CN108440590A - The method for preparing borate using fatty aldehyde - Google Patents
The method for preparing borate using fatty aldehyde Download PDFInfo
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- CN108440590A CN108440590A CN201810336759.5A CN201810336759A CN108440590A CN 108440590 A CN108440590 A CN 108440590A CN 201810336759 A CN201810336759 A CN 201810336759A CN 108440590 A CN108440590 A CN 108440590A
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- CN
- China
- Prior art keywords
- aldehyde
- borine
- borate
- hydroboration
- crown ether
- 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.)
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- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 150000002192 fatty aldehydes Chemical class 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 8
- 229910000085 borane Inorganic materials 0.000 claims abstract description 28
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 26
- 238000006197 hydroboration reaction Methods 0.000 claims abstract description 24
- 150000003983 crown ethers Chemical class 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000018044 dehydration Effects 0.000 claims abstract description 8
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 8
- 238000012545 processing Methods 0.000 claims abstract description 8
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012298 atmosphere Substances 0.000 claims abstract description 5
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011261 inert gas Substances 0.000 claims abstract description 5
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical group CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 12
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- -1 boric acid ester compound Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000005311 nuclear magnetism Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- XVTIGBVLQZAFQP-UHFFFAOYSA-N C=O.C1(CCCCC1)C1=CC=CC=C1 Chemical compound C=O.C1(CCCCC1)C1=CC=CC=C1 XVTIGBVLQZAFQP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003254 gasoline additive Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
Abstract
The application of open-chain crown ether base lithium of the present invention, and in particular to the method for preparing borate using fatty aldehyde.Under anhydrous and oxygen-free environment, in atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then catalyst open-chain crown ether base lithium is added, is uniformly mixed, adds aldehyde, hydroboration is carried out, is exposed in air and terminates reaction, obtain product borate；The aldehyde is selected from fatty aldehyde.Present invention firstly discovers that open-chain crown ether base lithium, which extremely can efficiently be catalyzed hexahydrobenzaldehyde, propionic aldehyde, n-Heptaldehyde and borine, occurs hydroboration, new scheme is provided to prepare borate with borine generation hydroboration using carbonyls.
Description
Technical field
It the present invention relates to the use of the method that fatty aldehyde prepares borate.
Technical background
The product boric acid ester compound of hydroboration can not only be used as polymeric additive, gasoline additive, resistance
Agent is fired, bactericidal agent uses, it is also possible to make special surfactant, lube oil additive and motor vehicle brake fluid etc., application range ten
Divide extensive.Various catalyst have been used for the hydroboration of aldehyde, especially in recent years, the report about this kind of reaction
Road is many.Since under no catalysts conditions, the hydroboration of carbonyls is difficult to occur.So a kind of anti-for this
The research emphasis answered exactly develops efficient catalyst system and catalyzing.But the catalyst system and catalyzing reported at present, catalyst are all relatively high
Expensive or reaction condition is more harsh.
Although belonging to carbonyls, ketone and aldehyde have different reaction properties, this is common sense, and the prior art exists simultaneously
Using keto-aldehyde as raw material, but only there is a situation where a kind of raw materials to react；Electron donating group can weaken the electropositive of carbonyl carbon simultaneously, from
And weakening the nucleophilic addition activity of carbonyl, aromatic aldehyde is since conjugation reduces carbonyl activity, to different the position of substitution, different electronics
The aromatic compound of effect and fatty compound, which have, larger reacts difference.It is efficiently urged so developing under new temperate condition
The catalyst system and catalyzing for changing the hydroboration of aldehyde is particularly urgent.
Invention content
The goal of the invention of the present invention is to provide a kind of method preparing borate, i.e., is efficiently to urge with open-chain crown ether base lithium
Agent is catalyzed aldehyde and hydroboration occurs with borine；The open-chain crown ether base lithium chemical formula is：4-Me-PhNHLi, chemistry
Structural formula is as follows：
To achieve the above object of the invention, the technical solution adopted by the present invention is：
A method of borate being prepared using fatty aldehyde, is included the following steps：
Under anhydrous and oxygen-free environment, in atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then adds
Enter catalyst open-chain crown ether base lithium, be uniformly mixed, add aldehyde, carry out hydroboration, is exposed in air and terminates reaction,
Obtain product borate；The aldehyde is selected from fatty aldehyde.
The present invention further discloses open-chain crown ether base lithium in catalysis aldehyde and the application in borine hydroboration；Institute
It states aldehyde and is selected from fatty aldehyde.
It is catalyzed aldehyde the invention also discloses open-chain crown ether base lithium and the method for hydroboration occurs for borine, including is following
Step：
Under anhydrous and oxygen-free environment, under atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then adds
Enter catalyst open-chain crown ether base lithium, be uniformly mixed, add aldehyde, carries out hydroboration.
