals Chemical class 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000004020 conductor Substances 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- JQQQEJZYKNGYBP-WXIWBVQFSA-N n-[4-[(e)-(carbamothioylhydrazinylidene)methyl]phenyl]acetamide;pyridine-4-carbohydrazide Chemical compound NNC(=O)C1=CC=NC=C1.CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 JQQQEJZYKNGYBP-WXIWBVQFSA-N 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/147—Saturated compounds having only one carboxyl group and containing —CHO groups
- C07C59/153—Glyoxylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/34—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with ozone; by hydrolysis of ozonides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- a) 일반식 R1OH(여기서, R1의 지방족 알콜에 알킬기의 탄소원자가 1 내지 10인 디알킬 말레이트를 용해시키고, 이 말레이트를 -80 내지 +20℃의 온도에서 오존당량과 반응시켜,b) 생성된 과산화물함유 용액을 단계 a)에서 가오존 분해하는데 사용한 일반식 R1OH의 알콜중의 수소화 촉매 현탁액에 연속적으로 공급하고,이때 용액을 계량하여 과산화물 함량이 수소 반응기내에서 수소화시키는 전공정을 통해 쳐 0.1몰/리터이하로 유지되도록 하며,수소화 반응을 1 내지 20바의 압력하 15℃내지 45℃의 온도 및 pH 2 내지 pH 7에서 수행한후, c) 적절하게는, 형성된 일반식(I)의 알킬 글리옥실레이트의 헤미아세탈을 가수분해함으로 특징으로 하여, 말레산 유도체를 가오존분해한후, 가오존분해 생성물을 촉매적 수소화하여, 일반식(I)의 글리옥실산 또는 글리옥실산 유도체를 제조하는 방법.상기식에서, R은 탄소원자 1내지 10의 알킬기를 나타내며, R1은탄소원자 1내지 4의 알킬기를 나타낸다.
- 제1항에 있어서, 단계 a)의 가오존 분해를 -10 내지 +5℃의 온도에서 수행하는 방법.
- 제1항 또는 제2항에 있어서, 메탄올을 일반식 R1OH의 알콜로서 사용하는 방법.
- 제1항내지 3항중 어느 하나에 있어서, 과산화물 함량을 단계 b)의 전수소화 공정을 통해 수소화 반응기에서 0.02/몰터이하로 유지하는 방법.
- 제1항내지 4항중 어느하나에 있어서, 담체를 함유하지 않은 백금 촉가를 단계 b)의 수소화 반응에 사용하는 방법.
- 제1항 내지 5항중 어느 하나에 있어서, 35 내지 40℃의 온도가 단계 b)의 수소화 반응중에 유지되는 방법.
- 제1항 내지 6항중 어느 하나에 있어서, 단계 b)의 수소화 반응중에 pH를 2 내지 4가 되도록하는방법.
- 제1항 내지 7항중 어느 하나에 있어서, 일반식(I)의 알킬 글리옥실레이트의 헤미아세탈을 물과 함께 가열하며 알콜/물 혼합물을 증류시켜 글리옥실산으로 전환시키는 방법.
- 제1항내지 8항중 어느 하나에 있어서, 수소화 반응후 및 촉매 제거후에 일반식(I)알킬글리옥실레이트를 분리시키지 않고 글리옥실산으로 가수분해시키는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3224795.8 | 1982-07-02 | ||
| DE19823224795 DE3224795A1 (de) | 1982-07-02 | 1982-07-02 | Verfahren zur herstellung von glyoxylsaeure und glyoxylsaeurederivaten |
| DEP3224795.8 | 1982-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840005422A true KR840005422A (ko) | 1984-11-12 |
| KR910000781B1 KR910000781B1 (ko) | 1991-02-08 |
Family
ID=6167474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830003023A KR910000781B1 (ko) | 1982-07-02 | 1983-07-01 | 글리옥실산 및 글리옥실산 유도체의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5015760A (ko) |
| EP (1) | EP0099981B1 (ko) |
| JP (1) | JPS5921643A (ko) |
| KR (1) | KR910000781B1 (ko) |
| AT (1) | ATE17232T1 (ko) |
| CA (1) | CA1217780A (ko) |
| DE (2) | DE3224795A1 (ko) |
| ES (1) | ES523725A0 (ko) |
| GR (1) | GR79213B (ko) |
| HU (1) | HU189710B (ko) |
| IE (1) | IE55562B1 (ko) |
| IL (1) | IL69124A (ko) |
| NZ (1) | NZ204693A (ko) |
| ZA (1) | ZA834756B (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6038247A (ja) * | 1983-08-10 | 1985-02-27 | Honda Motor Co Ltd | アンチロツク制動装置 |
| JPH0830026B2 (ja) * | 1987-05-27 | 1996-03-27 | 三井東圧化学株式会社 | グリオキシル酸類の製造法 |
| AT393504B (de) * | 1989-02-08 | 1991-11-11 | Mittelbach Martin | Verfahren zur herstellung von 3,3-dialkoxypropionsaeureestern durch ozonolyse von mehrfach ungesaettigten verbindungen |
| AT392638B (de) * | 1989-06-05 | 1991-05-10 | Chemie Linz Gmbh | Verfahren zur kontinuierlichen herstellung einer konzentrierten waessrigen loesung von glyoxylsaeure |
| AT396589B (de) * | 1990-06-05 | 1993-10-25 | Chemie Linz Gmbh | Verfahren zur herstellung von allantoin |
| TW299317B (ko) * | 1993-03-12 | 1997-03-01 | Chemie Linz Gmbh | |
| AT398759B (de) * | 1993-03-12 | 1995-01-25 | Chemie Linz Gmbh | Hydrogenolytische reduktion peroxidischer ozonolyseprodukte und vorrichtung zu ihrer durchführung |
