CN100463896C - 一种制备低级脂肪酸酯的方法 - Google Patents
一种制备低级脂肪酸酯的方法 Download PDFInfo
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- CN100463896C CN100463896C CNB2007102001475A CN200710200147A CN100463896C CN 100463896 C CN100463896 C CN 100463896C CN B2007102001475 A CNB2007102001475 A CN B2007102001475A CN 200710200147 A CN200710200147 A CN 200710200147A CN 100463896 C CN100463896 C CN 100463896C
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- -1 aliphatic ester Chemical class 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title 1
- 150000001336 alkenes Chemical class 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 11
- 229930195729 fatty acid Natural products 0.000 claims abstract description 11
- 239000000194 fatty acid Substances 0.000 claims abstract description 11
- 239000007791 liquid phase Substances 0.000 claims abstract description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000010936 titanium Substances 0.000 claims abstract description 7
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 7
- 239000012535 impurity Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 34
- 150000002632 lipids Chemical class 0.000 claims description 22
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 16
- 239000003456 ion exchange resin Substances 0.000 claims description 16
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- 239000011148 porous material Substances 0.000 claims description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
- 230000001627 detrimental effect Effects 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical group CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 17
- 150000004665 fatty acids Chemical class 0.000 abstract description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 230000009849 deactivation Effects 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 5
- 229940011051 isopropyl acetate Drugs 0.000 description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 208000012839 conversion disease Diseases 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000003822 preparative gas chromatography Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical class OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (9)
- 【权利要求1】一种制备低级脂肪酸酯的方法,其特征在于:反应物C1-C4脂肪酸和C2-C5烯烃或其中的一种先经过一个装有反应助剂的预处理器脱除有害杂质后,进入工业纯钛为材质装有催化剂的管式固定床反应器,在液相中反应以制备得到低级脂肪酸酯;所述反应助剂为离子交换树脂,所述催化剂是一种强酸性离子交换树脂。
- 【权利要求2】根据权利要求1所述的方法,其特征在于C1-C4脂肪酸选自甲酸、乙酸、丙酸、正丁酸、异丁酸、丙烯酸。
- 【权利要求3】根据权利要求1所述的方法,其特征在于C1-C4脂肪酸选自乙酸。
- 【权利要求4】根据权利要求1或2或3所述的方法,其特征在于C2-C5烯烃可以是乙烯、丙烯、1-丁烯、2-丁烯、异丁烯、1-戊烯或2-戊烯。
- 【权利要求5】根据权利要求1或2或3所述的方法,其特征在于预处理器的反应温度为20~80℃,所述离子交换树脂的交换容量不小于3mmol/gH。
- 【权利要求6】根据权利要求1或2或3所述的方法,其特征在于所述催化剂的比表面积为20~50m2/g,孔容为0.1~0.3ml/g,粒度为0.1~1.5mm;反应混合物中C1-C4脂肪酸与C2-C5烯烃的摩尔比为0.7:1~3.0:1,C1-C4脂肪酸进料空速为0.1~10.0hr-1,反应温度30~150℃,反应压力0.8~2.0MPa。
- 【权利要求7】根据权利要求5所述的方法,其特征在于所述催化剂的比表面积为20~50m2/g,孔容为0.1~0.3ml/g,粒度为0.1~1.5mm;反应混合物中C1-C4脂肪酸与C2-C5烯烃的摩尔比为0.7:1~3.0:1,C1-C4脂肪酸进料空速为0.1~10.0hr-1,反应温度30~150℃,反应压力0.8~2.0MPa。
- 【权利要求8】根据权利要求1或2或3所述的方法,其特征在于所述催化剂的比表面积为20~50m2/g,孔容为0.1~0.3ml/g,粒度为0.1~1.5mm;反应混合物中C1-C4脂肪酸与C2-C5烯烃的摩尔比为0.8:1~2.5:1,C1-C4脂肪酸进料空速为0.2~5.0hr-1,反应温度65~135℃,反应压力0.8~1.8MPa。
- 【权利要求9】根据权利要求5所述的方法,其特征在于所述催化剂的比表面积为20~50m2/g,孔容为0.1~0.3ml/g,粒度为0.1~1.5mm;反应混合物中C1-C4脂肪酸与C2-C5烯烃的摩尔比为0.8:1~2.5:1,C1-C4脂肪酸进料空速为0.2~5.0hr-1,反应温度65~135℃,反应压力0.8~1.8MPa。
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Families Citing this family (4)
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CN101139284B (zh) * | 2007-08-30 | 2010-06-02 | 湖南中创化工有限责任公司 | 一种脱除乙酸仲丁酯中臭味方法 |
CN102911044B (zh) * | 2011-08-01 | 2014-06-25 | 中国石油化工股份有限公司 | 一种正丁烯加成制备醋酸仲丁酯的方法 |
CN102909077B (zh) * | 2011-08-01 | 2015-04-15 | 中国石油化工股份有限公司 | 金属改性阳离子交换树脂催化剂及其制备方法和应用 |
CN103769215B (zh) * | 2012-10-24 | 2015-09-02 | 中国石油化工股份有限公司 | 一种改性阳离子交换树脂催化剂及其制备方法和应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0483826A2 (en) * | 1990-10-31 | 1992-05-06 | Nippon Petrochemicals Company, Limited | Method for producing lower alkyl acetate |
US5189201A (en) * | 1992-03-25 | 1993-02-23 | Showa Denko K.K. | Process for preparation of lower fatty acid ester |
CN1483717A (zh) * | 2003-06-13 | 2004-03-24 | 华南理工大学 | 乙酸异丙酯的合成工艺及其催化剂的制备方法 |
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2007
- 2007-02-02 CN CNB2007102001475A patent/CN100463896C/zh not_active Ceased
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0483826A2 (en) * | 1990-10-31 | 1992-05-06 | Nippon Petrochemicals Company, Limited | Method for producing lower alkyl acetate |
US5457228A (en) * | 1990-10-31 | 1995-10-10 | Daicel Chemical Industries, Ltd. | Method for producing lower alkyl acetate |
US5189201A (en) * | 1992-03-25 | 1993-02-23 | Showa Denko K.K. | Process for preparation of lower fatty acid ester |
CN1483717A (zh) * | 2003-06-13 | 2004-03-24 | 华南理工大学 | 乙酸异丙酯的合成工艺及其催化剂的制备方法 |
Non-Patent Citations (2)
Title |
---|
乙酸异丙酯合成技术开发. 王伟等.山东化工,第33卷第2期. 2004 |
乙酸异丙酯合成技术开发. 王伟等.山东化工,第33卷第2期. 2004 * |
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