In above-mentioned technical proposal, the fatty aldehyde hexahydrobenzaldehyde, propionic aldehyde, n-Heptaldehyde；
The borine is selected from pinacol borine.
In above-mentioned technical proposal, the catalyst amount is the 0.1% of aldehyde mole, and the molar ratio of aldehyde and borine is 1:
1.1。
In above-mentioned technical proposal, the temperature of hydroboration is room temperature, and the reaction time is 10 minutes.
Above-mentioned technical proposal can indicate as follows：
R1Come from raw material aldehyde.
Due to the application of the above technical scheme, the present invention has the following advantages compared with prior art：
1. present invention firstly discovers that open-chain crown ether base lithium extremely can efficiently be catalyzed hexahydrobenzaldehyde, propionic aldehyde, n-Heptaldehyde and boron
Hydroboration occurs for alkane, and new side is provided to prepare borate with borine generation hydroboration using carbonyls
Case.
2. the catalytic activity height that hydroboration occurs with borine for open-chain crown ether base lithium catalysis aldehyde disclosed by the invention (is urged
Agent dosage is only that 0.1%), reaction condition is mild (room temperature), and the reaction time is short (10 min), and reaction yield is high, and reaction is simple
Controllably, post-processing is simple, and reaction uses solvent-free system, reduces the pollution to environment.
3. catalyst disclosed by the invention has the fatty aldehyde of different size, different electronic effects preferable pervasive
Property, the boric acid ester compound to obtain different substituents structure provides more selections.
Specific implementation mode
The present invention is described further with reference to embodiment：
Embodiment one：Open-chain crown ether base lithium is catalyzed cyclohexyl benzene formaldehyde and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran that 20ul open-chain crown ether base lithiums are added of argon gas protection is molten
Liquid (0.05M) (0.1 mol% dosages, similarly hereinafter), then with syringe be added 0.1596 mL borines, be uniformly mixed, then with inject
0.095 mL2- pyridine carboxaldehydes are added in device, and mixture is stirred at room temperature, and after reacting 10 min, nuclear-magnetism yield is 99%, is subtracted later
Pressure removes a small amount of tetrahydrofuran and excessive borine to get to corresponding pinacol borate C6H5COCH2OB(OC(CH3)2C
(CH3)2O)。1H NMR (400 MHz, CDCl3) δ 8.61 (d, J = 5.4 Hz, 1H, Ar-H), 7.91 (t, J
= 7.7 Hz, 1H, Ar-H), 7.49-7.41 (m, 2H, Ar-H), 5.10 (s, 2H, OCH2), 1.32 (s,
12H, CH3). 13C NMR (101 MHz, CDCl3) δ 159.82 (Ar-C), 143.72 (Ar-C), 139.56
(Ar-C), 123.39 (Ar-C), 120.09 (Ar-C), 81.04 (OC), 66.47 (OCH2), 25.47 (CH3)。
Embodiment two：Open-chain crown ether base lithium is catalyzed propionic aldehyde and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran that 20ul open-chain crown ether base lithiums are added of argon gas protection is molten
Then 0.1596 mL borines are added with syringe in liquid (0.05M) (0.1 mol% dosages), are uniformly mixed, then be added with syringe
0.072 mL propionic aldehyde, mixture are stirred at room temperature, and after reacting 10 min, nuclear-magnetism yield is 99%, is removed under reduced pressure later a small amount of
Tetrahydrofuran and excessive borine are to get to corresponding pinacol borate CH3CH2COCH2OB(OC(CH3)2C(CH3)2O)。1H
NMR (400 MHz, CDCl3) δ 3.80 (t, J = 6.6 Hz, 2H, OCH2), 1.63-1.54 (m, 2H, CH2),
1.25 (s, 12H, CH3), 0.91 (t, J = 7.4 Hz, 3H, CH3). 13C NMR (101 MHz, CDCl3) δ
82.04 (OC), 66.02 (OCH2), 24.14 (CH3CH2), 24.05 (CH3), 9.55 (CH2CH3)。
Embodiment three：Open-chain crown ether base lithium is catalyzed n-Heptaldehyde and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran that 20ul open-chain crown ether base lithiums are added of argon gas protection is molten
Then 0.1596 mL borines are added with syringe in liquid (0.05M) (0.1 mol% dosages), are uniformly mixed, then be added with syringe
0.1392 mL n-Heptaldehydes, mixture are stirred at room temperature, and after reacting 10 min, nuclear-magnetism yield is 99%, are removed under reduced pressure later few
The tetrahydrofuran of amount and excessive borine are to get to corresponding pinacol borate C6H13COCH2OB(OC(CH3)2C(CH3)2O)
。1H NMR (400 MHz, CDCl3) δ 3.82 (t, J = 8 Hz, 2H, OCH2), 1.52-1.58 (m, 2H,
CH2), 1.27-1.34 (m, 8H, CH2), 1.24 (s, 12H, CH3), 0.87 (t, J = 8 Hz, 3H, CH3).13C NMR (100 MHz, CDCl3) δ 82.02 (OC), 64.40 (OCH2), 31.29 (CH2), 30.92 (CH2),
28.44 (CH2), 25.02 (CH2), 24.00 (CH3), 22.05 (CH2), 13.51 (CH3)。
Open-chain crown ether base lithium is replaced with to the amido lithium compound of formula I, it is virtually impossible to obtain product, yield is less than 10%.
