KR0165620B1 - 사이클로헥실아세테이트의 제조방법 - Google Patents
사이클로헥실아세테이트의 제조방법 Download PDFInfo
- Publication number
- KR0165620B1 KR0165620B1 KR1019950009575A KR19950009575A KR0165620B1 KR 0165620 B1 KR0165620 B1 KR 0165620B1 KR 1019950009575 A KR1019950009575 A KR 1019950009575A KR 19950009575 A KR19950009575 A KR 19950009575A KR 0165620 B1 KR0165620 B1 KR 0165620B1
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst
- reaction
- cyclohexene
- acetic acid
- cyclohexyl acetate
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 96
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 74
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 70
- 238000006243 chemical reaction Methods 0.000 claims abstract description 63
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 4
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 4
- 229910021645 metal ion Inorganic materials 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 27
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 17
- 230000000694 effects Effects 0.000 abstract description 23
- 239000011973 solid acid Substances 0.000 abstract description 17
- 239000000376 reactant Substances 0.000 abstract description 14
- 230000007423 decrease Effects 0.000 abstract description 3
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 230000003197 catalytic effect Effects 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000011949 solid catalyst Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052792 caesium Inorganic materials 0.000 description 5
- 230000008929 regeneration Effects 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- 229910021536 Zeolite Inorganic materials 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000012958 reprocessing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003930 superacid Substances 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- -1 cation salt Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/16—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
- C07C13/18—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexane ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (6)
- 하기 일반식 (I)의 헤테로폴리산 금속이온 염 촉매의 존재하에 사이클로헥센과 아세트산을 80 내지 120℃의 온도 및 1 내지 35기압의 압력하에서 30분 내지 4시간 동안 반응시켜 사이클로헥실아세테이트를 제조하는 방법:AxHn-xSM12O40bH2O (I)상기 식에서, A는 K 또는 Cs이고,x는 0.1 내지 3 또는 4이고, n은 3 또는 4이고, S는 P 또는 Si 이고, M은 Mo 또는 W, 또는 이들의 조합이며, b는 0 내지 20이다.
- 제1항에 있어서, 상기 촉매가 A가 Cs이고, x가 2.3-2.7범위이고, S가 P이고, M이 W인 방법.
- 제1항에 있어서, 상기 반응을 사이클로헥센:아세트산의 몰비를 1:1 내지 1:3, 사이클로헥센:촉매의 몰비를 160:1 내지 2600:1로 하여 수행하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 촉매를 100 내지 300℃에서 초기 열처리하는 단계를 더욱 포함하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 반응에서 상기 촉매를 분리하여 300℃에서 열처리하거나 또는 헤테로폴리산을 첨가한 후 동일한 방법으로 열처리하여 재사용함을 특징으로 하는 방법.
- 제1항에 있어서, 상기 반응에서 무수 아세트산을 가하여 수분을 제거하는 단계를 더욱 포함하는 것을 특징으로 하는 방법.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019950009575A KR0165620B1 (ko) | 1995-04-24 | 1995-04-24 | 사이클로헥실아세테이트의 제조방법 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019950009575A KR0165620B1 (ko) | 1995-04-24 | 1995-04-24 | 사이클로헥실아세테이트의 제조방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR960037625A KR960037625A (ko) | 1996-11-19 |
KR0165620B1 true KR0165620B1 (ko) | 1999-03-20 |
Family
ID=19412745
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019950009575A Expired - Fee Related KR0165620B1 (ko) | 1995-04-24 | 1995-04-24 | 사이클로헥실아세테이트의 제조방법 |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR0165620B1 (ko) |
-
1995
- 1995-04-24 KR KR1019950009575A patent/KR0165620B1/ko not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR960037625A (ko) | 1996-11-19 |
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Legal Events
Date | Code | Title | Description |
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A201 | Request for examination | ||
PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19950424 |
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PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19950424 Comment text: Request for Examination of Application |
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PG1501 | Laying open of application | ||
E902 | Notification of reason for refusal | ||
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19980331 Patent event code: PE09021S01D |
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E701 | Decision to grant or registration of patent right | ||
PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19980625 |
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GRNT | Written decision to grant | ||
PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19980917 Patent event code: PR07011E01D |
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PR1002 | Payment of registration fee |
Payment date: 19980917 End annual number: 3 Start annual number: 1 |
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PG1601 | Publication of registration | ||
PR1001 | Payment of annual fee |
Payment date: 20010605 Start annual number: 4 End annual number: 4 |
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PR1001 | Payment of annual fee |
Payment date: 20020718 Start annual number: 5 End annual number: 5 |
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FPAY | Annual fee payment |
Payment date: 20030407 Year of fee payment: 6 |
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PR1001 | Payment of annual fee |
Payment date: 20030407 Start annual number: 6 End annual number: 6 |
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LAPS | Lapse due to unpaid annual fee | ||
PC1903 | Unpaid annual fee |
Termination category: Default of registration fee Termination date: 20050610 |