CN114436775A - 一种由含缩醛的粗品加氢精制1,4-丁二醇的方法 - Google Patents
一种由含缩醛的粗品加氢精制1,4-丁二醇的方法 Download PDFInfo
- Publication number
- CN114436775A CN114436775A CN202011195991.5A CN202011195991A CN114436775A CN 114436775 A CN114436775 A CN 114436775A CN 202011195991 A CN202011195991 A CN 202011195991A CN 114436775 A CN114436775 A CN 114436775A
- Authority
- CN
- China
- Prior art keywords
- butanediol
- hydrogen
- temperature
- crude product
- crude
- 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
Links
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims abstract description 186
- 238000000034 method Methods 0.000 title claims abstract description 41
- 239000012043 crude product Substances 0.000 title claims abstract description 38
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 title claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 239000001257 hydrogen Substances 0.000 claims abstract description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000007789 gas Substances 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 11
- 239000000945 filler Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 14
- 150000002431 hydrogen Chemical class 0.000 abstract description 13
- 238000009833 condensation Methods 0.000 abstract description 10
- 230000005494 condensation Effects 0.000 abstract description 10
- 230000001965 increasing effect Effects 0.000 abstract description 8
- 238000004090 dissolution Methods 0.000 abstract description 5
- 239000006185 dispersion Substances 0.000 abstract description 3
- 230000001737 promoting effect Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000007670 refining Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- -1 polybutylene terephthalate Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 150000002373 hemiacetals Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000012229 microporous material Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Images
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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C07C29/90—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound using hydrogen only
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (14)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011195991.5A CN114436775B (zh) | 2020-10-31 | 2020-10-31 | 一种由含缩醛的粗品加氢精制1,4-丁二醇的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011195991.5A CN114436775B (zh) | 2020-10-31 | 2020-10-31 | 一种由含缩醛的粗品加氢精制1,4-丁二醇的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN114436775A true CN114436775A (zh) | 2022-05-06 |
CN114436775B CN114436775B (zh) | 2024-05-31 |
Family
ID=81356900
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202011195991.5A Active CN114436775B (zh) | 2020-10-31 | 2020-10-31 | 一种由含缩醛的粗品加氢精制1,4-丁二醇的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114436775B (zh) |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1216973A (zh) * | 1996-03-29 | 1999-05-19 | 科瓦内加工技术有限公司 | 1,4-丁二醇的纯化方法 |
JP2003026622A (ja) * | 2001-07-17 | 2003-01-29 | Mitsubishi Chemicals Corp | 1,4−ブタンジオールの製造方法 |
CN102311790A (zh) * | 2010-07-07 | 2012-01-11 | 中国石油化工股份有限公司 | 一种提高混氢量的液相循环加氢处理方法 |
CN106590732A (zh) * | 2015-10-15 | 2017-04-26 | 神华集团有限责任公司 | 一种费托合成油低温液相加氢精制的方法和*** |
CN107778141A (zh) * | 2016-08-30 | 2018-03-09 | 中国石油化工股份有限公司 | 一种1,4‑丁二醇的纯化方法 |
