JPS61246173A - γ−ブチロラクトンの製造方法 - Google Patents
γ−ブチロラクトンの製造方法Info
- Publication number
- JPS61246173A JPS61246173A JP60085438A JP8543885A JPS61246173A JP S61246173 A JPS61246173 A JP S61246173A JP 60085438 A JP60085438 A JP 60085438A JP 8543885 A JP8543885 A JP 8543885A JP S61246173 A JPS61246173 A JP S61246173A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- copper
- chromium
- butyrolactone
- butanediol
- 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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 21
- SXKJCXWNWBRZGB-UHFFFAOYSA-N chromium copper manganese Chemical compound [Mn][Cr][Cu] SXKJCXWNWBRZGB-UHFFFAOYSA-N 0.000 claims abstract description 4
- XUZDJUDKWXESQE-UHFFFAOYSA-N chromium copper zinc Chemical compound [Cr].[Zn].[Cu] XUZDJUDKWXESQE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 abstract description 8
- 239000011701 zinc Substances 0.000 abstract description 8
- 229910052804 chromium Inorganic materials 0.000 abstract description 6
- 239000011572 manganese Substances 0.000 abstract description 6
- 229910052802 copper Inorganic materials 0.000 abstract description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 239000002243 precursor Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000007791 liquid phase Substances 0.000 abstract description 2
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000012808 vapor phase Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JOSWYUNQBRPBDN-UHFFFAOYSA-P ammonium dichromate Chemical compound [NH4+].[NH4+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O JOSWYUNQBRPBDN-UHFFFAOYSA-P 0.000 description 7
- 239000011651 chromium Substances 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000010949 copper Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000006356 dehydrogenation reaction Methods 0.000 description 5
- 229910017813 Cu—Cr Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229930188620 butyrolactone Natural products 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 2
- PWGQHOJABIQOOS-UHFFFAOYSA-N copper;dioxido(dioxo)chromium Chemical compound [Cu+2].[O-][Cr]([O-])(=O)=O PWGQHOJABIQOOS-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- JGPSMWXKRPZZRG-UHFFFAOYSA-N zinc;dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O JGPSMWXKRPZZRG-UHFFFAOYSA-N 0.000 description 2
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- YMKHJSXMVZVZNU-UHFFFAOYSA-N manganese(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YMKHJSXMVZVZNU-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60085438A JPS61246173A (ja) | 1985-04-23 | 1985-04-23 | γ−ブチロラクトンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60085438A JPS61246173A (ja) | 1985-04-23 | 1985-04-23 | γ−ブチロラクトンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61246173A true JPS61246173A (ja) | 1986-11-01 |
| JPH0417954B2 JPH0417954B2 (enrdf_load_stackoverflow) | 1992-03-26 |
Family
ID=13858861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60085438A Granted JPS61246173A (ja) | 1985-04-23 | 1985-04-23 | γ−ブチロラクトンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61246173A (enrdf_load_stackoverflow) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992000973A1 (en) * | 1990-07-11 | 1992-01-23 | E.I. Du Pont De Nemours And Company | Dehydrogenation of diols |
