JPS6121538B2 - - Google Patents
Info
- Publication number
- JPS6121538B2 JPS6121538B2 JP8737580A JP8737580A JPS6121538B2 JP S6121538 B2 JPS6121538 B2 JP S6121538B2 JP 8737580 A JP8737580 A JP 8737580A JP 8737580 A JP8737580 A JP 8737580A JP S6121538 B2 JPS6121538 B2 JP S6121538B2
- Authority
- JP
- Japan
- Prior art keywords
- formaldehyde
- compound
- molar ratio
- reaction
- general formula
- 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
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 141
- 238000006243 chemical reaction Methods 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 18
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 14
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 14
- 239000006227 byproduct Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- -1 methylol group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 15
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 14
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 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 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 6
- 239000008098 formaldehyde solution Substances 0.000 description 5
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000008094 contradictory effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- KDHYEQYWOYBACO-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propan-2-ylpropane-1,3-diol Chemical compound CC(C)C(CO)(CO)CO KDHYEQYWOYBACO-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- HJIYDQCBJVTQAO-UHFFFAOYSA-N 2-butyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CCCCC(CO)(CO)CO HJIYDQCBJVTQAO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8737580A JPS5711934A (en) | 1980-06-26 | 1980-06-26 | Production of ditrimethylolalkane or dipentaerythritol in high ratio as by-product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8737580A JPS5711934A (en) | 1980-06-26 | 1980-06-26 | Production of ditrimethylolalkane or dipentaerythritol in high ratio as by-product |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5711934A JPS5711934A (en) | 1982-01-21 |
| JPS6121538B2 true JPS6121538B2 (de) | 1986-05-27 |
Family
ID=13913141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8737580A Granted JPS5711934A (en) | 1980-06-26 | 1980-06-26 | Production of ditrimethylolalkane or dipentaerythritol in high ratio as by-product |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5711934A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8642816B2 (en) | 2008-08-16 | 2014-02-04 | Lanxess Deutschland Gmbh | Method for isolating di-trimethylol propane |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57142929A (en) * | 1981-02-27 | 1982-09-03 | Koei Chem Co Ltd | Forming method of dipentaerythritol or ditrimethylolalkane as by-product at given ratio |
| JPS60190729A (ja) * | 1984-12-28 | 1985-09-28 | Kuraray Co Ltd | トリメチロ−ルヘプタンの製法 |
| DE4002961C1 (de) * | 1990-02-01 | 1991-03-07 | Fa. Carl Freudenberg, 6940 Weinheim, De | |
| JP3368957B2 (ja) * | 1993-12-14 | 2003-01-20 | 三井化学株式会社 | ジペンタエリスリトールの製造方法 |
| JP4599664B2 (ja) * | 2000-06-27 | 2010-12-15 | 三菱瓦斯化学株式会社 | 多価アルコールの製造法 |
| KR101564119B1 (ko) * | 2007-10-30 | 2015-10-28 | 미츠비시 가스 가가쿠 가부시키가이샤 | 디트리메틸올프로판의 제조 방법 |
-
1980
- 1980-06-26 JP JP8737580A patent/JPS5711934A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8642816B2 (en) | 2008-08-16 | 2014-02-04 | Lanxess Deutschland Gmbh | Method for isolating di-trimethylol propane |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5711934A (en) | 1982-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4465866A (en) | Preparation process of 2-hydroxy-3-alkoxypropylglyceryl ether | |
| HU198437B (en) | Process for producing mono- or bis-carbonyl-compounds | |
| EP0173714B1 (de) | Herstellung optisch aktiver 1,3-dioxolan-4-methanol-verbindungen | |
| JPS6121538B2 (de) | ||
| EP0799815B1 (de) | Verfahren zur Herstellung von Ditrimethylolpropan | |
| JP5434595B2 (ja) | ジトリメチロールプロパンの製造方法 | |
| JPH0144689B2 (de) | ||
| US4608443A (en) | Method for the preparation of 1,4-butandial | |
| US6080896A (en) | Process for producing polyhydric alcohol | |
| JPS61194043A (ja) | ２‐アルキル‐１，４‐ブタンジアールの製造方法 | |
| JPS6259104B2 (de) | ||
| JPH11124348A (ja) | トリメチロールアルカンを製造する方法 | |
| JPH0234330B2 (de) | ||
| JP3795970B2 (ja) | α，β−不飽和アルデヒドの製造方法 | |
| JP3557237B2 (ja) | ヒドロキシピバルアルデヒドの製造方法 | |
| KR20030027005A (ko) | 5-[(4-클로로페닐)메틸]-2,2-디메틸시클로펜탄온의 제조방법 | |
| JP2006513246A (ja) | 水溶性β−ヒドロキシニトリルの製造 | |
| EP0031909B1 (de) | 3-Hydroxycyclopent-4-enone und Verfahren zu deren Herstellung | |
| JPWO2003104177A1 (ja) | アリルエーテル類の製法 | |
| JP3791960B2 (ja) | ジペンタエリスリトールの製造方法 | |
| JP2814941B2 (ja) | Ｎ−ブトキシメチル（メタ）アクリルアミド類の製法 | |
| JP2649555B2 (ja) | ２−ｎ−ブチル−２−エチル−１，３−プロパンジオールの製造方法 | |
| JPH11209323A (ja) | ２，２’−ビス（ヒドロキシメチル）アルカナールおよび２，２’−ビス（ヒドロキシメチル）アルカン酸の製造方法 | |
| JPS6156224B2 (de) | ||
| HU190939B (en) | Process for preparing cyanohydrines |