JPS59128342A - Preparation of glutaraldehyde acetals - Google Patents

Abstract

PURPOSE:To obtain the titled substance by reacting a monohydric or polyhydric alcohol with a cyclopentyl peroxide compound in the presence of a catalyst containing an element selected from copper, silver, Al, Ti, Cr, Fe, Pd, Pt, etc. and a compound containing it. CONSTITUTION:An alcohol shown by the formula R1OH (R1 is 1-12C aliphatic or alicyclic group) or formula HO-Z1-OH (Z1 is 2-12C aliphatic or alicyclic group) is reacted with a compound shown by the formula II (R3 and R4 are H, or 1-10C organic group) in the presence of a catalyst containing an element selected from Cu, Ag, B, Al, Sn, Pb, Ti, Zr, V, Cr, Mo, Fe, W, Mn, Co, Ni, Ru, Rh, Pd, Os, Ir, and Pt and/or its compound, to give a compound shown by the formula III [X and Y are group shown by the formula IV, of formula V (R5 and R6 are R1 or HO-Z1), or formyl] or a compound shown by the formula IV (R7 and R8 are R1 or HO-Z1).

Description

[Detailed description of the invention] Glutaraldehyde is an expensive intermediate raw material for Tanyu chemical products, and is also used in many applications such as leather tanning agents, microcapsule hardening agents, bactericidal agents, crosslinking agents, and enzyme immobilization agents. It is a compound that is

Currently, curcuraldehyde is produced mainly through the Diets-Aldar reaction between acrolein and vinyl ether.
-Produced by hydrolyzing an alkoxine dihydropyran compound. However, this method has the disadvantage that raw materials are expensive and generally difficult to obtain.

In addition, a method of oxidizing 7,5-bentanediol is also known, but this method also has disadvantages in that the raw materials are expensive and the purity of the curcuraldehyde obtained is very poor. Therefore, curcuraldehyde is extremely expensive compared to other chemical products, and it is hoped that a method for producing curcuraldehyde with good purity using inexpensive raw materials that can be easily synthesized chemically will be developed. There is.

From such an industrial standpoint, it is hoped that a method for producing glutaraldehyde using cyclopentene or cyclopentene R conductor, which can be obtained industrially at relatively low cost, as a raw material will be developed. The method for producing curcuraldehyde by oxidizing cyclopentene or cyclopentene derivatives generally involves synthesizing 7,2-cyclobentanediol from cyclopentene, and converting this 2-cyclobentanediol into tetraacetic acid (>1) or periodic acid. A method of oxidizing with an oxidizing agent such as Although this method has good selectivity,
The drawback is that lead tetranodes and periodic acid are theoretically consumed as oxidizing agents rather than catalysts.

In addition, a method is known in which cyclopentene is reacted with ozone to form oscinite, which is reductively decomposed to obtain glutaraldehyde. However, this method has the disadvantage that it is not suitable for production on an industrial scale because it produces oscinite, which has a high risk of explosion, as a reaction intermediate.

Recently, a method has been proposed in which cyclopentene or cyclopentene oxide is catalytically oxidized with hydrogen peroxide in the presence of a molybtene compound (for example, Tokko Sho J, 2-! j/, No. 336.2). However, this method also has some serious drawbacks. The first is that the reaction must be carried out in a non-aqueous system because the reaction stops due to the presence of water. That is, a commercially available low-concentration hydrogen peroxide aqueous solution cannot be used, and water-free hydrogen peroxide obtained by extraction with an organic bath medium must be used. Even if you do that,
Since water is produced when hydrogen peroxide reacts with 7-chloropentene or cyclopentene oxide, this water must be continuously removed.

The second problem is that /, 2-cyclobentanediol is produced as a by-product in multiple stages. This diol is a substance that is very difficult to separate from curcuraldehyde, and it is necessary to eliminate as many by-products as possible in order to reduce the purity of the product curcuraldehyde.

The third and most serious problem is that the generated curcuraldehyde reacts further.

Glutaraldehyde is a very unstable substance, and if the reaction continues without being separated from the reaction system even after it has been produced, the glutaraldehyde that has been produced will be further oxidized and become carbo/acid.

It ends up being wasted in the condensation reaction.

For the reasons mentioned above, it is clear that it is difficult to produce highly pure glutaraldehyde using this method, and it is also difficult to improve the yield. Therefore, it is considered to be very difficult to industrialize the method for producing glutarartecht by oxidizing cyclopentene using hydrogen peroxide.

