CN108623437A - 一种连续生产新戊二醇的方法 - Google Patents
一种连续生产新戊二醇的方法 Download PDFInfo
- Publication number
- CN108623437A CN108623437A CN201810555219.6A CN201810555219A CN108623437A CN 108623437 A CN108623437 A CN 108623437A CN 201810555219 A CN201810555219 A CN 201810555219A CN 108623437 A CN108623437 A CN 108623437A
- Authority
- CN
- China
- Prior art keywords
- neopentyl glycol
- continuous production
- reaction
- catalyst
- hydrogenation
- 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.)
- Granted
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000010924 continuous production Methods 0.000 title claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 46
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 31
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000012530 fluid Substances 0.000 claims abstract description 23
- 239000007788 liquid Substances 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 12
- 238000006482 condensation reaction Methods 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 238000006423 Tishchenko reaction Methods 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 6
- CZZVAVMGKRNEAT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)CO.OCC(C)(C)C(O)=O CZZVAVMGKRNEAT-UHFFFAOYSA-N 0.000 claims abstract description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 229910052759 nickel Inorganic materials 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- -1 pentyl ester Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HNWHVVWRJAXEEC-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 2-methylpropanoate Chemical compound CC(C)C(=O)OCC(C)(C)CO HNWHVVWRJAXEEC-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RKQWXDAZJYDNKJ-UHFFFAOYSA-N C=O.OCC(C)(CO)C Chemical compound C=O.OCC(C)(CO)C RKQWXDAZJYDNKJ-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 238000012850 discrimination method Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910001679 gibbsite Inorganic materials 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000004845 hydriding Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000010433 powder painting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/44—Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201810555219.6A CN108623437B (zh) | 2018-06-01 | 2018-06-01 | 一种连续生产新戊二醇的方法 |
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CN201810555219.6A CN108623437B (zh) | 2018-06-01 | 2018-06-01 | 一种连续生产新戊二醇的方法 |
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CN108623437A true CN108623437A (zh) | 2018-10-09 |
CN108623437B CN108623437B (zh) | 2021-07-27 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109400473A (zh) * | 2018-11-14 | 2019-03-01 | 江苏开磷瑞阳化工股份有限公司 | 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 |
CN112500418A (zh) * | 2020-12-31 | 2021-03-16 | 山东中科新材料研究院有限公司 | 一种采用回路反应器合成1,8-二氮杂二环十一碳-7-烯的方法 |
CN112537998A (zh) * | 2020-12-18 | 2021-03-23 | 上海翼湍科技有限责任公司 | 连续催化加氢生产新戊二醇的工艺 |
CN115819185A (zh) * | 2022-12-28 | 2023-03-21 | 南京大学扬州化学化工研究院 | 一种合成新戊二醇的方法 |
CN116178105A (zh) * | 2022-12-08 | 2023-05-30 | 万华化学集团股份有限公司 | 一种催化分解季先科酯提高新戊二醇收率的方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5146012A (en) * | 1991-04-26 | 1992-09-08 | Aristech Chemical Corporation | Manufacture of neopentyl glycol (III) |
CN1224414A (zh) * | 1996-05-03 | 1999-07-28 | 伊斯曼化学公司 | 制备二羟基酯的可溶性镁催化剂 |
CN103351277A (zh) * | 2013-06-28 | 2013-10-16 | 万华化学集团股份有限公司 | 一种新戊二醇的制备方法 |
CN103449970A (zh) * | 2012-05-28 | 2013-12-18 | 北京三聚环保新材料股份有限公司 | 一种新戊二醇的制备方法 |
CN107540521A (zh) * | 2016-06-29 | 2018-01-05 | 中国石油化工股份有限公司 | 羟基新戊醛加氢制新戊二醇的方法 |
-
2018
- 2018-06-01 CN CN201810555219.6A patent/CN108623437B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5146012A (en) * | 1991-04-26 | 1992-09-08 | Aristech Chemical Corporation | Manufacture of neopentyl glycol (III) |
CN1224414A (zh) * | 1996-05-03 | 1999-07-28 | 伊斯曼化学公司 | 制备二羟基酯的可溶性镁催化剂 |
CN103449970A (zh) * | 2012-05-28 | 2013-12-18 | 北京三聚环保新材料股份有限公司 | 一种新戊二醇的制备方法 |
CN103351277A (zh) * | 2013-06-28 | 2013-10-16 | 万华化学集团股份有限公司 | 一种新戊二醇的制备方法 |
CN107540521A (zh) * | 2016-06-29 | 2018-01-05 | 中国石油化工股份有限公司 | 羟基新戊醛加氢制新戊二醇的方法 |
Non-Patent Citations (2)
Title |
---|
张东升: "羟基特戊酸新戊二醇单酯的合成及应用研究新进展", 《精细与专用化学品》 * |
郝子健: "我国新戊二醇生产技术进展及市场分析", 《化工中间体》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109400473A (zh) * | 2018-11-14 | 2019-03-01 | 江苏开磷瑞阳化工股份有限公司 | 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 |
CN109400473B (zh) * | 2018-11-14 | 2022-01-14 | 江苏开磷瑞阳化工股份有限公司 | 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 |
CN112537998A (zh) * | 2020-12-18 | 2021-03-23 | 上海翼湍科技有限责任公司 | 连续催化加氢生产新戊二醇的工艺 |
CN112537998B (zh) * | 2020-12-18 | 2022-12-23 | 上海翼湍科技有限责任公司 | 连续催化加氢生产新戊二醇的工艺 |
CN112500418A (zh) * | 2020-12-31 | 2021-03-16 | 山东中科新材料研究院有限公司 | 一种采用回路反应器合成1,8-二氮杂二环十一碳-7-烯的方法 |
CN116178105A (zh) * | 2022-12-08 | 2023-05-30 | 万华化学集团股份有限公司 | 一种催化分解季先科酯提高新戊二醇收率的方法 |
CN116178105B (zh) * | 2022-12-08 | 2024-05-14 | 万华化学集团股份有限公司 | 一种催化分解季先科酯提高新戊二醇收率的方法 |
CN115819185A (zh) * | 2022-12-28 | 2023-03-21 | 南京大学扬州化学化工研究院 | 一种合成新戊二醇的方法 |
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Date of cancellation: 20231123 Granted publication date: 20210727 Pledgee: Industrial and Commercial Bank of China Limited Lijin sub branch Pledgor: LIHUAYI GROUP Co.,Ltd. Registration number: Y2022980009431 |