CN1636962A - 多品种、低消耗增塑剂生产方法 - Google Patents
多品种、低消耗增塑剂生产方法 Download PDFInfo
- Publication number
- CN1636962A CN1636962A CN 03113054 CN03113054A CN1636962A CN 1636962 A CN1636962 A CN 1636962A CN 03113054 CN03113054 CN 03113054 CN 03113054 A CN03113054 A CN 03113054A CN 1636962 A CN1636962 A CN 1636962A
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- Prior art keywords
- acid
- phthalate
- esterification
- plasticizer
- ethyl
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- 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
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 239000004014 plasticizer Substances 0.000 title abstract description 9
- 238000005886 esterification reaction Methods 0.000 claims abstract description 30
- 230000032050 esterification Effects 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 16
- -1 di (2-ethyl) hexyl phthalate Chemical compound 0.000 claims abstract description 15
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims abstract description 12
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000007670 refining Methods 0.000 claims abstract description 10
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 8
- 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 abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 claims abstract description 6
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims abstract description 6
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 claims abstract description 6
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000004902 Softening Agent Substances 0.000 claims description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 5
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical group C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000005591 trimellitate group Chemical group 0.000 claims description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
- IHLDEDLAZNFOJB-UHFFFAOYSA-N 6-octoxy-6-oxohexanoic acid Chemical compound CCCCCCCCOC(=O)CCCCC(O)=O IHLDEDLAZNFOJB-UHFFFAOYSA-N 0.000 claims description 2
- 244000248349 Citrus limon Species 0.000 claims description 2
- 235000005979 Citrus limon Nutrition 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 150000007520 diprotic acids Chemical class 0.000 claims 1
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 239000012752 auxiliary agent Substances 0.000 abstract description 2
- 238000010923 batch production Methods 0.000 abstract 2
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- LNYCJZRLMAMTQW-UHFFFAOYSA-N trioctyl 2-hydroxy-4-oxopentane-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCC)C(C(C)=O)C(=O)OCCCCCCCC LNYCJZRLMAMTQW-UHFFFAOYSA-N 0.000 abstract 1
- APVVRLGIFCYZHJ-UHFFFAOYSA-N trioctyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCC)CC(=O)OCCCCCCCC APVVRLGIFCYZHJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002932 luster Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 3
- 239000004439 Isononyl alcohol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000004440 Isodecyl alcohol Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CNB031130542A CN100404496C (zh) | 2003-03-26 | 2003-03-26 | 多品种、低消耗增塑剂生产方法 |
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CNB031130542A CN100404496C (zh) | 2003-03-26 | 2003-03-26 | 多品种、低消耗增塑剂生产方法 |
Publications (2)
Publication Number | Publication Date |
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CN1636962A true CN1636962A (zh) | 2005-07-13 |
CN100404496C CN100404496C (zh) | 2008-07-23 |
Family
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Family Applications (1)
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CNB031130542A Expired - Fee Related CN100404496C (zh) | 2003-03-26 | 2003-03-26 | 多品种、低消耗增塑剂生产方法 |
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1326829C (zh) * | 2005-09-05 | 2007-07-18 | 吉化集团公司 | 一种邻苯二甲酸二异癸酯的生产方法 |
CN100363328C (zh) * | 2005-11-08 | 2008-01-23 | 江南大学 | 一种偏苯三酸三(c8-10醇)酯的制备方法 |
CN101139293B (zh) * | 2007-08-17 | 2010-08-25 | 郭立耀 | 对苯二甲酸二辛酯的生产方法 |
