CN100400489C - 双三羟甲基丙烷和三羟甲基丙烷甲缩醛生产工艺 - Google Patents
双三羟甲基丙烷和三羟甲基丙烷甲缩醛生产工艺 Download PDFInfo
- Publication number
- CN100400489C CN100400489C CNB200610086255XA CN200610086255A CN100400489C CN 100400489 C CN100400489 C CN 100400489C CN B200610086255X A CNB200610086255X A CN B200610086255XA CN 200610086255 A CN200610086255 A CN 200610086255A CN 100400489 C CN100400489 C CN 100400489C
- Authority
- CN
- China
- Prior art keywords
- trimethylolpropane
- tmp
- ditrimethylolpropane
- methylal
- reaction
- 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.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 238000005516 engineering process Methods 0.000 title description 3
- GQPBUEXGBKVDDE-UHFFFAOYSA-N COCOC.OC(CCC)(O)O Chemical compound COCOC.OC(CCC)(O)O GQPBUEXGBKVDDE-UHFFFAOYSA-N 0.000 title 1
- 235000013847 iso-butane Nutrition 0.000 title 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 title 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 title 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract description 84
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims abstract description 58
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 238000007323 disproportionation reaction Methods 0.000 claims abstract description 8
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006266 etherification reaction Methods 0.000 claims abstract description 3
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 48
- 238000000605 extraction Methods 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 19
- 230000018044 dehydration Effects 0.000 claims description 15
- 238000006297 dehydration reaction Methods 0.000 claims description 15
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 7
- 230000008020 evaporation Effects 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 241000282326 Felis catus Species 0.000 claims description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 238000007701 flash-distillation Methods 0.000 claims description 5
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 239000003637 basic solution Substances 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 238000012856 packing Methods 0.000 claims description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 238000010612 desalination reaction Methods 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 3
- UFZHRTLJOSFQNY-UHFFFAOYSA-N dimethoxymethane 2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound COCOC.C(O)C(CC)(CO)CO UFZHRTLJOSFQNY-UHFFFAOYSA-N 0.000 abstract 2
- 238000005829 trimerization reaction Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 150000001241 acetals Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200610086255XA CN100400489C (zh) | 2006-08-24 | 2006-08-24 | 双三羟甲基丙烷和三羟甲基丙烷甲缩醛生产工艺 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200610086255XA CN100400489C (zh) | 2006-08-24 | 2006-08-24 | 双三羟甲基丙烷和三羟甲基丙烷甲缩醛生产工艺 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1911886A CN1911886A (zh) | 2007-02-14 |
CN100400489C true CN100400489C (zh) | 2008-07-09 |
Family
ID=37720981
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB200610086255XA Expired - Fee Related CN100400489C (zh) | 2006-08-24 | 2006-08-24 | 双三羟甲基丙烷和三羟甲基丙烷甲缩醛生产工艺 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN100400489C (zh) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101092410B (zh) * | 2007-05-21 | 2010-04-14 | 吉化集团公司 | 用三羟甲基丙烷重质残液制备环状三羟甲基丙烷缩甲醛的方法及设备 |
EP2204356B1 (en) * | 2007-10-30 | 2015-12-09 | Mitsubishi Gas Chemical Company, Inc. | Process for production of ditrimethylolpropane |
DE102008038021A1 (de) * | 2008-08-16 | 2010-02-18 | Lanxess Deutschland Gmbh | Verfahren zur Isolierung von Di-Trimethylolpropan |
CN101550070B (zh) * | 2008-12-30 | 2013-07-17 | 湖北三江化工有限责任公司 | 双三羟甲基丙烷生产工艺 |
JP5817730B2 (ja) * | 2010-09-07 | 2015-11-18 | 三菱瓦斯化学株式会社 | ジトリメチロールプロパンの製造方法 |