In general, when manufacturing each Shinkasei product, there are a few simple steps.
! Of course, it is required that the reaction rate be high, but in the production of glutarartechite, its instability must be fully taken into account in the method. Therefore, even if the reaction rate is high, a production method in which the produced glutarartechite reacts further or wastes labor and materials in removing impurities is not considered to be an industrially appropriate method.

The present inventors have conducted intensive research to achieve the above-mentioned purpose and have proposed a method for producing glutarartechite using a 7-clopentyl peroquinto compound as a raw material (Special feature 1). Ryōsho 57-3 and 47, Ryōsho 57-/jri 27
).

The present inventors conducted further research to facilitate stabilization and high purification of the glutarartechite precursor, and as a result, discovered the following new method and completed the present invention. That is, the present invention provides copper, silver, boron, aluminum, tin, lead, titanium, zirconium, vanadium,
In the presence of a catalyst containing at least seven elements and/or compounds thereof selected from the group consisting of chromium, molybdenum, tungsten, manganese, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium and platinum, General formula (R, is the number of carbon atoms / ~ /,
A monohydric alcohol represented by a linear or branched aliphatic group (2, which is still an alicyclic organic group); It is a branched aliphatic or alicyclic organic group.
A number of hydroxyl groups may be bonded. However, the hydroxyl group is on the same carbon! At least 1 selected from the group of polyhydric alcohols shown in
German alcohol and the general formula (R2 is hydrogen or a straight chain of carbon fibers/-branched aliphatic, alicyclic or aromatic organic group -C) or the general formula (ft, and R4 are hydrogen or carbon u,'
~10 organic groups. R6 and R4 may be linked to form a quick-forming compound). be. R5 & Hibi R6 are R, Kashi or HO-Z, respectively. The present invention relates to a method for producing glutaraldehyde acetals represented by the general formula (%) and (%), although X and Y may be the same and may be the same, excluding the case where both are formyl groups.

The present inventors have shown that a compound with an aldehyde platform structure by decomposition of a compound that breaks down the cyclopentylbero structure is shown in the 1st section of this % revision, and an alcohol of the 1st section of the 6th section in the presence of a fCC financial catalyst. We have newly discovered that an acetal compound can be obtained by reacting with acetal compound.

That is, the general formula % formula % (where a, b, c and I+ are real numbers, 4ta+,
It was discovered that the following reaction (necessitated by 2b-1c=n+n) occurs, but such a reaction was completely unknown until now, and is a rare reaction.

When the method of the present invention is used for the production of curcuraldehyde, the operation is safe! It has been found that it is possible to produce pure IW glutaraldehyde.

In other words, cyclopentene must be synthesized industrially from cyclobentene oxide%l*! %j By catalytically decomposing the cyclopentyl peroxide-8-compound described in the desired range in an alcohol with i of a theoretically short or higher value to convert an unstable peroxide compound into a stable acetal, the reaction may run away or The risk of explosion can be completely eliminated. Although it was impossible to separate the by-produced noklope/tanediol and oligomers using the hydroquine cyclopentyl oxide compound, the acetals obtained in the present invention are thermally stable and can be easily purified by distillation. A highly purified glutaraldehyde precursor can be obtained. Furthermore, these acetals have the advantage that they are chemically stable and can be stored for long periods of time if care is taken to prevent contamination with acids and moisture.

The acetals thus obtained are hydrolyzed using the well-known 7i method, and by distilling off the by-product alcohol, a highly pure aqueous glutaraldehyde solution can be obtained.

The acetals produced by the method of the present invention have the general formula % or formyl group. R6 and R6 are each R
, or Hoz. X and Y may be the same, but the case where both are formyl groups is excluded) and the general formula % is represented by the formula %. Here are some specific examples of these acetals.

etc. can be opened. Depending on reaction conditions, individual acetals such as those described above may be produced during IUJ.

However, acetals can easily be separated into sheaths.
All of them can be converted into glutaraltehyde by hydrolysis.

In the method of Fudatsu J (historically used catalysts are planes and iron.

Boron, aluminum, tin, lead, titanium, zirconium, vanadium, chromium, molybdenum, tanksten,
Manganese, iron, cobalt, nickel.