CN101973884A (zh) * | 2010-09-26 | 2011-02-16 | 昆山合峰化工有限公司 | 偏苯三甲酸三异壬酯的制备方法 |
CN102219688A (zh) * | 2011-05-05 | 2011-10-19 | 江南大学 | 一种提高邻苯二甲酸二丁酯/二异丁酯热稳定性的方法 |
CN103080066A (zh) * | 2010-08-27 | 2013-05-01 | 罗狄亚聚酰胺特殊品有限公司 | 用于制备己二酸二-α-甲基苄基酯的方法 |
CN105399625A (zh) * | 2015-12-18 | 2016-03-16 | 安徽香枫新材料股份有限公司 | 一种耐寒增塑剂癸二酸二辛酯的制备方法 |
CN105504347A (zh) * | 2015-12-11 | 2016-04-20 | 安徽律正科技信息服务有限公司 | 一种塑胶用耐光耐热抗老化增塑剂 |
WO2016126080A1 (ko) * | 2015-02-04 | 2016-08-11 | 한화케미칼 주식회사 | 친환경 가소제 조성물, 및 이를 포함하는 염화비닐 수지 조성물 |
CN109153630A (zh) * | 2016-05-25 | 2019-01-04 | 沙特基础工业全球技术有限公司 | 三苯甲酸烷基酯的合成 |
CN109208340A (zh) * | 2018-11-05 | 2019-01-15 | 加通汽车内饰(常熟)有限公司 | 一种可降解pvc人造革及其制备工艺及其生产工艺 |
CN111040246A (zh) * | 2019-11-14 | 2020-04-21 | 东莞市世泰贸易有限公司 | 一种改进的己二酸二辛酯的制备方法 |
CN112209824A (zh) * | 2020-10-20 | 2021-01-12 | 山东朗晖石油化学股份有限公司 | 柠檬酸混酯生产方法 |
CN112958065A (zh) * | 2021-03-17 | 2021-06-15 | 江苏正丹化学工业股份有限公司 | 用于对苯二甲酸二辛酯生产的复合型催化剂、其制备方法和用途 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1169420A (zh) * | 1996-06-21 | 1998-01-07 | 巴陵石油化工公司鹰山石油化工厂 | 一种制备邻苯二甲酸二环己酯的方法 |
-
2003
- 2003-03-26 CN CNB031130542A patent/CN100404496C/zh not_active Expired - Fee Related
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1326829C (zh) * | 2005-09-05 | 2007-07-18 | 吉化集团公司 | 一种邻苯二甲酸二异癸酯的生产方法 |
CN100363328C (zh) * | 2005-11-08 | 2008-01-23 | 江南大学 | 一种偏苯三酸三(c8-10醇)酯的制备方法 |
CN101139293B (zh) * | 2007-08-17 | 2010-08-25 | 郭立耀 | 对苯二甲酸二辛酯的生产方法 |
CN103080066A (zh) * | 2010-08-27 | 2013-05-01 | 罗狄亚聚酰胺特殊品有限公司 | 用于制备己二酸二-α-甲基苄基酯的方法 |
CN101973884A (zh) * | 2010-09-26 | 2011-02-16 | 昆山合峰化工有限公司 | 偏苯三甲酸三异壬酯的制备方法 |
CN102219688A (zh) * | 2011-05-05 | 2011-10-19 | 江南大学 | 一种提高邻苯二甲酸二丁酯/二异丁酯热稳定性的方法 |
CN102219688B (zh) * | 2011-05-05 | 2014-03-26 | 江南大学 | 一种提高邻苯二甲酸二丁酯/二异丁酯热稳定性的方法 |
WO2016126080A1 (ko) * | 2015-02-04 | 2016-08-11 | 한화케미칼 주식회사 | 친환경 가소제 조성물, 및 이를 포함하는 염화비닐 수지 조성물 |
CN107428989A (zh) * | 2015-02-04 | 2017-12-01 | 韩华化学株式会社 | 环境友好的增塑剂组合物及含有该增塑剂组合物的氯乙烯树脂组合物 |
CN105504347A (zh) * | 2015-12-11 | 2016-04-20 | 安徽律正科技信息服务有限公司 | 一种塑胶用耐光耐热抗老化增塑剂 |
CN105399625A (zh) * | 2015-12-18 | 2016-03-16 | 安徽香枫新材料股份有限公司 | 一种耐寒增塑剂癸二酸二辛酯的制备方法 |
CN109153630A (zh) * | 2016-05-25 | 2019-01-04 | 沙特基础工业全球技术有限公司 | 三苯甲酸烷基酯的合成 |
CN109208340A (zh) * | 2018-11-05 | 2019-01-15 | 加通汽车内饰(常熟)有限公司 | 一种可降解pvc人造革及其制备工艺及其生产工艺 |
CN111040246A (zh) * | 2019-11-14 | 2020-04-21 | 东莞市世泰贸易有限公司 | 一种改进的己二酸二辛酯的制备方法 |
CN112209824A (zh) * | 2020-10-20 | 2021-01-12 | 山东朗晖石油化学股份有限公司 | 柠檬酸混酯生产方法 |
CN112958065A (zh) * | 2021-03-17 | 2021-06-15 | 江苏正丹化学工业股份有限公司 | 用于对苯二甲酸二辛酯生产的复合型催化剂、其制备方法和用途 |
CN112958065B (zh) * | 2021-03-17 | 2023-02-24 | 江苏正丹化学工业股份有限公司 | 用于对苯二甲酸二辛酯生产的复合型催化剂、其制备方法和用途 |
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CN100404496C (zh) | 2008-07-23 |
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Assignee: Jiangsu Lemon Chemical Industry Technology Co., Ltd. Assignor: Jiangnan University Contract fulfillment period: 2008.8.21 to 2014.12.31 contract change Contract record no.: 2009320001036 Denomination of invention: Production method of multi variety and low consumption plasticizer Granted publication date: 20080723 License type: General permission Record date: 2009.6.29 Assignee: Jiangsu Lemon Chemical Industry Technology Co., Ltd. Assignor: Jiangnan University Contract fulfillment period: 2009.7.10 to 2015.12.31 contract change Contract record no.: 2009320001207 Denomination of invention: Production method of multi variety and low consumption plasticizer Granted publication date: 20080723 License type: Exclusive license Record date: 2009.7.23 |
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Assignee: Jianye Organic Chemical Co Ltd, Jiande City, Zhejiang Assignor: Jiangnan University Contract record no.: 2010330002259 Denomination of invention: Production process of plasticizer with multiple variety and low consumption Granted publication date: 20080723 License type: Exclusive License Open date: 20050713 Record date: 20101215 |
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