TWI510535B - 酯類塑化劑之製備方法及其所製備之酯類塑化劑 - Google Patents
酯類塑化劑之製備方法及其所製備之酯類塑化劑 Download PDFInfo
- Publication number
- TWI510535B TWI510535B TW103100334A TW103100334A TWI510535B TW I510535 B TWI510535 B TW I510535B TW 103100334 A TW103100334 A TW 103100334A TW 103100334 A TW103100334 A TW 103100334A TW I510535 B TWI510535 B TW I510535B
- Authority
- TW
- Taiwan
- Prior art keywords
- ester plasticizer
- weight percent
- weight
- terephthalate
- reaction
- Prior art date
Links
- 239000004014 plasticizer Substances 0.000 title claims description 78
- 150000002148 esters Chemical class 0.000 title claims description 71
- 238000000034 method Methods 0.000 title claims description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 53
- 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 claims description 50
- 238000005809 transesterification reaction Methods 0.000 claims description 40
- XFADVSXRQFGART-UHFFFAOYSA-N 1-o-butyl 4-o-octyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCC)C=C1 XFADVSXRQFGART-UHFFFAOYSA-N 0.000 claims description 35
- LQLQDKBJAIILIQ-UHFFFAOYSA-N Dibutyl terephthalate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C=C1 LQLQDKBJAIILIQ-UHFFFAOYSA-N 0.000 claims description 25
- 238000004821 distillation Methods 0.000 claims description 25
- 239000011347 resin Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 12
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 10
- -1 dibutyl terephthalate ester Chemical class 0.000 claims description 10
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 6
- 239000011342 resin composition Substances 0.000 claims description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 229960002380 dibutyl phthalate Drugs 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 230000035484 reaction time Effects 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- 239000003377 acid catalyst Substances 0.000 description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000001747 exhibiting effect Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000005187 foaming Methods 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- DMIMWGHYIPFAIF-UHFFFAOYSA-N 5-nitro-2-piperidin-1-ylaniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1N1CCCCC1 DMIMWGHYIPFAIF-UHFFFAOYSA-N 0.000 description 2
- NWVGLJGUHISDBN-UHFFFAOYSA-N C(C1=CC=C(C(=O)O)C=C1)(=O)O.C(CCC)C1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45 Chemical compound C(C1=CC=C(C(=O)O)C=C1)(=O)O.C(CCC)C1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45 NWVGLJGUHISDBN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MURWRBWZIMXKGC-UHFFFAOYSA-N Phthalsaeure-butylester-octylester Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC MURWRBWZIMXKGC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000000750 endocrine system Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
- C07C69/82—Terephthalic acid esters
-
- C—CHEMISTRY; METALLURGY
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20130068197 | 2013-06-14 | ||
| KR1020130077986A KR101447376B1 (ko) | 2013-06-14 | 2013-07-03 | 에스테르계 가소제의 제조방법 및 이로부터 제조된 에스테르계 가소제 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201446852A TW201446852A (zh) | 2014-12-16 |
| TWI510535B true TWI510535B (zh) | 2015-12-01 |
Family
ID=52469546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103100334A TWI510535B (zh) | 2013-06-14 | 2014-01-06 | 酯類塑化劑之製備方法及其所製備之酯類塑化劑 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9200138B2 (enExample) |
| EP (1) | EP2851392B1 (enExample) |
| KR (1) | KR101447376B1 (enExample) |
| CN (1) | CN104395386B (enExample) |
| IN (1) | IN2015DN01460A (enExample) |
| PL (1) | PL2851392T3 (enExample) |
| TW (1) | TWI510535B (enExample) |
| WO (1) | WO2014200138A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140027014A (ko) * | 2012-08-23 | 2014-03-06 | 주식회사 엘지화학 | 가소제 조성물 |