It is a mixture of at least one or more of ruthenium, rhodium, palladium, osmium, iridium and platinum bodies and compounds. These compounds are used in the form of elements of zero valence, or inorganic or organic compounds with a certain valence.

These base compounds include oxides, mixed oxides, hydroxides, oxidants, heteropolyacids, salts and esters thereof. These include those derived from inorganic hydroacids, oxyacids, organic carboxylic acids having less than 0 carbon atoms, and sulfonic acids.

Complexes of these elements are mainly called organometallic complexes, which are coordinated by organic groups and/or inorganic groups.

Examples of catalysts that can be used in the present invention are as follows.

i.e. copper, silver, aluminum, tin, lead, titanium,
Vanadium, chromium, molybdenum.

Elemental metals such as tungsten, manganese, iron, cobalt, nickel, rhodium, palladium and platinum - copper-nickel, copper-platinum, copper-palladium, copper-gold, silver-platinum, silver-palladium, gold-platinum, cobalt iridium,
Cobalt-palladium, cobalt-rhodium, cobalt-iron, nickel-palladium, nickel-iron alloys, copper, silver, boron, aluminum, tin, lead, titanium,
Oxides of vanadium, chromium, molybdenum, tungsten, manganese, iron, cobalt, nickel, rhodium, palladium, osmium, iridium and platinum (Cu
20, Cub, Ag2O, Ago, Fed, Fe
,,03,F e 304 t Co O* C030
4t N i Oi Ru O2, Pdo1oso4,
I r 02 * P is also 021MnO2, Cr 02,
Cr 203, Cr05. MoO2, Mq205Mob
, , WO2, W, 05. 'W06, VO2, v2
05. ZrO2, TlO2, B2O3, AJ20. ,
PI) O nato) i cholera 17), t# chloride,
Fluoride, chloride, bromide, iodide, inorganic acid salts of these elements such as nitrates, sulfates, phosphates, pyrophosphates,
PoIJ IJ phosphate, borate, carbonate, formate, acetate, propionate, butyrate, inobutyrate, caproate, caprylate.

Organic acid salts such as laurate, nanthenate, stearate, oxalate, succinate, glutarate, adipate, benzoate, phthalate, benzenesulfonate; acetyl of these elements acetonate, phthalo7-anine complex 1 metal carbonyl of these elements (■(CO)6
．． Cr(CO)6lMo(CO)6゜w(co)6,F
e (co)5. Ni(Co)4, Ru3(Co)
12.033(CO)12, etc.) - Oxyacids such as morintic acid, chromic acid, osmic acid, tungstic acid, and corresponding heteropolyacids and alkali gold pA salts or alkaline earth gold camphor salts of superacids, etc. can be opened.

・The use of a mixture of at least one of the above single substances and compounds ("1, no problem").

Further alumina, silica according to known methods.

It is also possible to use silica alumina, zeolite, etc., or in some cases supported on a carrier such as an organic electrolyte.

In the present invention, a cyclopentyl peroxide compound represented by the following general formula is used.

Here, R2 is hydrogen or a group having 1 to 2 carbon atoms. Typical examples of these groups include alkyl groups, cycloalkyl groups, aryl groups, acyl groups, etc., and halogens, hydroxy groups, formyl groups, hydrobar groups, and baroxyalkyl groups. Yushinki, who does this, can also do 1 Fumii. This cyclopentyl peroxide compound contains sulfuric acid,
Presence of vinegar such as hydrochloric acid or cation exchange
It can be synthesized with a high areal yield by reacting cyclopentene oxide with hydrogen peroxide or an organic hydroperoxide.

The cyclopentyl peroxide compound with mata has the general formula %, where R' is an alkyl group, cycloalkyl group, or aryl group having 1 to 1 carbon atoms. It can also be synthesized by reacting hydroperoxides or organic hydroperoxides.

In the present invention, a cyclopentyl peroxide compound represented by the following general formula can also be used.

Here, R5 and R4 are each hydrogen or carbon number/
~10 mounds (base groups). Typical examples of this organic group include alkyl groups, cycloalkyl groups, halogens, bitroxy groups, polmyl groups, hydroxyl groups, peroxyalkyl groups, and cyclic peroxy groups. It is a metallurgical group containing oxyketal.

kt and 1ζ4 may be connected to form a term. This cyclopentyl peroxide compound can be synthesized by reacting cyclopentene oxide with ketone peroxide in the presence of an alcohol such as sulfuric acid, hydrochloric acid, or a li, iti ion exchange resin. Moreover, this cyclopentyl peroxide compound is converted into β-hydroxycyclopentyl hydroperoxide which can be synthesized by the method described above.
It can also be synthesized by reacting a ketone or an aldehyde with pf in the presence of L-hydrochloric acid or a cation exchange resin.

