JP2021511287A - フタレート化合物の水素化方法 - Google Patents
フタレート化合物の水素化方法 Download PDFInfo
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- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 74
- -1 phthalate compound Chemical class 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 39
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- 239000007795 chemical reaction product Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 239000004800 polyvinyl chloride Substances 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
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- 239000011342 resin composition Substances 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005498 phthalate group Chemical class 0.000 claims description 2
- 239000012808 vapor phase Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 9
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 7
- OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
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- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 4
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 4
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
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- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 4
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- LQLQDKBJAIILIQ-UHFFFAOYSA-N Dibutyl terephthalate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C=C1 LQLQDKBJAIILIQ-UHFFFAOYSA-N 0.000 description 2
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- PEIIRIVDOVFUIW-UHFFFAOYSA-N bis(7-methyloctyl) benzene-1,4-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCC(C)C)C=C1 PEIIRIVDOVFUIW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- GOPWOUQJIMLDDM-UHFFFAOYSA-N dibutyl benzene-1,3-dicarboxylate Chemical compound CCCCOC(=O)C1=CC=CC(C(=O)OCCCC)=C1 GOPWOUQJIMLDDM-UHFFFAOYSA-N 0.000 description 2
- 229960002380 dibutyl phthalate Drugs 0.000 description 2
- LERGDXJITDVDBZ-UHFFFAOYSA-N dioctyl benzene-1,3-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=CC(C(=O)OCCCCCCCC)=C1 LERGDXJITDVDBZ-UHFFFAOYSA-N 0.000 description 2
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- 150000003624 transition metals Chemical class 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 1
- 241001411320 Eriogonum inflatum Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CRPXFUDVZZLWAP-UHFFFAOYSA-N bis(8-methylnonyl) benzene-1,3-dicarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC(C(=O)OCCCCCCCC(C)C)=C1 CRPXFUDVZZLWAP-UHFFFAOYSA-N 0.000 description 1
- DUQLDVZUQAAAMU-UHFFFAOYSA-N bis(8-methylnonyl) benzene-1,4-dicarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC(C)C)C=C1 DUQLDVZUQAAAMU-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000598 endocrine disruptor Substances 0.000 description 1
- 208000030172 endocrine system disease Diseases 0.000 description 1
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- 239000012785 packaging film Substances 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- JQCXWCOOWVGKMT-UHFFFAOYSA-N phthalic acid diheptyl ester Natural products CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 238000007086 side reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/75—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a six-membered ring
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08K5/00—Use of organic ingredients
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- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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Abstract
Description
本出願は、2017年11月29日付の韓国特許出願第10−2017−0161950号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示された全ての内容は本明細書の一部として含まれる。
水素を含む気相原料;およびフタレート化合物を含む液相原料を反応器に投入して、水素およびフタレート化合物を水素化触媒存在下で反応させる段階を含むフタレート化合物の水素化方法であって、
前記液相原料のレイノルズ数は、1〜100であり、
前記反応後、分離された水素化反応生成物中のシス異性体の含有量が70%以上である、フタレート化合物の水素化方法を提供する。
本発明の好ましい一実施形態によれば、水素を含む気相原料;およびフタレート化合物を含む液相原料を反応器に投入して、水素およびフタレート化合物を水素化触媒存在下で反応させる段階を含むフタレート化合物の水素化方法であって、
前記液相原料のレイノルズ数は、1〜100であり、
前記反応後、分離された水素化反応生成物中のシス異性体の含有量が70%以上である、フタレート化合物の水素化方法が提供される。
レイノルズ数(Reynold’s number、NRE)は、流体の「慣性による力」と「粘性による力」の比であり、下記数式1で表される。
図1を参照すると、前記水素化反応装置は、熱交換器(a、b)、反応器cおよび気相−液相分離器dなどからなる。
実施例1
液相原料として純度99%であるジオクチルテレフタレート(dioctyl terephthalate,DOTP)、気相原料として水素を反応器に注入し、反応圧力150bar、反応温度150℃で水素付加反応を行った。
この時、液相原料のレイノルズ数は17.1に設定して運転した。ここでレイノルズ数は、下記数式1から計算された値である。
実施例1で、液相のレイノルズ数が4.9であることを除いては同様の水素化反応を行った。
実施例1で、液相のレイノルズ数が40.3であることを除いては同様の水素化反応を行った。
実施例1で、液相のレイノルズ数が110.2であることを除いては同様の水素化反応を行った。
前記実施例1〜3および比較例1の水素化反応の終了後、反応混合物から未反応の気相原料を分離して水素化反応生成物を得た。実施例および比較例それぞれに対して転換率、水素化反応生成物中のシス異性体の含有量を測定し、その結果を下記表1に示す。
c:反応器
d:気相−液相分離器
1、2:気相原料
3、4:液相原料
5:反応混合物
6:気相の未反応物
7:液相の反応生成物
Claims (9)
- 水素を含む気相原料、およびフタレート化合物を含む液相原料を反応器に投入し、水素およびフタレート化合物を水素化触媒存在下で反応させる段階を含むフタレート化合物の水素化方法であって、
前記液相原料のレイノルズ数は1〜100であり、
前記反応後、分離された水素化反応生成物中のシス異性体の含有量が70%以上である、フタレート化合物の水素化方法。 - 前記反応器に投入する水素の量は、フタレート化合物1モルに対して3〜300モルである、請求項1に記載のフタレート化合物の水素化方法。
- 前記フタレート化合物はフタレート、テレフタレート、イソフタレートおよびこれらのカルボン酸化合物からなる群より選ばれる1種以上である、請求項1に記載のフタレート化合物の水素化方法。
- 前記気相原料は反応器の上部または下部から供給され、前記液相原料は反応器の上部から供給される、請求項1に記載のフタレート化合物の水素化方法。
- 前記水素化触媒の活性成分はルテニウム(Ru)、ロジウム(Rh)、パラジウム(Pd)および白金(Pt)からなる群より選ばれる1種以上である、請求項1に記載のフタレート化合物の水素化方法。
- 前記水素化触媒は、担体100重量%に対して触媒活性成分が3重量%以下である、請求項1に記載のフタレート化合物の水素化方法。
- 請求項1〜6のいずれか一項に記載の方法により製造される、水素化されたフタレートあるいはテレフタレート化合物。
- 請求項7に記載の水素化されたフタレートあるいはテレフタレート化合物を含む、可塑剤。
- 請求項8に記載の可塑剤;およびエチレン酢酸ビニル、ポリエチレン、ポリプロピレン、ポリ塩化ビニル、ポリスチレン、ポリウレタン、ポリブタジエン、シリコン、熱可塑性エラストマーまたはこれらの共重合体の中から選ばれた樹脂;を含む、樹脂組成物。
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US11136284B2 (en) | 2021-10-05 |
WO2019107771A1 (ko) | 2019-06-06 |
US20200361846A1 (en) | 2020-11-19 |
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