| JP5907311B2 (ja) * | 2013-05-08 | 2016-04-26 | エルジー・ケム・リミテッド | エステル系組成物、その製造方法、及びこれを含む樹脂組成物 |
| PL3059221T3 (pl) * | 2015-02-18 | 2018-02-28 | Evonik Degussa Gmbh | Tereftalany pentylo-nonylowe |
| KR101907252B1 (ko) | 2015-03-20 | 2018-10-11 | 주식회사 엘지화학 | 가소제 조성물, 수지 조성물 및 이들의 제조 방법 |
| KR101939160B1 (ko) | 2015-05-14 | 2019-01-16 | 주식회사 엘지화학 | 에스테르계 화합물, 이를 포함하는 조성물, 이의 제조방법, 및 이를 포함하는 수지 조성물 |
| EP3112409A1 (en) * | 2015-06-30 | 2017-01-04 | Scg Chemicals Co. Ltd. | Plasticizer composition |
| KR101793383B1 (ko) | 2015-07-24 | 2017-11-20 | 주식회사 엘지화학 | 가소제 조성물, 수지 조성물 및 이들의 제조 방법 |
| CN107428992B (zh) * | 2015-07-24 | 2020-02-07 | Lg化学株式会社 | 增塑剂组合物、树脂组合物及其制备方法 |
| ES2744073T3 (es) * | 2015-09-30 | 2020-02-21 | Basf Se | Composición de plastificante que contiene ésteres de ácido dicarboxílico poliméricos y dialquilésteres de ácido tereftálico |
| RU2633963C2 (ru) * | 2015-12-29 | 2017-10-20 | Публичное акционерное общество "СИБУР Холдинг" | Композиция пластификатора для поливинилхлорида, пластизоль и пластификат на ее основе |
| WO2018167718A1 (en) * | 2017-03-15 | 2018-09-20 | Sabic Global Technologies B.V. | Method of making dialkyl terephthalate from terephthalic acid |
| CN107857896B (zh) * | 2017-11-16 | 2019-07-09 | 上海炼升化工股份有限公司 | 一种源自pta副品的酯类组合物及其制备方法 |
| KR102325729B1 (ko) | 2018-11-28 | 2021-11-15 | 주식회사 엘지화학 | 가압 구간을 포함하는 테레프탈레이트계 조성물의 제조방법 |
| TW202402914A (zh) * | 2022-02-25 | 2024-01-16 | 南韓商Ｌｇ化學股份有限公司 | 塑化劑組成物及包括彼之樹脂組成物 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200421021A (en) * | 2002-09-03 | 2004-10-16 | Kolon Inc | Photopolymerizable resin composition for sandblast resist |
| CN1563159A (zh) * | 2004-03-18 | 2005-01-12 | 杨家勇 | 对苯二甲酸和辛醇制备对苯二甲酸二辛酯增塑剂的工艺 |
| TW200734300A (en) * | 2006-01-12 | 2007-09-16 | Oxeno Olefinchemie Gmbh | Dialkyl terephthalates and their use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4204305B2 (ja) | 2002-11-08 | 2009-01-07 | 株式会社Ａｄｅｋａ | ポリエステル系可塑剤及び塩素含有樹脂組成物 |
| US7276621B2 (en) * | 2005-08-12 | 2007-10-02 | Eastman Chemical Company | Production of di-(2-ethylhexyl) terephthalate |
| US7361779B1 (en) * | 2007-04-18 | 2008-04-22 | Eastman Chemical Company | Low-melting mixtures of di-n-butyl and diisobutyl terephthalate |
| KR101536380B1 (ko) * | 2011-09-30 | 2015-07-14 | 주식회사 엘지화학 | 에스터 가소제 조성물 |
| KR20130042743A (ko) * | 2011-10-19 | 2013-04-29 | 주식회사 엘지화학 | 테레프탈산 유래 에스테르의 제조방법 |
-
2013
- 2013-07-03 EP EP13886163.8A patent/EP2851392B1/en active Active
- 2013-07-03 KR KR1020130077986A patent/KR101447376B1/ko active Active
- 2013-07-03 CN CN201380034504.9A patent/CN104395386B/zh active Active
- 2013-07-03 WO PCT/KR2013/005919 patent/WO2014200138A1/ko not_active Ceased
- 2013-07-03 IN IN1460DEN2015 patent/IN2015DN01460A/en unknown
- 2013-07-03 PL PL13886163T patent/PL2851392T3/pl unknown
-
2014
- 2014-01-06 TW TW103100334A patent/TWI510535B/zh active
- 2014-10-09 US US14/510,816 patent/US9200138B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200421021A (en) * | 2002-09-03 | 2004-10-16 | Kolon Inc | Photopolymerizable resin composition for sandblast resist |
| CN1563159A (zh) * | 2004-03-18 | 2005-01-12 | 杨家勇 | 对苯二甲酸和辛醇制备对苯二甲酸二辛酯增塑剂的工艺 |
| TW200734300A (en) * | 2006-01-12 | 2007-09-16 | Oxeno Olefinchemie Gmbh | Dialkyl terephthalates and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| US9200138B2 (en) | 2015-12-01 |
| TW201446852A (zh) | 2014-12-16 |
| KR101447376B1 (ko) | 2014-12-18 |
| IN2015DN01460A (enExample) | 2015-07-03 |
| CN104395386A (zh) | 2015-03-04 |
| PL2851392T3 (pl) | 2017-02-28 |
| EP2851392A1 (en) | 2015-03-25 |
| CN104395386B (zh) | 2016-09-07 |
| EP2851392B1 (en) | 2016-09-07 |
| WO2014200138A1 (ko) | 2014-12-18 |
| EP2851392A4 (en) | 2015-06-24 |
| US20150025186A1 (en) | 2015-01-22 |
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