JPH08511776A - シクロヘキサンジカルボン酸エステルの低圧製造方法 - Google Patents
シクロヘキサンジカルボン酸エステルの低圧製造方法Info
- Publication number
- JPH08511776A JPH08511776A JP7501973A JP50197395A JPH08511776A JP H08511776 A JPH08511776 A JP H08511776A JP 7501973 A JP7501973 A JP 7501973A JP 50197395 A JP50197395 A JP 50197395A JP H08511776 A JPH08511776 A JP H08511776A
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- hydrogenation
- hydrogenation zone
- hydrogen gas
- cyclohexanedicarboxylate
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- -1 cyclohexanedicarboxylic acid ester Chemical class 0.000 title description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 32
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 84
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 47
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- GGCUUOGRTPMFQK-UHFFFAOYSA-N dimethyl cyclohexane-1,1-dicarboxylate Chemical compound COC(=O)C1(C(=O)OC)CCCCC1 GGCUUOGRTPMFQK-UHFFFAOYSA-N 0.000 claims description 36
- NIQCNGHVCWTJSM-UHFFFAOYSA-N dimethyl benzenedicarboxylate Natural products COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 26
- LYMMFQAKPGXADS-UHFFFAOYSA-N dimethyl benzene-1,2-dicarboxylate;dimethyl benzene-1,3-dicarboxylate;dimethyl benzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1.COC(=O)C1=CC=CC(C(=O)OC)=C1.COC(=O)C1=CC=CC=C1C(=O)OC LYMMFQAKPGXADS-UHFFFAOYSA-N 0.000 claims description 25
- 239000000047 product Substances 0.000 claims description 23
- 229910052763 palladium Inorganic materials 0.000 claims description 22
- 239000000376 reactant Substances 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 15
- 239000012263 liquid product Substances 0.000 claims description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000010926 purge Methods 0.000 claims description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000012141 concentrate Substances 0.000 claims 1
- CXVAUNIKYTWEFC-UHFFFAOYSA-N dimethoxyborinic acid Chemical compound COB(O)OC CXVAUNIKYTWEFC-UHFFFAOYSA-N 0.000 claims 1
- QWDKIPDCCCVFSX-UHFFFAOYSA-N dimethyl 2-pentylpropanedioate Chemical compound CCCCCC(C(=O)OC)C(=O)OC QWDKIPDCCCVFSX-UHFFFAOYSA-N 0.000 claims 1
- 238000009825 accumulation Methods 0.000 abstract description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 229910000510 noble metal Inorganic materials 0.000 abstract description 3
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 24
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical class OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- YKFWNIZZOFAZMW-UHFFFAOYSA-N C1(CCCCC1)(C(=O)O)C(=O)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O Chemical compound C1(CCCCC1)(C(=O)O)C(=O)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O YKFWNIZZOFAZMW-UHFFFAOYSA-N 0.000 description 1
- WJJGAKCAAJOICV-UHFFFAOYSA-N N-dimethyltyrosine Natural products CN(C)C(C(O)=O)CC1=CC=C(O)C=C1 WJJGAKCAAJOICV-UHFFFAOYSA-N 0.000 description 1
- ZVOOGERIHVAODX-UHFFFAOYSA-N O-demycinosyltylosin Natural products O=CCC1CC(C)C(=O)C=CC(C)=CC(CO)C(CC)OC(=O)CC(O)C(C)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(O)C(C)(O)C2)C(C)O1 ZVOOGERIHVAODX-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 229910001680 bayerite Inorganic materials 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
Classifications
-
- 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