DE102011118953B4 (de) * | 2011-11-19 | 2014-06-05 | Oxea Gmbh | Destillatives Verfahren zur Gewinnung von Di-Trimethylolpropan |
CN102807477A (zh) * | 2012-09-12 | 2012-12-05 | 上海北凯实业有限公司 | 由单季戊四醇合成双季戊四醇的方法 |
CN104496960A (zh) * | 2014-11-24 | 2015-04-08 | 张家港保税区冠祥贸易有限公司 | 一种基于双(三羟甲基)丙烷可生物降解环缩醛烯类单体及其制备方法 |
CN108383826A (zh) * | 2018-03-09 | 2018-08-10 | 天津博奥新材料科技有限公司 | 一种环状三羟甲基丙烷缩甲醛的制备方法 |
CN109369333A (zh) * | 2018-11-27 | 2019-02-22 | 濮阳市永安化工有限公司 | 从三羟甲基丙烷轻组分中分离出三羟甲基丙烷的方法 |
CN110372475A (zh) * | 2019-08-16 | 2019-10-25 | 南通百川新材料有限公司 | 一种低酸度高收率三羟甲基丙烷的合成工艺 |
CN110577462A (zh) * | 2019-10-09 | 2019-12-17 | 江苏汉凯工程技术有限公司 | 双三羟甲基丙烷回收方法及回收装置 |
CN114181044B (zh) * | 2021-12-03 | 2024-05-17 | 宁夏百川科技有限公司 | 高纯度双三羟甲基丙烷的制备方法 |
CN115925540B (zh) * | 2022-11-09 | 2024-06-14 | 广东聚石科技研究有限公司 | 一种三羟甲基丙烷中碳链酯及其制备方法和应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4076721A (en) * | 1975-06-11 | 1978-02-28 | Ihara Chemical Industry Co., Ltd. | Process for producing saccharin |
CN1572761A (zh) * | 2003-06-13 | 2005-02-02 | 三菱瓦斯化学株式会社 | 二(三羟甲基丙烷)的制备方法 |
-
2006
- 2006-08-24 CN CNB200610086255XA patent/CN100400489C/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4076721A (en) * | 1975-06-11 | 1978-02-28 | Ihara Chemical Industry Co., Ltd. | Process for producing saccharin |
CN1572761A (zh) * | 2003-06-13 | 2005-02-02 | 三菱瓦斯化学株式会社 | 二(三羟甲基丙烷)的制备方法 |
Non-Patent Citations (2)
Title |
---|
三羟甲基丙烷缩合工艺的研究. 聂勇,李晶.化工科技,第10卷第2期. 2002 |
三羟甲基丙烷缩合工艺的研究. 聂勇,李晶.化工科技,第10卷第2期. 2002 * |
Also Published As
Publication number | Publication date |
---|---|
CN1911886A (zh) | 2007-02-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN100400489C (zh) | 双三羟甲基丙烷和三羟甲基丙烷甲缩醛生产工艺 | |
CN101003614B (zh) | 用于生产环氧树脂的方法 | |
CN100999442B (zh) | 含有二氯丙醇的假共沸组合物以及用于生产该组合物的方法 | |
US8906205B2 (en) | Process for separating ethylene glycol and 1,2-butanediol | |
CN109096062B (zh) | 用于提纯聚甲氧基二甲醚的方法 | |
CN101244983B (zh) | 一种低温费托合成反应水中有机物的分离回收方法 | |
EP2821384A1 (en) | Production process for preparing cyclohexanol and cyclohexanone by cyclohexane oxidation | |
CN105399603A (zh) | 同时合成2,2,4-三甲基-1,3-戊二醇双异丁酸酯和2,2,4-三甲基-1,3-戊二醇的方法 | |
CN106866366B (zh) | 一种去除乙二醇中二元醇或多元醇杂质并增产乙二醇的方法 | |
CN101830788A (zh) | 变压精馏分离甲乙酮和水共沸物的方法 | |
CN100447120C (zh) | 三羟甲基丙烷精制的工艺方法 | |
CN106699511A (zh) | 一种甘油氯化馏出液中有/无机物的回收利用方法 | |
CN106588658B (zh) | 一种合成碳酸二甲酯的方法 | |
CN105152860A (zh) | 一种精馏-渗透蒸发耦合工艺精制混合醇的方法 | |
CN113387801B (zh) | 一种十二碳醇酯的连续生产系统 | |
CN101544546B (zh) | 一种萃取精馏分离乙二醇二甲醚和水的方法 | |
CN103910659B (zh) | 2-硝基-4-甲磺酰基苯甲酸的精制方法及其中间体 | |
CN102701908B (zh) | 一种钙法制备新戊二醇的工艺 | |
CN109400473B (zh) | 一种羟基新戊酸新戊二醇单酯和新戊二醇联产的制备方法 | |
CN108329204B (zh) | 一种含氯化氢的甲酸水溶液提浓方法 | |
CN102633644A (zh) | 三氟乙酰乙酸乙酯的一种合成工艺 | |
CN114181044A (zh) | 高纯度双三羟甲基丙烷的制备方法 | |
CN201694976U (zh) | 连续生产高效磺化合成装置 | |
CN105085165A (zh) | 乙二醇和二乙二醇的分离方法 | |
CN110606609B (zh) | 一种回收f-t合成反应水中有机物的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: JIANGSU BOLI'AO CHEMICAL CO.,LTD. Free format text: FORMER OWNER: WANG QIANG Effective date: 20081107 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20081107 Address after: Jiangsu province Liyang City Nandu town Qiang Bu strong industrial park Patentee after: Jiangsu bourriau Chemical Co. Ltd. Address before: Jiangsu province Liyang City Nandu town Qiang Bu strong industrial park Patentee before: Wang Qiang |
|
ASS | Succession or assignment of patent right |
Owner name: LANXESS (LIYANG) POLYOL CO., LTD. Free format text: FORMER OWNER: JIANGSU BOLI'AO CHEMICAL CO.,LTD. Effective date: 20090918 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20090918 Address after: Jiangsu province Liyang City Nandu town Qiang Bu strong Road No. 36 Patentee after: LANXESS (Liyang) Co., Ltd. polyol Address before: Jiangsu province Liyang City Nandu town Qiang Bu strong industrial park Patentee before: Jiangsu bourriau Chemical Co. Ltd. |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080709 Termination date: 20190824 |
|
CF01 | Termination of patent right due to non-payment of annual fee |