Specific examples of these cyclopentyl oxide compounds include the following compounds.

In this inverse comparison, there is no problem in using the above cyclobentyl permoxide compound as a mixture.

The general formula of the alcohol used in the method of the present invention (R is a straight chain or branched JIi with a carbon number of /~/2)
& aliphatic or alicyclic organic group) -hydric alcohol, general formula %) It is an organic group with the formula.・Z, has an awn / on the carbon.
... hydroxyl groups may be bonded.

However, alcohols other than at least seven alcohols selected from the group of polyhydric alcohols shown in (excluding those in which one or more hydroxyl groups are bonded to the same carbon) are included.

Specific examples of these alcohols include methanol, ethanol, n-gloyl alcohol, isopropyl alcohol, n-fufur alcohol, sec-phthyl alcohol, n-7m)real alcohol, in-amyl alcohol, n- Hexanol, Octatool, Totecanol, Cyclopentanol, /Clohexanol, /Clototicarol, Ethylene glycol, Flopylenc I
J −r − beg/,. 5-bentanediol, /,2
-hexanediol, glycerin, /,2-cyclopentanediol, /,2-cyclohexanediol, /,3
-There is cyclododecanol.

In carrying out the present invention, the cyclopentyl peroxide compound described above is used in the above A/L without using any other solvent.

The reaction may be carried out in contact with the catalyst by dissolving it only in coal, or the reaction may be carried out by diluting it with a solvent other than the above-mentioned alcohol. The solvents used for this purpose are those that do not react with the antiphase alcohol, cyclopentyl peroxide compound, and acetals produced.
Can be used as an official. As such a solvent, carbon number j ~ 7.2
These include hydrocarbons, carboxylic acid esters, phosphoric acid esters, sulfonic acid esters, carboxylic acid amines, and ethers containing an organic group having 1 to 2 carbon atoms.

Specific examples of these solvents include n-penta/,
Impentane, cyclopenkune, cyclopentene, n-
hexane, inhexane, cyclohexane, octane,
Totican, benzene, toluene, xylene, ethylbenzene, ethyl acetate, butyl acetate, inamyl acetate, cyclohexyl acetate, butyl propionate, ethyl benzoate, dimethyl phthalate, diethyl phthalate, dimethylformamide, dimethylacetamide, triethyl phosphate, trihexyl phosphate , trioctyl phosphate, dimethyl methanephosphonate, diethyl ether, anisole, etc.

When carrying out the method of the present invention, the α degree in the reaction solution of the 7 clopentel peroxide compound is 0,/-30 wt%, preferably 0,j, in order to prevent heat generation and runaway risk due to rapid reaction. -, it is desirable to be in the 20s/L category.

The amount of alcohol to be used may be determined within a range that satisfies such concentration conditions, but it is preferable that the amount of alcohol used is at least 1 mol per mol of the hanclopentyl peroxide compound (< 1 mol). The dosage may be any value as long as it falls within the agglomeration range of the above-mentioned 7 clopentel peroquinide compound.

The number of catalysts used in acetalizing cyclopentyl peroxide compounds according to the method of the present invention can vary over a wide range depending on their activity;
10 per mole of cyclopentyl peroxide compound
-6 mol to 10-1 mol, especially 10-5 mol to 10
It is preferred to use an amount of -1 mol.

The temperature at which the method of the present invention is carried out is undesirable, such that the isocropentyl peroxide compound thermally decomposes non-catalytically and produces by-products other than acetal, and at low temperatures, the reaction rate is slow and economical. It's not a good situation. Therefore, the temperature range of this method is preferably from 0° C. to 200″G, and it is particularly desirable to carry out the process at a temperature below the v-point of the alcohol used in the reaction.

This inverse reaction can be carried out either batchwise or continuously.Although the time required for the inverse reaction varies depending on the reaction temperature and the composition of the reaction system, it is sufficient to carry out the reaction for 10 hours.

Example/ Raw material β-hydroxyclopentyl hydroperoxyte (2) was prepared by the following method.

