KR100830718B1 - 알킬케텐다이머의 수소화 반응에 의한 알킬 β-락톤의제조방법 - Google Patents
알킬케텐다이머의 수소화 반응에 의한 알킬 β-락톤의제조방법 Download PDFInfo
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- KR100830718B1 KR100830718B1 KR1020070008006A KR20070008006A KR100830718B1 KR 100830718 B1 KR100830718 B1 KR 100830718B1 KR 1020070008006 A KR1020070008006 A KR 1020070008006A KR 20070008006 A KR20070008006 A KR 20070008006A KR 100830718 B1 KR100830718 B1 KR 100830718B1
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst
- alkyl
- hydrogenation
- lactone
- reaction
- Prior art date
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- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 37
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 67
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 46
- -1 alkyl ketene dimer Chemical compound 0.000 claims abstract description 34
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 13
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 claims description 8
- 239000000539 dimer Substances 0.000 claims description 8
- 150000002596 lactones Chemical class 0.000 claims 2
- 229910017813 Cu—Cr Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 33
- 150000003839 salts Chemical class 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 8
- 238000001577 simple distillation Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 208000012839 conversion disease Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 239000003876 biosurfactant Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- CUEQHYJSSUSIFI-UHFFFAOYSA-N corynomycolic acid Chemical compound CCCCCCCCCCCCCCCC(O)C(C(O)=O)CCCCCCCCCCCCCC CUEQHYJSSUSIFI-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- IYRDVAUFQZOLSB-UHFFFAOYSA-N copper iron Chemical compound [Fe].[Cu] IYRDVAUFQZOLSB-UHFFFAOYSA-N 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 238000003900 soil pollution Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
구 분 | 실시예 2 | 실시예 3 | 실시예 4 | 비교예 1 | 비교예 2 |
출발물질 | C8 알킬케텐다이머 | C8 알킬케텐다이머 | C8 알킬케텐다이머 | C8 알킬케텐다이머 | C12 알킬케텐다이머 |
반응기 형태 | 고정층 | 고정층 | 고정층 | 회분식 | 회분식 |
정제여부 | 정제 | 정제 | 정제 | 미정제 | 미정제 |
전환율 (%) | 92 | 95 | 96 | 30 | 50 |
Claims (5)
- 삭제
- 알킬케텐다이머의 수소화 반응에 의해 알킬 β-락톤을 제조하는 방법에 있어서,상기 수소화 반응은 알루미나 및 실리카에 담지된 입상형 팔라듐 담지 촉매 또는 입상형 구리-크롬 촉매가 장착된 고정층 반응기를 이용하여 수행되는 것을 특징으로 하는 알킬 β-락톤의 제조방법.
- 제 2 항에 있어서, 상기 수소화 반응은 알루미나 및 실리카에 담지된 입상형 팔라듐 촉매가 장착된 고정층 반응기를 이용하여 20 ∼ 100 ℃ 온도 범위와, 0.1 ∼ 10 기압 범위하에서 수행하는 것을 특징으로 하는 알킬 β-락톤의 제조방법.
- 제 2 항에 있어서, 상기 수소화 반응은 입상형 구리-크롬 촉매가 장착된 고정층 반응기를 이용하여 80 ∼ 300 ℃ 온도 범위와, 0.1 ∼ 30 기압 범위하에서 수 소화 반응을 수행하는 것을 특징으로 하는 알킬 β-락톤의 제조방법.
- 제 2 항 내지 제 4 항 중에서 선택된 어느 한 항에 있어서, 상기 알킬케텐다이머는 증류로 정제하여 사용하는 것을 특징으로 하는 알킬 β-락톤의 제조방법.
Priority Applications (1)
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---|---|---|---|
KR1020070008006A KR100830718B1 (ko) | 2007-01-25 | 2007-01-25 | 알킬케텐다이머의 수소화 반응에 의한 알킬 β-락톤의제조방법 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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KR1020070008006A KR100830718B1 (ko) | 2007-01-25 | 2007-01-25 | 알킬케텐다이머의 수소화 반응에 의한 알킬 β-락톤의제조방법 |
Publications (1)
Publication Number | Publication Date |
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KR100830718B1 true KR100830718B1 (ko) | 2008-05-19 |
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KR1020070008006A KR100830718B1 (ko) | 2007-01-25 | 2007-01-25 | 알킬케텐다이머의 수소화 반응에 의한 알킬 β-락톤의제조방법 |
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KR (1) | KR100830718B1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104870712B (zh) * | 2012-11-08 | 2018-01-02 | 索理思科技开曼公司 | 氢化烷基烯酮二聚体的组合物和用途 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20040106720A (ko) * | 2003-06-11 | 2004-12-18 | (주)네오팜 | 2-알킬-3-히드록시지방산 및 그 유도체의 제조방법 |
KR20070009574A (ko) * | 2004-02-17 | 2007-01-18 | 토마스 이. 존슨 | 매크로사이클릭 화합물의 형성을 위한 방법, 조성물 및장치 |
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- 2007-01-25 KR KR1020070008006A patent/KR100830718B1/ko active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20040106720A (ko) * | 2003-06-11 | 2004-12-18 | (주)네오팜 | 2-알킬-3-히드록시지방산 및 그 유도체의 제조방법 |
KR20070009574A (ko) * | 2004-02-17 | 2007-01-18 | 토마스 이. 존슨 | 매크로사이클릭 화합물의 형성을 위한 방법, 조성물 및장치 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104870712B (zh) * | 2012-11-08 | 2018-01-02 | 索理思科技开曼公司 | 氢化烷基烯酮二聚体的组合物和用途 |
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