| EP0584408A3 (en) * | 1992-08-25 | 1994-06-22 | Tonen Sekiyukagaku Kk | Process for the preparation of gamma-butyrolactone |
| EP0628552A1 (de) * | 1993-06-11 | 1994-12-14 | Hüls Aktiengesellschaft | Verfahren zur katalytischen Dehydrierung von Diolen |
| CN1044866C (zh) * | 1994-05-05 | 1999-09-01 | 化学工业部北京化工研究院 | 顺酐气相加氢制γ－丁内酯的催化剂 |
| CN1045174C (zh) * | 1994-05-05 | 1999-09-22 | 化学工业部北京化工研究院 | 一种γ－丁内酯的生产方法 |
| CN1046216C (zh) * | 1994-06-04 | 1999-11-10 | 中国石油化工总公司 | 制备1,4-丁二醇和/或γ-丁内酯的催化剂 |
| CN1054843C (zh) * | 1996-08-12 | 2000-07-26 | 中国石油化工总公司 | N－甲基吡咯烷酮的制备方法 |
| US6323347B2 (en) | 2000-01-14 | 2001-11-27 | Dairen Chemical Corporation | Catalyst for preparing lactone and a method for preparing lactone |
| JP2005523148A (ja) * | 2002-04-22 | 2005-08-04 | エギョン ペトロケミカル カンパニー リミテッド | 水素添加反応触媒、その製造方法、およびその触媒を使用して無水マレイン酸からガンマ−ブチロラクトンを製造する方法 |
| WO2009082086A1 (en) * | 2007-12-21 | 2009-07-02 | Isu Chemical Co., Ltd. | Process for preparing of n-methyl pyrrolidone |
| WO2021045153A1 (ja) * | 2019-09-06 | 2021-03-11 | 昭和電工株式会社 | ガンマブチロラクトンの製造方法およびｎ－メチルピロリドンの製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB583344A (en) * | 1944-10-20 | 1946-12-16 | John George Mackay Bremner | Process for the production of lactones |
| JPS4924906A (enrdf_load_stackoverflow) * | 1972-06-26 | 1974-03-05 |
-
1985
- 1985-04-23 JP JP60085438A patent/JPS61246173A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB583344A (en) * | 1944-10-20 | 1946-12-16 | John George Mackay Bremner | Process for the production of lactones |
| JPS4924906A (enrdf_load_stackoverflow) * | 1972-06-26 | 1974-03-05 |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992000973A1 (en) * | 1990-07-11 | 1992-01-23 | E.I. Du Pont De Nemours And Company | Dehydrogenation of diols |
| EP0584408A3 (en) * | 1992-08-25 | 1994-06-22 | Tonen Sekiyukagaku Kk | Process for the preparation of gamma-butyrolactone |
| EP0628552A1 (de) * | 1993-06-11 | 1994-12-14 | Hüls Aktiengesellschaft | Verfahren zur katalytischen Dehydrierung von Diolen |
| CN1044866C (zh) * | 1994-05-05 | 1999-09-01 | 化学工业部北京化工研究院 | 顺酐气相加氢制γ－丁内酯的催化剂 |
| CN1045174C (zh) * | 1994-05-05 | 1999-09-22 | 化学工业部北京化工研究院 | 一种γ－丁内酯的生产方法 |
| CN1046216C (zh) * | 1994-06-04 | 1999-11-10 | 中国石油化工总公司 | 制备1,4-丁二醇和/或γ-丁内酯的催化剂 |
| CN1054843C (zh) * | 1996-08-12 | 2000-07-26 | 中国石油化工总公司 | N－甲基吡咯烷酮的制备方法 |
| US6323347B2 (en) | 2000-01-14 | 2001-11-27 | Dairen Chemical Corporation | Catalyst for preparing lactone and a method for preparing lactone |
| JP2005523148A (ja) * | 2002-04-22 | 2005-08-04 | エギョン ペトロケミカル カンパニー リミテッド | 水素添加反応触媒、その製造方法、およびその触媒を使用して無水マレイン酸からガンマ−ブチロラクトンを製造する方法 |
| WO2009082086A1 (en) * | 2007-12-21 | 2009-07-02 | Isu Chemical Co., Ltd. | Process for preparing of n-methyl pyrrolidone |
| JP2011507830A (ja) * | 2007-12-21 | 2011-03-10 | イス・ケミカル・カンパニー・リミテッド | Ｎ−メチルピロリドンの製造方法 |
| WO2021045153A1 (ja) * | 2019-09-06 | 2021-03-11 | 昭和電工株式会社 | ガンマブチロラクトンの製造方法およびｎ－メチルピロリドンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0417954B2 (enrdf_load_stackoverflow) | 1992-03-26 |
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