300 equipped with stirrer, reflux condenser and dropping o-toe
Three CC bottles, one flask, and one amber IJ.
-/, t (manufactured by Rohm and Haas, strong acid cation exchange 14 fat) I 9 and/methyl phthalate Og
Then, while keeping the flask at 30°C, from the dropping funnel into the stirring F, dimethyl tutalate solution containing 7 clopentene oquindo≠og and hydrogen peroxide/J'wL%/1 was added.
0 g of the mixture was added dropwise over 7 hours.

After the dropwise addition was completed, the reaction was further carried out at 30°C for 3 hours, and then the catalyst was separated. The ρ solution was subjected to preparative liquid chromatography using silica gel as the stationary phase and benzene-niethanol=20:/ as the mobile phase to obtain β-hydroxycyclopentyl hydroperoxide ≠θg.

The reaction between the prepared β-hydroxycyclopentyl hydroperoxide and ethanol was carried out as follows.

30 equipped with stirrer, reflux condenser and dropping funnel
Put 7.0 g of Pd/C (5% Pd supported) powder and tjg of ethanol into a 0 cc capacity tri-Solo flask and heat.
Under boiling ethanol, add β-methyl hydroperoxide from the dropping funnel, 2/, 0
A solution prepared by diluting 9 with 701/ml of ethanol was added dropwise over 7 hours.

After the dropwise addition was completed, the reaction was continued at boiling temperature for another 2 hours.

The reaction solution was treated with FFAP (freefatty acid).
Analysis by gas chromatography using a column with a liquid phase of cis-
and t r a II δ-i, o-diethoxy7tetra-hydropyran 10. Otsu V, jt, J-diethoxopentanal J, 7g and /1/.

j, j-tetraethoxypentane/! ;, /,9 were found to be generated. Yield of acetals is 90%
Met. It was confirmed by I. I. Lee that no unreacted peroxide remained in the reaction solution.

Example λ A cyclopentyl peroxide compound prepared from cyclopentene oxide and methyl ethyl ketone peroxide in the same manner as in Example 4, 4'-ethyl-Hiro-methyl-
λ, J, j −) Riokizabicyclo [Hiroshi.

3, O]nonane ■ was synthesized. However, the reaction temperature is Hiro θ
℃, and a solution prepared by diluting cyclopentene oxide 4toy, methyl ethyl ketone peroxide i, txg with dimethyl phthalate of >>Og was used. 4to after completion of dripping
After reacting for 3 hours at °C, fractionation was carried out using liquid chromatography in the same manner as in Example.
Methyl-2.3.5-trioxabicyclo[tx, 3.
o] Nonane ■Hiro 0.9 was obtained.

Acetalization of this compound was carried out in exactly the same manner as in Example. However, as a catalyst, Pd/At20°(P(
1 supported amount/%) powder/ /i, Og, 311.41 g of ■ as a cyclopentyl peroxy compound, and ethanol was used in soybean flask and 70 g in dropping funnel, respectively.

After the reaction was completed, gas chromatography analysis revealed cis- and trans-,2,! ;-dietquintetrahydropyran/, 2,19, ta,! −
Shedkin Pentanal 6.0g and/,/,! ;,
! ;-Tetraethoxypentane/7°gg was produced. The yield of these acetals was 0%.

Example 3 Cyclopentene oxide was reacted with t-butyl hydroperoxide to prepare raw material β-hydroxycyclopentyl monobutyl peroxide (2) in the following manner.

After stirring, tilt the reflux condenser and dropping funnel! θOa
After putting 7 g of Amberlyst/O and Ioo g of monobutanol into an a-sized Mitsuro flask, the temperature was raised to 70°C, and while stirring, added lysoclopentene oquinide v4tg and t-butylhydroperoquinide S to the dropping funnel. , :zg
and a solution consisting of 700 g of butanol was added over a period of one hour.

After reacting at θ° C. for 1 hour, the reaction solution was distilled under reduced pressure to obtain β-hydroxyclopentyl monobutyl peroxide.

β-Hydroloki/cyclopentyl was also reacted with monobutyl peroxide in ethanonyl using palladium black as a catalyst in the same manner as in Example. That is, in a flask similar to Example/, palladium black 0. Add 2g of ethanol and Og of ethanol, and add β-hydroxycyclopentyl L from the dropping funnel.
-Butylperoxyfluoride/13g was dissolved in ethanol tug and a solution of 0g of 0SO was added dropwise at the boiling temperature of ethanol.

