Processes for producing dialdehyde monoacetals

• US 6,166,225 A
• Filed: 10/15/1999
• Issued: 12/26/2000
• Est. Priority Date: 02/17/1998
• Status: Expired due to Fees

• Current Assignee: Daicel Chemical Industries Limited
• Original Assignee: Daicel Chemical Industries Limited
• Inventors: Tanaka, Yasutaka, Shimada, Giichi, Uenakai, Hiroaki
• Primary Examiner(s): OWENS, AMELIA A
• Application Number:
  US09/403,215
• Time in Patent Office: 438 Days
• Field of Search: 549/347
• US Class Current: 549/347
• CPC Class Codes: C07D 317/26 Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom

Abstract

In a method of producing a dialdehyde monoacetal(s) (III) from dialdehyde(s) (I) and diol(s) (II), the present invention provides a method comprising a first step wherein said dialdehyde(s) (I) and said diol(s) (II) are reacted to produce dialdehyde bisacetal(s) (IV), the amount by mole of said diol(s) (II) being at least twice the amount by mole of said dialdehyde (I) and a second step wherein said dialdehyde bisacetal(s) (IV) is reacted with said dialdehyde (I). The present invention also provides a method of producing a glutaraldehyde monoacetal via reacting 2-Y-3, 4-dihydro-2H-pyran or a ring-substituted derivative thereof with diol. This method comprises a second step reaction wherein glutaraldehyde (iv) which is one of the by-products of the first step reaction is reacted with glutaraldehyde bisacetal (v) which is another by-product of said first reaction. According to the present invention, in the above-mentioned method of producing a glutaraldehyde monoacetal (iii), after the end of the first step reaction, the crude reaction solution is heated at a temperature of from 100° C. to 200° C. to produce the glutaraldehyde monoacetal (iii) from the by-products, low boiling-point components produced from the substituant group Y being removed via distillation.

Claims

1. A method of producing a dialdehyde monoacetal (III) from a dialdehyde (I) and a diol (II) characterised in that it comprises:

a first step where said dialdehyde (I) and said diol(II) are reacted to obtain a dialdehyde bisacetal (IV), the mole amount of said diol(s) (II) being at least twice amount of said dialdehyde (I); and

a second step where said dialdehyde bisacetal (IV) is reacted with said dialdehyde (I);

said dialdehyde (I), diol (II), dialdehyde monoacetal (III) and dialdehyde bisacetal (IV) being shown in the following Formulae (I) to (III) ##STR10## wherein R¹ is a hydrocarbon group

space="preserve" listing-type="equation">HO--R.sup.2 --OH (II)

wherein R² is a hydrocarbon group ##STR11## (wherein R¹ and R² are the same as in Formulae (I) and (II) respectively ##STR12## wherein R¹ and R² are the same as in Formulae (I) and (II) respectively.

2. The method for producing a dialdehyde monoacetal of claim 1, wherein the first step and/or the second step are carried out in the presence of an acidic catalyst.

3. The method for producing dialdehyde monoacetal(s) of claim 1, wherein said dialdehyde (I) used in the reaction with dialdehyde bisacetal(s) (IV) is anhydrous.

4. A method for producing a glutaraldehyde monoacetal via reacting a 2-Y-3, 4-dihydro-2H-pyran or a ring-substituted derivative thereof as shown in General Formula (i) with a diol as shown in General Formula (ii) to obtain glutaraldehyde monoacetal as shown in General Formula (iii), characterised in that said glutaraldehyde monoacetal (iii) is produced in a second step reaction wherein said glutaraldehyde (iv) which is a by-product of the first step reaction is reacted with glutaraldehyde bisacetal (v) which is another by-product of the same reaction;

2-Y-3, 4-dihydro-2H-pyran, diol (ii), glutaraldehyde monoacetal (iii), glutaraldehyde (iv) and glutaraldehyde bisacetal (v) being as shown in the following General Formulae;

##STR13## wherein Y is a hydroxy group, an alkoxy group, an aryloxy group or an aralkyloxy group

space="preserve" listing-type="equation">HO--R--OH (ii)

wherein R is a divalent saturated or unsaturated hydrocarbon group having from 1 to 10 carbon atoms ##STR14## wherein R is as defined in General Formula (ii) ##STR15## wherein R is as defined in General Formula (ii).

5. The method of producing a glutaraldehyde monoacetal of claim 4, wherein in the process for isolating glutaraldehyde monoacetal via distillation of the crude reaction solution of the first step, the initial distillation operation for removing low boiling-point components is carried out while maintaining the temperature of the solution in the bottom flask of the distillation column in the range of 100°

C. to 200°

C.

6. The method for producing a glutaraldehyde monoacetal of claim 4, wherein after the end of the first step reaction, the crude solution is heated until a temperature comprised between 100°

C. and 200°

C., glutaraldehyde monoacetal (iii) being produced from by-products and the low boiling-point components produced from the substituant group Y being distilled out during the production of said glutaraldehyde monoacteal (iii).

7. The method of producing a glutaraldehyde monoacetal of claim 4, wherein said 2-Y-3, 4-dihydro-2H-pyran is 2-methoxy-3, 4-dihydro-2H-pyran and said diol is ethylene glycol.

8. The method of producing a glutaraldehyde monoacetal of claim 7, wherein a crude reaction solution in said first step is separated into a fraction primarily containing glutaraldehyde and a fraction primarily containing glutaraldehyde monoacetal via distillation.

9. The method for producing a glutaraldehyde monoacetal of claim 8, wherein the separation of the fraction primarily containing glutaraldehyde is carried out at a temperature of the solution of the bottom flask of the column of 130°

C. to 142°

C. and under a pressure of the top of the column of from 25 torr to 35 torr and at a temperature of the top of the column of from 95°

C. to 119°

C.

10. The method for producing a glutaraldehyde monoacetal of claim 8 or 9, wherein the separation of the fraction primarily containing glutaraldehyde monoacetal is carried out at a temperature of the solution of the bottom of the column of from 142°

C. to 168°

C. and under a pressure of the top of the column of from 25 torr to 35 torr and at a temperature of the top of the column of from 119°

C. to 124°

C.