Present invention firstly discovers that open-chain crown ether base lithium can be catalyzed the hydroboration of aldehyde with high catalytic activity, and
And there is very wide substrate usage range.Cheap catalyst and lower catalyst amount, mild catalysis item
Part provides possibility for industrial applications.
Claims (10)
1. a kind of method preparing borate using fatty aldehyde, includes the following steps：
Under anhydrous and oxygen-free environment, in atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then adds
Enter catalyst open-chain crown ether base lithium, is uniformly mixed, adds aldehyde, reacted；It is then exposed to terminate reaction in air, obtain
To borate；The aldehyde is selected from fatty aldehyde.
2. the preparation method of borate according to claim 1, which is characterized in that the fatty aldehyde be selected from hexahydrobenzaldehyde,
Propionic aldehyde, n-Heptaldehyde；The borine is selected from pinacol borine.
3. the preparation method of borate according to claim 1, which is characterized in that the dosage of the catalyst is aldehyde mole
0.1 % of amount.
4. the preparation method of borate according to claim 1, which is characterized in that the temperature of reaction be room temperature, reaction when
Between be 10 min.
5. the preparation method of borate according to claim 1, which is characterized in that the molar ratio of aldehyde and borine is 1: 1.1.
6. open-chain crown ether base lithium is in catalysis aldehyde and the application in borine hydroboration；The aldehyde is fatty aldehyde.
7. application according to claim 6, which is characterized in that the hydroboration includes the following steps：
Under anhydrous and oxygen-free environment, under atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then adds
Enter open-chain crown ether base lithium, be uniformly mixed, add aldehyde, carries out hydroboration.
8. application according to claim 6, which is characterized in that the fatty aldehyde is selected from hexahydrobenzaldehyde, propionic aldehyde, positive heptan
Aldehyde；The borine is selected from pinacol borine.
9. application according to claim 6, which is characterized in that the dosage of the catalyst is 0.1 % of aldehyde mole,
The molar ratio of aldehyde and borine is 1: 1.1.
10. application according to claim 6, which is characterized in that the temperature of the hydroboration is room temperature, and the time is
10 min。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810336759.5A CN108440590A (en) | 2018-04-16 | 2018-04-16 | The method for preparing borate using fatty aldehyde |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810336759.5A CN108440590A (en) | 2018-04-16 | 2018-04-16 | The method for preparing borate using fatty aldehyde |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503318A (en) * | 2018-12-24 | 2019-03-22 | 苏州大学 | A method of alcoholic compound is prepared by the non-catalytic reaction of aliphatic carboxylic acid |
| CN109651083A (en) * | 2018-12-29 | 2019-04-19 | 苏州大学 | The method for preparing aliphatic alcohol based on n-BuLi |
| WO2019200523A1 (en) * | 2018-04-17 | 2019-10-24 | 南通纺织丝绸产业技术研究院 | Application of p-methylanilino lithium in catalyzing hydroboration of carbonyl compound and borane |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749372A (en) * | 2016-12-07 | 2017-05-31 | 厦门大学 | A kind of preparation method of organic boronic ester compounds |
-
2018
- 2018-04-16 CN CN201810336759.5A patent/CN108440590A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749372A (en) * | 2016-12-07 | 2017-05-31 | 厦门大学 | A kind of preparation method of organic boronic ester compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019200523A1 (en) * | 2018-04-17 | 2019-10-24 | 南通纺织丝绸产业技术研究院 | Application of p-methylanilino lithium in catalyzing hydroboration of carbonyl compound and borane |
| CN109503318A (en) * | 2018-12-24 | 2019-03-22 | 苏州大学 | A method of alcoholic compound is prepared by the non-catalytic reaction of aliphatic carboxylic acid |
| CN109651083A (en) * | 2018-12-29 | 2019-04-19 | 苏州大学 | The method for preparing aliphatic alcohol based on n-BuLi |
| CN109651083B (en) * | 2018-12-29 | 2021-11-05 | 苏州大学 | Method for preparing aliphatic alcohol based on n-butyl lithium |
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Application publication date: 20180824 |