After the dropwise addition was completed, the mixture was heated and stirred for a period of time. After distilling off excess ethanol from the reaction solution, fractional distillation was performed using a rotary bundt type rectification column, and cis-2,j-shedquin tetrahydropyran was obtained! /℃/3 mmHg node, 9, trans-,2,j-jetoxytetrahydrobilane (tj-C/2 to H9) 2
．． ri g, z, z-jetoxypentanal (za/ ℃/
2 iamH,? )ri, / p, /, /, j
, j-tetraeth♀cibentane (Tata ℃ 72 mmHg
)/ri, og was obtained. The yield of acetals was uneven.

Example 1 Amber list ijk was prepared in exactly the same manner as in Example 1.
Cyclopentene oxide and hydrogen peroxide were reacted as a catalyst, and after one reaction, the catalyst was separated to obtain a dinotyl phthalate solution containing 23.1% of β-hydroxyclopentyl hydroperoxide.

Using this reaction solution without separating β-hydroxycyclopentylhydroberoxate, the reaction with methanol was carried out as follows.

JOOc equipped with stirrer, reflux condenser and dropping funnel
Platinum black 0.0% in a c-capacity Mitsuro flask. OP and 720 g of methanol were added and heated, and 700 g of the above reaction solution was added from the dropping funnel over 7 hours while the methanol was boiling.

After the dropwise addition was completed, the mixture was further heated and stirred for ♂ hours, and then analyzed by gas chromatography. Otsu-dimethoxytetrahydropyran 10. ．． 29.3j-,J-dimethoxypentanal, 7g and/, /,J,j-tetramethoxypentane//,! It was found that 59 were generated. The yield of these acetals was 16%.

EXAMPLE The reaction between β-hydroxycyclopentylhydroberoxide (1) obtained in the same manner as in Example 1 and ethylene glycol was carried out as follows.

TIO (Cs
)(,O□)2/,/217 and ethylene glycol jO
The mixture was heated to 20° C., and a common solution consisting of β-hydroxycyclopentyl hydroperoxide 309 and ethylene glycol OP was added dropwise through the dropping funnel over a period of 7 hours.

After completing Mj lower, go back to O''C and continue with j time counter y6.

After the reaction was completed, the acetal was separated by preparative liquid chromatography, and the result was t-(,2',j'-dioxacyclopentyl)butyl-a,3-bis(2',3/-dioxacyclopentyl). :/Roban 23, 7g was given ii4. The yield of these J setals was 65%.

Examples 6 to 26 Various cyclopentyl peroxide compounds were prepared in the same manner as in Examples 1 to 3, and acetalized in the presence of various catalysts. The results are shown in Table 1.

23/24 7624-4G2
3/34 7624-4 G2
3/40 7624-4 G2
3150 7624-4 G2
3/72 6674-4 G2
3/74 6674-4G23
/88 6674-4 G23/
89 6674-4 G271
08 7059-4 G311
04 7059-4 G31/
16 7059-4 GC07
D 323104 8214-
4C@ Inventor Mitsuo Matsuno 2-228 Kosugi-cho, Nakahara-ku, Kawasaki City 0 Inventor Kosuke Imai 1393-3 Hakusan-cho, Midori-ku, Yokohama City

Claims (1)

[Claims] Copper, silver, boron, aluminum, tin, lead, titanium,
A catalyst containing at least seven elements and/or compounds thereof selected from the group consisting of zirconium, vanadium, chromium, molybdenum, tungsten, manganese, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium and platinum. % (2 , is a linear or branched aliphatic or alicyclic organic group having carbon number λ~/2.On the carbon of Zl, there is further /~
A large number of hydroxyl groups may be bonded. However, polyhydric alcohols with the general formula (R2 is hydrogen or the number of carbon atoms/~ A linear or branched aliphatic, alicyclic or aromatic organic group) General formula (R and R4 are hydrogen or carbon fiber number/~I
It is an organic group of O. R6 and R4 may be linked to form a cyclopentyl peroxide compound represented by the general formula x-(.R2), -Y or formyl group. , R and R8 are each 5 R1 or HO-Z. However, X and Y may be the same, but both of them are formyl groups (excluding the lifter) and the general formula (%).