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.(1)水素ガス及びシクロヘキサンジカルボン酸ジメチル生成物と対応す るベンゼンジカルボン酸ジメチル反応剤との液状混合物を、少なくとも1個のア ルミナ担持パラジウム水素化触媒の固定床を含む水素化帯域に連続的に供給する 工程、並びに (2)水素化帯域から水素ガス及びシクロヘキサンジカルボン酸ジメチル生成物 からなる液状生成物を連続的に取り出す工程を含んでなり、10〜205バール絶対 圧(1,000〜20,500kPa)の圧力及び150〜230℃の温度でベンゼンジカルボン酸ジ メチルをシクロヘキサンジカルボン酸ジメチルに水素化し、水素化帯域から取り 出す水素ガス中の一酸化炭素の濃度を200体積部/百万(ppmv)より低く維持す る、シクロヘキサンジカルボン酸ジメチルの連続製造方法。 2.水素化帯域を通過する水素の気体空間速度が少なくとも2である請求の範 囲第1項記載の方法。 3.水素化帯域を通過する水素の気体空間速度が少なくとも2であり、ベンゼ ンジカルボン酸ジメチルのシクロヘキサンジカルボン酸ジメチルに対する重量化 が1:20〜1:10の範囲内である請求の範囲第1項記載の方法。 4.(1)水素ガス及びシクロヘキサンジカルボン酸ジメチル生成物と対応す るベンゼンジカルボン酸ジメチル反応剤との液状混合物を、少なくとも1個のア ルミナ担持パラジウム水素化触媒の固定床を含む水素化帯域に連続的に供給する 工程、並びに (2)水素化帯域から水素ガス及びシクロヘキサンジカルボン酸ジメチル生成物 からなる液状生成物を連続的に取り出す工程 を含んでなり、10〜205バール絶対圧(1,000〜20,500kPa)の圧力 及び150〜230℃の温度で、少なくとも99モル%の転化率でベンゼンジカルボン酸 ジメチルをシクロヘキサンジカルボン酸ジメチルに水素化し、水素化帯域から取 り出す水素ガス中の一酸化炭素の濃度を100体積部/百万より低く維持し、水素 化帯域を通過する水素の気体空間速度が3〜10であり、ベンゼンジカルボン酸ジ メチルのシクロヘキサンジカルボン酸ジメチルに対する重量比が1:20〜1:10 の範囲内であり、そしてベンゼンジカルボン酸ジメチルの液体空間速度が0.3〜 5である、シクロヘキサンジカルボン酸ジメチルの連続製造方法。 5.I.水素ガス及びシクロヘキサンジカルボン酸ジメチル生成物と対応する ベンゼンジカルボン酸ジメチル反応剤との液状混合物を、そこでベンゼンジカル ボン酸ジメチルがシクロヘキサンジカルボン酸ジメチルに水素化される、少なく とも1個のアルミナ担持パラジウム水素化触媒の固定床を含む第一水素化帯域に 連続的に供給する工程、 II.第一水素化帯域から、水素ガス並びにシクロヘキサンジカルボン酸ジメチル 生成物及び未反応ベンゼンジカルボン酸ジメチルからなる液状生成物を連続的に 取り出す工程 III.工程IIからの液状生成物の80〜95重量%を第一水素化帯域に連続的に循環 する工程、 IV.工程IIからの循環しない液状生成物及び水素ガスを、そこで未反応のベンゼ ンジカルボン酸ジメチルがシクロヘキサンジカルボン酸ジメチルに水素化される 第二水素化帯域に連続的に供給する工程、 V.第二水素化帯域から、水素ガス及び少なくとも99モル%の純度を有するシク ロヘキサンジカルボン酸ジメチル生成物からなる液状生成物を連続的に取り出す 工程、 VI.工程Vからの水素ガスの5〜30体積%を水素化プロセスからパージする工程 、並びに VII.プロセスからパージしない工程Vからの水素ガスを第一水素化帯域に循環 させる工程 を含んでなり、水素化を10〜205バール絶対圧(1,000〜20,500kPa)の圧力及び1 50〜270℃の温度で行い、水素化帯域から取り出す水素ガス中の一酸化炭素の濃 度を200体積部/百万(ppmv)より低く維持する、シクロヘキサンジカルボン酸 ジメチルの製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7667693A | 1993-06-15 | 1993-06-15 | |
US076,676 | 1993-06-15 | ||
PCT/US1994/006267 WO1994029261A1 (en) | 1993-06-15 | 1994-06-03 | Low pressure process for the manufacture of cyclohexanedicarboxylate esters |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH08511776A true JPH08511776A (ja) | 1996-12-10 |
JP3510890B2 JP3510890B2 (ja) | 2004-03-29 |
Family
ID=22133540
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50197395A Expired - Fee Related JP3510890B2 (ja) | 1993-06-15 | 1994-06-03 | シクロヘキサンジカルボン酸エステルの低圧製造方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US5399742A (ja) |
EP (1) | EP0703896B1 (ja) |
JP (1) | JP3510890B2 (ja) |
KR (1) | KR100329890B1 (ja) |
CN (1) | CN1058959C (ja) |
CA (1) | CA2165205C (ja) |
DE (1) | DE69409519T2 (ja) |
ES (1) | ES2115241T3 (ja) |
SG (1) | SG47884A1 (ja) |
WO (1) | WO1994029261A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018500273A (ja) * | 2014-10-29 | 2018-01-11 | エクソンモービル ケミカル パテンツ インコーポレイテッド | ベンゼンポリカルボン酸およびその誘導体の水素化のための改善された方法 |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1089082C (zh) * | 1996-06-28 | 2002-08-14 | Sknjc株式会社 | 制备环己烷二甲醇的方法 |
JP4898079B2 (ja) * | 2001-02-16 | 2012-03-14 | ビーエーエスエフ ソシエタス・ヨーロピア | シクロヘキサンジカルボン酸およびその誘導体を製造する方法 |
EP1432758B1 (en) | 2001-09-25 | 2008-11-26 | ExxonMobil Chemical Patents Inc. | Plasticised polyvinyl chloride |
US6803341B2 (en) * | 2002-01-18 | 2004-10-12 | Chinese Petroleum Corporation | Method of a high stability selectable hydrogenate catalyst producing and using for DMCHD manufacturing |
DE102004063637A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Carbonsäuren oder deren Derivaten |
US7632962B2 (en) * | 2006-04-26 | 2009-12-15 | Eastman Chemical Company | Hydrogenation process and catalysts |
US8877984B2 (en) | 2011-07-29 | 2014-11-04 | Eastman Chemical Company | Process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid |
US8410317B2 (en) | 2011-07-29 | 2013-04-02 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol |
US8410318B2 (en) | 2011-07-29 | 2013-04-02 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid |
US8766017B2 (en) | 2011-07-29 | 2014-07-01 | Eastman Chemical Company | Integrated process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid |
CN102746144A (zh) * | 2012-07-30 | 2012-10-24 | 江苏恒祥化工有限责任公司 | 一种1,4-环己烷二甲酸的制备方法 |
ITMI20121641A1 (it) | 2012-10-02 | 2014-04-03 | Polynt S P A | Procedimento per l'idrogenazione di esteri di acidi carbossilici aromatici a dare loro omologhi saturi, nuovi usi per detti omologhi, e nuove miscele polimeriche plastificate. |
EP2716623A1 (de) * | 2012-10-05 | 2014-04-09 | Basf Se | Verfahren zur Herstellung von Cyclohexanpolycarbonsäure-Derivaten mit geringem Nebenproduktanteil |
US9090553B2 (en) | 2012-10-05 | 2015-07-28 | Basf Se | Process for preparing cyclohexanepolycarboxylic acid derivatives having a low proportion of by-products |
CN102935365B (zh) * | 2012-11-12 | 2014-12-03 | 中国石油化工股份有限公司 | 一种制备1,4-环己烷二甲酸二甲酯的催化剂及方法 |
EP2757088B1 (de) * | 2013-01-22 | 2016-08-03 | Covestro Deutschland AG | Verfahren zur Herstellung von aromatischen Aminen |
KR102413118B1 (ko) | 2015-11-02 | 2022-06-24 | 에스케이케미칼 주식회사 | 1,4-사이클로헥산디메탄올의 제조 부산물의 처리 방법 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2070770A (en) * | 1935-10-18 | 1937-02-16 | Du Pont | Hydrogenation of alkyl phthalates |
US2675390A (en) * | 1950-05-19 | 1954-04-13 | Edgar F Rosenblatt | Hydrogenation of cyclic-compounds |
US3027398A (en) * | 1960-02-01 | 1962-03-27 | Du Pont | Process for preparing dimethyl 1, 4-cyclohexanedicarboxylate |
US3205278A (en) * | 1963-03-14 | 1965-09-07 | California Research Corp | Preparation of complex organic metallic hydrogenation catalysts and their use |
US3334149A (en) * | 1964-07-21 | 1967-08-01 | Eastman Kodak Co | Plural stage hydrogenation of dialkyl terephthalate using palladium and then copper chromite |
US3824193A (en) * | 1972-03-30 | 1974-07-16 | Eastman Kodak Co | Alkaline reactivation of alumina supported palladium catalysts |
DE2823165A1 (de) * | 1978-05-26 | 1979-11-29 | Bayer Ag | Verfahren zur herstellung von cycloaliphatischen carbonsaeureestern |
-
1994
- 1994-04-11 US US08/225,871 patent/US5399742A/en not_active Expired - Lifetime
- 1994-06-03 DE DE69409519T patent/DE69409519T2/de not_active Expired - Lifetime
- 1994-06-03 WO PCT/US1994/006267 patent/WO1994029261A1/en active IP Right Grant
- 1994-06-03 CA CA002165205A patent/CA2165205C/en not_active Expired - Fee Related
- 1994-06-03 ES ES94920702T patent/ES2115241T3/es not_active Expired - Lifetime
- 1994-06-03 KR KR1019950705693A patent/KR100329890B1/ko not_active IP Right Cessation
- 1994-06-03 SG SG1996004993A patent/SG47884A1/en unknown
- 1994-06-03 JP JP50197395A patent/JP3510890B2/ja not_active Expired - Fee Related
- 1994-06-03 EP EP94920702A patent/EP0703896B1/en not_active Expired - Lifetime
- 1994-06-10 CN CN94106439A patent/CN1058959C/zh not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018500273A (ja) * | 2014-10-29 | 2018-01-11 | エクソンモービル ケミカル パテンツ インコーポレイテッド | ベンゼンポリカルボン酸およびその誘導体の水素化のための改善された方法 |
Also Published As
Publication number | Publication date |
---|---|
KR100329890B1 (ko) | 2002-10-18 |
EP0703896A1 (en) | 1996-04-03 |
CN1099744A (zh) | 1995-03-08 |
CN1058959C (zh) | 2000-11-29 |
CA2165205C (en) | 1999-05-11 |
JP3510890B2 (ja) | 2004-03-29 |
WO1994029261A1 (en) | 1994-12-22 |
US5399742A (en) | 1995-03-21 |
DE69409519T2 (de) | 1998-08-06 |
ES2115241T3 (es) | 1998-06-16 |
EP0703896B1 (en) | 1998-04-08 |
CA2165205A1 (en) | 1994-12-22 |
SG47884A1 (en) | 1998-04-17 |
DE69409519D1 (de) | 1998-05-14 |
KR960703104A (ko) | 1996-06-19 |
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