| AT401930B (de) * | 1993-12-27 | 1996-12-27 | Chemie Linz Gmbh | Verfahren zur herstellung von n-substituierten glycinestern und verfahren zur indigosynthese aus den so hergestellten glycinestern |
| AT404593B (de) * | 1996-11-21 | 1998-12-28 | Chemie Linz Gmbh | Verfahren zur herstellung von glyoxylsäureestern und deren hydraten |
| CN1142194C (zh) | 2000-01-25 | 2004-03-17 | 阿克佐诺贝尔股份有限公司 | 胺化聚烯烃的制备方法 |
| CN1312100C (zh) * | 2005-06-07 | 2007-04-25 | 中国科学院新疆理化技术研究所 | 马来酸臭氧化物氧化乙二醛合成乙醛酸的方法 |
| FR2986704B1 (fr) | 2012-02-09 | 2015-08-21 | Oreal | Procede de traitement cosmetique et composition comprenant un ester d'acide glyoxylique |
| EA035462B1 (ru) | 2015-10-16 | 2020-06-19 | Акцо Нобель Кемикалз Интернэшнл Б.В. | Простые эфиры целлюлозы с временными поперечно сшитыми связями, способ их получения и их применение |
| CN111333493B (zh) * | 2018-12-18 | 2022-08-05 | 万华化学集团股份有限公司 | 一种二醛半缩醛的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3145232A (en) * | 1959-11-03 | 1964-08-18 | Monsanto Co | Ozonization and reduction of unsaturated organic compounds |
| US3644508A (en) * | 1969-07-23 | 1972-02-22 | United States Steel Corp | Process for the recovery of glyoxylic acid |
| US3637721A (en) * | 1970-06-25 | 1972-01-25 | Inmont Corp | Process for producing aldehydes by ozonizing and reducing certain aromatic and heterocyclic compounds containing carbon-to-carbon unsaturation |
| US3705922A (en) * | 1970-08-11 | 1972-12-12 | United States Steel Corp | Process for the preparation of glyoxylic acid methyl hemiacetal |
| FR2383911A1 (fr) * | 1977-03-17 | 1978-10-13 | Hoechst France | Procede permettant d'augmenter les rendements en hemiacetal-esters de l'acide glyoxylique au cours de leur obtention ou leurs taux de recuperation dans les milieux les contenant |
-
1982
- 1982-07-02 DE DE19823224795 patent/DE3224795A1/de not_active Withdrawn
-
1983
- 1983-06-10 DE DE8383105712T patent/DE3361696D1/de not_active Expired
- 1983-06-10 GR GR71636A patent/GR79213B/el unknown
- 1983-06-10 EP EP83105712A patent/EP0099981B1/de not_active Expired
- 1983-06-10 AT AT83105712T patent/ATE17232T1/de not_active IP Right Cessation
- 1983-06-21 IE IE1458/83A patent/IE55562B1/en not_active IP Right Cessation
- 1983-06-24 NZ NZ204693A patent/NZ204693A/xx unknown
- 1983-06-29 ZA ZA834756A patent/ZA834756B/xx unknown
- 1983-06-30 ES ES523725A patent/ES523725A0/es active Granted
- 1983-06-30 CA CA000431579A patent/CA1217780A/en not_active Expired
- 1983-06-30 IL IL69124A patent/IL69124A/xx not_active IP Right Cessation
- 1983-07-01 JP JP58118417A patent/JPS5921643A/ja active Granted
- 1983-07-01 HU HU832398A patent/HU189710B/hu unknown
- 1983-07-01 KR KR1019830003023A patent/KR910000781B1/ko not_active IP Right Cessation
-
1989
- 1989-03-29 US US07/331,026 patent/US5015760A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1217780A (en) | 1987-02-10 |
| DE3224795A1 (de) | 1984-01-05 |
| EP0099981A1 (de) | 1984-02-08 |
| JPS5921643A (ja) | 1984-02-03 |
| GR79213B (ko) | 1984-10-22 |
| ATE17232T1 (de) | 1986-01-15 |
| KR910000781B1 (ko) | 1991-02-08 |
| IL69124A (en) | 1986-07-31 |
| IE831458L (en) | 1984-01-02 |
| ZA834756B (en) | 1984-03-28 |
| ES8500212A1 (es) | 1984-10-01 |
| EP0099981B1 (de) | 1986-01-02 |
| DE3361696D1 (en) | 1986-02-13 |
| JPH0253426B2 (ko) | 1990-11-16 |
| US5015760A (en) | 1991-05-14 |
| NZ204693A (en) | 1985-04-30 |
| IL69124A0 (en) | 1983-10-31 |
| ES523725A0 (es) | 1984-10-01 |
| HU189710B (en) | 1986-07-28 |
| IE55562B1 (en) | 1990-11-07 |
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