CN109225073A (zh) * | 2018-09-17 | 2019-01-18 | 清华大学 | 一种微填充床内加氢反应装置及其进行加氢反应的方法 |
CN109679690A (zh) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | 一种液相加氢***及液相加氢方法 |
CN109679682A (zh) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | 一种溶氢设备和溶氢方法 |
CN110862302A (zh) * | 2018-08-27 | 2020-03-06 | 中国石化扬子石油化工有限公司 | 一种浆态床加氢与固定床加氢组合制备1,4-丁二醇的方法 |
-
2020
- 2020-10-31 CN CN202011195991.5A patent/CN114436775B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1216973A (zh) * | 1996-03-29 | 1999-05-19 | 科瓦内加工技术有限公司 | 1,4-丁二醇的纯化方法 |
JP2003026622A (ja) * | 2001-07-17 | 2003-01-29 | Mitsubishi Chemicals Corp | 1,4−ブタンジオールの製造方法 |
CN102311790A (zh) * | 2010-07-07 | 2012-01-11 | 中国石油化工股份有限公司 | 一种提高混氢量的液相循环加氢处理方法 |
CN106590732A (zh) * | 2015-10-15 | 2017-04-26 | 神华集团有限责任公司 | 一种费托合成油低温液相加氢精制的方法和*** |
CN107778141A (zh) * | 2016-08-30 | 2018-03-09 | 中国石油化工股份有限公司 | 一种1,4‑丁二醇的纯化方法 |
CN109679690A (zh) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | 一种液相加氢***及液相加氢方法 |
CN109679682A (zh) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | 一种溶氢设备和溶氢方法 |
CN110862302A (zh) * | 2018-08-27 | 2020-03-06 | 中国石化扬子石油化工有限公司 | 一种浆态床加氢与固定床加氢组合制备1,4-丁二醇的方法 |
CN109225073A (zh) * | 2018-09-17 | 2019-01-18 | 清华大学 | 一种微填充床内加氢反应装置及其进行加氢反应的方法 |
Non-Patent Citations (1)
Title |
---|
张志炳 等: "Marangoni效应与汽液传质过程", 《化工学报》, vol. 54, no. 4, 30 April 2003 (2003-04-30), pages 508 - 515 * |
Also Published As
Publication number | Publication date |
---|---|
CN114436775B (zh) | 2024-05-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106164028B (zh) | 复合金属催化剂组合物及使用其用于制备1,4-环己烷二甲醇的方法和装置 | |
CN107473954A (zh) | 一种丁二酸的绿色化生产方法 | |
US10189766B2 (en) | Process for producing 2-ethylhexanal helping to improve yield | |
CN114436775B (zh) | 一种由含缩醛的粗品加氢精制1,4-丁二醇的方法 | |
CN114433100B (zh) | 加氢催化剂及其制备方法和应用以及顺酐加氢制丁二酸酐的方法 | |
CN112125792B (zh) | 一种联产羟基香茅醛和羟基香茅醇的方法 | |
CN114929658B (zh) | 1,4-环己烷二甲醇的制备方法 | |
CN114436778A (zh) | 一种缩醛加氢精制1,4-丁二醇的方法 | |
US8569442B2 (en) | Hydrogenation process for improving yield of hydrogenated bisphenol-A-based epoxy resin | |
KR102670911B1 (ko) | 1,4-사이클로헥산디메탄올의 제조 방법 | |
CN107915579A (zh) | 丁二烯合成1,4‑丁二醇的方法 | |
CN111825526B (zh) | 1,4-环己烷二甲醇的制备方法 | |
CN114945546B (zh) | 制备1,4-环己烷二甲醇的方法 | |
CN114539191B (zh) | 一种顺酐马来酐加氢和1,4丁二醇脱氢耦合法制备gbl的方法 | |
CN113042040A (zh) | 一种铂碳催化剂及用铂碳催化剂制备氨甲环酸的方法 | |
CN1245369C (zh) | 2—乙基己醛的制备方法 | |
CN114929657B (zh) | 制备1,4-环己烷二甲酸的方法 | |
CN109647472B (zh) | 加氢催化剂及其制备方法和四氢糠醇的制备方法 | |
CN114105846B (zh) | 一种己内酰胺的加氢精制方法和装置 | |
CN114716397B (zh) | 一种苯酐常压加氢制苯酞的制备方法 | |
CN112473725B (zh) | 一种改性分子筛催化剂的制备方法及连续合成3-甲氧基-3-甲基丁醇的方法 | |
CN106554268A (zh) | 一种水相催化合成甲基琥珀酸的方法 | |
CN118164823A (zh) | 一种乙二醇液相加氢制备精乙二醇的方法 | |
CN107913706B (zh) | 丁二烯制备1,4-二乙酰氧基丁烷的加氢催化剂 | |
CN114805032A (zh) | 氧芴还原制备邻苯基苯酚的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20240107 Address after: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Applicant after: CHINA PETROLEUM & CHEMICAL Corp. Applicant after: Sinopec (Dalian) Petrochemical Research Institute Co.,Ltd. Address before: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Applicant before: CHINA PETROLEUM & CHEMICAL Corp. Applicant before: DALIAN RESEARCH INSTITUTE OF PETROLEUM AND PETROCHEMICALS, SINOPEC Corp. |
|
TA01 | Transfer of patent application right | ||
GR01 | Patent grant | ||
GR01 | Patent grant |